A method for quantitating the intracellular metabolism of AZT amino acid phosphoramidate pronucleotides by capillary high-performance liquid chromatography - Electrospray ionization mass spectrometry

Molecular Pharmaceutics

Volumn 2, Issue 3, 2005, Pages 233-241

  Kim, Jisook ^a   Park, Soobong ^b   Tretyakova, Natalia Y ^b   Wagner, Carston R ^a  

^a UNIVERSITY OF MINNESOTA   (United States)

^b UNIVERSITY OF MINNESOTA   (United States)

Author keywords

Antiviral agent; AZT; Phosphoramidate; Prodrugs

Indexed keywords

DEXTRO PHENYLALANINE METHYL ESTER ZIDOVUDINE PHOSPHORAMIDATE; DEXTRO TRYPTOPHAN METHYL ESTER ZIDOVURINE PHOSPHORAMIDATE; PHENYLALANINE METHYL ESTER ZIDOVUDINE PHOSPHORAMIDATE; PRODRUG; TRYPTOPHAN METHYL ESTER ZIDOVUDINE PHOSPHORAMIDATE; UNCLASSIFIED DRUG; ZIDOVUDINE DERIVATIVE; ZIDOVUDINE PHOSPHORAMIDATE;

ARTICLE; CANCER CELL; CAPILLARY CHROMATOGRAPHY; CELL METABOLISM; CELL TRANSPORT; CONTROLLED STUDY; DRUG METABOLISM; DRUG UPTAKE; ELECTROSPRAY MASS SPECTROMETRY; HUMAN; HUMAN CELL; LYMPHOBLASTOID CELL; METHODOLOGY; PRIORITY JOURNAL; QUANTITATIVE ANALYSIS; REVERSED PHASE HIGH PERFORMANCE LIQUID CHROMATOGRAPHY; T LYMPHOBLAST; VALIDATION PROCESS;

AMIDES; AMINO ACIDS; ANTI-HIV AGENTS; CHROMATOGRAPHY, HIGH PRESSURE LIQUID; HUMANS; LEUKEMIA, T-CELL; PHOSPHORIC ACIDS; PRODRUGS; SENSITIVITY AND SPECIFICITY; SPECTROMETRY, MASS, ELECTROSPRAY IONIZATION; THYMINE NUCLEOTIDES; TUMOR CELLS, CULTURED; ZIDOVUDINE;

EID: 21444433356     PISSN: 15438384     EISSN: None     Source Type: Journal    
DOI: 10.1021/mp0500162     Document Type: Article

References (37)

1. Cheson, B. D.; Keating, M. J.; Plunkett, W. Nucleoside analogs in cancer therapy; Marcel Dekker: New York, 1990.
2. Chabner, B. A.; Longo, D. L. Cancer Chemotherapy and Biotherapy; Lippincott-Raven: New York, 1996.
3. De Clercq, E. Antiviral activity spectrum and target of action of different classes of nucleoside. Nucleosides Nucleotides 1994, 13, 1271.
4. Herdewijn, P. Structural requirements for antiviral activity in nucleosides. Drug Discovery Today 1997, 2, 235.
5. Ledneva, R. K.; Preobrazhenskaya, N. N.; Shinskii, N. G.; Shabarova, Z. A.; Prokofev, M. A. Analogs of uridine-5′-phosphoramides and thier hydrolysis by ribonucleoside-5′-phosphoramidase. Dokl. Akad. Nauk SSSR 1970, 193, 1308-1310.
6. Vrang, L.; Bazin, H.; Remaud, G.; Chattopadhyaya, J.; Oberg, B. Inhibition of the reverse transcriptase from HIV by 3′-azido- 3′deoxythymidine triphosphate and its threo analogue. Antiviral Res. 1987, 7, 139-149.
7. Mitsuya, H.; Jarett, R. F.; Matsukura, M.; Veronese, F. D. M.; De Vico, A. L.; et al. 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. U.S.A. 1987, 84, 2033-2037.
8. Furman, P. A.; St. Clair, M. H.; Weinhold, K.; Rideout, J. L.; Freeman, G. A.; et al. Phosphorylation of 3′-azido-3′deoxythymidine and selective interaction of the 5′-triphosphate with human immunodeficiency virus reverse transcriptase. Proc. Natl. Acad. Sci. U.S.A. 1986, 83, 8333-8337.
9. De Clercq, E. New perspectives for the treatment of HIV infections. Collect. Czech. Chem. Commun. 1998, 63, 449-479.
10. Cheng, Y. C.; Dutschman, G. E.; Bastow, K. F.; Sarngadharan, M. G.; Ting, R. Y. Human immunodeficiency virus reverse transcriptase: general properties and its interactions with nucleoside triphosphate analogs. J. Biol. Chem. 1987, 262, 2187-2189.
11. Schuetz, J. D.; Connelly, M. C.; Sun, D.; Paibir, S. G.; Flynn, P. M.; et al. MRP4: A previously unidentified factor in resistance to nucleoside-based antiviral drugs. Nat. Med. 1999, 5, 1048-1051.
12. Abraham, T. W.; Kalman, T. I.; McIntee, E. J.; Wagner, C. R. Synthesis and biological activity of aromatic amino acid phosphoramidates of 5-fluoro-2′-deoxyuridine and 1-β-arabinofuranosylcytosine: evidence of phosphoramidase activity. J. Med. Chem. 1996, 39, 4569-4575.
13. Molema, G.; Jansen, R. W.; Pauwels, R. D. Targeting of antiviral drugs to T4-lymphocytes. Anti-HIV activity of neoglycoprotein-AZTMP conjugates in vitro. Biochem. Pharmacol. 1990, 40, 2603-2610.
14. McIntee, E. J.; Remmel, R. P.; Schinazi, R. F.; Abraham, T. W.; Wagner, C. R. Probing the mechanism of action and decomposition of amino acid phosphomonoester amidates of antiviral nucleoside prodrugs. J. Med. Chem. 1997, 40, 3323-3331.
15. Jones, A. S.; McGuigan, C.; Walker, R. T.; Balzarini, J.; De Clercq, E. Synthesis, properties, and biological activity of some nucleoside cyclic phosphoramidates. J. Chem. Soc., Perkin Trans. 1 1984, 1471-1474.
16. Wagner, C. R.; Chang, S.-I.; Griesgraber, G. W.; Song, H.; McIntee, E. J.; et al. Antiviral nucleoside drug delivery via amino acid phosphoramidates. Nucleosides Nucleotides 1999, 18, 913-919.
17. Chang, S.-I.; Griesgraber, G. W.; Southern, P. J.; Wagner, C. R. Amino acid phosphoramidate monoesters of 3′-azido-3′-deoxythymidine: Relationship between antiviral potency and intracellular metabolism. J. Med. Chem. 2001, 44, 223-231.
18. 31P NMR. Nucleosides, Nucleotides Nucleic Acids 2004, 23, 483-493.
19. Yoshida, S.; Urakami, K.; Kito, M.; Takeshima, S.; Hirose, S. High-performance liquid chromatography with chemiluminescence detection of serum levels of pre-column derivatized fluoropyrimidine compounds. J. Chromatogr. A 1990, 530, 57-64.
20. Iwamoto, M.; Yoshida, S.; Hirose, S. High performance liquid chromatographic determination of pyrimidine nucleobases and 5-fluorouracil labeled with a fluorescent reagent. Yakugaku Zasshi 1984, 104, 1251-1256.
21. Dass, C. Principles and practice of biological mass spectrometry; John Wiley & Sons: New York, 2001.
22. Henner, G.; Becher, F.; Pruvost, A.; Goujard, C.; Grassi, J.; et al. Liquid chromatography-tandem mass spectrometry assays for intracellular deoxyribonucleotide triphosphate competitors of nucleoside antiretrovirals. J. Chromatogr. B 2003, 789, 273-281.
23. Hua, Y.; Wainhaus, S. B.; Yang, Y.; Shen, L.; Xiong, Y.; et al. Comparison of negative and positive Ion electospray tandem mass spectrometry for the liquid chromatography tandem mass spectrometry analysis of oxidized deoxynucleosides. J. Am. Soc. Mass Spectrom. 2001, 12, 80-87.
24. Lefebvre, I.; Perigaud, C.; Pompon, A.; Aubertin, A. M.; Girardet, J. L.; et al. Mononucleoside phosphotriester derivatives with S-acyl-2-thioethyl bioreversible phosphate-protecting groups: intracellular delivery of 3′-azido-2′,3′-dideoxythymidine 5′-monophosphate. J. Med. Chem. 1995, 38, 3941-3950.
25. Lin, C.-c.; Yeh, L.-T.; Johnson, Y.; Lau, N. Specific, sensitive and accurate liquid chromatographic-tandem mass spectrometric method for the measurement of ribavirin in rat and monkey plasma. J. Chromatogr. B 2002, 779, 241-248.
26. Lynch, T.; Eisenberg, G.; Kernan, M. LC/MS determination of the intracellular concentration of two novel aryl phosphoramidate prodrugs of PMPA and their metabolites in dog PBMC. Nucleosides, Nucleotides Nucleic Acids 2001, 20, 1415-1419.
27. Rentsch, K. M. Sensitive and specific determination of eight antiretroviral agents in plasma by high-performance liquid chromatography-mass spectrometry. J. Chromatogr. B 2003, 788, 339-350.
28. Roboz, J. Mass spectrometry in cancer reserach; CRC Press: Boca Raton, FL, 2002.
29. Siuzdak, G. Mass spectrometry for biotechnology; Academic Press: San Diego, CA, 1996.
30. St Claire, R. L. Positive ion electrospray ionization tandem mass spectrometry coupled to ion-pairing high-performance liquid chromatography with a phosphate buffer for the quantitative analysis of intracellular nucleotides. Rapid Commun. Mass Spectrom. 2000, 14, 1625-1634.
31. Van den Driessche, B.; Lemiere, F.; Van Dongen, W.; Esmans, E. L. Alkylation of DNA by melphalan: investigation of capillary liquid chromatography-electrospray ionization tandem mass spectrometry in the study of the adducts at the nucleoside level. J. Chromatogr. B 2003, 785, 21-37.
32. Witters, E.; Van Dongen, W.; Esmans, L. E.; Van Onckelen, A. H. Ion-pair liquid chromatography-electrospray mass spectrometry for the analysis of cyclic nucleotides. J. Chromatogr. B 1997, 694, 55-63.
33. Kim, J.; Chou, T.-f.; Griesgraber, G. W.; Wagner, C. R. Direct measurement of nucleoside monophosphate delivery from a phosphoramidate pronucleotide by stable isotope labeling and LC-ESI-MS/MS. Mol. Pharm. 2004, 1, 102-111.
34. Iyer, I. V.; Griesgraber, G. W.; Radmer, M. R.; McIntee, E. J.; Wagner, C. R. Synthesis, in vitro anti-breast cancer activity, and intracellular decomposition of amino acid methyl ester and alkyl amide phosphoramidate monoesters of 3′-azido-3′-deoxythymidine (AZT). J. Med. Chem. 2000, 43, 2266-2274.
35. Monkkonen, H.; Moilanen, P.; Monkkonen, J.; Frith, C. J.; Rogers, J. M.; et al. Analysis of an adenine nucleotide-containing metabolite of clodronate using ion pair high-performance liquid chromatography-electrospray ionisation mass spectrometry. J. Chromatogr. B 2000, 738, 395-403.
36. Auriola, S.; Frith, J.; Rogers, J. M.; Koivuniemi, A.; Monkkonen, J. Identification of adenine nucleotide-containing metabolites of bisphosphonate drugs using ion-pair liquid chromatography-electrospray mass spectrometry. J. Chromatogr. B 1997, 704, 187-195.
37. Esmans, E. L.; Broes, D.; Hoes, I.; Lemire, F.; Vanhoutte, K. Liquid chromatography-mass spectrometry in nucleoside, nucleotide and modified nucleotide characterization. J. Chromatogr. A 1998, 794, 109-127.