Amphiphilic Cyclodextrins, Synthesis, Utilities and Application of Molecular Modeling in Their Design

Jabbari, Atena; Sadeghian, Hamid

doi:10.5772/50220

Cited by 13 publications

(11 citation statements)

References 37 publications

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“…In particular, amphiphilic CDs have attracted a significant interest and several review articles can be found that survey the state of art and future prospects of various nanocarriers. 10,11,[14][15][16][17] Amphiphilic CDs are prepared by grafting hydrophobic substituents on the primary or secondary face, or both. They can be designed to respond to external stimuli, 18 insert themselves in bilayer membranes 19 or form aggregates able to encapsulate and carry active compounds and drugs to specific targets.…”

Section: Introductionmentioning

confidence: 99%

Self-Assembly of Amphiphilic Biotransesterified β-Cyclodextrins: Supramolecular Structure of Nanoparticles and Surface Properties

et al. 2017

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A series of β-cyclodextrin (βCD) amphiphilic derivatives with varying degrees of substitution were prepared by acylating βCDs on their secondary face using thermolysin to catalyze the transesterification. After dissolution in acetone, the βCD-C derivatives (n = 8, 10, 12, 14) were nanoprecipitated in water, where they self-organized into structured particles that were characterized using cryo-transmission electron microscopy (cryo-TEM) images and small-angle X-ray scattering (SAXS) data. Two types of morphologies and ultrastructures were observed depending on the total degree of substitution (TDS) of the parent derivative. The molecules with TDS < 5 formed nanospheres with a multilamellar organization, whereas those with TDS > 5 self-assembled into barrel-like (n = 8, 10, 12) or more tortuous (n = 14) particles with a columnar inverse hexagonal structure. In particular, faceted βCD-C particles (TDS = 7) appeared to be composed of several domains with different orientations that were separated by sharp interfaces. Ultrastructural models were proposed on the basis of cryo-TEM images and the analysis of the contrast distribution in different projections of the lattice. Complementary compression isotherm experiments carried out at the air-water interface also suggested that differences in the molecular conformation of the series of derivatives existed depending on whether TDS was lower or higher than 5.

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Section: Introductionmentioning

confidence: 99%

Self-Assembly of Amphiphilic Biotransesterified β-Cyclodextrins: Supramolecular Structure of Nanoparticles and Surface Properties

et al. 2017

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“…Among the various types of CD derivatives, amphiphilic CDs are largely used to form supramolecular nanoassemblies, and have had many applications in the biomedical field [ 153 , 154 , 155 , 156 , 157 ]. Researchers have developed the concept of amphiphilic CDs to adjust the hydrophobic/hydrophilic balance of their construction, leading to the formation of various types of supramolecular nanoassemblies (vesicles, micelles, NPs…) [ 158 , 159 , 160 , 161 ]. Amphiphilic CDs can be obtained by enzymatic pathways or by grafting various substituent groups via amino, amido, thio, ester, and ether bonds [ 155 ].…”

Section: Cyclodextrins For Anticancer Photodynamic Therapymentioning

confidence: 99%

Use of Cyclodextrins in Anticancer Photodynamic Therapy Treatment

et al. 2018

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Photodynamic therapy (PDT) is mainly used to destroy cancerous cells; it combines the action of three components: a photoactivatable molecule or photosensitizer (PS), the light of an appropriate wavelength, and naturally occurring molecular oxygen. After light excitation of the PS, the excited PS then reacts with molecular oxygen to produce reactive oxygen species (ROS), leading to cellular damage. One of the drawbacks of PSs is their lack of solubility in water and body tissue fluids, thereby causing low bioavailability, drug-delivery efficiency, therapeutic efficacy, and ROS production. To improve the water-solubility and/or drug delivery of PSs, using cyclodextrins (CDs) is an interesting strategy. This review describes the in vitro or/and in vivo use of natural and derived CDs to improve antitumoral PDT efficiency in aqueous media. To achieve these goals, three types of binding modes of PSs with CDs are developed: non-covalent CD–PS inclusion complexes, covalent CD–PS conjugates, and CD–PS nanoassemblies. This review is divided into three parts: (1) non-covalent CD-PS inclusion complexes, covalent CD–PS conjugates, and CD–PS nanoassemblies, (2) incorporating CD–PS systems into hybrid nanoparticles (NPs) using up-converting or other types of NPs, and (3) CDs with fullerenes as PSs.

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“…In some cases, the addition of amphiphilic molecules as a phase transfer catalyst is useful to control the properties. 23 We also investigated the inclusion complex with MGS as a potential anticancer drug 24 and an agent for removal of reactive oxygen species during ischemia-reperfusion (paper and patent in preparation), but the molecular mechanism of the inclusion of MGS by CDNPs still remains unclear. Although not for epichlorohydrin-linked CDs, Ma and Li found that the binding constant dramatically increased by about 5 orders of magnitude for diisocyanate-linked CDs by measuring UV absorbance.…”

Section: Introductionmentioning

confidence: 99%

Dramatically Increased Binding Constant of Water-Soluble Cyclodextrin Hyperbranched Polymers: Explored with Diffusion Ordered NMR Spectroscopy (DOSY)

Doan

Katsuki

et al. 2022

ACS Omega

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We report that the polymerization of cyclodextrin (CD) with epichlorohydrin (ECH) dramatically increases the binding constant of CD to vanillin, from 55 to 8.4 × 10 3 M –1 , by approximately 100 times, as determined by diffusion ordered spectroscopy (DOSY)– 1 H NMR. The binding constant increased with an increase of the ECH content of the polymer, although ECH polymers without CDs showed no affinity at all, suggesting that the hydrophobicity of the ECH network outside of CDs helps to enhance the binding. This increased binding constant allows CD–ECH polymers to increase the drug loading ratio, which may be one of the most critical issues for drug delivery systems.

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Amphiphilic Cyclodextrins, Synthesis, Utilities and Application of Molecular Modeling in Their Design

Cited by 13 publications

References 37 publications

Self-Assembly of Amphiphilic Biotransesterified β-Cyclodextrins: Supramolecular Structure of Nanoparticles and Surface Properties

Self-Assembly of Amphiphilic Biotransesterified β-Cyclodextrins: Supramolecular Structure of Nanoparticles and Surface Properties

Use of Cyclodextrins in Anticancer Photodynamic Therapy Treatment

Dramatically Increased Binding Constant of Water-Soluble Cyclodextrin Hyperbranched Polymers: Explored with Diffusion Ordered NMR Spectroscopy (DOSY)

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