Comparison of cytotoxicity of mononucleoside phosphotriester derivatives bearing biolabile phosphate protecting groups in normal human bone marrow progenitor cells

Antiviral Chemistry and Chemotherapy

Volumn 7, Issue 6, 1996, Pages 338-345

  Perigaud C ^a   Girardet, J L ^a   Lefebvre, I ^a   Xie, M Y ^b   Aubertin, A M ^c   Kirn, A ^c   Gosselin, G ^a   Imbach, J L ^a   Somrnadossi, J P ^b  

^a CNRS   (France)

^b UNIVERSITY OF ALABAMA AT BIRMINGHAM   (United States)

^c UNIVERSITÉ DE STRASBOURG   (France)

Author keywords

antiviral agents; biolabile phosphate protecting groups; nucleotide prodrugs; toxicity

Indexed keywords

2',3' DIDEOXYURIDINE; 2',3' DIDEOXYURIDINE DERIVATIVE; ANTI HUMAN IMMUNODEFICIENCY VIRUS AGENT; PRODRUG; ZIDOVUDINE; ZIDOVUDINE DERIVATIVE;

ANTIVIRAL ACTIVITY; ARTICLE; BLOOD CELL; CELL LINE; CLONOGENIC ASSAY; COLONY FORMING UNIT GM; CONTROLLED STUDY; CYTOTOXICITY; HEMATOPOIETIC STEM CELL; HUMAN; HUMAN CELL; HUMAN IMMUNODEFICIENCY VIRUS 1; MONONUCLEAR CELL; PRIORITY JOURNAL; STEM CELL; VIRUS INFECTION;

EID: 0029796002     PISSN: 09563202     EISSN: None     Source Type: Journal    
DOI: 10.1177/095632029600700607     Document Type: Article

References (41)

1. Alexander, P., and Holy, A. (1994) Prodrugs of analogs of nucleic acid components. Collect Czech Chem Commun 59: 2127-2165.
2. Baba, M., Pauwels, R., Herdewijn, P., De Clercq, E., Desmyter, J., and Vandeputte, M. (1987) Both 2′,3′-dideoxythymidine and its 2′,3′-unsaturated denvative (2′,3′-dideoxythymidinene) are potent and selective inhibitors of human immunodeficiency virus replication in vitro. Biochem Biophys Res Commun 142: 128-134.
3. Balzarini, J. (1994) Metabolism and mechanism of antiretroviral action of purine and pyrimidine derivatives. Pharm World Sci 16: 113-126.
4. Balzarini, J., Kang, G.J., Dalal, M., Herdewijn, P., De Clercq, E., Broder, S., and Johns, D.G. (1987) The anti-HTLV-III (anti-HIV) and cytotoxic activity of 2′,3′-didehydro-2′,3′-dideoxyribonucleosides: a comparison with their parental 2′,3′-dideoxyribonucleosides. Mol Pharmacol 32: 162-167.
5. Balzarini, J., Baba, M., Pauwels, R., Herdewijn, P., and De Clercq, E. (1988) Anti-retrovirus activity of 3′-fluoro- and 3′-azido-substituted pyrimidine 2′,3′-dideoxynucleoside analogues. Biochem Pharmacol 37: 2847-2856.
6. Chu, C.K., Schinazi, R.F., Arnold, B.H., Cannon, D.L., Doboszewski, B., Bhadti, V.B., and Gu, Z. (1988) Comparative activity of 2′,3′-saturated and unsaturated pyrimidine and purine nucleosides against human immunodeficiency virus type 1 in peripheral blood mononuctear cells. Biochem Pharmacol 37: 3543-3548.
7. De Clercq, E. (1992) HIV inhibitors targeted at the reverse transcriptase. AIDS Res Human Retrov 8: 119-134.
8. De Flora, A., Zocchi, E., Guida, L., Polvani, C., and Benatti, U. (1988) Conversion of encapsulated 5-fluoro-2′-deoxyuridine 5′-monophosphate to the antineoplastic drug 5-fluoro-2′-deoxyuridine in human erythrocytes. Proc Natl Acad Sci USA 85: 3145-3149.
9. Frick, L.W., Nelson, D.J., St Clair, M.H., Furman, P.A., and Krenitsky, T.A. (1988) Effects of 3′-azido-3′-deoxythymidine on the deoxynucleotide triphosphate pools of cultured human cells. Biochem Biophys Res Commun 154: 124-129.
10. Fridland, A., Connelly, M.C., and Ashmun, R. (1990) Relation of deoxynucleotide changes to inhibition of DMA synthesis induced by the antiretroviral agent 3′-azido-3′-deoxythymidine and release of its monophosphate by human lymphoid cells (CCRF-CEM). Mol Pharmacol 37: 665-670.
11. Furman, P.A., and Barry, D.W. (1988) Spectrum of antiviral activity and mechanism of action of Zidovudine. Am J Med 85: 176-181.
12. Furman, P.A., Fyfe, J.A., St Clair, M.H., Weinhold, K., Rideout, J.L., Freeman, G.A., Nusinoff Lehrman, S., Bolognesi, D.P., Broder, S., Mitsuya, H., and Barry, D.W. (1986) Phosphorylation of 3′-azidothymidine and selective interaction of the 5′-triphosphate with human immunodeficiency virus reverse transcriptase. Proc Natl Acad Sci USA 83: 8333-8337.
13. Gao, W.Y., Agbaria, R., Driscoll, J.S., and Mitsuya, H. (1994) Divergent anti-human immunodeficiency virus activity and anabolic phosphorylation of 2′,3′-dideoxynucleoside analogs in resting and activated human cells. J Biol Chem 259: 12633-12638; and references cited therein.
14. Girardet, J.-L., Péngaud, C., Aubertin, A.-M., Gosselin, G., Kirn, A., Imbach, J.-L. (1995) Increase of the anti-HIV activity of d4T in human T-cell culture by the use of the SATE pronucleotide approach. Bioorg Med Chem Lett 5: 2981-2984.
15. Gosselin, G., and Imbach, J.-L. (1993) The anti-HIV nucleoside phosphotriester approach: controversial comments and complementary data. Int Antiviral News 1: 100-102.
16. Hao, Z., Farquhar, D., De Vico, A.L., Sarngadharan, M.G., Cooney, D.A., and Johns, D.G. (1988) 2′,3′-Dideoxyuridine triphosphate: a potent inhibitor of HIV reverse transcriptase. Proc Am Assoc Cancer Res 29: 348.
17. Hao, Z., Cooney, D.A., Farquhar, D., Perno, C.F., Zhang, K., Masood, R., Wilson, Y., Hartman, N.R., Balzarini, J., and Johns, D.G. (1990) Potent DMA chain termination activity and selective inhibition of human immunodeficiency virus reverse transcriptase by 2′,3′-dideoxyuridine-5′-triphosphate. Mol Pharmacol 37: 157-163.
18. Harrington, J.A., Miller, W.H., and Spector, T. (1987) Effector studies of 3′-azidothymidine nucleotides with human ribonucleotide reductase. Biochem Pharmacol 36: 3757-3761.
19. Jones, R.J., and Bischofberger, N. (1995) Minireview: nucleotide prodrugs. Antiviral Res 27: 1-17.
20. Kern, E.R. (1990) Preclinical evaluation of antiviral agents: in vitro and animal model testing. In: Antiviral Agents and Viral Diseases of Man. Galasso, G.J., Whitley, R.J., and Merigan, T.C. (eds). New York: Raven Press, pp. 87-123.
21. Lefebvre, I., Périgaud, C., Pompon, A., Aubertin, A.-M., Girardet, J.-L., Kirn, A., Gosselin, G., and Imbach, J.-L. (1995) Mononucleoside phosphotriester derivatives with S-acyl-2-thioethyl bioreversible phosphate protecting groups. Intracellutar delivery of 3′-azido-2′,3′-dideoxythymidine 5′-monophosphate (AZTMP). J Med Chem 38: 3941-3950.
22. 32P-labeled ribonucleotides in tissue slices and cell suspensions. J Biol Chem 216: 823-830.
23. Lichtenstein, J., Barner, H.D., and Cohen, S.S. (1960) The metabolism of exogenously supplied nucleotides by Escherichia coli. J Biol Chem 235: 457-465.
24. Magnani, M., Bianchi, M., Rossi, L., and Stocchi, V. (1989) Human red blood cells as bioreactors for the release of 2′,3′-dideoxycytidine, an inhibitor of HIV infectivity. Biochem Biophys Res Commun 164: 446-452.
25. Nilsson, S., Reichard, P., and Skoog, L. (1980) Deoxyuridine triphosphate pools after polyoma virus infection. J Biol Chem 255: 9552-9555.
26. Ohmori, H., and Yamamoto, I. (1983) Mechanism of augmentation of the antibody response in vitro by 2-mercaptoethanol in murine lymphocytes. Cell Immunol 79: 173-185.
27. Périgaud, C., Gosselin, G., Lefebvre, I., Girardet, J.-L., Benzana, S., Barber, I., and Imbach, J.-L. (1993) Rational design for cytosolic delivery of nucleoside monophosphates: « SATE »and « DTE » as enzyme-labile transient phosphate protecting groups. Bioorg Med Chem Lett 3: 2521-2526.
28. Périgaud, C., Aubertin, A.-M., Benzana, S., Pelicano, H., Girardet, J.-L., Maury, G., Gosselin, G., Kirn, A., and Imbach, J.-L. (1994) Equal inhibition of the replication of human immunodeficiency virus in human T-cell culture by ddA bis (SATE)phosphotriester and 3′-azido-2′,3′-dideoxythymidine. Biochem Pharmacol 48: 11-14.
29. Périgaud, C., Girardet, J.-L., Gosselin, G., and Imbach, J.-L. (1995) Comments on nucleotide delivery forms. In: Advances in Antiviral Drug Design. De Clercq, E. (ed.). Greenwich: JAI Press Inc., pp. 147-172.
30. Pompon, A., Lefebvre, I., Imbach, J.-L., Kahn, S., and Farquhar, D. (1994) Decomposition pathways of the monoand bis (pivaloyloxymethyl) esters of azidothymidine 5′-monophosphate in cell extract and in tissue culture medium: an application of the 'on-line ISRP-cleaning' HPLC technique. Antiviral Chem Chemother 5: 91-98.
31. Puech, F., Gosselin, G., Lefebvre, I., Pompon, A., Aubertin, A.-M., Kirn, A., and Imbach, J.-L. (1993) Intracellular delivery of nucleoside monophosphates through a reductase-mediated activation process. Antiviral Res 22: 155-174.
32. Ratto, G.M., Payne, R., Owen, W.G., and Tsien, R.Y. (1988) The concentration of cytosolic free calcium in vertebrate rod outer segments measured with Fura-2. J Neurosci 8: 3240-3246.
33. Roll, P.M., Weinfeld, H., Caroll, E., and Brown, G.B. (1956) The utilisation of nucleotides by the mammal. IV. Triply labeled purine nucleotides. J Biol Chem 220: 439-454.
34. Sastry, J.K., Nehete, P.N., Khan, S., Nowak, B.J., Plunkett, W., Arlinghaus, R.B., and Farquhar, D. (1991) Membranepermeable dideoxyuridine 5′-monophosphate analogue inhibits human immunodeficiency virus infection. Mol Pharmacol 41: 441-445.
35. Shimizu, S.I., Balzarini, J., De Clercq, E., and Walker, R.T. (1992) The synthesis and biological properties of some aryl bis (nucleosid-5′-yl) phosphates using nucleosides with proven anti-HIV activity. Nucleosides & Nucleotides 11: 583-594.
36. Sommadossi, J.-P. (1993) Nucleoside analogs: similarities and differences. Clin Infect Dis 16 (Suppl 1): S7-S15.
37. Sommadossi, J.-P., and Carlisle, R. (1987) Toxicity of 3′-azido-3′-deoxythyrnidine and 9-(1,3-dihydroxy-2-propoxymethyl)-guanine for normal human hematopoietic progenitor cells in vitro. Antimicrob Agents Chemother 31: 452-454.
38. Sommadossi, J.-P., Carlisle, R., Schinazi, R.F., and Zhou, Z. (1988) Uridine reverses the toxicity of 3′-azido-3′-deoxythymidine in normal human granulocyte-macrophage progenitor cells in vitro without impairment of antiretroviral activity. Antimicrob Agents Chemother 32: 997-1001.
39. Tiffert, T., Garcia-Sancho, J., and Lew, V.L. (1984) Irreversible depletion caused by low concentrations of formaldehyde and of calcium-chelator esters in intact human red cells. Biochim Biophys Acta 773: 143-156.
40. 2+ with Quin2. Methods Enzymol 172: 230-262.
41. Zelphati, O., Degols, G., Loughrey, H., Leserman, L., Pompon, A., Puech, F., Maggio, A.-F., Imbach, J.-L., and Gosselin, G. (1993) Inhibition of HIV-1 replication in cultured cells with phosphorylated dideoxyuridine derivatives encapsulated in immunoliposomes. Antiviral Res 21: 181-195.