162615-68-1Relevant articles and documents
Synthesis and characterization of novel multifunctional host compounds. 4. Cyclodextrin derivatives bearing chromophores
Gao,Tong,Inoue,Tai
, p. 703 - 710 (1995)
Nine novel cyclodextrin derivatives were synthesized and characterized by 1H-NMR, 13C-NMR, FT-IR, TLC, and elemental analysis. A solvent mixture consisting of acetone and water (5:1) was found effective for separation and purificatio
Amino alcohol-modified β-cyclodextrin inducing biomimetic asymmetric oxidation of thioanisole in water
Shen, Hai-Min,Ji, Hong-Bing
, p. 49 - 58 (2012)
Inspired by β-CD, a macrocyclic oligomers of d-(+)-glucopyranose and a renewable material, which could be obtained from starch, that can promote a lot of organic reactions in water, a green solvent, several amino alcohol-modified β-CDs CD-1 to CD-7 were synthesized in the yields of 36-61%. Their conformations in vacuum and in aqueous solution were optimized by quantum calculation. Their complexes with sodium molybdate prepared in situ were characterized by 1H NMR and were applied in the asymmetric oxidation of thioanisole. Their performance in inducing enantioselectivity was investigated in detail. For the optimal one, CD-1, moderate enantioselectivity (56% ee) was achieved in aqueous CH3COONa-HCl buffer solution (pH 7.0). The abilities of CD-1 to CD-7 to induce asymmetry are highly dependent on the pH value of the reaction medium and the structure of the modifying group. The origin of the moderate enantioselectivity and the reaction mechanism were investigated with the aid of 1H ROESY NMR studies and quantum calculation. The moderate enantioselectivity was attributed to the two different binding models between CD-1 and thioanisole, which could be defined as intramolecular catalysis and intermolecular catalysis, in which intramolecular catalysis gave (S)-methyl phenyl sulfoxide and intermolecular catalysis gave (R,S)-methyl phenyl sulfoxide.
Polyethylenimine-Bisphosphonate-Cyclodextrin Ternary Conjugates: Supramolecular Systems for the Delivery of Antineoplastic Drugs
Blanco, Victor,Garcia-Cerezo, Pablo,Giron-Gonzalez, María Dolores,Hernandez-Mateo, Fernando,Plesselova, Simona,Reche-Perez, Francisco J.,Salto-Gonzalez, Rafael,Santoyo-Gonzalez, Francisco
, p. 12245 - 12260 (2021)
Bisphosphonates (BPs) are bone-binding molecules that provide targeting capabilities to bone cancer cells when conjugated with drug-carrying polymers. This work reports the design, synthesis, and biological evaluation of polyethyleneimine-BP-cyclodextrin (PEI-BP-CD) ternary conjugates with supramolecular capabilities for the loading of antineoplastic drugs. A straightforward, modular, and versatile strategy based on the click aza-Michael addition reaction of vinyl sulfones (VSs) allows the grafting of BPs targeting ligands and βCD carrier appendages to the PEI polymeric scaffold. The in vitro evaluation (cytotoxicity, cellular uptake, internalization routes, and subcellular distribution) for the ternary conjugates and their doxorubicin inclusion complexes in different bone-related cancer cell lines (MC3T3-E1 osteoblasts, MG-63 sarcoma cells, and MDA-MB-231 breast cancer cells) confirmed specificity, mitochondrial targeting, and overall capability to mediate a targeted drug transport to those cells. The in vivo evaluation using xenografts of MG-63 and MDA-MB-231 cells on mice also confirmed the targeting of the conjugates.
Monovinyl sulfone B-cyclodextrin. a flexible drug carrier system
Del Castillo, Teresa,Marales-Sanfrutos, Julia,Santoyo-Gonzlez, Francisco,Magez, Stefan,Lopez-Jaramillo, F. Javier,Garcia-Salcedo, Jose A.
, p. 383 - 389 (2014)
Cyclodextrins have been conjugated to target various receptors and have also been functionalized with carbohydrates for targeting specific organs. However, this approach is based on a rigid design that implies the ad hoc synthesis of each cyclodextrin- targeting agent conjugate. We hypothesized that: 1) a modular design that decouples the carrier function from the targeting function leads to a flexible system, 2) combining the reactivity of the vinyl sulfone group toward biomolecules that act as targeting agents with the ability of cyclodextrin to form complexes with a wide range of drugs may yield a versatile system that allows the targeting of different organs with different drugs, and 3) the higher reactivity of histidine residues toward the vinyl sulfone group can be exploited to couple the cyclodextrin to the targeting system with a degree of regioselectivity. As a proof of concept, we synthesized a monovinyl sulfone b-cyclodextrin (module responsible for the payload), which, after coupling to recombinant antibody fragments raised against Trypanosoma brucei (module responsible for targeting) and loading with nitrofurazone (module responsible for therapeutic action) resulted in an effective delivery system that targets the surface of the parasites and shows trypanocidal activity.
