Intracellular metabolism of 3'-azido-3'-deoxythimidine (AZT): A nuclear magnetic resonance study on T-lymhoblastoid cell lines with different resistance to AZT

Biochemical Pharmacology

Volumn 54, Issue 9, 1997, Pages 979-990

  Di Vito, Massimo ^a   Bozzi, Argante ^b   Ferretti, Amalia ^a   Cianfriglia, Maurizio ^a   Barca, Stefano ^a   Signoretti, Claudia ^a   Lenti, Luisa ^c   D'Agostino, Federica ^c   Strom, Roberta ^c   Podo, Franca ^a  

^a ISTITUTO SUPERIORE DI SANITÀ   (Italy)

^b UNIVERSITY OF L'AQUILA   (Italy)

^c SAPIENZA UNIVERSITY OF ROME   (Italy)

Author keywords

AZT; AZT resistance; Lymphoid cells; MDR; NMR; Pyrimidine 5' nucleotidase; Thymidine kinase

Indexed keywords

NUCLEOSIDE ANALOG; ZIDOVUDINE;

ARTICLE; CELLULAR DISTRIBUTION; CONTROLLED STUDY; DRUG METABOLISM; HUMAN; HUMAN CELL; MULTIDRUG RESISTANCE; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; PRIORITY JOURNAL; T LYMPHOBLAST;

ANTI-HIV AGENTS; CELL LINE; HUMANS; MAGNETIC RESONANCE SPECTROSCOPY; PHOSPHORYLATION; T-LYMPHOCYTES; THYMIDINE KINASE; ZIDOVUDINE;

EID: 0030725330     PISSN: 00062952     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0006-2952(97)00253-0     Document Type: Article

References (44)

1. Mitsuya H and Broder S, Strategies for antiviral therapy in AIDS. Nature 325: 773-778, 1987.
2. Herdewijn P, Balzarini J, De Clercq E, Pauwels R, Baba M, Broder S and Vanderhaeghe H, 3′-substituted 2′,3′-dideoxy-nucleoside analogues as potential anti-HIV (HTLV-III/LAV) agents. J Med Chem 30: 1270-1278, 1987.
3. Mitsuya H, Jarett RF, Matsukura M, Veronese FDM, De Vico AL, Sarngadharan MG, Johns DG, Reitz MS and Broder S, Long-term inhibition of human T-lymphotropic virus type III/lymphadenopathy-associated virus (human immunodeficiency virus) DNA synthesis and RNA expression in T cells protected by 2′,3′-dideoxynucleosides in vitro. Proc Natl Acad Sci USA 84: 2033-2037, 1987.
4. Fischl MA, Richman DD, Grieco MH, Gottlieb MS, Volberding PA, Laskin OL, Leedom JM, Groopman JE, Mildvan D, Schooley RT, Jackson GG, Durack DT, King D and the AZT Collaborative Working Group, The efficacy of azidothymidine (AZT) in the treatment of patients with AIDS and AIDS-related complex: a double-blind, placebo-controlled trial. N Engl J Med 317: 185-191, 1987.
5. Yarchoan R, Mitsuya H, Myers CE and Broder S, Clinical pharmacology of 3′-azido-2′,3′-dideoxythymidine (zidovudine) and related dideoxynucleosides. N Engl J Med 321: 726-738, 1989.
6. Zimmerman TP, Mahony WB and Prus KL, 3′-Azido-3′-deoxythymidine: an unusual nucleoside analog that permeates the membrane of human erythrocytes and lymphocytes by nonfacilitated diffusion. J Biol Chem 262: 5748-5754, 1987.
7. Domin BA, Mahony WB and Zimmerman TP, Purine nucleobase transport in human erythrocytes: reinvestigation with a novel "inhibitor-stop" assay. J Biol Chem 263: 9276-9284, 1988.
8. Furman PA, Fyfe JA, St. Clair MH, Weinhold K, Rideout JL, Freeman GA, Nusinoff Lehrman S, Bolognesi DP, Broder S, Mitsuya H and Barry DW, Phosphorylation of 3′-azido-3′-deoxythymidine and selective interaction of the 5′-triphosphate with human immunodeficiency virus reverse transcriptase. Proc Natl Acad Sci USA 83: 8333-8337, 1986.
9. Balzarini J, Pauwels R, Baba M, Herdewijn P, De Clercq E, Broder S and Johns DG, The in vitro and in vivo anti-retrovirus activity, and intracellular metabolism of 3′-azido-2′,3′-dideoxythymidine and 2′,3′-dideoxycytidine are highly dependent on the cell species. Biochem Pharmacol 37: 897-903, 1988.
10. Waqar MA, Evans MJ, Manly KF, Hughes RG and Huberman JA, Effects of 2′,3′-dideoxynucleosides on mammalian cells and viruses. J Cell Physiol 121: 402-408, 1984.
11. Cheng YC, Dutschman GE, Bastow KF, Samgadharan MG and Ting RY, Human immunodeficiency virus reverse transcriptase: general properties and its interactions with nucleoside triphosphate analogs. J Biol Chem 262: 2187-2189, 1987.
12. Vrang L, Bazin H, Remaud G, Chattopadhyaya J and Oberg B, Inhibition of the reverse transcriptase from HIV by 3′-azido-3′-deoxythymidine triphosphate and its threo analogue. Antiviral Res 7: 139-149, 1987.
13. Kedar PS, Abbots J, Kovacs T, Lesiak K, Torrence W and Wilson SH, Mechanism of HIV reverse transcriptase: enzyme-primer interaction as revealed through studies of a dNTP analogue, 3′-azido-dTTP. Biochemistry 29: 3603-3611, 1990.
14. Tornevik Y, Ullman B, Balzarini J, Wahren B and Eriksson S, Cytotoxicity of 3′-azido-3′-deoxythymidine correlates with 3′-azidothymidine-5′-monophosphate (AZTMP) levels, whereas anti-human immunodeficiency virus (HIV) activity correlates with 3′-azidothymidine-5′-triphosphate (AZTTP) levels in cultured CEM T-lymphoblastoid cells. Biochem Pharmacol 49: 829-837, 1995.
15. Cretton EM, Xie MY, Bevan RJ, Goudgaon NM, Schinazi RF and Sommadossi JP, Catabolism of 3′-azido-3′-deoxythymidine in hepatocytes and liver microsomes, with evidence of formation of 3′-amino-3′-deoxythymidine, a highly toxic catabolite for human bone marrow cells. Mol Pharmacol 39: 258-266, 1991.
16. Starnes MC and Cheng YC, Cellular metabolism of 2′,3′-dideoxycytidine, a compound active against human immuno-deficiency virus in vitro. J Biol Chem 262: 988-991, 1987.
17. Bradley G, Juranka PF and Ling V, Mechanism of multidrug resistance. Biochim Biophys Acta 948: 87-128, 1988.
18. Endicott JA and Ling V, The biochemistry of P-glycoprotein-mediated multidrug resistance. Annu Rev Biochem 58: 137-171, 1989.
19. Yusa K, Oh-hara T, Yamazaki A, Tsukahara S, Satoh W and Tsuruo T, Cross-resistance to anti-HIV nucleoside analogues in multidrug-resistant human cell. Biochem Biophys Res Commun 169: 986-990, 1990.
20. Antonelli G, Turriziani O, Cianfriglia M, Riva E, Dong G, Fattorossi A and Dianzani F, Resistance of HIV-1 to AZT might also involve the cellular expression of multidrug resistance P-glycoprotein. AIDS Res Hum Retroviruses 8: 1839-1843, 1992.
21. Gadian DG, Nuclear Magnetic Resonance and its Applications to Living Systems. Clarendon Press, Oxford, 1982.
22. De Certaines JD, Bovée WMMJ and Podo F (Eds.) Magnetic Resonance Spectroscopy in Biology and Medicine. Functional and Pathological Tissue Characterization. Pergamon Press, Oxford, 1992.
23. 1H-NMR of acid extracts. Biochim Biophys Acta 1054: 181-197, 1990.
24. 19F-NMR spectroscopy of the antimetabolite 5-fluorouracil and its analogues. Biochem Pharmacol 39: 857-863, 1990.
25. Malet-Martino MC and Martino R, Uses and limitations of nuclear magnetic resonance (NMR) spectroscopy in clinical pharmacokinetics. Clin Pharmacokinet 20: 337-349, 1991.
26. Newell DR, Maxwell RJ and Golding BT, In vivo and ex vivo magnetic resonance spectroscopy as applied to pharmacokinetic studies with anticancer agents: a review. NMR Biomed 5: 273-278, 1992.
27. Toyoshima T, Kimura S, Muramatsu S, Takahagi H and Shimada K, A sensitive nonisotopic method for the determination of intracellular azidothymidine 5′-mono-, 5′-di-, and 5′-triphospate. Anal Biochem 196: 302-307, 1991.
28. Singhal RP, Hughbanks D and Xian J, Separation of dideoxyribonucleosides in trace amounts by automated liquid chromatography and capillary electrophoresis. J Chromatogr 609: 147-161, 1992.
29. 31P NMR and HPLC studies of mouse L1210 leukemia cell extracts: the effect of Au(I) and Cu(I) diphosphine complexes on the cell metabolism. Magn Reson Med 18: 142-158, 1991.
30. Minowada J, Ohnuma T and Moore GE, Rosette-forming human lymphoid cell lines: establishment and evidence for origin of thymus-derived lymphocytes. J Natl Cancer Inst 49: 891-895, 1972.
31. Foley GE, Lazarus H, Farber S, Uzman BG, Boone BA and McCarthy RE, Continuous culture of human lymphoblasts from peripheral blood of a child with acute leukemia. Cancer 18: 522-529, 1965.
32. Singlas E, Pioger JC, Taburet AM, Colaneri S and Fillastre JP, Comparative pharmacokinetics of zidovudine (AZT) and its metabolite (G.AZT) in healthy subjects and HIV seropositive patients. Eur J Clin Pharmacol 36: 639-640, 1989.
33. Avramis VI, Markson W, Jackson RL and Gomperts E, Biochemical pharmacology of zidovudine in human T-lymphoblastoid cells (CEM). AIDS 3: 417-422, 1989.
34. Avramis VI, Kwock R, Solorzano MM and Gomperts E, Evidence of in vitro development of drug resistance to azido-thymidine in T-lymphocytic leukemia cell lines (Jurkat E6-1/AZT-100) and in pediatric patients with HIV-1 infection. J AIDS 6: 1287-1296, 1993.
35. Dianzani F, Antonelli G, Turriziani O, Riva E, Simeoni E, Signoretti C, Strosselli S and Cianfriglia M, Zidovudine induces the expression of cellular resistance affecting its antiviral activity. AIDS Res Hum Retroviruses 10: 1471-1478, 1994.
36. Nyce J, Leonard S, Canupp D, Schulz S and Wong S, Epigenetic mechanisms of drug resistance: drug-induced DNA hypermethylation and drug resistance. Proc Natl Acad Sci USA 90: 2960-2964, 1993.
37. Wu S, Liu X, Solorzano MM, Kwock R and Avramis VI, Development of zidovudine (AZT) resistance in Jurkat T cells is associated with decreased expression of the thymidine kinase (TK) gene and hypermethylation of the 5′ end of human TK gene. J Acquir Immune Defic Syndr Human Retrovirol 8: 1-9, 1995.
38. Lucarelli M, Palitti F, Carotti D, Cianfriglia M, Signoretti C, Bozzi A and Strom R, AZT-induced hypermethylation of human thymidine kinase gene in the absence of total DNA hypermethylation. FEBS Lett 396: 323-326, 1996.
39. Beutler E, Pyrimidine 5′-nucleotidase. In: Red Cell Metabolism: a Manual of Biochemical Methods. Ed. Beutler E, pp. 100-102. Grune & Stratton Inc., New York, 1983.
40. 31P NMR and enzymatic studies. Anticancer Res 13: 867-872, 1993.
41. Gill PS, Rarick M, Brynes RK, Causey D, Loureiro C and Levine AM, Azidothymidine associated with bone marrow failure in the acquired immunodeficiency syndrome (AIDS). Ann Intern Med 107: 502-505, 1987.
42. Richman DD, Fischl MA, Grieco MH, Gottlieb MS, Volberding PA, Laskin OL, Leedom JM, Groopman JE, Mildvan D, Hirsh MS, Jackson GG, Durack DT, Phil D, Nusinoff-Lehrman S and the AZT Collaborative Working Group, The toxicity of azidothymidine (AZT) in the treatment of patients with AIDS and AIDS-related complex: a double-blind, placebo-controlled trial. N Engl J Med 317: 192-197, 1987.
43. Dalakas MC, Illa I, Pezeshkpour GH, Laukaitis JP, Cohen B and Griffin JL, Mitochondrial myopathy caused by long-term zidovudine therapy. N Engl J Med 322: 1098-1105, 1990.
44. Fridland A, Connelly MC and Ashmun R, Relationship of deoxynucleotide changes to inhibition of DNA 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, 1990.