30754-23-5Relevant academic research and scientific papers
Monodisperse nanoparticles from self-assembling amphiphilic cyclodextrins: Modulable tools for the encapsulation and controlled release of pharmaceuticals
Mendez-Ardoy, Alejandro,Gomez-Garcia, Marta,Geze, Annabelle,Putaux, Jean-Luc,Wouessidjewe, Denis,Mellet, Carmen Ortiz,Defaye, Jacques,Fernandez, Jose M. Garcia,Benito, Juan M.
, p. 524 - 532 (2012)
Selective chemical functionalization of cyclodextrins (CDs) is a readily amenable methodology to produce amphiphilic macromolecules endowed with modulable self-organizing capabilities. Herein, the synthesis of well-defined amphiphilic CD derivatives, with a "skirt-type" architecture, that incorporate long-chain fatty esters at the secondary hydroxyl rim and a variety of chemical functionalities (e. g. iodo, bromo, azido, cysteaminyl or isothiocyanato) at the primary hydroxyls rim is reported. Nanoprecipitation of the new CD facial amphiphiles, or binary mixtures of them, resulted in nanoparticles with average hydrodynamic diameters ranging from 100 to 240 nm that were stable in suspension for several months. The precise size, zeta potential and topology of the nanoparticles are intimately dependent on the functionalization pattern at the CD scaffold. Highly efficient molecular encapsulation capabilities of poorly bioavailable drugs such as diazepam (DZ) were demonstrated for certain derivatives, the drug release profile being dependent on the type of formulation (nanospheres or nanocapsules). The efficiency and versatility of the synthetic strategy, together with the possibility of exploiting the reactivity of the functional groups at the nanoparticle surface, offer excellent opportunities to further manipulate the carrier capabilities of this series of amphiphilic CDs from a bottom-up approach.
A simple synthesis of a highly water soluble symmetrical β-cyclodextrin derivative
Roehri-Stoeckel, Christine,Dangles, Olivier,Brouillard, Raymond
, p. 1551 - 1554 (1997)
1,3-dipolar cycloaddition between peracetyl-heptakis-6-azido-6-deoxy-β-cyclodextrin and the dimethylester of 2-butyne dicarboxylic acid is a highly efficient route for the introduction of seven 1,2,3-triazole heterocycles and fourteen carboxyl groups on the small rim of the macrocycle.
Selective binding and controlled release of anticancer drugs by polyanionic cyclodextrins
Cheng, Jian-Guang,Yu, Hua-Jiang,Chen, Yong,Liu, Yu
, p. 2287 - 2290 (2018)
The binding stoichiometry, binding constants, and inclusion mode of some water-soluble negatively charged cyclodextrin derivatives, i.e. heptakis-[6-deoxy-6-(3-sulfanylpropanoic acid)]-β-cyclodextrin(H1), heptakis-[6-deoxy-6-(2-sulfanylacetic acid)]-β-cyclodextrin(H2), mono-[6-deoxy-6-(3-sulfanylpropanoic acid)]-β-cyclodextrin (H3) and mono-[6-deoxy-6-(2-sulfanylacetic acid)]-β-cyclodextrin (H4), with three anticancer drugs, i.e. irinotecan hydrochloride; topotecan hydrochloride; doxorubicin hydrochloride, were investigated by means of 1H NMR, UV–Vis spectroscopy, mass spectra and 2D NMR. Polyanionic cyclodextrins H1-H2 showed the significantly high binding abilities of up to 2.6 × 104–2.0 × 105 M?1 towards the selected anticancer drugs, which were nearly 50–1000 times higher than the corresponding Ks values of native β-cyclodextrin. In addition, these polyanionic cyclodextrins also showed the pH-controlled release behaviors. That is, the anticancer drugs could be efficiently encapsulated in the cyclodextrin cavity at a pH value similar to that of serum but sufficiently released at an endosomal pH value of a cancer cell, which would make these cyclodextrin derivatives the potential carriers for anticancer drugs.
Mono-benzimidazole functionalized β-cyclodextrins as supramolecular nanovalves for pH-triggered release of p-coumaric acid
Wang, Ting,Wang, Mingdong,Ding, Chendi,Fu, Jiajun
, p. 12469 - 12472 (2014)
The self-complexation of mono-benzimidazole functionalized β-cyclodextrins was investigated. The unique molecular structure employed as supramolecular nanovalves were installed on the external surface of mesoporous silica to assemble mechanized silica nanoparticles, which showed pH-triggered release property. This journal is
Sugar-grafted cyclodextrin nanocarrier as a "trojan Horse" for potentiating antibiotic activity
Li, Min,Neoh, Koon Gee,Xu, Liqun,Yuan, Liang,Leong, David Tai,Kang, En-Tang,Chua, Kim Lee,Hsu, Li Yang
, p. 1161 - 1174 (2016)
Purpose: The use of "Trojan Horse" nanocarriers for antibiotics to enhance the activity of antibiotics against susceptible and resistant bacteria is investigated. Methods: Antibiotic carriers (CD-MAN and CD-GLU) are prepared from β-cyclodextrin grafted with sugar molecules (D-mannose and D-glucose, respectively) via azide-alkyne click reaction. The sugar molecules serve as a chemoattractant enticing the bacteria to take in higher amounts of the antibiotic, resulting in rapid killing of the bacteria. Results: Three types of hydrophobic antibiotics, erythromycin, rifampicin and ciprofloxacin, are used as model drugs and loaded into the carriers. The minimum inhibitory concentration of the antibiotics in the CD-MAN-antibiotic and CD-GLU-antibiotic complexes for Gram-negative Escherichia coli, Pseudomonas aeruginosa and Acinetobacter baumannii strains, and a number of Gram-positive Staphylococcus aureus strains, including the methicillin-resistant strains (MRSA), are reduced by a factor ranging from 3 to >100. The CD-MAN-antibiotic complex is also able to prolong the stability of the loaded antibiotic and inhibit development of intrinsic antibiotic resistance in the bacteria. Conclusions: These non-cytotoxic sugar-modfied nanocarriers can potentiate the activity of existing antibiotics, especially against multidrug-resistant bacteria, which is highly advantageous in view of the paucity of new antibiotics in the pipeline.
Entirely oligosaccharide-based supramolecular amphiphiles constructed: Via host-guest interactions as efficient drug delivery platforms
Shi, Yuting,Li, Hongping,Cheng, Ju,Luan, Tingting,Liu, Di,Cao, Yufei,Zhang, Xiangdong,Wei, Hua,Liu, Yali,Zhao, Guanghui
, p. 12302 - 12305 (2017)
Entirely oligosaccharide-based supramolecular amphiphiles were constructed via host-guest interactions between ferrocene-terminated acetylated-maltoheptaose (Fc-AcMH) and β-cyclodextrin-terminated four-arm star maltoheptaose (MH4-β-CD). The amphiphiles could self-assemble to form spherical supramolecular nanoparticles to provide efficient drug delivery platforms. The combination of a pH-sensitive covalent acetal group and the oxidation-sensitive noncovalent host-guest interaction of β-CD and ferrocene provided the obtained fully oligosaccharide-based supramolecular amphiphiles. The structures of these amphiphiles could respond to the intracellular microenvironment.
Improved cyclodextrin-based receptors for camptothecin by inverse virtual screening
Steffen, Andreas,Thiele, Carolin,Tietze, Simon,Strassnig, Christian,Kaemper, Andreas,Lengauer, Thomas,Wenz, Gerhard,Apostolakis, Joannis
, p. 6801 - 6809 (2007)
We report the computeraided optimization of a synthetic receptor for a given guest molecule, based on inverse virtual screening of receptor libraries. As an example, a virtual set of β-cyclodextrin (β-CD) derivatives was generated as receptor candidates for the anticancer drug camptothecin. We applied the two docking tools AutoDock and GlamDock to generate camptothecin complexes of every candidate receptor. Scoring functions were used to rank all generated complexes. From the 10% top-ranking candidates nine were selected for experimental alidation. They were synthesized by reaction of heptakis-[6-deoxy-6-iodo]-β-CD with a thiol compound to form the hepta-substituted β-CDs. The stabilities of the camptothecin complexes obtained from solubility measurements of five of the nine CD derivatives were significantly higher than for any other CD derivative known from literature. The remaining four CD derivatives were insoluble in water. In addition, corresponding mono-substituted CD derivatives were synthesized that also showed improved binding constants. Among them the 9-H-purine derivative was the best, being comparable to the investigated hepta-substituted β-CDs. Since the measured binding free energies correlated satisfactorily with the calculated scores, the applied scoring functions appeared to be appropriate for the selection of promising candidates for receptor synthesis.
Multicharge β-cyclodextrin supramolecular assembly for ATP capture and drug release
Chen, Changhui,Chen, Yong,Dai, Xianyin,Li, Jingjing,Jia, Shanshan,Wang, Shuaipeng,Liu, Yu
, p. 2812 - 2815 (2021)
A hyaluronidase-responsive polysaccharide supramolecular assembly was constructed from an amphiphilic β-cyclodextrin bearing seven hexylimidazolium units (AMCD), adamantyl-grafted hyaluronic acid, and chlorambucil, which showed specific cancer cell targeting and controlled drug release abilities. Interestingly, ternary supramolecular assembly can disassemble in the presence of hyaluronidase, and the released AMCD can assemble with ATP to form a stable 1?:?1 complex, which enhanced the efficacy of chlorambucil on cancer chemotherapy by inhibiting ATP hydrolysis.
Synthesis of the dendritic type β-cyclodextrin on primary face via click reaction applicable as drug nanocarrier
Toomari, Yousef,Namazi, Hassan,Akbar, Entezami Ali
, p. 205 - 213 (2015)
Abstract The objective of this study was the syntheses of well-defined glycodendrimer with entrapment efficiency by click reactions, with β-cyclodextrins (β-CDs) moiety to keep the biocompatibility properties, besides especially increase their capacity to
Probing carbohydrate-carbohydrate interactions by photoswitchable supramolecular glycoclusters
Bavireddi, Harikrishna,Bharate, Priya,Kikkeri, Raghavendra
, p. 3988 - 3990 (2013)
The synthesis of photo-switchable glycoclusters with distinct sugar arrangements is described and the use of these clusters to study carbohydrate-carbohydrate interactions (CCIs) is demonstrated.
