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• W3113648052 abstract "Nucleotide analogues are used for treating viral infections such as HIV, hepatitis B, hepatitis C, influenza, and SARS-CoV-2. To become polymerase substrates, a nucleotide analogue must be phosphorylated by cellular kinases which is rate-limiting. The goal of this study is to develop dNTP/NTP analogues directly from nucleotides. Tenofovir (TFV) analogues were synthesized by conjugating with amino acids. We demonstrate that some conjugates act as dNTP analogues and HIV-1 reverse transcriptase (RT) catalytically incorporates the TFV part as the chain terminator. X-ray structures in complex with HIV-1 RT/dsDNA showed binding of the conjugates at the polymerase active site, however, in different modes in the presence of Mg2+ versus Mn2+ ions. The adaptability of the compounds is seemingly essential for catalytic incorporation of TFV by RT. 4d with a carboxyl sidechain demonstrated the highest incorporation. 4e showed weak incorporation and rather behaved as a dNTP-competitive inhibitor. This result advocates the feasibility of designing NTP/dNTP analogues by chemical substitutions to nucleotide analogues." @default.
• W3113648052 created "2021-01-05" @default.
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• W3113648052 date "2020-12-23" @default.
• W3113648052 modified "2023-10-16" @default.
• W3113648052 title "Tenofovir-Amino Acid Conjugates Act as Polymerase Substrates—Implications for Avoiding Cellular Phosphorylation in the Discovery of Nucleotide Analogues" @default.
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• W3113648052 doi "https://doi.org/10.1021/acs.jmedchem.0c01747" @default.
• W3113648052 hasPubMedId "https://pubmed.ncbi.nlm.nih.gov/33356231" @default.
• W3113648052 hasPublicationYear "2020" @default.
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