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001-es BibID:BIBFORM070763
Első szerző:Kaltner, Herbert
Cím:Bivalent O-glycoside mimetics with S/disulfide/Se substitutions and aromatic core: Synthesis, molecular modeling and inhibitory activity on biomedically relevant lectins in assays of increasing physiological relevance / Herbert Kaltner, Tamás Szabó, Krisztina Fehér, Sabine André, Sára Balla, Joachim C. Manning, László Szilágyi, Hans-Joachim Gabius
Dátum:2017
ISSN:0968-0896
Megjegyzések:The emerging significance of recognition of cellular glycans by lectins for diverse aspects of pathophysiology is a strong incentive for considering development of bioactive and non-hydrolyzable glycoside derivatives, for example by introducing S/Se atoms and the disulfide group instead of oxygen into the glycosidic linkage. We report the synthesis of 12 bivalent thio-, disulfido- and selenoglycosides attached to benzene/naphthalene cores. They present galactose, for blocking a plant toxin, or lactose, the canonical ligand of adhesion/growth-regulatory galectins. Modeling reveals unrestrained flexibility and inter-headgroup distances too small to bridge two sites in the same lectin. Inhibitory activity was first detected by solid-phase assays using a surface-presented glycoprotein, with relative activity enhancements per sugar unit relative to free cognate sugar up to nearly 10fold. Inhibitory activity was also seen on lectin binding to surfaces of human carcinoma cells. In order to proceed to characterize this capacity in the tissue context monitoring of lectin binding in the presence of inhibitors was extended to sections of three types of murine organs as models. This procedure proved to be well-suited to determine relative activity levels of the glycocompounds to block binding of the toxin and different human galectins to natural glycoconjugates at different sites in sections. The results on most effective inhibition by two naphthalene-based disulfides and a selenide raise the perspective for broad applicability of the histochemical assay in testing glycoclusters that target biomedically relevant lectins.
Tárgyszavak:Természettudományok Kémiai tudományok idegen nyelvű folyóiratközlemény külföldi lapban
Agglutinin
Glycosyldisulfides
Histochemistry
Lectin
Selenoglycosides
Sugar code
Thioglycosides
Megjelenés:Bioorganic & Medicinal Chemistry. - 25 : 12 (2017), p. 3158-3170. -
További szerzők:Szabó Tamás (1985-) (vegyész) Fehér Krisztina (1974-) (vegyész) André, Sabine Balla Sára Manning, Joachim C. Szilágyi László (1941-) (vegyész) Gabius, Hans-Joachim
Pályázati támogatás:NN-109671
OTKA
GINOP-2.3.2-15-2016-00008
GINOP
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