Effect of stereoisomerism on the cellular pharmacology of β-enantiomers of cytidine analogs in Hep-G2 cells

Biochemical Pharmacology

Volumn 53, Issue 1, 1997, Pages 75-87

  Martin, Lee T ^a   Faraj, Abdesslem ^a   Schinazi, Raymond F ^b,c   Gosselin, Gilles ^d   Mathe, Christophe ^d   Imbach, Jean Louis ^d   Sommadossi, Jean Pierre ^a,e  

^a University of Alabama at Birmingham   (United States)

^b ATLANTA VA MEDICAL CENTER   (United States)

^c EMORY UNIVERSITY SCHOOL OF MEDICINE   (United States)

^d CNRS   (France)

^e UNIVERSITY OF ALABAMA AT BIRMINGHAM   (United States)

Author keywords

antiviral; enantioselective; metabolism; nucleoside analog; stereoisomer

Indexed keywords

2',3' DIDEOXY 5 FLUOROCYTIDINE; 2',3' DIDEOXY 5 FLUOROCYTIDINE DIPHOSPHATE; 2',3' DIDEOXY 5 FLUOROCYTIDINE PHOSPHATE; 2',3' DIDEOXY 5 FLUOROCYTIDINE TRIPHOSPHATE; 2',3' DIDEOXYCYTIDINE 5' TRIPHOSPHATE; ANTIVIRUS AGENT; DRUG METABOLITE; UNCLASSIFIED DRUG; ZALCITABINE;

ARTICLE; CELL LEVEL; CONTROLLED STUDY; DRUG ELIMINATION; DRUG HALF LIFE; DRUG METABOLISM; ENANTIOMER; HEPATOMA CELL; HIGH PERFORMANCE LIQUID CHROMATOGRAPHY; HUMAN; HUMAN CELL; PHOSPHORYLATION; PRIORITY JOURNAL; STEREOISOMERISM; STEREOSPECIFICITY;

ANTIVIRAL AGENTS; CELLS, CULTURED; CHROMATOGRAPHY, HIGH PRESSURE LIQUID; HUMANS; LIVER; LIVER NEOPLASMS; PHOSPHORYLATION; STEREOISOMERISM; TUMOR CELLS, CULTURED; ZALCITABINE;

EID: 0031060704     PISSN: 00062952     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0006-2952(96)00653-3     Document Type: Article

References (37)

1. Eton JJ, Benoit SL, Jemsek J, MacArthur RD, Santana J, Quinn JB, Kuritzkes DR, Fallon MA and Rubin M, Treatment with lamivudine, zidovudine, or both in HIV-positive patients with 200 to 500 CD4+ cells per cubic millimeter. N Engl J Med 333: 1662-1669, 1995.
2. Dienstag JL, Perrillo RP, Schiff ER, Bartholomew M, Vicary C and Rubin M, A preliminary trial of Lamivudine for chronic hepatitis B infection. N Engl J Med 333: 1657-1661, 1995.
3. Condreay LD, Condreay JP, Jansen RW, Paff MT and Averett DR, (-)-Cis-5-fluoro-1-[2-(hydroxymethyl)-1,3-oxathiolan-5-yl]cytosine (524W91) inhibits hepatitis B virus replication in primary human hepatocytes. Antimicrob Agents Chemother 40: 520-523, 1996.
4. Furman PA, Davis M, Liotta DC, Paff M, Frick LW, Nelson DJ, Dornsife RE, Wurster JA, Wilson LJ, Fyfe JA, Tuttle JV, Miller WH, Condreay L, Averett DR, Schinazi RF and Painter GR, The anti-hepatitis B virus activities, cytotoxicities, and anabolic profiles of the (-) and ( + ) enantiomers of ds-5-fluoro-1-[2-(hydroxymethyl)-l,3-oxathiolan-5-yl]cytosine. Antimicrob Agents Chemother 36: 2686-2692, 1992.
5. Schinazi RF, McMillan A, Cannon D, Mathis R, Lloyd RM, Peck A, Sommadossi J-P, St. Clair M, Wilson J, Furman PA, Painter G, Choi W-B and Liotta DC, Selective inhibition of human immunodeficiency viruses by racemates and enantiomers of ds-5-fluoro-l-[2-(hydroxymethyl)-l,3-oxathiolan-5-yl]cytosine. Antimicrob Agents Chemother 36: 2423-2431, 1992.
6. Paff MT, Averett DR, Prus KL, Miller WH and Nelson DJ, Intracellular metabolism of (-)-and (+)-cis-5-fluoro-l-[2-(hydroxymethyl)-l,3-oxathiolan-5-yl]cytosine in HepG2 de-rivative 2.2.15 (subclone P5A) cells. Antimicrob Agents Chemother 38: 1230-1238, 1994.
7. Frick LW, St. John L, Taylor LC, Painter GR, Furman PA, Liotta DC, Furfine ES and Nelson DJ, Pharmacokinetics, oral bioavailability, and metabolic disposition in rats of (-)-cis-5-fluoro-l-[2-(hydroxymethyl)-l,3-oxathiolan-5-yl]cytosine, a nucleoside analog active against human immunodeficiency virus and hepatitis B virus. Antimicrob Agents Chemother 37: 2285-2292, 1993.
8. Furman PA, Wilson JE, Reardon JE and Painter GR, The effect of absolute configuration on the anti-HIV and anti-HBV activity of nucleoside analogues. Antiviral Chem Chemother 6: 345-355, 1995.
9. Skalski V, Chang C-N, Dutschman G and Cheng Y-C, The biochemical basis for the differential anti-human immunodeficiency virus activity of two cis enantiomers of 2′,3′-dideoxy-3′-thiacytidine. J Biol Chem 268: 23234-23238, 1993.
10. Chang C-N, Doong S-L, Zhou JH, Beach JW, Jeong LS, Chu CK, Tsai C-H and Cheng Y-C, Deoxycytidine deaminase-resistant stereoisomer is the active form of (±)-2′,3′-dideoxy-3′-thiacytidine in the inhibition of hepatitis B virus replication. J Biol Chem 267: 13938-13942, 1992.
11. Sommadossi J-P, Schinazi RF, Chu CK and Xie M-Y, Comparison of cytotoxicity of the (-)-and (+)-enantiomer of 2′,3′-dideoxy-3′-thiacytidine in normal human bone marrow progenitor cells. Biochem Pharmacol 44: 1921-1925, 1992.
12. Schinazi RF, Chu CK, Peck A, McMillan A, Mathis R, Cannon DL, Jeong L-S, Beach JW, Choi W-B, Yeola S and Liotta DC, Activities of the four optical isomers of 2′,3′-dideoxy-3′-thiacytidine (BCH-189) against human immunodeficiency virus type 1 in human lymphocytes. Antimicrob Agents Chemother 36: 672-676, 1992.
13. Coates JAV, Cammack N, Jenkinson HJ, Mutton IM, Pearson BA, Storer R, Cameron JM and Penn CR, The separated enantiomers of 2′-deoxy-3′-thiacytidine (BCH 189) both inhibit human immunodeficiency virus replication in vitro. Antimicrob Agents Chemother 36: 202-205, 1992.
14. Shewach DS, Liotta DC and Schinazi RF, Affinity of the antiviral enantiomers of oxathiolane cytosine nucleosides for human 2′-deoxycytidine kinase. Biochem Pharmacol 45: 1540-1543, 1993.
15. Doong S-L, Tsai C-H, Schinazi RF, Liotta DC and Cheng Y-C, Inhibition of the replication of hepatitis B virus in vitro by 2′,3′-dideoxy-3′-thiacytidine and related analogues. Proc Natl Acad Sci USA 88: 8495-8499, 1991.
16. Martin JL, Brown CE, Matthews-Davis N, and Reardon JE, Effects of antiviral nucleoside analogs on human DNA polymerases and mitochondrial DNA synthesis. Antimicrob Agents Chemother 38: 2743-2749, 1994.
17. Hart GJ, Orr DC, Penn CR, Figueiredo HT, Gray NM, Boehme RE and Cameron JM, Effects of (-)-2′-deoxy-3′thiacytidine (3TC) 5′-triphosphate on human immunodeficiency virus reverse transcriptase and mammalian DNA polymerases alpha, beta, and gamma. Antimicrob Agents Chemother 36: 1688-1694, 1992.
18. Faraj A, Agrofoglio LA, Wakefield JK, McPherson S, Morrow CD, Gosselin G, Mathé C, Imbach J-L, Schinazi RF and Sommadossi J-P, Inhibition of human immunodeficiency virus type I reverse transcriptase by the 5′-triphosphate β enantiomers of cytidine analogs. Antimicrob Agents Chemother 38: 2300-2305, 1994.
19. Gosselin G, Schinazi RF, Sommadossi J-P, Mathé C, Bergogne M-C, Aubertin A-M, Kirn A and Imbach J-L, Antihuman immunodeficiency virus activities of the β-L enantiomer of 2′,3′-dideoxycytidine and its 5-fluoro derivative in vitro. Antimicrob Agents Chemother 38: 1292-1297, 1994.
20. Gosselin G, Mathé C, Bergogne M-C, Aubertin A-M, Kirn A, Schinazi RF, Sommadossi J-P and Imbach J-L, Enantio-meric 2′,3′-dideoxycytidine derivatives are potent human immunodeficiency virus inhibitors in cell cultures. CR Acad Sci [III] 317: 85-89, 1994.
21. Lin T-S, Luo M-Z, Liu M-C, Pai SB, Dutschman GE and Cheng Y-C, Synthesis and biological evaluation of 2′,3′-dideoxy-L-pyrimidine nucleosides as potential antiviral agents against human immunodeficiency virus (HIV) and hepatitis B virus (HBV). J Med Chem 37: 798-803, 1994.
22. Lin T-S, Luo M-Z, Liu M-C, Pai SB, Dutschman GE and Cheng Y-C, Antiviral activity of 2′,3′-dideoxy-β-L-5-fluorocytidine (β-L-FddC) and 2′,3′-dideoxy-β-L-cytidine (β-L-ddC) against hepatitis B virus and human immunodeficiency virus type 1 in vitro. Biochem Pharmacol 47: 171-174, 1994.
23. van Draanen NA, Tisdale M, Parry NR, Jansen R, Dornsife RE, Tuttle JV, Averett DR and Koszalka GW, Influence of stereochemistry on antiviral activities and resistance profiles of dideoxycytidine nucleosides. Antirrucrob Agents Chemother 38: 868-871, 1994.
24. Larder BA, Kemp SD and Harrigan PR, Potential mechanism for sustained antiretroviral efficacy of AZT-3TC combination therapy. Science 269: 696-699, 1995.
25. Schinazi RF, Gosselin G, Faraj A, Korba BE, Liotta DC, Chu CK, Mathè C, Imbach J-L and Sommadossi J-P, Pure nucleoside enantiomers of β-2′,3′-dideoxycytidine analogs are selective inhibitors of hepatitis B virus in vitro. Antimicrob Agents Chemother 38: 2172-2174, 1994.
26. Placidi L, Cretton-Scott E, de Sousa G, Rahmani R, Placidi M and Sommadossi J-P, Disposition and metabolism of the angiogenic moderator O-(chloroacetyl-carbamoyl) fumagillol (TNP-470; AGM-1470) in human hepatocytes and tissue microsomes. Cancer Res 55: 3036-3042, 1995.
27. de Sousa G, Dou M, Barbe D, Lacarelle B, Placidi M and Rahmani R, Freshly isolated or cryopreserved human hepatocytes in primary culture: Influence of drug metabolism on hepatotoxicity. Toxicol in Vitro 5: 483-486, 1991.
28. Gomeni R and Gomeni C, Interactive graphic package for pharmacokinetic analysis. Comput Biol Med 9: 38-48, 1979.
29. Hao Z, Stowe EE, Ahluwalia G, Baker DC, Hebbier AK, Chisena C, Musser SM, Kelly JA, Perno CF, Johns DG and Cooney DA, Characterization of 2′,3′-dideoxycytidine diphosphocholine and 2′,3′-dideoxycytidine ethanolamine. Drug Metab Dispos 21: 738-744, 1993.
30. Zoulim F, Dannaoui E, Borel C, Hantz O, Lin T-S, Liu S-H, Trépo C and Cheng Y-C, 2′,3′-Dideoxy-β-L-5-fluorocytidine inhibits duck hepatitis B virus reverse transcription and suppresses viral DNA synthesis in hepatocytes, both in vitro and in vivo. Antimicrob Agents Chemother 40: 448-453, 1996.
31. Hao Z, Cooney DA, Farquhar D, Perno CF, Zhang K, Masood R, Wilson Y, Hartman NR, Balzarini J and Johns DG, Potent DNA chain termination activity and selective inhibition of human immunodeficiency virus reverse transcriptase by 2′,3′dideoxyuridine-5′-triphosphate. Mol Pharmacol 37: 157-163, 1990.
32. Amer ESJ and Eriksson S, Deoxycytidine and 2′,3′-dideoxycytidine metabolism in human monocyte-derived macrophages. Biochem Biophys Res Commun 197: 1499-1504, 1993.
33. Cammack N, Rouse P, Marr CLP, Reid PJ, Boehme RE, Coates JAV, Penn CR and Cameron JM, Cellular metabolism of (-)enantiomeric 2′-deoxy-3′-thiacytidine. Biochem Pharmacol 43: 2059-2064, 1992.
34. Aduma P, Connelly MC, Srinivas RV and Fridland A, Metabolic diversity and antiviral activities of acyclic nucleoside phosphonates. Mol Pharmacol 47: 816-822, 1995.
35. Voet D and Voet JG, Lipid metabolism. In: Biochemistry (Ed. Stiefel J), pp. 618-677. John Wiley, New York, 1990.
36. Sohal RS and Cornell RB, Sphingosine inhibits the activity of rat liver CTP:phosphocholine cytidylyltransferase. J Biol Chem 265: 11746-11750, 1990.
37. Yao Z and Vance DE, The active synthesis of phosphatidylcholine is required for very low density lipoprotein secretion from rat hepatocytes. J Biol Chem 263: 2998-3004, 1988.