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Original Articles

Monitoring the Intracellular Metabolism of Nucleoside Phosphoramidate Pronucleotides by 31P NMR

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Pages 483-493 | Received 12 Aug 2003, Accepted 03 Nov 2003, Published online: 01 Jun 2007

References

  • Herdewijn , P. 1997 . Structural requirements for antiviral activity in nucleosides . Drug Discov. Today , 2 : 235 [CSA]
  • De Clercq , E. 1994 . Antiviral activity spectrum and target of action of different classes of nucleoside . Nucleosides Nucleotides , 13 : 1271
  • Cheson , B. D. , Keating , M. J. and Plunkett , W. 1997 . Nucleoside Analogs in Cancer Therapy Vol. 12 , New York : Marcel Dekker, Inc. .
  • Chabner , B. A. and Longo , D. L. 1996 . Cancer Chemotherapy and Biotherapy New York : Lippincott‐Raven .
  • Vrang , L. , Bazin , H. , Remaud , G. , Chattopadhyaya , J. and Oberg , B. 1987 . Inhibition of the reverse transcriptase from HIV by 3′‐azido‐3′deoxythymidine triphosphate and its threo analogue . Antivir. Res. , 7 : 139 – 149 . [PUBMED] [INFOTRIEVE] [CROSSREF] [CSA]
  • Mitsuya , H. , Jarett , R. F. , Matsukura , M. , Veronese , F. D.M. , De Vico , A. L. , Sarngadharan , M. G. , Johns , D. G. , Reitz , M. S. and Broder , S. 1987 . Long‐term inhibition of human T‐lymphotropic virus type III lymphadenoparthy‐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. , 84 : 2033 – 2037 . [PUBMED] [INFOTRIEVE] [CSA]
  • Furman , P. A. , St. Clair , M. H. , Weinhold , K. , Rideout , J. L. , Freeman , G. A. , Nusinoff , L. S. , Bolognesi , D. P. , Broder , S. , Mitsuya , H. and Barry , D. W. 1986 . 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. , 83 : 8333 – 8337 . [PUBMED] [INFOTRIEVE]
  • De Clercq , E. 1998 . New perspectives for the treatment of HIV infections . Collect. Czechoslov. Chem. Commun. , 63 : 449 – 479 . [CROSSREF]
  • Cheng , Y. C. , Dutschman , G. E. , Bastow , K. F. , Sarngadharan , M. G. and Ting , R. Y. 1987 . Human immunodeficiency virus reverse transcriptase: general properties and its interactions with nucleoside triphosphate analogs . J. Biol. Chem. , 262 : 2187 – 2189 . [PUBMED] [INFOTRIEVE]
  • Avramis , V. I. , Kwock , R. , Solorzano , M. M. and Gomperts , E. 1993 . Evidence of in vitro development of drug resistance to azidothymidine in T‐lymphocytic leukemia cell lines (Jurkat E6‐1/AZT‐100) and in pediatric patients with HIV‐1 infection . J. Acquir. Immune Defic. Syndr. , 6 : 1287 – 1296 . [PUBMED] [INFOTRIEVE] [CSA]
  • Darby , G. and Field , H. J. 1981 . Altered substrate specificity of herpes simplex virus thymidine dinase confers acyclovir resistance . Nature , 289 : 81 – 83 . [PUBMED] [INFOTRIEVE] [CROSSREF]
  • Hall , A. , Cattan , A. R. and Proctor , S. J. 1989 . Mechanisms of drug resistance in acute leukemia . Leuk. Res. , 13 : 351 – 356 . [PUBMED] [INFOTRIEVE] [CROSSREF]
  • Antonelli , G. , Turriziani , O. , Verri , A. , Narciso , P. , Ferri , F. , D'Offizi , G. and Dianzini , F. 1996 . Long‐term exposure to zidovudine affects in vitro and in vivo the efficiency of thymidine kinase . AIDS Res. Hum. Retrovir. , 12 : 223 – 228 . [PUBMED] [INFOTRIEVE] [CSA]
  • Flasshove , M. , Strumberg , D. and Ayscue , L. 1994 . Structural analysis of the deoxycytidine kinase gene in patients with acute myeloid leukemia and resistance to cytosine arabinoside . Leukemia , 8 : 780 – 785 . [PUBMED] [INFOTRIEVE]
  • Reichard , P. , Skold , O. and Klein , G. 1962 . Studies on resistance against 5‐fluorouracil. I. Enzymes of the uracil pathway during the development of resistance . Cancer Res. , 22 : 235 – 243 . [PUBMED] [INFOTRIEVE]
  • Jacobsson , B. , Britton , S. and He , Q. 1995 . Decreased thymidine kinase levels in peripheral blood cells from HIV‐seropositive individuals: implications for zidovudine metabolism . AIDS Res. Hum. Retrovir. , 11 : 805 – 811 . [PUBMED] [INFOTRIEVE] [CSA]
  • Schrecker , A. W. and Goldin , A. 1968 . Antitumor effect and mode of action of 1‐β‐d‐arabinofuranosylcytosine 5′‐phosphate in leukemia L 1210 . Cancer Res. , 28 : 802 – 803 . [PUBMED] [INFOTRIEVE]
  • LePage , G. A. , Naik , S. R. , Katakkar , S. B. and Khaliq , A. 1975 . 9‐Beta‐d‐arabinofuranosyladenine 5′‐phosphate metabolism and excretion in humnas . Cancer Res. , 35 ( 111 ) : 3036 – 3040 . [PUBMED] [INFOTRIEVE]
  • Leibman , K. C. and Heidelberg , C. 1955 . The metabolism of 32P‐labeled ribonucleotides in tissue slices and cell suspensions . J. Biol. Chem. , 216 : 823 – 830 . [PUBMED] [INFOTRIEVE]
  • Meier , C. 1998 . Pronucleotides recent advances in the design of efficient tools for the delivery of biologically active nucleoside monophosphates . Synth. Lett. , : 233 – 242 .
  • Lorcy , M. , Meier , C. , De Clercq , E. and Balzarini , J. 1997 . Cyclo‐saligenyl‐5‐fluoro‐2′‐deoxyuridinemonophosphate (cycloSal‐FdUMP)—a new prodrug approach for FdUMP . Nucleosides Nucleotides , 16 : 1303 – 1306 .
  • McGuigan , C. , Devine , K. G. , O'Connor , T. J. , Galpin , S. A. , Jeffries , D. J. and Kinchington , D. 1990 . Synthesis and evaluation of some novel phosphoramidate derivatives of AZT as anti‐HIV compounds . Antivir. Chem. Chemother. , 1 : 107 – 113 .
  • McGuigan , C. , Sheeka , H. M. , Mahmood , N. and Hay , A. J. 1993 . Phosphate derivatives of d4T as inhibitors of HIV . Bioorg. Med. Chem. Lett. , 3 : 1203 – 1206 . [CROSSREF]
  • Turcotte , J. G. , Srivastava , S. P. , Steim , J. M. , Calabresi , P. , Tibbetts , L. M. and Chu , M. Y. 1980 . Cytotoxic liponucleotide analogs. II. Antitumor activity of CDP‐diacylglycerol analogs containing the cytosine arabinoside moiety . Biochem. Biophys. , 619 : 619 – 631 .
  • Hong , C. I. , Kirisits , A. J. , Nechaev , A. , Buchheit , D. J. and West , C. R. 1985 . Synthesis and comparison of antitumor activity of 1‐beta‐d‐arabinofuranosylcytosine conjugates of corticosteroids and selected lipophilic alcohols . J. Med. Chem. , 28 : 171 – 177 . [PUBMED] [INFOTRIEVE] [CSA]
  • McIntee , E. J. , Remmel , R. P. , Schinazi , R. F. , Abraham , T. W. and Wagner , C. R. 1997 . Probing the mechanism of action and decomposition of amino acid phosphomonoester amidates of antiviral nucleoside prodrugs . J. Med. Chem. , 40 : 3323 – 3331 . [PUBMED] [INFOTRIEVE] [CROSSREF] [CSA]
  • Wagner , C. R. , Chang , S.‐I. , Griesgraber , G. W. , Song , H. , McIntee , E. J. and Zimmerman , C. L. 1999 . Antiviral nucleoside drug delivery via amino acid phosphoramidates . Nucleosides Nucleotides , 18 : 913 – 919 . [PUBMED] [INFOTRIEVE]
  • Molema , G. , Jansen , R. W. and Pauwels , R. D. 1990 . Targeting of antiviral drugs to T4‐lymphocytes. Anti‐HIV activity of neoglycoprotein‐AZTMP conjugates in vitro . Biochem. Pharmacol. , 40 : 2603 – 2610 . [PUBMED] [INFOTRIEVE] [CROSSREF]
  • Jones , A. S. , McGuigan , C. , Walker , R. T. , Balzarini , J. and De Clercq , E. 1984 . Synthesis, properties, and biological activity of some nucleoside cyclic phosphoramidates . J. Chem. Soc., Perkin Trans. , 40 : 2603 – 2610 .
  • Abraham , T. W. and Wagner , C. R. 1994 . A phosphoramidate‐based synthesis of phosphoramidate amino acid diesters of antiviral nucleosides . Nucleosides Nucleotides , 1994 : 1891 – 1903 .
  • Chang , S.‐I. , Griesgraber , G. W. , Southern , P. J. and Wagner , C. R. 2001 . Amino Acid phosphoramidate monoesters of 3′‐azido‐3′‐deoxythymidine: relationship between antiviral potency and intracellular metabolism . J. Med. Chem. , 44 : 223 – 231 . [PUBMED] [INFOTRIEVE] [CROSSREF] [CSA]
  • Iyer , I. V. , Griesgraber , G. W. , Radmer , M. R. , McIntee , E. J. and Wagner , C. R. 2000 . 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. , 43 : 2266 – 2274 . [PUBMED] [INFOTRIEVE] [CROSSREF] [CSA]
  • Vito , M. D. , Bozzi , A. , Ferretti , A. , Cianfriglia , M. , Stefano , B. , Signoretti , C. , Lenti , L. , d'Agostino , F. , Strom , R. and Podo , F. 1997 . Intracellular metabolism of 3′‐azido‐3′‐deoxythymidine (AZT): a nuclear magnetic resonance study on T‐lymphoblastoid cell lines with different resistance to AZT . Biochem. Pharmacol. , 54 : 979 – 990 . [PUBMED] [INFOTRIEVE] [CROSSREF] [CSA]
  • Lefebvre , I. , Perigaud , 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: intracellular delivery of 3′‐azido‐2′,3′‐dideoxythymidine 5′‐monophosphate . J. Med. Chem. , 38 ( 20 ) : 3941 – 3950 . [PUBMED] [INFOTRIEVE] [CSA]
  • Huang , D. , Zhang , Y. and Chen , X. 2003 . Analysis of intracellular nucleoside triphosphate levels in normal and tumor cell lines by high‐performance liquie chromatography . J. Chromatogr., B , 784 : 101 – 109 . [CROSSREF] [CSA]
  • Balzarini , J. , Herdewijn , P. and De Clercq , E. 1989 . Differential patterns of intracellular metabolism of 2′,3′‐didehydro‐2′,3′‐dideoxythymidine and 3′‐azido‐2′,3′‐dideoxythymidine two potent anti‐human immunodeficiency virus compounds . J. Biol. Chem. , 264 ( 15 ) : 6127 – 6133 . [PUBMED] [INFOTRIEVE]

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