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• W2029944114 abstract "Bevirimat (2), the first-in-class HIV-1 maturation inhibitor, shows a low efficacy due essentially to the natural polymorphism of its target, the CA-SP1 junction. Moreover, its low hydrosolubility makes it difficult to study its interaction with the CA-SP1 junction. We have synthesized new derivatives of bevirimat by adding different hydrophilic substituents at the C-28 position to improve their hydrosolubility and perform the structural study of a complex by NMR. Synthesis of the new derivatives, the effect of substituents at the C-28 position and their hydrosolubility are discussed. The ability of these molecules to inhibit viral infection and their cytotoxicity is assessed. Compared to the well-known bevirimat (2), one of our compounds (16) shows a higher hydrosolubility associated with a 2.5 fold increase in activity, a higher selectivity index and a better antiviral profile. Moreover, for the first time a direct interaction between a derivative of bevirimat (16) and the domain CA-SP1–NC is shown by NMR. Information from this study should allow us to decipher the mechanism by which bevirimat inhibits HIV-1 maturation and how the natural polymorphism of the spacer peptide SP1 triggers resistance to inhibitors." @default.
• W2029944114 created "2016-06-24" @default.
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• W2029944114 date "2013-04-01" @default.
• W2029944114 modified "2023-10-13" @default.
• W2029944114 title "Synthesis and biological evaluation of a new derivative of bevirimat that targets the Gag CA-SP1 cleavage site" @default.
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• W2029944114 doi "https://doi.org/10.1016/j.ejmech.2013.01.013" @default.
• W2029944114 hasPubMedId "https://pubmed.ncbi.nlm.nih.gov/23399723" @default.
• W2029944114 hasPublicationYear "2013" @default.
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