29390-67-8Relevant articles and documents
Preparation, characterization and biological evaluation of β-cyclodextrin-biotin conjugate based podophyllotoxin complex
Zhao, Xiu,Qiu, Neng,Ma, Yingyu,Liu, Junda,An, Lianying,Zhang, Teng,Li, Ziqin,Han, Xu,Chen, Lijuan
, (2021)
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.
Aminated β-cyclodextrin-grafted Fe3O4-loaded gambogic acid magnetic nanoparticles: Preparation, characterization, and biological evaluation
Fang, Wei,Dai, Ya Ji,Wang, Ting,Gao, Hai Tao,Huang, Peng,Yu, Juan,Huang, He Ping,Wang, Dian Lei,Zong, Wei Lu
, p. 27136 - 27146 (2019)
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.
Synthesis, characterization, and in vitro evaluation of artesunate-β-cyclodextrin conjugates as novel anti-cancer prodrugs
Jiang, Rui-Jian,Zhao, Yu-Lin,Chen, Yun-Jian,Xiao, Dan,Wang, Fen,Han, Bin,Yang, Jian,Liao, Xia-Li,Yang, Li-Juan,Gao, Chuan-Zhu,Yang, Bo
, p. 19 - 25 (2014)
A novel series of artesunate-β-cyclodextrin (ATS-β-CD) conjugates, in which artesunate (ATS) was coupled covalently to one of the primary hydroxyl groups of β-cyclodextrin (β-CD) through amino bond formation, were synthesized and characterized by 1H NMR, HRMS, 2D NMR (ROESY), X-ray diffraction (XRD), and thermogravimetric analysis (TGA). The results showed that the aqueous solubility of ATS-β-CD conjugates was 26-45 times better than that of free ATS. The cytotoxicity of the ATS-β-CD conjugates was evaluated on human colon cancer cell lines HCT116, LOVO, SW480, and HT-29, and the results indicated that ATS-2NβCD exhibited a very high cytotoxicity against HCT116, LOVO, and HT-29 with IC50 values of 0.58, 1.62, and 5.18 μmol/L, respectively. In addition, the supposition of better cytotoxicity was further supported by the control experiment of fluorescent cyclodextrin.
pH-sensitive β-cyclodextrin derivatives for the controlled release of Podophyllotoxin
Gao, Chuanzhu,Li, Fanjie,Liao, Xiali,Yang, Bo,Yang, Jing,Yang, Lei,Yang, Waixiang,Zhao, Yulin
, (2021)
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.
Fuel-Driven and Enzyme-Regulated Redox-Responsive Supramolecular Hydrogels
Jain, Mehak,Ravoo, Bart Jan
, p. 21062 - 21068 (2021)
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.
Fluorescent sensors of molecular recognition. Modified cyclodextrins capable of exhibiting guest-responsive twisted intramolecular charge transfer fluorescence
Hamasaki, Keita,Ikeda, Hiroshi,Nakamura, Asao,Ueno, Akihiko,Toda, Fujio,Suzuki, Iwao,Osa, Tetsuo
, p. 5035 - 5040 (1993)
α-, β-, and γ-cyclodextrin derivatives bearing a p-(dimethylamino)benzoyl (DMAB) moiety (DMAB-αCyD, DMAB-βCyD, and DMAB-γCyD, respectively) have been synthesized as fluorescent sensors of molecular recognition. These compounds show dual fluorescence emission arising from normal planar (NP) and twisted intramolecular charge transfer (TICT) exited states, and among them strong TICT emission was observed for DMAB-βCyD. The induced circular dichroism spectra of the derivatives suggest that only DMAB-βCyD among other derivatives binds the DMAB moiety into its own cavity, forming an intramolecular inclusion complex. This conformation was confirmed by the analysis of its 1H-NMR data and was related to its strong TICT emission. The intensity of the TICT emission of DMAB-βCyD decreased markedly with increasing the concentration of cyclic alchols, monoterpenes, or steroids. This observation was explained by the guest-induced location change of the DMAB moiety from inside to outside of the cavity. Since the TICT emission intensity depended on the size, shape, and polarity of the guest molecules, DMAB-βCyD was useful as a fluorescent chemosensor of molecular recognition.
Homodimerization and heteroassociation of 6-O-(2-sulfonato-6-naphthyl)-γ-cyclodextrin and 6-deoxy-(pyrene-1-carboxamido)-β-cyclodextrin
Park, Joon Woo,Song, Hee Eun,Lee, Soo Yeon
, p. 7071 - 7076 (2003)
6-O-(2-Sulfonato-6-naphthyl)-γ-cyclodextrin (1) and 6-deoxy-(pyrene-1-carboxamido)-β-cyclodextrin (2) were prepared. Homodimerizations of 1 and 2 and heteroassociation between 1 and 2 were investigated by 1H NMR, circular dichroism, and fluorescence spectroscopic methods. The compounds 1 and 2 form head-to-head dimers with dimerization constants of 140 ± 50 and 270 ± 70 M-1, respectively. We also determined the association constants of 1 with β-CD as 270 ± 20 M-1 and 2 with γ-CD as 100 ± 30 M-1 from fluorescence and circular dichroism titration data, respectively. The heteroassociation between 1 and 2 was manifested in increased circular dichroism ellipticities of 2, downfield shift of the H-2 proton of the pyrene group of 2, and upfield shift of the H-5 proton of the naphthyl group of 1 upon mixing 1 and 2. The analysis of circular dichroism titration data of 2 with 1 gave the association constant as 9300 ± 1600 M-1. The NMR and circular dichroism spectra suggested that the naphthyl group of 1 is deeply included into the β-CD cavity of 2, while the pyrene group of 2 is partially inserted in the γ-CD cavity of 1 in the complex. The energy-minimized structure from molecular modeling of the complex supports this. We believe that the facile heteroassociation of two cyclodextrin derivatives having different sizes of cavity and pendant group could be utilized as a useful strategy for assembling functionalized CDs for various applications.
Insight into the Excitation-Dependent Fluorescence of Carbon Dots
Divya, Sasi,Narayan, Satya,Ainavarapu, Sri Rama Koti,Khushalani, Deepa
, p. 984 - 990 (2019)
High quantum yield, photoluminescence tunability, and sensitivity to the environment are a few distinct trademarks that make carbon nanodots (CDs) interesting for fundamental research, with potential to replace the prevalent inorganic semiconductor quantum dots. Currently, application and fundamental understanding of CDs are constrained because it is difficult to make a quantitative comparison among different types of CDs simply because their photoluminescence properties are directly linked to their size distribution, the surface functionalization, the carbon core structures (graphitic or amorphous) and the number of defects. Herein, we report a facile one-step synthesis of mono-dispersed and highly fluorescent nanometre size CDs from a ‘family’ of glucose-based sugars. These CDs are stable in aqueous solutions with photoluminescence in the visible range. Our results show several common features in the family of CDs synthesized in that the fluorescence, in the visible region, is due to a weak absorption in the 300–400 nm from a heterogeneous population of fluorophores. Fluorescence quenching experiments suggest the existence of not only surface-exposed fluorophores but more importantly solvent inaccessible fluorophores present within the core of CDs. Interestingly, time-resolved fluorescence anisotropy experiments directly suggest that a fast exchange of excitation energy occurs that results in a homo-FRET based depolarization within 150 ps of excitation.
β-Cyclodextrin-Modified Magnetic Nanoparticles Immobilized on Sepharose Surface Provide an Effective Matrix for Protein Refolding
Ghaeidamini, Marziyeh,Kharat, Ali N.,Haertlé, Thomas,Ahmad, Faizan,Saboury, Ali A.
, p. 9907 - 9919 (2018)
In this article, we propose an impressive and facile strategy to improve protein refolding using solid phase artificial molecular chaperones consisting of the surface-functionalized magnetic nanoparticles. Specifically, monotosyl-β-cyclodextrin connected to the surface of 3-aminopropyltriethoxysilane (APES)-modified magnetic nanoparticles is immobilized on the sepharose surface to promote interaction with exposed hydrophobic surfaces of partially folded (intermediates) and unfolded states of proteins. Their efficiencies were investigated by circular dichroism spectroscopy and photoluminescence spectroscopy of the protein. Although the mechanism of this method is based on principles of hydrophobic chromatography, this system is not only purging the native protein from inactive inclusion bodies but also improving the protein refolding process. We chose β-cyclodextrin (β-CD) considering multiple reports in the literature about its efficiency in protein refolding and its biocompatibility. To increase the surface area/volume ratio of the sepharose surface by nanoparticles, more β-CD molecules are connected to the sepharose surface to make a better interaction with proteins. We suppose that proteins are isolated in the nanospace created by bound cyclodextrins on the resin surface so intermolecular interactions are reduced. The architecture of nanoparticles was characterized by Fourier transform infrared spectra, X-ray diffraction, scanning electron microscopy images, energy dispersive X-ray spectroscopy, nuclear magnetic resonance (1H NMR and 13C NMR), and dynamic light scattering.
Supramolecular self-assembled aggregates formed by pentacosa-10,12-diynyl amidomethyl-β-cyclodextrin
Cho, Eunae,Kim, Hwanhee,Yang, Jee Eun,Jun, Bong-Hyun,Paik, Seung R.,Jung, Seunho
, p. 37 - 42 (2014)
Mono[6-deoxy-6-(pentacosa-10,12-diynyl amidomethyl)]-β-cyclodextrin was successfully synthesized by reacting mono-6-amino-6-deoxy-β- cyclodextrin with N-hydroxysuccinimide ester of 10,12-pentacosadiynoic acid in DMF. The modified β-cyclodextrin self-assembled and aggregated to form a worm-like supramolecular structure, and the novel supramolecular aggregates were studied using 2D nuclear magnetic resonance spectroscopy, X-ray powder diffraction, thermogravimetry, and electron microscopy. Interestingly, the synthesized pentacosa-10,12-diynyl amidomethyl-β-cyclodextrin formed columnar type self-aggregates and it was clearly differentiated from cage-like structure of native β-cyclodextrin.
