Abstract
Twenty analogues of the anti-HIV-1 integrase (IN) inhibitors dicaffeoylquinic acids (DCQAs) were prepared. Their IC50 values for 3’-end processing and strand transfer against recombinant HIV-1IN were determined in vitro, and their cell toxicities and EC50 against HIV-1 were measured in cells (ex vivo). Acetylated or benzylated and/or with cyclohexylidene group compounds exhibited no inhibition of integration in biochemical assays or viral replication in HIV-infected cells, with the exception of 16 and 36. Removal of these groups, however, correlated with potent inhibition. Compounds 19, 31, and 38, all digalloyls, exhibited the most robust inhibitory performance in biochemical assays as well as in cell culture and less toxicity than other molecules in the current study.
Keywords: Integrase inhibitor, HIV-1, dicaffeoyl, digalloyl, second generation inhibitor, esters, quinic acid, cyclitol, anti-HIV agents, catechol.
Current Medicinal Chemistry
Title:Synthesis and HIV-1 Inhibitory Activities of Dicaffeoyl and Digalloyl Esters of Quinic Acid Derivatives
Volume: 20 Issue: 5
Author(s): C. O.R. Junior, S. C. Verde, C. A.M. Rezende, W. Caneschi, M. R.C. Couri, B. R. McDougall, W. E. Robinson, Jr. and M. V. de Almeida
Affiliation:
Keywords: Integrase inhibitor, HIV-1, dicaffeoyl, digalloyl, second generation inhibitor, esters, quinic acid, cyclitol, anti-HIV agents, catechol.
Abstract: Twenty analogues of the anti-HIV-1 integrase (IN) inhibitors dicaffeoylquinic acids (DCQAs) were prepared. Their IC50 values for 3’-end processing and strand transfer against recombinant HIV-1IN were determined in vitro, and their cell toxicities and EC50 against HIV-1 were measured in cells (ex vivo). Acetylated or benzylated and/or with cyclohexylidene group compounds exhibited no inhibition of integration in biochemical assays or viral replication in HIV-infected cells, with the exception of 16 and 36. Removal of these groups, however, correlated with potent inhibition. Compounds 19, 31, and 38, all digalloyls, exhibited the most robust inhibitory performance in biochemical assays as well as in cell culture and less toxicity than other molecules in the current study.
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Junior O.R. C., Verde C. S., Rezende A.M. C., Caneschi W., Couri R.C. M., McDougall R. B., Robinson, Jr. E. W. and de Almeida V. M., Synthesis and HIV-1 Inhibitory Activities of Dicaffeoyl and Digalloyl Esters of Quinic Acid Derivatives, Current Medicinal Chemistry 2013; 20 (5) . https://dx.doi.org/10.2174/092986713804999349
DOI https://dx.doi.org/10.2174/092986713804999349 |
Print ISSN 0929-8673 |
Publisher Name Bentham Science Publisher |
Online ISSN 1875-533X |
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