Recognition ability and cytotoxicity of some oligosaccharidylsubstituted β‐cyclodextrins

Abstract

This paper reports a chemico-enzymatic synthesis of beta-CD derivatives. The recognition properties of these derivatives were tested using flocculating yeast and isolated lectins. It was observed that the substitution of beta-cyclodextrins with galactose end arms induces the better recognition by a cell-linked galactose-specific lectin. The physicochemical effects of the beta-CD derivatives on membranes were estimated using red blood cells and the effects on the viability of yeast and human rectal tumor cells were appreciated by measuring the mitochondrial deshydrogenase activity. The substitutions of the beta-CD ring by sugar antennae decrease the negative physicochemical effects of the beta-CD, ie their hemolytic properties. However, these substitutions induce significant modifications of the biological properties of the molecules, particularly the cytotoxicity and the growth of eukaryotic cells.

Pharmaceutical Applications of Cyclodextrins. III. Toxicological Issues and Safety Evaluation

“…When the character of the lipophilic cavity of CDs is modified by chemical derivatization, the effects on cell membranes can be dramatically changed [81][82][83][84][85][86][87][88] ; some of the results are depicted in Figure 6. The hemolytic activity of CDs correlates with their inclusion ability toward membrane lipids rather than their intrinsic solubility or surface activity.…”

Improvement of Drug Properties by Cyclodextrins

“…160 It is reported that some galactose and fucose conjugates have a signifi cant cytotoxic effect on the human rectal adenocarcinoma cell line, with P-glycoprotein-positive multidrug resistance. 161 The sugar-substituted CyD derivatives may offer a new way of delivering drugs selectively to specifi c cell surfaces of organs such as liver and colon, although the uptake of drugs into cells may decrease due to the presence of a bulky, hydrophilic CyD moiety.…”

Multivalent Cyclooligosaccharides: Versatile Carbohydrate Clusters with Dual Role as Molecular Receptors and Lectin Ligands

“…Stoddart and Fulton [28] prepared the per- Scheme 6. Thus, d-galactopyranosyl ligands bind to the cell wall lectin of Kluyveromyces bulgaricus (KbCWL), [13,15,29] Arachis hypogea (peanut), [26b] Ricinus communis [11b] and Griffonia simplicifolia I (GSI) lectins; [25] d-glucopyranosyl ligands to Pisum sativum (pea) lectin; [26a] d-mannopyranosyl ligands to Pisum sativum [60] and Concanavalia ensiformis (concanavalin A, Con A) lectins; [14, 16, 25, 26a] N-acetylglucosamine and Nacetyllactosamine ligands to Triticum vulgaris (WGA, wheat germ agglutinin) [23a, 23b, 25, 26a] and Erythrina corallodendron (EcorL) lectins. [27,28] Lectin-binding and inclusion ability of monovalent versus multivalent polysubstituted cyclodextrin neoglycoconjugates: b-CD neoglycoconjugates bearing biorecognizable saccharide markers have been shown to bind to complementary lectins in vitro.…”