Synthesis and properties of 3′-azido-3′-deoxythymidine derivatives of glycerolipids

Author: Lonshakov D.   Baranova E.   Lyutik A.   Shastina N.   Shvets V.  

Publisher: Springer Publishing Company

ISSN: 0091-150X

Source: Pharmaceutical Chemistry Journal, Vol.44, Iss.10, 2011-01, pp. : 557-563

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Abstract

A promising approach to enhancing the bioavailability of hydrophilic therapeutic agents including anti-HIV nucleosides is designing their pseudotriglyceride derivatives that may mimic natural lipids and take advantage of their metabolic pathways resulting in improved delivery to target cells. The synthesis of a series of new 1,3-diglycerides and AZT conjugates employing various linkage types between the pharmacophore residue and the spacer part of the hydrophobic moiety (ester or phosphodiester) is described. The hydrolytic properties of the synthesized liponucleosides (in buffer solutions and under the action of pancreatic lipase) have been studied. Liposomes based on these AZT-containing prodrugs have been obtained.

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