60984-63-6Relevant articles and documents
Electrochemical redox responsive polymeric micelles formed from amphiphilic supramolecular brushes
Feng, Anchao,Yan, Qiang,Zhang, Huijuan,Peng, Liao,Yuan, Jinying
, p. 4740 - 4742 (2014)
The end-decorated homopolymer poly(ε-caprolactone)-ferrocene threaded onto a β-cyclodextrin-functionalized main-chain polymer can form a class of amphiphilic noncovalent graft copolymers based on the host-guest interactions of the terminal groups on the side chains. These new supramolecular polymer brushes can further self-assemble into micellar aggregates that exhibit reversible assembly and disassembly behavior under an electrochemical redox trigger, which opens up a new route to building dynamic block copolymer topologies. This journal is the Partner Organisations 2014.
Thio[2-(benzoylamino)ethylamino]-β-CD fragment modified gold nanoparticles as recycling extractors for [60]fullerene
Liu, Yu,Yang, Ying-Wei,Chen, Yong
, p. 4208 - 4210 (2005)
Gold particles are modified with surface-attached bis(β-cyclodextrin)s bearing S-S bridges to give water-soluble cyclodextrin-modified gold nanoparticles, which are successfully used as recycling extractors for [60]fullerene. The Royal Society of Chemistry 2005.
Synthesis of novel indolyl modified β-cyclodextrins and their molecular recognition behavior controlled by the solution's pH value
Liu, Yu,You, Chang-Cheng,He, Song,Chen, Guo-Song,Zhao, Yan-Li
, p. 463 - 469 (2002)
In order to investigate the effects of substituent and tether length in molecular recognition, three novel indolyl-contained β-cyclodextrin derivatives were synthesized by the condensation of indol-3-ylbutyric acid with the corresponding oligo(aminoethylamino)-β-cyclodextrin in the presence of DCC. Their molecular recognition behavior with some representative dye guests, i.e. Acridine Red, Rhodamine B, Neutral Red, Brilliant Green and Methyl Orange, was studied by using absorption, fluorescence and circular dichroism spectrometry. From the results of induced circular dichroism spectra and two-dimensional NMR spectroscopy, it was found that the initial conformations of these compounds are dramatically different in aqueous buffers of pH 2.0 and 7.2, which intrinsically determine the molecular binding ability of the host. It was also revealed that both the guest structure and the host tether length were responsible for the inclusion complexation stability. Therefore, on the one hand the hydrophobicity and substituent effect of the guest simultaneously determine the stability of host-guest complex through hydrophobic, van der Waals, and electrostatic interactions. On the other hand, the size/shape-matching relationship and induced-fit concept working between host and guest also play crucial roles in the selective molecular binding process of cyclodextrin hosts.
Influence of supramolecular layer-crosslinked structure on stability of dual pH-Responsive polymer nanoparticles for doxorubicin delivery
Feng, Hailiang,Sun, Yu,Zhang, Jianhua,Deng, Liandong,Dong, Anjie
, p. 81 - 92 (2018)
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.
Synthesis and photodynamic therapy properties of a water-soluble hypocrellin modified by cyclodextrin
Ou, Zhi-Ze,Chen, Jing-Rong,Wang, Xue-Song,Zhang, Bao-Wen,Cao, Yi
, p. 838 - 839 (2001)
For improving water solubility of hypocrellin B (HB), a cyclodextrin modified hypocrellin B (HBCD) was designed and synthesized. Electron spin resonance (ESR) measurement indicated that this HB derivative remained photodynamically active in terms of type I and type II mechanisms. HBCD is water-soluble and possesses stronger photosensitized damage ability to calf thymus DNA than hypocrellin B.
Interactions of some modified mono- and bis-β-cyclodextrins with bovine serum albumin
Gao, Hui,Wang, Yi-Nong,Fan, Yun-Ge,Ma, Jian-Biao
, p. 131 - 137 (2006)
Two mono-substituted β-cyclodextrins and two bridged bis-β-cyclodextrins, that is, mono(6-(2-aminoethylamino)-6-deoxy)-β- cyclodextrin (1), mono(6-(2-(2-aminoethylamino)ethylamino)-6-deoxy)-β- cyclodextrin (2), ethylene-1,2-diamino bis-6-(6-deoxy-β-cyclodextrin) (3), and iminodiethylene-2,2′-diamino bis-6-(6-deoxy-β-cyclodextrin) (4), were prepared from β-cyclodextrin. Their binding ability with bovine serum albumin as a model protein was investigated through proton magnetic resonance (1H NMR), ultraviolet visible spectroscopy (UV-vis), circular dichroism (CD), and fluorescence spectroscopy. In the 1H NMR spectra of the modified cyclodextrins, the resolution of proton signals decreases after the addition of BSA. From the UV and CD spectra, it is found that both the UV absorption and the α-helix content of BSA increase with the concentration of the modified cyclodextrins. The protein-ligand interactions cause a fluorescence quenching. The quenching constants are determined using the Stern-Volmer equation to provide an observation of the binding affinity between modified cyclodextrins and BSA. All these results indicate that the modified cyclodextrins can interact with BSA and the bridged bis(β-cyclodextrin)s (3 and 4) have much stronger interactions than the mono-substituted β-cyclodextrins (1 and 2). The strong binding stability of bis-cyclodextrins should be attributed to the cooperative effect of two adjacent cyclodextrin moieties. Job's plot shows that the complex stoichiometries of BSA to the modified cyclodextrins were 1:4 for 1 and 2, as well as 1:3 for 3 and 4, respectively.
Leading neuroblastoma cells to die by multiple premeditated attacks from a multifunctionalized nanoconstruct
Jiao, Peifu,Zhou, Hongyu,Otto, Mario,Mu, Qingxin,Li, Liwen,Su, Gaoxing,Zhang, Yi,Butch, Elizabeth R.,Snyder, Scott E.,Jiang, Guibin,Yan, Bing
, p. 13918 - 13921 (2011)
To conquer complex and devastating diseases such as cancer, more coordinated and combined attack strategies are needed. We suggest that these can be beautifully achieved by using nanoconstruct design. We present an example showing that neuroblastoma cells are selectively killed by a nanoconstruct that specifically targets neuroblastoma cells, pushes cells to the vulnerable phase of the cell cycle, and greatly enhances radiation-induced cell death. The success of this multipronged attack approach launched by cell-embedded nanoconstructs demonstrates the power and flexibility of nanotechnology in treating cancer, a difficult task for a small molecule.
Synthesis of amphiphilic polyaspartamide derivatives and construction of reverse micelles
Liu, De-E,Han, Hui,Lu, Hongguang,Wu, Guolin,Wang, Yinong,Ma, Jianbiao,Gao, Hui
, p. 37130 - 37137 (2014)
A series of amphiphilic graft copolymers based on biodegradable and biocompatible poly(aspartic acid)s were synthesized by a successive aminolysis reaction of polysuccinimide using octadecylamine/dodecylamine, and ethylenediamine-β-cyclodextrin/ethanediamine. The chemical structures of the copolymers were confirmed by FT-IR and 1H NMR spectroscopy. Large compound reverse micelles consisting of numerous small reverse micelles with polar cores and hydrophobic shells were formed in octanol solution. The reverse micelles showed various particle sizes based on the different length of hydrophobic alkyl chains and molecular weight of polysuccinimide, as determined by dynamic light scattering. Interestingly, the particle size of micelles showed temperature dependence, the diameter decreased continuously with increasing temperature. Their morphology and assembly properties were characterized using scanning electron microscopy, transmission electron microscopy and fluorescence spectroscopy. The reverse micelles were extremely efficient in extracting Congo red from water into octanol, exhibiting a potential application as delivery vehicles in the pharmaceutical and cosmetic fields, and as nanocontainers for separation of inorganic molecules as well. the Partner Organisations 2014.
Supramolecular Fluorescent Nanoparticles Constructed via Multiple Non-Covalent Interactions for the Detection of Hydrogen Peroxide in Cancer Cells
Wei, Xuan,Dong, Ruijiao,Wang, Dali,Zhao, Tianyu,Gao, Yongsheng,Duffy, Patrick,Zhu, Xinyuan,Wang, Wenxin
, p. 11427 - 11434 (2015)
Overabundance of hydrogen peroxide originating from environmental stress and/or genetic mutation can lead to pathological conditions. Thus, the highly sensitive detection of H2O2 is important. Herein, supramolecular fluorescent nanoparticles self-assembled from fluorescein isothiocyanate modified β-cyclodextrin (FITC-β-CD)/rhodamine B modified ferrocene (Fc-RB) amphiphile were prepared through host-guest interaction between FITC-β-CD host and Fc-RB guest for H2O2 detection in cancer cells. The self-assembled nanoparticles based on a combination of multiple non-covalent interactions in aqueous medium showed high sensitivity to H2O2 while maintaining stability under physiological condition. Owing to the fluorescence resonance energy transfer (FRET) effect, addition of H2O2 led to obvious fluorescence change of nanoparticles from red (RB) to green (FITC) in fluorescent experiments. In vitro study showed the fluorescent nanoparticles could be efficiently internalized by cancer cells and then disrupted by endogenous H2O2, accompanying with FRET from "on" to "off". These supramolecular fluorescent nanoparticles constructed via multiple non-covalent interactions are expected to have potential applications in diagnosis and imaging of diseases caused by oxidative stresses.
Pip-HoGu: An Artificial Assembly with Cooperative DNA Recognition Capable of Mimicking Transcription Factor Pairs
Yu, Zutao,Guo, Chuanxin,Wei, Yulei,Hashiya, Kaori,Bando, Toshikazu,Sugiyama, Hiroshi
, p. 2426 - 2429 (2018)
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.
Pseudo-graft polymer based on adamantyl-terminated poly(oligo(ethylene glycol) methacrylate) and homopolymer with cyclodextrin as pendant: Its thermoresponsivity through polymeric self-assembly and host-guest inclusion complexation
Li, Yinwen,Guo, Huilong,Zhang, Yunfei,Zheng, Jian,Gan, Jianqun,Guan, Xiaoxiao,Lu, Mangeng
, p. 17768 - 17779 (2014)
A series of well-defined adamantyl-terminated thermally responsive copolymers (Ad-POEGMAs) were synthesized by atom transfer radical polymerization (ATRP), in which 2-(2-methoxyethoxy) ethyl methacrylate (MEO2MA) and oligo(ethylene glycol) methacrylate (OEGMA) served as the thermosensitive building blocks. Moreover, cyclodextrins (CDs) as bulky pendant grafted polymers (PGCD) were synthesized by homopolymerization of aminoethyl methacrylate β-cyclodextrin (GCD). The thermal-responsive behaviors were investigated by a combination of 1H NMR, UV-vis spectroscopy, dynamic light scattering (DLS), and transmission electron microscopy (TEM). In comparison to other thermal-responsive copolymers based on POEGMAs, Ad-POEGMAs exhibited unusual thermally induced aggregation processes. The Ad group assembled and POEGMA chains associated to produce stable water-soluble nano-aggregates, followed by a rearrangement process at the second thermal transition. Moreover, it was found that a noncovalently connected supramolecular pseudo-graft polymer was formed via inclusion complexation in aqueous solution. This pseudo-graft polymer underwent a reversible temperature-induced transition from solution to micelle under suitable conditions. The cyclodextrin (CD) moiety attached to the main chain played two roles. As supramolecular host moieties, CDs formed inclusion complexes with guest-ended polymers, leading to graft-like polymers. As bulky hydrophilic moieties, CDs stabilized the micelles induced by the coil-to-globule transition of POEGMA segments. This journal is the Partner Organisations 2014.
Fluorescent behaviour in host-guest interactions. Part 3. Fluorescent sensing for organic guests using three types of amino-β-cyclodextrins
Takenaka, Yasushi,Higashi, Miwako,Yoshida, Noboru
, p. 615 - 620 (2002)
The pH- and temperature-dependent fluorescence behaviour in aqueous solution of three amino-β-cyclodextrins (amino-β-CDx), 1, 2 and 3, bearing an amide-linked naphthalene probe has been investigated. The emission intensity at λmax(em) of 1 decreased dramatically with increasing temperature. The pH-dependent fluorescence spectrum was also recorded. Operation of the in-out equilibrium of the naphthalene probe of 1 was mainly analyzed using 1H NMR and circular dichroism spectra. The application of 1 to organic-guest sensing is demonstrated by several examples. These findings suggest that the new host molecule, 1, will be an excellent CDx-based fluorescent sensor for temperature, pH and neutral organic guests.
Synthesis of bridged and metallobridged bis(β-cyclodextrin)s containing fluorescent oxamidobisbenzoyl linkers and their selective binding towards bile salts
Liu, Yu,Yu, Hong-Mei,Chen, Yong,Zhao, Yan-Li
, p. 3858 - 3868 (2006)
A series of β-cyclodextrin (β-CD) dimers containing fluorescent 2,2′-oxamidobisbenzoyl and 4,4′-oxamidobisbenzoyl linkers - that is, 6,6′-[2,2′-oxamidobis(benzoylamino)]ethyleneamino-6,6′-deoxy- bis(β-CD) (2), 6,6′-[2,2′-oxamidobis(benzoylamino)] diethylenediamino-6,6′-deoxy-bis(β-CD) (3), 6,6′-[4,4′- oxamidobis(benzoylamino)]ethyleneamino-6,6′-deoxy-bis(β-CD) (4), and 6,6′-[4,4′-oxamidobis(benzoylamino)]-diethylenediamino-6, 6′-deoxy- bis(β-CD) (5) - were synthesized from the corresponding oxamidobis(benzoic acid)s through treatment with mono[6-aminoethyleneamino-6- deoxy]-β-CD or mono[6-diethylenetriamino-6-deoxy]-β-CD. Further treatment of 2-5 with copper perchlorate gave their CuII complexes 6-9 in satisfactory yields. The conformation and binding behavior of 2-9 towards two bile salt guests - sodium cholate (CA) and sodium deoxycholate (DCA) - was comprehensively investigated by circular dichroism, 2D NMR spectroscopy, and fluorescence spectroscopy in TrisHCl buffer solution (pH 7.2) at 25 °C. Thanks to the cooperative host-linker-guestbinding mode, the stoichiometric 1:1 complexes formed by bis(β-CD)s 2-5 with bile salts gave high stability constants (KS values) of up to 103-104M-1. Significantly, benefiting from the intramolecular 1:2 or 2:4 binding stoichiometry, the resulting complexes of metallobis(β-CD)s 6-9 with bile salts gave much higher KS values of up to 106-107M -2. The enhanced binding abilities of bis(β-CD)s and metallobridged bis(β-CD)s are discussed from the viewpoints of induced-fit interactions and multiple recognition between host and guest.
Hyper-Cross-linked Porous MoS2-Cyclodextrin-Polymer Frameworks: Durable Removal of Aromatic Phenolic Micropollutant from Water
Liu, Jian,Yang, Yanmei,Bai, Jingwei,Wen, Huang,Chen, Fengjuan,Wang, Baodui
, p. 3621 - 3627 (2018)
A reasonable and efficient strategy for the construction of hyper-cross-linked porous MoS2-CD-polymer frameworks (MoS2CDPFs) was demonstrated. Here, MoS2 nanosheets (NSs) can be decorated with amino functionalized β-cyclodextrin, producing a nanoscale structural motif (MoS2@CD) for the synthesis of MoS2CDPFs. We demonstrated that CD polymer (CDP) as linker can be uniformly incorporated into the frameworks. Except for the pores created between MoS2 NSs, polymer doping generates extra interspace between MoS2 NSs and CD monomer. Interestingly, the resultant MoS2CDPFs can rapidly sequester aromatic phenolic micropollutant bisphenol A (0.1 mM) from water with 93.2% adsorption capacity, which is higher than that of MoS2, MoS2@CD, and CDP. The intercalation between MoS2 sheets with CDP imparts the frameworks durability in adsorption/desorption of aromatic phenolic micropollutants. Remarkably, the removal efficiency reduced only 3% after 10 regeneration-reuse cycles. These findings demonstrated that the porous MoS2-CD-polymer-based frameworks are promising adsorbents for rapid, flow-through water remediation.
Surface immobilization of β-cyclodextrin on hybrid silica and its fast adsorption performance of p-nitrophenol from the aqueous phase
Shen, Hai-Min,Zhu, Gong-Yuan,Yu, Wu-Bin,Wu, Hong-Ke,Ji, Hong-Bing,Shi, Hong-Xin,Zheng, Yi-Fan,She, Yuan-Bin
, p. 84410 - 84422 (2015)
Renewable β-cyclodextrin (β-CD) was immobilized onto the surface of hybrid silica using ethylenediamine as linking groups to construct an adsorbent in water treatment (CD@Si), and the obtained CD@Si was characterized through FT-IR, XPS, EDX, contact angle measurement, TGA, solid-state 13C NMR, SEM, and XRD analyses. The effect of initial pH, contact time on the adsorption performance of CD@Si for p-nitrophenol, and the adsorption kinetics, adsorption isotherms, adsorption thermodynamics, reusability and adsorption mechanism were investigated systematically, which indicate that the adsorption of p-nitrophenol onto CD@Si is a very fast process. The adsorption equilibrium can be reached in 15 s with an acceptable equilibrium adsorption capacity of 69.6 mg g-1 at pH 7.0, which is much faster than many reported adsorbents based on β-CD. The adsorption of p-nitrophenol onto CD@Si follows the pseudo-second-order model, obeys the Freundlich model, and is a feasible, spontaneous, and exothermic process which is more favorable at lower temperatures. And the formation of an inclusion complex and a hydrogen bond interaction are two origins of p-nitrophenol being adsorbed onto CD@Si. Additionally, CD@Si can be recycled and reused for at least five runs with an acceptable adsorption capacity, and is a very promising adsorbent for the fast adsorption of p-nitrophenol or its analogues from the aqueous phase. Additionally, this work also provides a strategy to increase the adsorption rate of adsorbents based on β-CD.
Functional carrier based on alkylamino cyclodextrin in entrapment of ferulic acid
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Paragraph 0039; 0050-0052, (2020/04/02)
The invention discloses application of a functional carrier based on alkylamino cyclodextrin in entrapment of ferulic acid. On the one hand, alkylamino-modified beta-cyclodextrin is designed as a mainbody to prepare a ferulic acid clathrate compound; and on the other hand, an alkylamino cyclodextrin high-molecular polymer connected with linear polymer molecules is designed to load ferulic acid. Compared with the ferulic acid monomer, the ferulic acid entrapped by the carrier has advantages that the water solubility is obviously improved and the thermal stability is also enhanced; and a certain theoretical reference is provided for developing a novel water-soluble ferulic acid material and expanding the application of ferulic acid in the field of food and medicine.
