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Synthesis and Anti-Human Immunodeficiency Virus Type 1 Integrase Activity of Hydroxybenzoic and Hydroxycinnamic Acid Flavon-3-yl Esters:

Synthesis and Anti-Human Immunodeficiency Virus Type 1 Integrase Activity of Hydroxybenzoic and... A series of new hydroxybenzoic and hydroxycinnamic acid flavon-3-yl esters were synthesized in order to obtain compounds targeting the human immunodeficiency virus (HIV) type 1 integrase (IN). The esters were tested for anti-IN and anti-reverse transcriptase (RT) activity in enzyme assays and for anti-HIV-1, anti-proliferative and anti-topoisomerase activity in cell-based assays. In enzyme assays, the two gallic acid flavon-3-yl esters showed a notable IN inhibition (IC50 values were 8.3 and 9.1 µM, respectively), while the two caffeic acid flavon-3-yl esters exhibited a modest activity (IC50 75 and 60 µM, respectively). Replacement of hydroxyl groups resulted in loss of potency. Caffeic acid 3′,4′-dichloroflavon-3-yl ester also inhibited the RT activity whereas it was not active on human topoisomerases. It therefore represents an interesting example of a compound specifically targeting more than one step of the virus replication cycle. http://www.deepdyve.com/assets/images/DeepDyve-Logo-lg.png Antiviral Chemistry and Chemotherapy SAGE

Synthesis and Anti-Human Immunodeficiency Virus Type 1 Integrase Activity of Hydroxybenzoic and Hydroxycinnamic Acid Flavon-3-yl Esters:

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Publisher
SAGE
Copyright
Copyright © 2019 by SAGE Publications Ltd unless otherwise noted. Manuscript content on this site is licensed under Creative Commons Licenses
ISSN
2040-2066
eISSN
2040-2066
DOI
10.1177/095632029800900606
Publisher site
See Article on Publisher Site

Abstract

A series of new hydroxybenzoic and hydroxycinnamic acid flavon-3-yl esters were synthesized in order to obtain compounds targeting the human immunodeficiency virus (HIV) type 1 integrase (IN). The esters were tested for anti-IN and anti-reverse transcriptase (RT) activity in enzyme assays and for anti-HIV-1, anti-proliferative and anti-topoisomerase activity in cell-based assays. In enzyme assays, the two gallic acid flavon-3-yl esters showed a notable IN inhibition (IC50 values were 8.3 and 9.1 µM, respectively), while the two caffeic acid flavon-3-yl esters exhibited a modest activity (IC50 75 and 60 µM, respectively). Replacement of hydroxyl groups resulted in loss of potency. Caffeic acid 3′,4′-dichloroflavon-3-yl ester also inhibited the RT activity whereas it was not active on human topoisomerases. It therefore represents an interesting example of a compound specifically targeting more than one step of the virus replication cycle.

Journal

Antiviral Chemistry and ChemotherapySAGE

Published: Jun 24, 2016

Keywords: HIV-1,integrase inhibitors,flavonoids,caffeic acid esters,gallic acid esters

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