- Influence of degree of substitution on the host-guest inclusion complex between ionic liquid substituted β-cyclodextrins with 2,4-dichlorophenol: An electrochemical, NMR and molecular docking studies
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A mono- and di-substituted ionic liquid-β-cyclodextrin (β-CD-ILs) were synthesized and their host-guest inclusion complex with 2, 4-dichlorophenol (2,4-DCP) were evaluated by electrochemical study. First, both β-CD-ILs which is β-CD-1-BIMOTs and β-CD-2-BIMOTs were fabricated on carbon paste electrode (CPE) for determination of 2,4-DCP. The cyclic voltammetry results indicate that both β-CD-IL/CPEs exhibit higher oxidation peak current compared to native β-CD/CPE. Both complexes possess high sensitivity, stability and reproducibility. However, as the degree of substitution of ionic liquid (IL) increases, the selectivity of β-CD-IL towards 2,4-DCP decreases. Thus, it can be deduced that the degree of substitution of IL is influencing the host-guest inclusion complex of β-CD-ILs with 2,4-DCP.
- Rasdi, Fairuz Liyana Mohd,Rahim, Nurul Yani,Hasim, Fara Wahida,Prabu, Samikannu,Jumbri, Khairulazhar,Manan, Ninie Suhana Abdul,Mohamad, Sharifah
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- Characterization and enhanced antioxidant activity of the cysteinyl β-cyclodextrin-baicalein inclusion complex
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Baicalein is a type of flavonoid isolated from the roots of a medicinal plant, Scutellaria baicalensis. Although it has attracted considerable attention due to its antiviral, anti-tumor, and anti-inflammatory activities, its limited aqueous solubility inhibits the clinical application of this flavonoid. The present study aimed to prepare and characterize a host-guest complex in an effort to improve the solubility and antioxidant activity of baicalein. The host molecule is a macrocyclic β-cyclodextrin (β-CD) functionalized with cysteine for a synergetic effect. The structure of the synthesized cysteinyl β-CD was analyzed using nuclear magnetic resonance (NMR) spectroscopy and mass spectrometry. The inclusion complex with baicalein was studied by UV-vis, NMR spectroscopy, scanning electron microscopy, and X-ray powder diffractometry. The formed cysteinyl β-CD/baicalein inclusion complex efficiently improved the solubility and antioxidant ability of baicalein. Therefore, we suggest that the present cysteinyl β-CD is a potential host molecule for inclusion complexation and for bioavailability augmentation.
- Kim, Hwanhee,Yiluo, Hu,Park, Seyeon,Lee, Jae Yung,Cho, Eunae,Jung, Seunho
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- Preparation of 2D molecularly imprinted materials based on mesoporous silicas via click reaction
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The two-dimensional (2D) molecular imprinting approach has attracted extensive research interest in recent years due to its potential advantages such as simple construction, fast template removal and rapid mass transfer. In this study, a new 2D imprinting
- Xu, Zhifeng,Deng, Peihong,Tang, Siping,Kuang, Daizhi,Zhang, Fuxing,Li, Junhua
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- Pseudopolyanions based on poly(NIPAAM-co-β-cyclodextrin methacrylate) and ionic liquids
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(Chemical Equation Presented) A fine host: Copolymers from methacrylated β-cyclodextrin and N-isopropylacrylamide form inclusion complexes with anions of ionic liquids (IL; see picture). Complex formation alters the solubility properties of the copolymer,
- Amajjahe, Sadik,Choi, Soowhan,Munteanu, Maricica,Ritter, Helmut
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- Biotinylated cyclooligosaccharides for paclitaxel solubilization
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The poor water solubility of paclitaxel causes significant problems in producing cancer therapeutic formulations. Here, we aimed to solubilize paclitaxel using biocompatible cyclic carbohydrates. Generally recognized as safe, labeled β-cyclodextrin (β-CD), a cyclic α-1,4-glucan consisting of seven glucoses, was prepared, and bio-sourced cyclosophoraoses (CyS), which are unbranched cyclic β-1,2-glucans with 17–23 glucose units, were purified using various chromatographic methods from Rhizobium leguminosarum cultural broth. For effective targeting, CyS and β-CD were modified with a biotinyl moiety in a reaction of mono-6-amino CyS and mono-6-amino-β-CD with N-hydroxysuccinimide ester of biotinamidohexanoic acid. Interestingly, the aqueous solubility of paclitaxel was enhanced 10.3- and 3.7-fold in the presence of biotinyl CyS and biotinyl β-CD, respectively. These findings suggest that biotin-appended cyclooligosaccharides can be applied to improve the delivery of paclitaxel.
- Cho, Eunae,Jung, Seunho
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- Fabrication of new generation of co-delivery systems based on graphene-g-cyclodextrin/chitosan nanofiber
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Although many techniques have been devoted to promote therapeutic purposes of drug carrier systems, however, there are still many challenges in this area. Here, we designed co-loaded delivery systems, composed of curcumin loaded cyclodextrin-graphene oxid
- Adeli, Mohsen,Rashidipour, Marzieh,Sattari, Shabnam,Soleimani, Khadijeh,Tehrani, Abbas Dadkhah
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- Supramolecular poly(N-acryloylmorpholine)-b-poly(D,L-lactide) pseudo-block copolymer via host-guest interaction for drug delivery
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In the present study, a pseudo-block copolymer was prepared from β-cyclodextrin terminated poly(N-acryloylmorpholine) (β-CD-PNAM) and adamantine-terminated linear poly(D,L-lactide) (AD-PDLLA), through host-guest interaction between β-CD and AD groups. Ini
- Ramesh, Kalyan,Anugrah, Daru Seto Bagus,Lim, Kwon Taek
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- Rational design for cooperative recognition of specific nucleobases using β-cyclodextrin-modified DNAs and fluorescent ligands on DNA and RNA scaffolds
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We propose a binary fluorimetric method for DNA and RNA analysis by the combined use of two probes rationally designed to work cooperatively. One probe is an oligonucleotide (ODN) conjugate bearing a β-cyclodextrin (β-CyD). The other probe is a small repo
- Futamura, Akika,Uemura, Asuka,Imoto, Takeshi,Kitamura, Yusuke,Matsuura, Hirotaka,Wang, Chun-Xia,Ichihashi, Toshiki,Sato, Yusuke,Teramae, Norio,Nishizawa, Seiichi,Ihara, Toshihiro
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- Efficient synthesis of pure monotosylated beta-cyclodextrin and its dimers
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6-O-Monotosyl-β-cyclodextrin (mono-Ts-βCD) is one of the most important intermediates in the production of substituted βCD. So far, performing the monotosylation reaction and, in particular, the purification steps was challenging, relied on toxic solvents
- Tripodo, Giuseppe,Wischke, Christian,Neffe, Axel T.,Lendlein, Andreas
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- Preparation and Stability Evaluation of Size-Controllable PDHCA-β-CD Nanoparticles as Drug Carrier
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A novel biocompatible polymer was prepared by grafting the derivate of β-cyclodextrin (6-SH-β-CD) onto poly(3,4-dihydroxycinnamic acid) (PDHCA) via Michael addition. PDHCA-β-CD nanoparticles were prepared by the self-assembly of amphiphilic PDHCA-β-CD pol
- Chu, Hong,Zhao, Xue,Liu, Shirong,Ni, Zhongbin,Shi, Dongjian,Chen, Mingqing
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- Novel supramolecular liquid crystals: Cyclodextrin-triphenylene column liquid crystals based on click chemistry
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Three new cyclodextrin-triphenylene derivatives 6, 7a and 7b were designed and synthesized by introducing a triphenylene unit into cyclodextrin based on click chemistry and further acylation of hydroxyl groups of the cyclodextrin unit. The column liquid c
- Yang, Fafu,Zhang, Yingmei,Guo, Hongyu
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- The first successful investigation into a cyclodextrin-based enzyme model as an efficient catalyst for luminol chemiluminescent reaction.
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The chemiluminescence of the luminol-H2O2 system is found for the first time to be remarkably enhanced by the Ce(IV) complexes of cyclodextrin dimers.
- Yuan, De-Qi,Lu, Jianzhong,Atsumi, Masato,Izuka, Ayako,Kai, Masaaki,Fujita, Kahee
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- Magnetic poly(β-cyclodextrin-ionic liquid) nanocomposites for micro-solid phase extraction of selected polycyclic aromatic hydrocarbons in rice samples prior to GC-FID analysis
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Poly(β-cyclodextrin functionalized ionic liquid) immobilized magnetic nanoparticles (Fe3O4@βCD-Vinyl-TDI) as sorbent in magnetic μ-SPE was developed for the determination of selected polycyclic aromatic hydrocarbons (PAHs) in rice samples coupled with gas chromatographic-flame ionization detector (GC-FID). The nanocomposite was characterized by various tools and significant parameters that affected the extraction efficiency of PAHs were investigated. The calibration curves were linear for the concentration ranging between 0.1 and 500 μg kg?1 with correlation determinations (R2) from 0.9970 to 0.9982 for all analytes. Detection limits ranged at 0.01–0.18 μg kg?1 in real matrix. The RSD values ranged at 2.95%–5.34% (intra-day) and 4.37%–7.05% (inter-day) precision for six varied days. The sorbents showed satisfactory reproducibility in 2.9% to 9.9% range and acceptable recovery values at 80.4%–112.4% were obtained for the real sample analysis. The optimized method was successfully applied to access content safety of selected PAHs for 24 kinds of commercial rice available in Malaysia.
- Boon, Yih Hui,Mohamad Zain, Nur Nadhirah,Mohamad, Sharifah,Osman, Hasnah,Raoov, Muggundha
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- Modular synthesis of propargylamine modified cyclodextrins by a gold(iii)-catalyzed three-component coupling reaction
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An efficient modular approach for the synthesis of propargylamine modified β-cyclodextrins has been developed. Using mono-(6-benzylamino-6-deoxy)-β-cyclodextrins, formaldehyde, and alkynes, mono-(6-(benzylpropargyl)amino-6-deoxy)-β-cyclodextrins have been synthesized through a three-component coupling reaction catalyzed by gold(iii) salt in water at 40 °C.
- Hui, Tsz-Wai,Cui, Jian-Fang,Wong, Man-Kin
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- Effects of β-cyclodextrin-based Schiff-base Zn(II) complexes: synthesis, physicochemical characterization and their role in alleviating oxidative stress related disorder
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Two water-soluble zinc(II) complexes of β-cyclodextrin-based Schiff bases, viz., mono-6-deoxy-6-(4-(5-chloro-2-hydroxybenzylideneamino)-3,4-diaminotolune)-β-cyclodextrin (4a) and mono-6-deoxy-6-(4-(5-nitro-2-hydroxybenzylideneamino)-3,4-diaminotolune)-β-c
- Das, Ananya,Dutta, Somit,Sinha, Biswajit
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- Inclusion complexes of cysteinyl β-cyclodextrin with baicalein restore collagen synthesis in fibroblast cells following ultraviolet exposure
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Baicalein, a bioactive flavonoid, has poor water solubility, thereby limiting its use in a wide range of biological applications. In the present study, we used inclusion complexes of cysteinyl β-cyclodextrin (β-CD) with baicalein to enhance the stability and solubility of baicalein in aqueous solution. We examined the effects of inclusion complexes of cysteinyl β-CD on collagen synthesis following ultraviolet (UV) irradiation, as well as the mechanisms underlying its effects. Our findings demonstrated that baicalein significantly restored collagen synthesis in the UV-exposed human fibroblast Hs68 cells. In addition, synthetic cysteine functionalized β-CDs were found to promote baicalein-induced collagen synthesis. Inclusion complexes of cysteinyl β-CDs with baicalein significantly upregulated the protein expression of type I collagen and activated the transcription of type I, II, and III collagen. Inclusion complexes of cysteinyl β-CDs with baicalein also downregulated matrix metalloproteinase -1 and -3, and α-smooth muscle actin expression. In addition, inclusion complexes of cysteinyl β-CDs with baicalein attenuated the expression of caveolin-1, but this treatment enhanced the UV-induced phosphorylation of Smad in the transforming growth factor-β pathway. These results suggested that the newly synthesized derivative of CD can be used as a complexing agent to enhance the bioavailability of flavonoids such as baicalein, especially in restoring collagen synthesis.
- Lee, Joomin,Ahn, Eunsook,Kim, Seon-Y.,Shin, Yujeong,Ahn, Seunghyun,Sung, Jiha,Kim, Hwanhee,Cho, Eunae,Jung, Seunho,Park, Seyeon
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- Supramolecular ABC miktoarm star terpolymer based on host-guest inclusion complexation
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A facile strategy for the construction of supramolecular star-shaped ABC terpolymer was proposed and realized via the molecular recognition between β-cyclodextrin- (β-CD-) based host and adamantane- (AD-)modified guest. In the first step, β-CD with two di
- Huan, Xiuying,Wang, Dali,Dong, Ruijiao,Tu, Chunlai,Zhu, Bangshang,Yan, Deyue,Zhu, Xinyuan
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- Electrochemical signal modulation in homogeneous solutions using the formation of an inclusion complex between ferrocene and β-cyclodextrin on a DNA scaffold
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Two DNA conjugates modified with ferrocene and β-cyclodextrin were prepared as a pair of probes that work cooperatively for DNA sensing, in which the electrochemical signal of ferrocene on one probe was significantly "quenched" by the formation of an incl
- Ihara, Toshihiro,Wasano, Tsugutoshi,Nakatake, Ryuta,Arslan, Pelin,Futamura, Akika,Jyo, Akinori
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- A supramolecular strategy to assemble multifunctional viral nanoparticles
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Using a one-pot approach driven by the supramolecular interaction between β-cyclodextrin and adamantyl moieties, multifunctional viral nanoparticles can be facilely formulated for biomedical applications. The Royal Society of Chemistry 2013.
- Chen, Limin,Zhao, Xia,Lin, Yuan,Huang, Yubin,Wang, Qian
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- RETRACTED ARTICLE: Novel supramolecular liquid crystal: Synthesis of cyclodextrin-triphenylene column liquid crystal based on click chemistry
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Three new cyclodextrin-triphenylene derivatives 6, 7a and 7b were designed and synthesized by introducing triphenylene unit on cyclodextrin based on click chemistry and further acylation of hydroxyl groups of cyclodextrin unit. The column liquid crystal b
- Yang, Fafu,Zhang, Yingmei,Guo, Hongyu,Lin, Jianrong
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- Synthesis and comparative lectin-binding affinity of mannosyl-coated β-cyclodextrin-dendrimer constructs
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Targeted drug delivery systems have been built from β-cyclodextrin by monoconjugation with mannosyl-coated dendritic branches following an iterative thiourea-forming convergent strategy; the multivalent adducts showed high Concanavalin A lectin binding ability and intact inclusion capabilities.
- Baussanne,Benito,Mellet,Fernandez,Law,Defaye
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- Supramolecular host-guest interaction for labeling and detection of cellular biomarkers
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Be my guest: A supramolecular host-guest interaction is utilized for highly efficient bioorthogonal labeling of cellular targets. Antibodies labeled with a cyclodextrin host molecule bind to adamantane-labeled magnetofluorescent nanoparticles (see picture
- Agasti, Sarit S.,Liong, Monty,Tassa, Carlos,Chung, Hyun Jung,Shaw, Stanley Y.,Lee, Hakho,Weissleder, Ralph
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- A plug and socket approach for tightening polyelectrolyte multilayers
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A plug and socket approach for tightening polyelectrolyte multilayers is introduced based on the use pendant β-cyclodextrin groups. Prototypical multilayers derived from poly(sodium 4-styrene sulfonate) and β-cyclodextrin-containing poly(4-vinylbenzyltrim
- Lin, Cen,Stedronsky, Erwin R.,Jordan, Luke R.,Wittenberg, Nathan J.,Regen, Steven L.
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- Trimerization of β-cyclodextrin through the click reaction
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Triprop-2-ynyl benzene-1,3,5-tricarboxylate (A) is synthesized by the reaction of 1,3,5-benzenetricarbonyl trichloride with propargyl alcohol and (A) is clicked with mono-6-deoxy-6-azido-β-cyclodextrin (N3-β- CD) in the presence of copper(I) bromide catalyst. N3-β-CD has been prepared from β-cyclodextrin (β-CD) on treatment with toluenesulfonyl chloride (TsCl) and then with sodium azide (NaN3) in two consecutive steps. Further trimer of β-CD is characterized by 1H NMR and FTIR studies. Solubility of β-cyclodextrin (β-CD) in water can be increased by increasing the number of alcoholic OH functionalities and hydrophobic cavities in a molecule by the trimerization of β-CD.
- Tungala, Kranthikumar,Adhikary,Krishnamoorthi
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- Harnessing the energy of molecular recognition in a nanomachine having a photochemical on/off switch
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6A-Deoxy-6A-(N-methyl-3-phenylpropionamido)-β-cyclodextrin operates as a molecular machine, where the amide group serves as a torsion bar to harness the work output resulting from extraction of 1-adamantanol and consequent complexati
- Coulston, Roger J.,Onagi, Hideki,Lincoln, Stephen F.,Easton, Christopher J.
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- Tadpole-shaped β-cyclodextrin-tagged poly(N-vinylpyrrolidone): Synthesis, characterization and studies of its complexation with phenolphthalein and anti tumor activities
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Tadpole-shaped β-cyclodextrin-tagged poly(N-vinylpyrrolidone) (β-CD-PNVP) has been synthesised via the click reaction of alkyne-terminated PNVP and azide-functionalized β-CD. The formed polymer is characterized by 1H NMR, FTIR, and TGA study. T
- Vishwakarma, Niraj Kumar,Patel, Vijay Kumar,Hira, Sumit Kumar,Ramesh,Srivastava, Prateek,Mitra, Kheyanath,Singh, Shikha,Chattopadhyay, Dipankar,Maiti, Pralay,Misra, Nira,Manna, Partha Pratim,Ray, Biswajit
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- Functionalization of cyclodextrins with N-hydroxyphthalimide moiety: A new class of supramolecular pro-oxidant organocatalysts
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N-hydroxyphthalimide (NHPI) is an organocatalyst for free-radical processes able to promote the aerobic oxidation of a wide range of organic substrates. In particular, NHPI can catalyze the hydroperoxidation of polyunsaturated fatty acids (PUFA). This pro
- Melone, Lucio,Petroselli, Manuel,Pastori, Nadia,Punta, Carlo
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- Syntheses of subtractively modified 2-chloro-4-nitrophenyl-β-maltopentaosides and their application to the differential assay of human alpha-amylases
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Three novel maltopentaosides, 2-chloro-4-nitrophenyl O-(6-deoxy-α-D-xylo-hex-5-enopyranosyl)-(1->4)-tris4)>-β-D-glucopyranoside (3), 2-chloro-4-nitrophenyl O-(6-deoxy-α-D-glucopyranosyl)-(1->4)-tris4)>-β
- Tokutake, Shoichi,Oguma, Tetsuya,Tobe, Kouichirou,Kotani, Kazuo,Saito, Kazunori,Yamaji, Nobuyuki
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- Supramolecular intracellular delivery of an anionic porphyrin by octaarginine-conjugated per-O-methyl-β-cyclodextrin
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A convenient and efficient method for intracellular delivery of a water-soluble anionic porphyrin has been developed by utilizing its supramolecular interaction with per-O-methyl-β-cyclodextrin bearing an octaarginine chain as a cell-penetrating peptide.
- Kitagishi, Hiroaki,Chai, Fumihiko,Negi, Shigeru,Sugiura, Yukio,Kano, Koji
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- Dendrimeric β-Cyclodextrin/GdIII chelate supramolecular host-guest adducts as high-relaxivity MRI probes
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We have synthesized a new macromolecular architecture, (PAMAM)-CD 8, which consists of eight β-cyclodextrin units (β-CD) attached to a generation 1 poly(amidoamine) (PAMAM) dendrimer through a disulfide bond, which can be cleaved under reducing conditions. This system shows a pronounced hosting capability towards GdIII chelates functionalized with hydrophobic groups, thus leading to well-defined supramolecular adducts. 1H NMR relaxometric investigations were carried out to follow the formation of adducts with three GdIII chelates based on the ligand architectures of 6-amino-6-methylperhydro-1,4- diazepinetetraacetic acid (AAZTA) or 1,4,7,10-tetraazacyclododecane-1,4,7,10- tetraacetic acid (DOTA) suitably functionalized with benzyl or adamantyl (Ad) pendant groups. In particular, the ditopic complex composed of two AAZTA chelating units connected to a central aromatic ring that bears an adamantyl group showed a strong affinity (ca. 106 M-1) for the CD units of the dendrimer, which is two orders of magnitude higher than toward human serum albumin (HSA). Remarkable relaxivity enhancements (i.e., up to 71 % at 1 T and 25 C) were observed upon the formation of the macromolecular host-guest adducts due to a decrease in the molecular tumbling rate and fast water-exchange. Reduction experiments and competition studies between the paramagnetic dendrimer and HSA were carried out by relaxometric techniques. The results show that the metal complexes are not displaced by the protein, thus suggesting that this novel macromolecular probe is potentially suitable for applications in vivo.
- Martinelli, Jonathan,Thangavel, Kalaivani,Tei, Lorenzo,Botta, Mauro
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- β-Cyclodextrin functionalized ionic liquid as chiral stationary phase of high performance liquid chromatography for enantioseparation of β-blockers
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Two covalently bonded β-Cyclodextrin (β-CD) based CSPs were prepared by immobilizing the native β-CD and mono-6-deoxy-6-(3-benzylimidazolium tosylate)-β-CD (β-CD-BIMOTs) onto modified silica gel. β-CD-BIMOTs is a β-CD based CSP with ionic liquid (3-benzylimidazolium tosylate) substituent. The enantioseparation capability of the synthesized CSPs was examined using 4 racemic mixtures of β-blockers (propranolol, metoprolol, pindolol and atenolol). The results indicated that β-CD-BIMOTs based CSP afforded more favorable enantioseparations than native β-CD based CSP. In order to study the mechanism of enantioseparation, inclusion complexes β-CD-BIMOTs and β-blockers were prepared and these inclusion complexes were characterized by using 1H NMR and NOESY. In addition, the separation conditions such as pH and composition of mobile phase were varied to study the role of β-CD and ionic liquid in enantioseparation. In general, it can be concluded that the complete enantioseparation of propranolol and metoprolol is achieved through the formation of inclusion complex with β-CD-BIMOTs and the formation π-π interaction with the ionic liquid moiety of β-CD-BIMOTs. The result also showed the poor enantioseparation of pindolol and atenolol on the β-CD-BIMOTs based CSP due to the strong interaction at the exterior torus of β-CD-BIMOTs.
- Rahim, Nurul Yani,Tay, Kheng Soo,Mohamad, Sharifah
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- Supramolecular interaction of 2,4-dichlorophenol and β-cyclodextrin functionalized ionic liquid and its preliminary study in sensor application
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The supramolecular interaction of 2,4-dichlorophenol (2,4-DCP) and β-cyclodextrin functionalized ionic liquid, a mono-6-deoxy-6-(3-benzylimidazolium)-β-cyclodextrin tosylate (β-CD-BIMOTs) has been investigated. The inclusion complex of β-CD-BIMOTs-2,4-DCP complex was analyzed with conventional spectroscopic techniques and compared with native β-CD-2,4-DCP complex. The mechanism of the inclusion too was studied and discussed based on FTIR, 1H NMR and 2D NOESY analysis. β-CD-BIMOTs has a stronger binding affinity towards 2,4-DCP compared to native β-CD based on the formation constant value calculated. In this work, modified electrodes were fabricated by mixing β-CD-BIMOTs and carbon paste electrode (CPE) for determination of 2,4-DCP. The electrochemical behavior of 2,4-DCP at β-CD-BIMOTs/CPE exhibits higher electrochemical performance than that of native β-CD/CPE and CPE, revealing that CPE modified β-CD-BIMOTs not only displays good electrical properties of the ionic liquid but also exhibits high supramolecular recognition properties of β-CD-BIMOTs through the formation of an inclusion complex between β-CD-BIMOTs and 2,4-DCP molecules. This preliminarily study shows that β-CD-BIMOTs can act as an inexpensive electrochemical sensor that is suitable for the determination of 2,4-DCP.
- Mohamad, Sharifah,Chandrasekaram, Kumuthini,Rasdi, Fairuz Liyana Mohd,Manan, Ninie Suhana Abdul,Raoov, Muggundha,Sidek, Nadiah,Fathullah, Syed Fariq
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- Comparative studies on molecular induced aggregation of hepta-imidazoliumyl-β-cyclodextrin towards anionic surfactants
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A β-cyclodextrin derivative bearing seven cationic arms and its singly charged analogue, i.e., per-6-deoxy-6-(1-methylimidazol-3-ium-3-yl)-β-cyclodextrin (3) and mono-6-deoxy-6-(1-methylimidazol-3-ium-3-yl)-β-cyclodextrin (4) were synthesized and fully characterized. Their induced aggregation behaviours towards two anionic surfactant, that is, sodium dodecyl sulfonate (SDS) and dioctyl sodium sulfosuccinate (Aerosol OT, AOT), were investigated by UV-vis, NMR, Zeta-potential, dynamic light scattering (DLS), and transmission electron microscopy. The results revealed that host 3 can induce the molecular aggregation of anionic surfactant at concentration far lower than its original CAC, leading to the larger diameter, the narrower size distribution and the higher thermal stability of the induced aggregate towards the anionic surfactant possessing more hydrophobic tails.
- Zhao, Di,Chen, Yong,Liu, Yu
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- The adsorption of mercury(II) on the surface of silica modified with β-cyclodextrin
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Multistage chemical modification of the surface of silica with β-cyclodextrin was performed. IR spectroscopy and quantitative analysis of surface compounds were used to prove the structure of modified silica. The adsorption of Hg(II) from dilute solutions
- Belyakova,Shvets,De Namor, A. F. Denil
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- Poly(N-vinylpyrrolidone) bearing covalently attached cyclodextrin via click-chemistry: Synthesis, characterization, and complexation behavior with phenolphthalein
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We report about modification of poly(N-vinylpyrrolidone) (PVP) with monofunctional β-cyclodextrin (βCD) via click-chemistry. The modification was carried out by copper(I)-catalyzed microwave-assisted Huisgen-type cycloaddition of 3-propargyl-N-vinylpyrrol
- Trellenkamp, Taina,Ritter, Helmut
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- Development of Protein-Cage-Based Delivery Nanoplatforms by Polyvalently Displaying β-Cyclodextrins on the Surface of Ferritins Through Copper(I)-Catalyzed Azide/Alkyne Cycloaddition
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Protein cages are spherical hollow macromolecules that are attractive platforms for the construction of nanoscale cargo delivery vehicles. Human heavy-chain ferritin (HHFn) is modified genetically to control the number and position of functional groups per cage. 24 β-CDs are conjugated precisely to the modified HHFn in specific locations through thiol-maleimide Michael-type addition followed by copper(I)-catalyzed azide/alkyne cycloaddition (CuAAC). The resulting human ferritins displaying β-CDs (β-CD-C90 HHFn) can form inclusion complexes with FITC-AD, which can slowly release the guest molecule reversibly in a buffer solution via non-covalent β-CD/AD interactions. β-CD-C90 HHFn can potentially be used as delivery vehicles for insoluble drugs. 24 β-cyclodextrins are displayed on the surface of a human ferritin in distinct positions through thiol-mediated conjugation followed by copper(I)-catalyzed azide/alkyne cycloaddition. These β-cyclodextrins displayed on the surface show an excellent capability to form inclusion complexes with FITC-ADs via molecular recognition and to release them reversibly.
- Kwon, Chanho,Kang, Young Ji,Jeon, Sangbin,Jung, Seunho,Hong, Sung You,Kang, Sebyung
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- A new hyaluronan modified with β-cyclodextrin on hydroxymethyl groups forms a dynamic supramolecular network
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A new hyaluronan derivative modified with β-cyclodextrin units (CD-HA) was prepared via the click reaction between propargylated hyaluronan and monoazido-cyclodextrin (CD) to achieve a degree of substitution of 4%. The modified hyaluronan was characterize
- Kova?evi?, Jelica,Prucková, Zdeňka,Pospí?il, Tomá?,Ka?párková, Věra,Rouchal, Michal,Vícha, Robert
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- Novel permethylated β-cyclodextrin derivatives appended with chromophores as efficient fluorescent sensors for the molecular recognition of bile salts
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(Figure Presented) Two novel permethylated β-cyclodextrin (PM-β-CD) derivatives, i.e., 6I-O-(1-naphtholxy)-2 I,31-di-O-methylhexakis(2II-VII,3 II-VII,6II-VII-tri-O-methyl)-β-cyclodextrin(1)
- Liu, Yu,Shi, Jun,Guo, Dong-Sheng
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- Mono-6-deoxy-6-aminopropylamino-Β-cyclodextrin as a supramolecular catalyst for the synthesis of indolyl 1H-pyrrole via one-pot four component reaction in water
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We report here the synthesis of mono-6-deoxy-6-aminopropylamino-β-cyclodextrin (Pr-β-CD) as a supramolecular organic base catalyst. Pr-β-CD was characterized by FT-IR, NMR, MALDI-TOF mass spectrometry and SEM analysis. Using this Pr-β-CD, biologically important indolyl 1H-pyrrole derivatives were synthesized with good to excellent yields in an aqueous medium via one-pot four-component reaction. Furthermore, the catalytic mechanism was elucidated in detail by using 2D NMR (ROESY), FE-SEM and FT-IR studies. The credit of the presented protocol includes the use of novel efficacious, reusable eco-friendly supramolecular carbohydrate catalyst, and precludes the use of organic solvents and column chromatography.
- Shinde, Vijay Vilas,Jeong, Daham,Joo, Sang Woo,Cho, Eunae,Jung, Seunho
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Read Online
- Synthesis of 6I-O-(4-Methylbenzenesulfonyl)-β-cyclodextrin
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An improved procedure has been proposed for the synthesis of 6I-O-(4-methylbenzenesulfonyl)-β-cyclodextrin by reaction of β-cyclodextrin with p-toluenesulfonyl chloride in aqueous alkali. Repeated use of unreacted p-toluenesulfonyl chloride and reduction of the volume of water by half in combination with optimized conditions make it possible to obtain the target product in up to 58% yield without loss of purity.
- Novokshonov,Xuan, Nguyen Thi Thu,Shaglaeva
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Read Online
- An attempt to synthesize the two monomers of CDTOH: Unexpected NMR and X-ray diffraction crystal analysis
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Two monomer compounds of CDTOH, 6A-deoxy-6A-(4-(2-hydroxyethyl)-1H-1,2,3-triazol-1-yl)-per-O-methylated β-cyclodextrin 4 and 6A-deoxy-6A-(4-(2-hydroxyethyl)-1H-1,2,3-triazol-1-yl) β-cyclodextrin 7, have been syn
- Chu, Xindang,Gao, Qianqian,Li, Haiwei,Liu, Ruiwen,Ma, Xinyuan,Xiao, Sulong,Yi, Yanliang,Zhang, Jiayi,Zhang, Lihe,Zhang, Yongmin,Zhou, Demin
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- Fuel-Driven and Enzyme-Regulated Redox-Responsive Supramolecular Hydrogels
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Chemical reaction networks (CRN) embedded in hydrogels can transform responsive materials into complex self-regulating materials that generate feedback to counter the effect of external stimuli. This study presents hydrogels containing the β-cyclodextrin (CD) and ferrocene (Fc) host–guest pair as supramolecular crosslinks where redox-responsive behavior is driven by the enzyme–fuel couples horse radish peroxidase (HRP)–H2O2 and glucose oxidase (GOx)–d-glucose. The hydrogel can be tuned from a responsive to a self-regulating supramolecular system by varying the concentration of added reduction fuel d-glucose. The onset of self-regulating behavior is due to formation of oxidation fuel in the hydrogel by a cofactor intermediate GOx[FADH2]. UV/Vis spectroscopy, rheology, and kinetic modeling were employed to understand the emergence of out-of-equilibrium behavior and reveal the programmable negative feedback response of the hydrogel, including the adaptation of its elastic modulus and its potential as a glucose sensor.
- Jain, Mehak,Ravoo, Bart Jan
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supporting information
p. 21062 - 21068
(2021/08/13)
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- Biodegradable supramolecular micellesviahost-guest interaction of cyclodextrin-terminated polypeptides and adamantane-terminated polycaprolactones
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Biodegradable supramolecular micelles were prepared exploiting the host-guest interaction of cyclodextrin and adamantane. Cyclodextrin-initiated polypeptides acted as the hydrophilic corona, whereas adamantane-terminated polycaprolactones served as the hydrophobic core.
- Pottanam Chali, Sharafudheen,Azhdari, Suna,Galstyan, Anzhela,Gr?schel, André H.,Ravoo, Bart Jan
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supporting information
p. 9446 - 9449
(2021/09/22)
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- pH-sensitive β-cyclodextrin derivatives for the controlled release of Podophyllotoxin
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An effective tumor targeting drug delivery systems was designed and synthesized by conjugating pH-sensitive maleamide derivatives to Mono-(6-deoxy-6-amino)-β-CD. Their characteristics and inclusion behaviors with insoluble anticancer drug PPT were investigated in both solution and solid state by means of 1H NMR and 2D-ROESY, XRD, DSC and SEM, which reveal PPT is successfully encapsulated in the cavity of CD derivatives with different stability constants (Ks). Water solubility of PPT are significantly increased to 60.35 and 22.89 mg·mL?1 after formation of inclusion complexes with host-1 and host-2, compared with free PPT (0.12 mg·mL?1). Their acid-controlled release has been studied in vitro by 1H NMR and UV-Vis spectra, living cells incubated with host 1-2 were observed by Inverted fluorescence microscope to confirm pH-response releasing. Moreover, host-1/PPT and host-2/PPT maintain effective cell proliferation inhibition to human cancer, while their cytotoxicity to normal cell is significantly reduced. Our work shows inspiring potential in tumor-targeted delivery and acid-controlled release of PPT both in vitro.
- Gao, Chuanzhu,Li, Fanjie,Liao, Xiali,Yang, Bo,Yang, Jing,Yang, Lei,Yang, Waixiang,Zhao, Yulin
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- Functionalization using biocompatible carboxylated cyclodextrins of iron-based nanoMIL-100
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Here we report the first example of nanoMIL-100 particles modified with monomeric cyclodextrin derivatives of different length by exploiting strong interactions between non-saturated iron trimers at the external surface and carboxylate functionalities located at the end of biocompatible and flexible linkers of cyclodextrins. The main results revealed that, after the functionalization, the cyclodextrins are selectively located at the external surfaces covering the nanoparticles. Z potential measurements show that this functionalization induced changes respect to the bare nanoMIL-100 particles, however, the presence of the cyclodextrins does not modify the size neither porosity of the nanoparticles. The amount of cyclodextrins attached, investigated by thermogravimetry, increases with the length of the linker between CD cavity and nanoparticle surface, reaching up a 9 % wt. Auger spectroscopy suggested a clear predominant sp3 character after the functionalizations (vs. sp2 predominance in the unmodified nanoMIL-100). This study supposes the creation of an alternative family of hybrids based on carboxylated monomeric cyclodextrins.
- Ca?ón-Mancisidor, Walter,Carmona, Thais,Giménez-Marqués, Mónica,Gutiérrez-Cuti?o, Marlen,Hermosilla-Ibá?ez, Patricio,Mínguez Espallargas, Guillermo,Marco, José F.,Pérez, Edwin G.,Venegas-Yazigi, Diego
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supporting information
(2021/10/21)
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- Preparation, characterization and biological evaluation of β-cyclodextrin-biotin conjugate based podophyllotoxin complex
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Podophyllotoxin is a natural occurring aryltetralin lignin with pronounced cytotoxic activity. However, its clinical application for cancer treatment has been blocked due to its poor water solubility and selectivity. In this work, biotin as a tumor specific ligand was coupled with β-cyclodextrin and the resulting biotin modified β-cyclodextrin was used to complex with podophyllotoxin to improve its aqueous solubility and tumor selectivity. The solubility of β-cyclodextrin was greatly enhanced(>16 times) by conjugating with biotin. podophyllotoxin/ mono-6-biotin-amino-6-deoxy-β-cyclodextrin inclusion complex was prepared by freeze-drying method and the complex behavior between mono-6-biotin-amino-6-deoxy-β-cyclodextrin and podophyllotoxin was studied by water solubility, phase solubility, Job's plot, UV spectroscopy, Proton Nuclear Magnetic Resonance, Rotating-frame Overhauser Effect Spectroscopy, Powder X-ray diffraction and Scanning electron microscopy. The solubility of podophyllotoxin/ mono-6-biotin-amino-6-deoxy-β-cyclodextrin complex was greatly improved(9 times) compared with Podophyllotoxin. The stability constant of podophyllotoxin/ mono-6-biotin-amino-6-deoxy-β-cyclodextrin complex (Ks= 415.29 M?1) was 3.2 times that of podophyllotoxin/β-cyclodextrin complex. The possible inclusion mode of podophyllotoxin/mono-6-biotin-amino-6-deoxy-β-cyclodextrin complex was inferred from the Proton Nuclear Magnetic Resonance and Rotating-frame Overhauser Effect Spectroscopy. The cellular uptake study showed that the introduction of biotin increased the cellular uptake of rhodamine-B/mono-6-biotin-amino-6-deoxy-β-cyclodextrin complex. Moreover, cell cytotoxicity study showed that the antitumor activity of podophyllotoxin/ mono-6-biotin-amino-6-deoxy-β-cyclodextrin complex was more potent than podophyllotoxin/β-cyclodextrin complex and free podophyllotoxin. The superior water solubility and enhanced cytotoxicity suggested that the mono-6-biotin-amino-6-deoxy-β-cyclodextrin associated inclusion complex might be a potential and promising delivery system for hydrophobic chemotherapeutics such as podophyllotoxin.
- Zhao, Xiu,Qiu, Neng,Ma, Yingyu,Liu, Junda,An, Lianying,Zhang, Teng,Li, Ziqin,Han, Xu,Chen, Lijuan
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- Efficient modification of PAMAM G1 dendrimer surface with β-cyclodextrin units by CuAAC: Impact on the water solubility and cytotoxicity
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The toxicity of the poly(amidoamine) dendrimers (PAMAM) caused by the peripheral amino groups has been a limitation for their use as drug carriers in clinical applications. In this work, we completely modified the periphery of PAMAM dendrimer generation 1 (PAMAM G1) with β-cyclodextrin (β-CD) units through the Cu(i)-catalyzed azide-alkyne cycloaddition (CuAAC) to obtain the PAMAM G1-β-CD dendrimer with high yield. The PAMAM G1-β-CD was characterized by 1H- and 13C-NMR and mass spectrometry studies. Moreover, the PAMAM G1-β-CD dendrimer showed remarkably higher water solubility than native β-CD. Finally, we studied the toxicity of PAMAM G1-β-CD dendrimer in four different cell lines, human breast cancer cells (MCF-7 and MDA-MB-231), human cervical adenocarcinoma cancer cells (HeLa) and pig kidney epithelial cells (LLC-PK1). The PAMAM G1-β-CD dendrimer did not present any cytotoxicity in cell lines tested which shows the potentiality of this new class of dendrimers.
- González-Méndez, Israel,Illescas, Javier,Martínez-Serrano, Ricardo D,Rivera, Ernesto,Ruiu, Andrea,Solano, José D,Sorroza-Martínez, Kendra,Zhu, Xiao Xia
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p. 25557 - 25566
(2020/10/02)
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- First class of phosphorus dendritic compounds containing β-cyclodextrin units in the periphery prepared by CuAAC
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A new class of phosphorus dendritic compounds (PDCs) having a cyclotriphosphazene (P3N3) core and decorated with six β-cyclodextrin (βCD) units, named P3N3-[O-C6H4-O-(CH2)n-βCD]6, where n = 3 or 4 was designed, and the synthesis was performed using copper (I) catalyzed alkyne-azide cycloaddition (CuAAC). To obtain the complete substitution of the P3N3, two linkers consisting of an aromatic ring and an aliphatic chain of two different lengths were assessed. We found that, with both linkers, the total modification of the periphery was achieved. The two new obtained dendritic compounds presented a considerably high water solubility (>1 g/mL). The compounds comprised in this new class of PDCs are potential drug carrier candidates, since the conjugation of the βCD units to the P3N3 core through the primary face will not only serve as surface cover but, also, provide them the faculty to encapsulate various drugs inside the βCDs cavities.
- Caminade, Anne-Marie,González-Méndez, Israel,Illescas, Javier,Moineau-Chane Ching, Kathleen I.,Rivera, Ernesto,Sorroza-Martínez, Kendra,Vonlanthen, Mireille
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- Water soluble homogeneous catalysts that are recoverable by phase selectivity and host-guest interactions
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A chemical reaction is catalyzed in an organic solvent using a water soluble N-heterocyclic carbene homogeneous catalyst to form a reaction mixture. An aqueous phase in the reaction mixture. A solvent in which the catalyst is insoluble is added to the reaction mixture, causing the catalyst to migrate to the aqueous phase to form a catalyst-laden aqueous phase. The catalyst is extracted from the catalyst-laden aqueous phase.
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Page/Page column 8; 9
(2020/08/30)
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- Synergetic effects in the enantiodifferentiating photocyclodimerization of 2-anthracenecarboxylic acid mediated by β-cyclodextrin-pillar[5]arene-hybridized hosts
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Tri-cavity hosts consisting of one pillar[5]arene (P5) sandwiched by two β-cyclodextrins (CDs) were synthesized, and their diastereoseparation was successfully accomplished. Photocyclodimerization of 2-anthracenecarboxylate with these hybrid hosts demonst
- Cheng, Guo,Gong, Qiyong,Ji, Jiecheng,Luo, Kui,Rao, Ming,Wei, Xueqin,Wu, Wanhua,Yang, Cheng,Zhou, Dayang
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supporting information
p. 6197 - 6200
(2020/06/22)
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- Novel chiral stationary phases based on 3,5-dimethyl phenylcarbamoylated β-cyclodextrin combining cinchona alkaloid moiety
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Novel chiral selectors based on 3,5-dimethyl phenylcarbamoylated β-cyclodextrin connecting quinine (QN) or quinidine (QD) moiety were synthesized and immobilized on silica gel. Their chromatographic performances were investigated by comparing to the 3,5-dimethyl phenylcarbamoylated β-cyclodextrin (β-CD) chiral stationary phase (CSP) and 9-O-(tert-butylcarbamoyl)-QN-based CSP (QN-AX). Fmoc-protected amino acids, chiral drug cloprostenol (which has been successfully employed in veterinary medicine), and neutral chiral analytes were evaluated on CSPs, and the results showed that the novel CSPs characterized as both enantioseparation capabilities of CD-based CSP and QN/QD-based CSPs have broader application range than β-CD-based CSP or QN/QD-based CSPs. It was found that QN/QD moieties play a dominant role in the overall enantioseparation process of Fmoc-amino acids accompanied by the synergistic effect of β-CD moiety, which lead to the different enantioseparation of β-CD-QN-based CSP and β-CD-QD-based CSP. Furthermore, new CSPs retain extraordinary enantioseparation of cyclodextrin-based CSP for some neutral analytes on normal phase and even exhibit better enantioseparation than the corresponding β-CD-based CSP for certain samples.
- Zhu, Lunan,Zhu, Junchen,Sun, Xiaotong,Wu, Yaling,Wang, Huiying,Cheng, Lingping,Shen, Jiawei,Ke, Yanxiong
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supporting information
p. 1080 - 1090
(2020/05/25)
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- Synthesis and immunostimulatory activity of sugar-conjugated TLR7 ligands
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Toll-like receptors (TLRs) are a type of pattern recognition receptors (PRRs), which are activated by recognizing pathogen-associated molecular patterns (PAMPs). The activation of TLRs initiates innate immune responses and subsequently leads to adaptive immune responses. TLR agonists are effective immuomodulators in vaccine adjuvants for infectious diseases and cancer immunotherapy. In exploring hydrophilic small molecules of TLR7 ligands using the cell-targeted property of a vaccine adjuvant, we conjugated 1V209, a small TLR7 ligand molecule, with various low or middle molecular weight sugar molecules that work as carriers. The sugar-conjugated 1V209 derivatives showed increased water solubility and higher immunostimulatory activity in both mouse and human cells compared to unmodified 1V209. The improved immunostimulatory potency of sugar-conjugates was attenuated by an inhibitor of endocytic process, cytochalasin D, suggesting that conjugation of sugar moieties may enhance the uptake of TLR7 ligand into the endosomal compartment. Collectively our results support that sugar-conjugated TLR7 ligands are applicable to novel drugs for cancer and vaccine therapy.
- Baba, Akihito,Wakao, Masahiro,Shinchi, Hiroyuki,Chan, Michael,Hayashi, Tomoko,Yao, Shiyin,Cottam, Howard B.,Carson, Dennis A.,Suda, Yasuo
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supporting information
(2019/12/27)
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- Aminated β-cyclodextrin-grafted Fe3O4-loaded gambogic acid magnetic nanoparticles: Preparation, characterization, and biological evaluation
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Based on aminated β-cyclodextrin (6-NH2-β-CD)-grafted Fe3O4 and gambogic acid (GA) clathrate complexes, a nanoparticle delivery system was developed with the aim to achieve low irritation, strong targeting, and high bioavailability of a gambogic acid magnetic nanopreparation. 6-NH2-β-CD grafted onto Fe3O4 MNPs was demonstrated by high-resolution transmission electron microscopy, Fourier transform infrared spectroscopy, X-ray diffraction, zeta potential, and magnetic measurements. The average particle size of the Fe3O4?NH2-β-CD MNPs was 147.4 ± 0.28 nm and the PDI was 0.072 ± 0.013. The encapsulation efficiency, drug loading, zeta potential, and magnetic saturation values of the Fe3O4?NH2-β-CD MNPs were 85.71 ± 3.47%, 4.63 ± 0.04%, -29.3 ± 0.42 mV, and 46.68 emu g-1, respectively. Compared with free GA, the in vitro release profile of GA from Fe3O4?NH2-β-CD MNPs was characterized by two phases: an initial fast release and a delayed-release phase. The Fe3O4?NH2-β-CD MNPs displayed continuously increased cytotoxicity against HL-60 and HepG2 cell lines in 24 h, whereas the carrier Fe3O4?NH2-β-CD MNPs showed almost no cytotoxicity, indicating that the release of GA from the nanoparticles had a sustained profile and Fe3O4?NH2-β-CD MNPs as a tumor tissue-targeted drug delivery system have great potential. Besides, blood vessel irritation tests suggested that the vascular irritation could be reduced by the use of Fe3O4?NH2-β-CD MNPs encapsulation for GA. The t1/2 and the AUC of the Fe3O4?NH2-β-CD?GA MNPs were found to be higher than those for the GA solution by approximately 2.71-fold and 2.42-fold in a pharmacokinetic study, respectively. The better biocompatibility and the combined properties of specific targeting and complexation ability with hydrophobic drugs make the Fe3O4?NH2-β-CD MNPs an exciting prospect for the targeted delivery of GA.
- Fang, Wei,Dai, Ya Ji,Wang, Ting,Gao, Hai Tao,Huang, Peng,Yu, Juan,Huang, He Ping,Wang, Dian Lei,Zong, Wei Lu
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p. 27136 - 27146
(2019/09/12)
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- Molecular encapsulation of berberine by a modified β-cyclodextrin and binding of host: guest complex to G-quadruplex DNA
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The capacity to control quadruplex formation, especially in cancer cells, is captivating and entails a reasonable comprehension of the ligand-G-quadruplex binding. Herein, we report an iminopyrenyl-β-cyclodextrin conjugate interacting with duplex and G-quadrulex DNAs. In addition, the host: guest association of the established G-quadruplex binder, berberine, with the β-cyclodextrin derivative is studied employing 2-D ROESY. NMR, UV-visible, and fluorescence spectroscopic techniques are utilized to explore the β-cyclodextrin conjugate's interaction with the quadruplexes. The Binding constants are accounted for the association of the ligands to each of the DNAs viz., calf thymus DNA (duplex), kit22, telo24, and myc22 (quadruplexes). The modulation of the iminopyrenyl-β-cyclodextrin binding to the DNAs are observed when berberine is loaded in the host molecule. A vivid distinction between the interactions of the ligands with duplex and quadruplex structures is inferred. Berberine-loaded iminopyrenyl-β-cyclodextrin shows a higher affinity for binding to kit22.
- Suganthi, Soundrapandian,Sivaraj, Ramasamy,Enoch, Israel V. M. V.
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p. 858 - 873
(2019/06/10)
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- Reusable shuttles for exchangeable functional cargos: Reversibly assembled, magnetically powered organocatalysts for asymmetric aldol reactions
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A supramolecular approach has been followed to support adamantyl substituted proline organocatalysts onto the surface of magnetite nanoparticles decorated with a β-cyclodextrin motif. The resulting magnetic nanoparticles (ca. ～10 nm diameter) were used as modular, magnetically recyclable catalysts in the asymmetric aldol reaction of aromatic aldehydes with cyclic ketones in water. The catalytic assemblies can be easily dismantled in organic media, and the recovered nanoparticles (magnetically powered chemical shuttles) re-complexed with another suitably substituted catalytic unit (replaceable functional cargo).
- Mendoza, Carolina,de la Croix, Augustin,Riente, Paola,Llorens, Lluís,de Mendoza, Javier,Pericàs, Miquel A.
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supporting information
(2019/09/17)
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- MICROSPHERES CONTAINING THERAPEUTIC AGENTS AND RELATED METHODS OF USE
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Microspheres, compositions including the microspheres, and methods of using the microspheres are disclosed herein. The microspheres can be substantially spherical and can include a copolymer of a monomer (such as an acrylic monomer) and a cyclodextrin or a derivative thereof. The microspheres can also include a therapeutic agent, such as a platinum-based drug.
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Paragraph 00124; 00125
(2019/03/05)
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- Remote loading of curcumin-in-modified β-cyclodextrins into liposomes using a transmembrane pH gradient
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Curcumin (CRM) is a natural polyphenol with antioxidative, anti-inflammatory, and anticancer therapeutic properties. However, CRM therapeutic potential is limited by low water solubility and bioavailability. Intraliposomal remote loading describes the ret
- Odeh, Fadwa,Nsairat, Hamdi,Alshaer, Walhan,Alsotari, Shrouq,Buqaien, Rula,Ismail, Said,Awidi, Abdalla,Al Bawab, Abeer
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p. 37148 - 37161
(2019/12/02)
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- Sustainable Gold Catalysis in Water Using Cyclodextrin-tagged NHC-Gold Complexes
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The synthesis of 10 water-soluble β-cyclodextrin-tagged NHC-gold(I) complexes is described. Key steps are nucleophilic substitutions, as well as, copper-(CuAAC)- and ruthenium-(RuAAC)-catalyzed azide alkyne cycloadditions. Whereas the CuAAC reliably affor
- Sak, Hülya,Mawick, Matthias,Krause, Norbert
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p. 5821 - 5829
(2019/11/14)
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- Assembly-enhanced triplet-triplet annihilation upconversion in the aggregation formed by Schiff-base Pt(II) complex grafting-permethyl-β-CD and 9, 10-diphenylanthracence dimer
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Water-soluble triplet sensitizer with permethyl-β-cyclodextrin (PMCD) grafting on a Schiff-base Pt(II) complex (Pt-2), in which PMCD unit serves as a host for binding the acceptors and the Schiff-base Pt(II) complex serves as a triplet sensitizer, was syn
- Lai, Hongxia,Zhao, Ting,Deng, Yurong,Fan, Chunyin,Wu, Wanhua,Yang, Cheng
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supporting information
p. 1979 - 1983
(2019/10/02)
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- NITRIC OXIDE-RELEASING CYCLODEXTRINS AS BIODEGRADABLE ANTIBACTERIAL SCAFFOLDS AND METHODS PERTAINING THERETO
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Disclosed herein are cyclodextrin molecules covalently modified to store and release nitric oxide, as well as methods of making and uses thereof. The covalently modified cyclodextrin molecules may be tailored, in several embodiments, to release nitric oxide in a controlled manner and are useful for reduction and/or eradication of bacteria and for the treatment of disease.
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Page/Page column 97-99
(2019/10/01)
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- Glutathione Responsive β-Cyclodextrin Conjugated S-Nitrothiols as a Carrier for Intracellular Delivery of Nitric Oxide
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Nitric oxide (NO) exerts multiple functions in many life processes and was of great significance in a variety of biomedical scenarios. However, the mismatches between releasing locations and NO active sites seriously limited the available NO at areas of i
- Jia, Fan,Deng, Yongyan,Fang, Yu,Jin, Qiao,Ji, Jian
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p. 583 - 591
(2019/03/26)
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- Facile preparation and characterization of novel oleanane-type triterpene functionalized β-cyclodextrin conjugates
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Oleanolic acid (OA) and echinocystic acid (EA), two naturally occurring pentacyclic oleanane triterpenes, are gaining increasing attention due to their promising pharmacological activities. Conjugation with amphiphilic α(β)-cyclodextrin (CD) via “click chemistry” can improve their solubility and anti-HCV entry potency. In the present work, four water-soluble β-CD-pentacyclic triterpene conjugates were designed and synthesized, in which OA and EA was coupled to one of the primary hydroxyl groups of β-CD via ester and amide bonds. The structures of the conjugates were unambiguously determined by 1H NMR, 13C NMR and HRMS or MALDI-TOF-MS. All the conjugates showed lower hydrophobicity (AlogP) than their parent compounds and no significant cytotoxicity was found to HL-60, A549, Hela and Bel-7402 cells at concentrations up to 10 μmol/L. Further anti-HCV entry activity and mechanism studies are under way in our laboratory.
- Jiao, Pingxuan,Wang, Shouxin,Liang, Shuobin,Li, Man,Gao, Qianqian,Ji, Dezhong,Chen, Yingying,Li, Haiwei,Ran, Fuxiang,Zhang, Yongmin,Zhang, Lihe,Zhou, Demin,Xiao, Sulong
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p. 690 - 693
(2018/10/24)
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- Synthesis and structure-activity relationship studies of water-soluble β-cyclodextrin-glycyrrhetinic acid conjugates as potential anti-influenza virus agents
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Glycyrrhetinic acid (GA) is a major constituent of the herb Glycyrrhiza glabra, and many of its derivatives demonstrate a broad spectrum of antiviral activities. In the current study, 18 water-soluble β-cyclodextrin (CD)-GA conjugates, in which GA was covalently coupled to the primary face of β-CD using 1,2,3-triazole moiety along with varying lengths of linker, were synthesized via copper-catalyzed azide-alkyl cycloaddition reaction. Benefited from the attached β-CD moiety, all these conjugates showed lower hydrophobicity (AlogP) compared with their parent compound GA. With the exception of per-O-methylated β-CD-GA conjugate (35), all other conjugates showed no significant cytotoxicity to MDCK cells, and these conjugates were then screened against A/WSN/33 (H1N1) virus using the cytopathic effect assay. The preliminary results indicated that six conjugates showed promising antiviral activity, and the C-3 and C-30 of GA could tolerate some modifications. Our findings suggested that GA could be used as a lead compound for the development of potential anti-influenza virus agents.
- Liang, Shuobin,Li, Man,Yu, Xiaojuan,Jin, Hongwei,Zhang, Yongmin,Zhang, Lihe,Zhou, Demin,Xiao, Sulong
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supporting information
p. 328 - 338
(2019/02/07)
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- Influence of supramolecular layer-crosslinked structure on stability of dual pH-Responsive polymer nanoparticles for doxorubicin delivery
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Undesired physiological instability remains a major limitation for nanoparticle-based drug delivery. To overcome this issue, a dual pH-responsive supramolecular layer-crosslinked nanoparticles (PCB-b-PCD/PBM-b-PDPA NPs, PDM NPs), which consisted of pH-responsive hydrophobic poly(diisopropylethyl methacrylate) (pKa ≈6.3) as the core, hydrophilic poly((methacrylic acid betaine) methyl methacrylate) as the shell and pH-responsive supramolecular crosslinked layer based on β-cyclodextrin and benzimidazole (pKa 6.0), was prepared. Effects of this supramolecular layer-crosslinked structure on dilution and stored stability, protein adsorption, and pH-responsibility were investigated. PDM NPs exhibited lower critical aggregation concentrations, good unimodal distribution and better dilution stability in comparison with non-crosslinked PCB-PDPA NPs. Moreover this pH-responsive supramolecular layer-crosslinked structure did not only influence the anti-protein adsorption ability, but also reduced the disintegrated pH (from 6.3 to below 6.0) of PDM NPs, which leads to the DOX was released from PDM NPs at the mildly acid condition effectively and sustainably in vitro. Therefore, this pH-responsive layer-crosslinked NPs held promising potentials as a smart nanocarriers for drug delivery.
- Feng, Hailiang,Sun, Yu,Zhang, Jianhua,Deng, Liandong,Dong, Anjie
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- Pip-HoGu: An Artificial Assembly with Cooperative DNA Recognition Capable of Mimicking Transcription Factor Pairs
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Cooperation between pairs of transcription factors (TFs) has been widely demonstrated to play a pivotal role in the spatiotemporal regulation of gene expression, but blocking cooperative TF pair-DNA interactions synergistically has been challenging. To achieve this, we designed programmable DNA binder pyrrole-imidazole polyamides conjugated to host-guest assemblies (Pip-HoGu) to mimic the cooperation between natural TF pairs. By incorporating cyclodextrin (Cyd)-adamantane (Ada), we synthesized Ada1 (PIP1-Ada) and Cyd1 (PIP2-Cyd), which were evaluated using Tm, EMSA, competitive, and SPR assays and molecular dynamics studies. The results consistently demonstrated that Pip-HoGu system formed stable noncovalent cooperative complexes, thereby meeting key criteria for mimicking a TF pair. The system also had a longer recognition sequence (two-PIP binding length plus gap distance), favorable sequence selectivity, higher binding affinity, and in particular, a flexible gap distance (0-5 bp). For example, Ada1-Cyd1 showed thermal stability of 7.2 °C and a minimum free energy of interaction of -2.32 kcal·mol-1 with a targeting length of 14 bp. Furthermore, cell-based evaluation validated the capability of Pip-HoGu to exhibit potent cooperative inhibitory effects on gene expression under physiological conditions by disrupting TF pair-DNA function. In conclusion, the modular design of Pip-HoGu defines a general framework for mimicking naturally occurring cooperative TF pair-DNA interactions that offers a promising strategy for applications in the precise manipulation of cell fate.
- Yu, Zutao,Guo, Chuanxin,Wei, Yulei,Hashiya, Kaori,Bando, Toshikazu,Sugiyama, Hiroshi
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supporting information
p. 2426 - 2429
(2018/02/28)
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- Removable Water-Soluble Olefin Metathesis Catalyst via Host-Guest Interaction
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A highly removable N-heterocyclic carbene ligand for a transition-metal catalyst in aqueous media via host-guest interactions has been developed. Water-soluble adamantyl tethered ethylene glycol in the ligand leads a hydrophobic inclusion into the cavity of β-cyclodextrin. Ruthenium (Ru) olefin metathesis catalyst with this ligand demonstrated excellent performance in various metathesis reactions in water as well as in CH2Cl2, and removal of residual Ru was performed via filtration utilizing a host-guest interaction and extraction.
- Kim, Cheoljae,Ondrusek, Brian A.,Chung, Hoyong
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supporting information
p. 736 - 739
(2018/02/09)
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- INCLUSION COMPLEX AND THE MANUFACTURING THE SAME
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An inclusion complex according to an embodiment of the present invention includes: cysteinyl beta-cyclodextrin containing a cavity in a central region thereof; and a baicalein partially embedded in the cavity of the cysteinyl beta-cyclodextrin. Accordingly, the present invention is able to improve an antioxidation effect.
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Paragraph 0029; 0054-0056
(2019/02/16)
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- Synthetic β-Cyclodextrin Dimers for Squaraine Binding: Effect of Host Architecture on Photophysical Properties, Aggregate Formation and Chemical Reactivity
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Reported herein is the synthesis and application of three novel β-cyclodextrin dimer hosts for the complexation of near infrared (NIR) squaraine dyes in aqueous solution. A series of eight different N-substituted N-methyl anilino squaraine dyes with variable terminal groups are investigated, with an optimal n-hexyl-substituted squaraine guest demonstrating binding constants orders of magnitude higher than the other squaraine–host combinations and comparable to literature-reported systems. Moreover, hydrophobic complexation of the squaraine dyes with the β-cyclodextrin dimer hosts causes drastic changes in the squaraine's photophysical properties, propensity for aggregation and susceptibility to hydrolytic decay.
- Chaudhuri, Sauradip,Verderame, Molly,Mako, Teresa L.,Bandara, Y. M. Nuwan D. Y.,Fernando, Ashvin I.,Levine, Mindy
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supporting information
p. 1964 - 1974
(2018/05/15)
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- Nitric Oxide-Releasing Cyclodextrins
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A series of secondary amine-modified cyclodextrin (CD) derivatives was synthesized with diverse exterior terminal groups (i.e., hydroxyl, methyl, methoxyl, and primary amine). Subsequent reaction with nitric oxide (NO) gas under alkaline conditions yieldedN-diazeniumdiolate-modified CD derivatives. Adjustable NO payloads (0.6-2.4 μmol/mg) and release half-lives (0.7-4.2 h) were achieved by regulating both the amount of secondary amine precursors and the functional groups around the NO donors. The bactericidal action of these NO-releasing cyclodextrin derivatives was evaluated againstPseudomonas aeruginosa, a Gram-negative pathogen, with antibacterial activity proving dependent on both the NO payload and exterior modification. Materials containing a high density of NO donors or primary amines exhibited the greatest ability to eradicateP. aeruginosa. Of the materials prepared, only the primary amine-terminated heptasubstituted CD derivatives exhibited toxicity against mammalian L929 mouse fibroblast cells. The NO donor-modified CD was also capable of delivering promethazine, a hydrophobic drug, thus demonstrating potential as a dual-drug-releasing therapeutic.
- Jin, Haibao,Yang, Lei,Ahonen, Mona Jasmine R.,Schoenfisch, Mark H.
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supporting information
p. 14178 - 14184
(2018/10/24)
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- Picolinamide modified β-cyclodextrin/Pd (II) complex: Asupramolecular catalyst for Suzuki-Miyaura coupling of aryl, benzyl and allyl halides with arylboronic acids in water
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Novel supramolecular catalysts for Suzuki-Miyaura coupling were prepared and characterized by NMR, FT-IR, TEM, XRD, TGA, and XPS. The resulting picolinamide-modified β-cyclodextrin/Pd(II) complex (Pd(II)@PCA-β-CD) showed very efficient catalytic activity for Suzuki-Miyaura coupling of aryl, benzyl, and allyl halides with arylboronic acids in an environmentally benign aqueous solution. Various organic halides including chlorides can produce good to excellent yields with phenyl-boronic acid and a catalytic amount of Pd(II)@PCA-β-CD. This hydro-soluble catalyst was capable of being reused for at least eight runs with only a slight loss of catalytic activity. A putative mechanism of the Pd(II)/Pd(IV) catalytic cycle was also explored and calculated by ab initio QM/MM methods.
- Luo, Kaixiu,Zhang, Lu,Yang, Rui,Jin, Yi,Lin, Jun
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p. 200 - 210
(2018/08/09)
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- Solubility and bioavailability enhancement of ciprofloxacin by induced oval-shaped mono-6-deoxy-6-aminoethylamino-β-cyclodextrin
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Ciprofloxacin is a broad-spectrum fluoroquinolone antibiotic used to treat bacterial infections; however, its limited aqueous solubility inhibits its broader clinical uses. This study investigated the complexation effect of mono-6-deoxy-6-aminoethylamino-β-cyclodextrin on the aqueous solubility and bioavailability of ciprofloxacin. During complexation, the oval-shaped cavity induced by mono-aminoethylamine substitution on the primary rim of β-cyclodextrin, was considered to be a key factor according to NMR spectroscopy and molecular modeling studies. The ciprofloxacin with mono-6-deoxy-6-aminoethylamino-β-cyclodextrin complex was characterized using FE-SEM, DSC, FT-IR, T1 relaxation, 2D NOESY, and DOSY NMR spectroscopy and molecular modeling studies. The solubility property of ciprofloxacin complexed with mono-6-deoxy-6-aminoethylamino-β-cyclodextrin was enhanced by seven-fold compared to that of pure ciprofloxacin. Furthermore antibacterial activity of that complex against methicillin-resistant Staphylococcus aureus was enhanced and it clearly showed the growth inhibition. The mono-6-deoxy-6-aminoethylamino-β-cyclodextrin has the potential to be utilized for other oblong guest molecules besides ciprofloxacin based on the novel induced elliptical cavity.
- Choi, Jae Min,Park, Kyeonghui,Choi, Youngjin,Park, Seyeon,Yu, Jae-hyuk,Dindulkar, Someshwar D,Lee, Benel,Cho, Eunae,Jeong, Daham,Jung, Seunho
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p. 118 - 128
(2017/02/05)
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- MICROSPHERES CONTAINING THERAPEUTIC AGENTS AND RELATED METHODS OF USE
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Microspheres, compositions including the microspheres, and methods of using the microspheres are disclosed herein. The microspheres can be substantially spherical and can include a copolymer of a monomer (such as an acrylic monomer) and a cyclodextrin or a derivative thereof. The microspheres can also include a therapeutic agent, such as a platinum-based drug.
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Paragraph 0115
(2017/09/02)
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- Cyclodextrin-based polymers for therapeutics delivery
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The present invention relates to novel compositions of therapeutic cyclodextrin containing polymeric compounds designed as a carrier for small molecule therapeutics delivery and pharmaceutical compositions thereof. These cyclodextrin-containing polymers i
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Page/Page column 66
(2017/02/28)
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- COMPLEXING AGENTS FOR COMPOSITIONS CONTAINING INCLUSION COMPLEXES
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The invention provides a composition containing particulate composite of a polymer and a therapeutic agent. The composition also contains a complexing agent. The polymer interacts with the complexing agent in a host-guest or a guest-host interaction to fo
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Paragraph 0162; 0163
(2017/03/21)
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- Upconversion Nanoprobes for the Ratiometric Luminescent Sensing of Nitric Oxide
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By taking advantage of the optical properties of upconversion nanoparticles (UCNPs), we have designed a luminescence ratiometric nanosensor for measuring nitric oxide (NO) in biological fluids, live cells, and tissues. This nanoconjugate consists of a UCN
- Wang, Ningning,Yu, Xinyan,Zhang, Ke,Mirkin, Chad A.,Li, Jishan
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supporting information
p. 12354 - 12357
(2017/09/23)
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- Supramolecular block copolymers for gene delivery: Enhancement of transfection efficiency by charge regulation
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A class of cationic supramolecular block copolymers with readily controlled charges has been exploited. Upon post-synthetic structural optimization, this copolymer exhibits comparable biocompatibility, greatly improved pDNA condensation capability and biostability, and further enhanced transfection efficiency in vitro. This work provides valuable insight into the creation of advanced nonviral vectors for gene delivery.
- Yasen, Wumaier,Dong, Ruijiao,Zhou, Linzhu,Huang, Yu,Guo, Dongbo,Chen, Dong,Li, Chuanlong,Aini, Aliya,Zhu, Xinyuan
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supporting information
p. 12782 - 12785
(2017/12/06)
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- UV light- and thermo-responsive supramolecular aggregates with tunable morphologies from the inclusion complexation of dendritic/linear polymers
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UV light- and thermo-responsive supramolecular aggregates with tunable morphologies were obtained through the inclusion complexation between a β-CD containing dendritic host polymer and an azobenzene containing linear guest polymer. Morphologies of the ag
- Zou, Hui,Yuan, Weizhong,Lu, Yeqiang,Wang, Shanfeng
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supporting information
p. 2463 - 2466
(2017/03/01)
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