Bis(pivaloyloxymethyl) thymidine 5′-phosphate is a cell membrane-permeable precursor of thymidine 5′-phosphate in thymidine kinase deficient CCRF CEM cells

Biochemical Pharmacology

Volumn 69, Issue 9, 2005, Pages 1307-1313

  Khan, Saeed R ^a   Nowak, Billie ^b   Plunkett, William ^b   Farquhar, David ^b  

^a JOHNS HOPKINS UNIVERSITY   (United States)

^b UNIVERSITY OF TEXAS   (United States)

Author keywords

Antitumor; Membrane permeable; Prodrugs; Thymidine 5 phosphate

Indexed keywords

ANTINEOPLASTIC AGENT; BIS(PIVALOYLOXYMETHYL)THYMIDINE 5' PHOSPHATE; THYMIDINE; THYMIDINE KINASE; THYMIDINE PHOSPHATE; TRITIUM; UNCLASSIFIED DRUG;

ANTINEOPLASTIC ACTIVITY; ARTICLE; CANCER INHIBITION; CELL LINE; CELL MEMBRANE PERMEABILITY; CELL MUTANT; CELL PROLIFERATION; CELL STRAIN; CONTROLLED STUDY; DRUG EFFECT; ENZYME DEFICIENCY; HUMAN; HUMAN CELL; IC 50; INCUBATION TIME; LINEAR SYSTEM; PRIORITY JOURNAL; RADIOACTIVITY; STATISTICAL SIGNIFICANCE; WILD TYPE;

EID: 17044407389     PISSN: 00062952     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.bcp.2005.02.008     Document Type: Article

References (17)

1. J.W. Erickson, and S.K. Burt Structural mechanisms of HIV drug resistance Annu Rev Pharmacol Toxicol 36 1996 545 571
2. B. Jacobsson, S. Britton, Q. He, A. Karlsson, and S. Eriksson Decreased thymidine kinase levels in peripheral blood cells from HIV-seropositive individuals, implications for zidovudine metabolism AIDS Res Hum Retroviruses 11 1998 805 811
3. 32P-labeled ribonucleotides in tissue slices and cell suspensions J Biol Chem 316 1955 823 830
4. P.M. Roll, H. Weinfeld, E. Carroll, and G.B. Brown The utilization of nucleotides by the mammal. IV. Triply labeled purine nucleotides J Biol Chem 220 1956 439 454
5. 131I labeled 5-iodo-2′-deoxyuridine 5′-phosphate Biochem Pharmacol 11 1962 155 159
6. H. Holmsen, and M.C. Rosenberg Adenine nucleotide metabolism of blood platelets. I. Adenosine kinase and nucleotide formation from exogenous adenosine and AMP Biochem Biophys Acta 155 1968 326 341
7. Farquhar D. Biologically-reversible phosphate and phosphonate protective groups. US Patent 4,816,570 (1989).
8. D. Farquhar, D.N. Srivastava, N.J. Kuttesch, and P.P. Saunders Biologically reversible phosphate protective groups J Pharm Sci 72 1983 324 325
9. J. Freed, D. Farquhar, and A. Hampton Evidence for acyloxymethylesters of pyridine 5′-deoxyribonucleotides as extracellular sources of active 5′-deoxyribonucleotides in cultured cells Biochem Pharmacol 38 1989 3193 3198
10. D. Farquhar, S. Khan, D.N. Srivastava, and P.P. Saunders Synthesis and antitumorevaluation of bis(pivaloyloxymethyl) 2′-deoxy-5-fluorouridine 5′-monophosphate (FdUMP): a strategy to introduce nucleosides into cells J Med Chem 37 1994 3902 3909
11. D. Farquhar, B. Nowak, S. Khan, and W. Plunkett Membrane-permeable anti HIV nucleotides Antiviral Res 15 1991 143 151
12. K.J. Sastry, P.N. Nehete, S. Khan, B.J. Nowak, W. Plunkett, and R.B. Arlinghaus Membrane-permeable dideoxyuridine 5′-monophosphate analogue inhibits human immunodeficiency virus infection Mol Pharmacol 41 1992 441 445
13. V. Gandhi, and W. Plunkett Modulatory activity of 2′,2′- diflurodeoxycytidine on the phosphorylation and cytotoxicity of arabinosyl nucleosides Cancer Res 50 1990 3675 3680
14. V. Heinemann, Y.Z. Xu, S. Chubb, A. Sen, L.W. Hertel, and G.B. Grindey Inhibition of ribonucleotide reduction in CCRF-CEM cells by 2′,2′- diflurodeoxycytidine Mol Pharmacol 38 1990 567 572
15. V. Heinemann, Y.Z. Xu, S. Chubb, A. Sen, L.W. Hertel, and G.B. Grindey Cellular elimination of inhibition of 2′,2′, diflurodeoxycytidine 5′-triphosphate: a mechanism of self potentiation Mol Pharmacol 52 1992 533 539
16. R.M. Fox, E.H. Tripp, and M.H. Tattersall Mechanism of deoxycytidine rescue of thymidine toxicity in human T-leukemic lymphocytes Cancer Res 40 1980 1718 1721
17. P. Huang, D. Farquhar, and W. Plunkett Selective action of 2′,3′-didehydro-2′,3′-dideoxythymidine triphosphate on human immunodeficiency virus reverse transcriptase and human DNA polymerises J Biol Chem 267 1992 2817 2822