Synthesis, Properties, and Anti-HIV Activity of New Lipophilic
3'-Azido-3'-Deoxythymidine Conjugates Containing
Functional Phosphoric Linkages

N. S. Shastina^{a, 1}, T. Yu. Maltseva^a, L. N. D’yakova^a, O. A. Lobach^b,
M. S. Chataeva^b, D. N. Nosik^b, and V. I. Shvetz^a

^a Lomonosov Moscow State University of Fine Chemical Technology, pr. Vernadskogo 86, Moscow, 119571 Russia

^b Ivanovsky Institute of Virology, Ministry of Health of Russian Federation,
ul. Gamalei 16, Moscow, 123098 Russia

Received July 3, 2012; in final form, August 29, 2012

Abstract—One of the approaches to enhance the bioavailability of nucleoside reverse transcriptase HIV inhib-
itors is the design of their prodrugs based on 1,3-diacylglycerols, which may simulate metabolic pathways of
natural lipids, thus supporting the efficacy of drug delivery to the target cells. Glycerolipid AZT conjugates with
different functional phosphoric centers were synthesized by the H-phosphonate technique. Stability of the pre-
pared prodrugs against chemical and enzymatic hydrolysis (in buffer solutions and in the presence of pancreatic
lipase), as well as their anti-HIV activity against the HIV-1_899A strain in human T-lymphoid MT-4 cells, were
studied.

Keywords: anti-HIV activity, 3'-azido-3'-deoxythymidine, bioavailability, 1,3-diacylglycerol, prodrugs

DOI: 10.1134/S1068162013020118

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