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Short Communication

Conjugation of phosphonoacetic acid to nucleobase promotes a mechanism-based inhibition

, , , , & ORCID Icon
Pages 384-389 | Received 06 Oct 2017, Accepted 06 Dec 2017, Published online: 26 Jan 2018

References

  • Oberg B. Rational design of polymerase inhibitors as antiviral drugs. Antiviral Res 2006;71:90–5.
  • Oberg B. Antiviral effects of phosphonoformate (PFA, foscarnet sodium). Pharmacol Ther 1989;40:213–85.
  • Huang H, Chopra R, Verdine GL, Harrison SC. Structure of a covalently trapped catalytic complex of HIV-1 reverse transcriptase: implications for drug resistance. Science 1998;282:1669–75.
  • Fauci AS, Folkers GK. Toward an AIDS-free generation. JAMA 2012;308:343–4.
  • Menéndez-Arias L. Molecular basis of human immunodeficiency virus drug resistance: an update. Antiviral Res 2010;85:210–31.
  • Menéndez-Arias L. Molecular basis of human immunodeficiency virus type 1 drug resistance: overview and recent developments. Antiviral Res 2013;98:93–120.
  • Margolis AM, Heverling H, Pham PA, Stolbach A. A review of the toxicity of HIV medications. J Med Toxicol 2014;10:26–39.
  • Velázquez S, Alvarez R, San-Félix A, et al. Synthesis and anti-HIV activity of [AZT]-[TSAO-T] and [AZT]-[HEPT] dimers as potential multifunctional inhibitors of HIV-1 reverse transcriptase. J Med Chem 1995;38:1641–9.
  • Renoud-Grappin M, Fossey C, Fontaine G, et al. Imidazo[1,5-b]pyridazine-d4T conjugates: synthesis and anti-human immunodeficiency virus evaluation. Antivir Chem Chemother 1998;9:205–23.
  • Pontikis R, Dollé V, Guillaumel J, et al. Synthesis and evaluation of “AZT-HEPT”, “AZT-pyridinone”, and “ddC-HEPT” conjugates as inhibitors of HIV reverse transcriptase. J Med Chem 2000;43:1927–39.
  • Adelfinskaya O, Herdewijn P. Amino acid phosphoramidate nucleotides as alternative substrates for HIV-1 reverse transcriptase. Angew Chem Int Ed Engl 2007;46:4356–8.
  • Giraut A, Song X-P, Froeyen M, et al. Iminodiacetic-phosphoramidates as metabolic prototypes for diversifying nucleic acid polymerization in vivo. Nucleic Acids Res 2010;38:2541–50.,
  • De S, Groaz E, Margamuljana L, et al. Sulfonate derived phosphoramidates as active intermediates in the enzymatic primer-extension of DNA. Org Biomol Chem 2015;13:3950–62.
  • Song Y, Zhan P, Li X, et al. Multivalent agents: a novel concept and preliminary practice in Anti-HIV drug discovery. Curr Med Chem 2013;20:815–32.
  • Giraut A, Abu El-asrar R, Marlière P, et al. 2′-Deoxyribonucleoside phosphoramidate triphosphate analogues as alternative substrates for E. coli polymerase III. ChemBioChem 2012;13:2439–44.
  • Hollenstein M. Nucleoside triphosphates-building blocks for the modification of nucleic acids. Molecules 2012;17:13569–91.
  • Hutchinson DW, Cload PA, Haugh MC. Organophosphorus compounds as antiviral agents. Phosphorus Sulfur 1983;14:285–93.
  • Hamilton CJ, Roberts SM. Synthesis of fluorinated phophonoacetate derivatives of carbocyclic nucleoside monophosphonates and activity as inhibitors of HIV reverse transcriptase. J Chem Soc Perkin Trans 1 1999; 1051–6.
  • Le Grice SF, Naas T, Wohlgensinger B, Schatz O. Subunit-selective mutagenesis indicates minimal polymerase activity in heterodimer-associated p51 HIV-1 reverse transcriptase. EMBO J 1991;10:3905–11.
  • Shinnick TM, Lerner RA, Sutcliffe JG. Nucleotide sequence of moloney murine leukaemia virus. Nature 1981;293:543–8.
  • Tauraitė D, Ražanas R, Mikalkėnas A, et al. Synthesis of pyridone-based nucleoside analogues as substrates or inhibitors of DNA polymerases. Nucleos. Nucleot. Nucl 2016;35:163–77.
  • Meyer PR, Matsuura SE, Zonarich D, et al. Relationship between 3′-azido-3′-deoxythymidine resistance and primer unblocking activity in foscarnet-resistant mutants of human immunodeficiency virus type 1 reverse transcriptase. J Virol 2003;77:6127–37.
  • Marchand B, Tchesnokov EP, Götte M. The pyrophosphate analogue foscarnet traps the pre-translocational state of HIV-1 reverse transcriptase in a Brownian ratchet model of polymerase translocation. J Biol Chem 2007;282:3337–46.
  • Zahn KE, Tchesnokov EP, Götte M, Doublié S. Phosphonoformic acid inhibits viral replication by trapping the closed form of the DNA polymerase. J Biol Chem 2011;286:25246–55.