Metabolism in human cells of the D and L enantiomers of the carbocyclic analog of 2'-deoxyguanosine: Substrate activity with deoxycytidine kinase, mitochondrial deoxyguanosine kinase, and 5'-nucleotidase

Antimicrobial Agents and Chemotherapy

Volumn 42, Issue 5, 1998, Pages 1045-1051

  Bennett Jr , L Lee ^a   Allan, Paula W ^a   Arnett, Gussie ^a   Shealy, Y Fulmer ^a   Shewach, Donna S ^b   Mason, William S ^c   Fourel, Isabelle ^c   Parker, William B ^a  

^a SOUTHERN RESEARCH INSTITUTE   (United States)

^b UNIVERSITY OF MICHIGAN HEALTH SYSTEM   (United States)

^c FOX CHASE CANCER CENTER   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

DEOXYCYTIDINE KINASE; DEOXYGUANOSINE; MITOCHONDRIAL ENZYME; NUCLEOSIDE ANALOG; NUCLEOTIDASE; NUCLEOTIDE;

ARTICLE; DRUG ACTIVITY; DRUG METABOLISM; ENANTIOMER; ENZYME ACTIVITY; ENZYME ASSAY; ENZYME ISOLATION; ENZYME SUBSTRATE COMPLEX; HUMAN; KINETICS; NONHUMAN; PHOSPHORYLATION; PRIORITY JOURNAL;

EID: 0344878893     PISSN: 00664804     EISSN: None     Source Type: Journal    
DOI: 10.1128/aac.42.5.1045     Document Type: Article

References (44)

1. Allan, P. W., W. B. Parker, G. Arnett, L. M. Rose, S. C. Shaddix, D. S. Shewach, I. Fourel, J. A. Secrist III, J. A. Montgomery, Y. F. Shealy, and L. L. Bennett, Jr. 1995. Metabolism of the carbocyclic analog of 2′-deoxyguanosine (CdG) in human cells. Antivir. Res. 26:A266.
2. Arner, E. S. J., and S. Eriksson. 1995. Mammalian deoxyribonucleoside kinases. Pharmacol. Ther. 67:155-186.
3. Balzarini, J., E. De Clercq, H. Baumgartner, M. Bodenteich, and H. Griengl. 1990. Carbocyclic 5-iodo-2′-deoxyuridine (C-IDU) and carbocyclic (E)-5-(2-bromovinyl)-2′-deoxyuridine (C-BVDU) as unique examples of chiral molecules where the two enantiomeric forms are biologically active: interaction of the (+)- and (-)-enantiomers of C-IDU and C-BVDU with the thymidine kinase of herpes simplex virus type 1. Mol. Pharmacol. 37:395-401.
4. Bennett, L. L., Jr., Y. F. Shealy, P. W. Allan, L. M. Rose, W. M. Shannon, and G. Arnett. 1990. Phosphorylation of the carbocyclic analog of 2′-deoxyguanosine in cells infected with herpes viruses. Biochem. Pharmacol. 40: 1515-1522.
5. Bennett, L. L., Jr., W. B. Parker, P. W. Allan, L. M. Rose, Y. F. Shealy, J. A. Secrist III, J. A. Montgomery, G. Arnett, R. L. Kirkman, and W. M. Shannon. 1993. Phosphorylation of the enantiomers of the carbocyclic analog of 2′-deoxyguanosine in cells infected with herpes simplex virus type 1 and in uninfected cells. Lack of enantiomeric selectivity with the viral thymidine kinase. Mol. Pharmacol. 44:1258-1266.
6. Biron, K. K., S. C. Stanat, J. B. Sorrell, J. A. Fyfe, P. M. Keller, C. U. Lambe, and D. J. Nelson. 1985. Metabolic activation of the nucleoside analog 9-{[2-hydroxy-1-(hydroxymethyl)ethoxy]-methyl}guanine in human diploid fibroblasts infected with human cytomegalovirus. Proc. Natl. Acad. Sci. USA 82:2473-2477.
7. Bogenhagen, D., and D. A. Clayton. 1974. The number of mitochondrial deoxyribonucleic acid genomes in mouse L and human HeLa cells. Quantitative isolation of mitochondrial deoxyribonucleic acid. J. Biol. Chem. 249: 7991-7995.
8. Estes, J. E., and E.-S. Huang. 1997. Stimulation of cellular thymidine kinases by human cytomegalovirus. J. Virol. 24:13-21.
9. Fourel, I., J. Saputelli, P. Schaffer, and W. S. Mason. 1994. The carbocyclic analog of 2′-deoxyguanosine induces a prolonged inhibition of duck hepatitis B virus DNA synthesis in primary hepatocyte cultures and in the liver. J. Virol. 68:1059-1065.
10. Furman, P. A., J. E. Wilson, J. E. Reardon, and G. R. Painter. 1995. The effect of absolute configuration on the anti-HIV and anti-HBV activity of nucleoside analogues. Antivir. Chem. Chemother. 6:345-355.
11. Grove, K. L., X. Guo, S.-H. Liu, Z. Gao, C. K. Chu, and Y. C. Cheng. 1995. Anticancer activity of β-L-dioxolane-cytidine, a novel nucleoside analogue with the unnatural L-configuration. Cancer Res. 55:3008-3011.
12. Harrison, P. T., R. Thompson, and A. J. Davison. 1991. Evolution of herpesvirus thymidine kinases from cellular deoxycytidine kinase. J. Gen. Virol. 72:2583-2586.
13. Higuchi, Y., and S. Linn. 1995. Purification of all forms of HeLa cell mitochondrial DNA and assessment of damage to it caused by hydrogen peroxide treatment of mitochondria or cells. J. Biol. Chem. 270:7950-7956.
14. Itoh, R. 1981. Purification and some properties of cytosol 5′-nucleotidase from rat liver. Biochim. Biophys. Acta 657:402-410.
15. Itoh, R. 1993. IMP-GMP 5′-nucleotidase. Comp. Biochem. Physiol. 105B: 13-19.
16. Johansson, M., and A. Karlsson. 1996. Cloning and expression of human deoxyguanosine kinase cDNA. Proc. Natl. Acad. Sci. USA 93:7258-7262.
17. Johnson, M. A., and A. Fridland. 1989. Phosphorylation of 2′,3′-dideoxyinosine by cytosolic 5′-nucleotidase of human lymphoid cells. Mol. Pharmacol. 36:291-295.
18. Kitos, T. E., and D. L. J. Tyrrell. 1995. Intracellular metabolism of 2′,3′-dideoxynucleosides in duck hepatocyte primary cultures. Biochem. Pharmacol. 49:1291-1302.
19. Kosovsky, M. J., and G. Soslau. 1991. Mitochondrial DNA topoisomerase I from human platelets. Biochim. Biophys. Acta 1078:56-62.
20. Krenitsky, T. A., J. V. Tuttle, G. W. Koszalka, I. S. Chen, L. M. Beacham III, J. L. Rideout, and G. B. Elion. 1976. Deoxycytidine kinase from calf thymus. Substrate and inhibitor specificity. J. Biol. Chem. 251:4055-4061.
21. Lewis, R. A., L. Watkins, and S. St. Jeor. 1985. Enhancement of deoxyguanosine kinase activity in human lung fibroblast cells infected with human cytomegalovirus. Mol. Cell. Biochem. 65:67-71.
22. Littler, E., A. D. Stuart, and M. S. Chee. 1992. Human cytomegalovirus UL97 open reading frame encodes a protein that phosphorylates the antiviral nucleoside analogue ganciclovir. Nature 358:160-162.
23. Meijer, H., C. A. Bruggeman, P. H. J. Dormans, and C. P. A. van Boven. 1984. Human cytomegalovirus induces a cellular deoxyguanosine kinase, also interacting with acyclovir. FEMS Microbiol. Lett. 25:283-287.
24. Miller, W. H., S. M. Daluge, E. P. Garvey, S. Hopkins, J. E. Reardon, F. L. Boyd, and R. L. Miller. 1992. Phosphorylation of carbovir enantiomers by cellular enzymes determines the stereoselectivity of antiviral activity. J. Biol. Chem. 267:21220-21224.
25. Montgomery, J. A., S. Niwas, J. D. Rose, J. A. Secrist III, Y. S. Babu, C. E. Bugg, M. D. Erion, W. C. Guida, and S. E. Ealick. 1993. Structure-based design of inhibitors of purine nucleoside phosphorylase. I. 9-(Arylmethyl) derivatives of 9-deazaguanine. J. Med. Chem. 36:55-69.
26. Nair, V., and T. S. Jahnke. 1995. Antiviral activities of isomeric dideoxynucleosides of D- and L-related stereochemistry. Antimicrob. Agents Chemother. 39:1017-1029.
27. Price, P. M., R. Banerjee, and G. Acs. 1989. Inhibition of the replication of hepatitis B virus by the carbocyclic analogue of 2′-deoxyguanosine. Proc. Natl. Acad. Sci. USA 86:8541-8544.
28. Shannon, W. M. 1990. Antiretroviral activity of carbocyclic nucleoside analogs, p. 75-95. In R. B. Diasio and J.-P. Sommadossi (ed.), Advances in chemotherapy of AIDS. Pergamon Press, Inc., New York, N.Y.
29. Shealy, Y. F., C. A. O'Dell, W. M. Shannon, and G. Arnett. 1984. Synthesis and antiviral activity of carbocyclic analogues of 2′-deoxyribofuranosides of 2-amino-6-substituted purines and of 2-amino-6-substituted-8-azapurines. J. Med. Chem. 27:1416-1421.
30. Shewach, D. S., K. K. Reynolds, and L. Hertel. 1992. Nucleotide specificity of human deoxycytidine kinase. Mol. Pharmacol. 42:518-524.
31. Shewach, D. S., D. C. Liotta, and R. F. Schinazi. 1993. Affinity of the antiviral enantiomers of oxathiolane cytosine nucleosides for human 2′-deoxycytidine kinase. Biochem. Pharmacol. 45:1540-1543.
32. Smee, D. F. 1985. Interaction of 9-(1,3-dihydroxy-2-propoxymethyl)guanine with cytosol and mitochondrial deoxyguanosine kinases: possible role in anti-cytomegalovirus activity. Mol. Cell. Biochem. 69:75-81.
33. Spadari, S., G. Maga, F. Focher, G. Ciarrocchi, R. Manservigi, F. Arcamone, M. Capobianco, A. Carcuro, F. Colonna, S. Iotti, and A. Garbesi. 1992. L-Thymidine is phosphorylated by herpes simplex virus type 1 thymidine kinase and inhibits viral growth. J. Med. Chem. 35:4214-4220.
34. Spadari, S., G. Maga, A. Verri, A. Bendiscioli, L. Tondelli, M. Capobianco, F. Colonna, A. Garbesi, and F. Focher. 1995. Lack of stereospecificity of some cellular and viral enzymes involved in the synthesis of deoxyribonucleotides and DNA: molecular basis for the antiviral activity of unnatural L-β-nucleosides. Biochimie 77:861-867.
35. Sullivan, V., C. L. Talarico, S. C. Stanat, M. Davis, D. M. Coen, and K. K. Biron. 1992. A protein kinase homologue controls phosphorylation of ganciclovir in human cytomegalovirus-infected cells. Nature 358:162-164.
36. Tuttleman, J. S., J. C. Pugh, and J. W. Summers. 1986. In vitro experimental infection of primary duck hepatocyte cultures with duck hepatitis B virus. J. Virol. 58:17-25.
37. Van Draanen, N. A., M. Tisdale, N. G. Parry, R. Jansen, R. E. Dornsife, J. V. Tuttle, D. R. Averett, and G. Koszalka. 1994. Influence of stereochemistry on antiviral activities and resistance profiles of dideoxycytidine nucleosides. Antimicrob. Agents Chemother. 38:868-871.
38. Verri, A., F. Focher, G. Priori, G. Gosselin, J.-L. Imbach, M. Capobianco, A. Garbesi, and S. Spadari. 1997. Lack of enantiospecificity of human 2′-deoxycytidine kinase: relevance for the activation of β-L-deoxycytidine analogs as antineoplastic and antiviral agents. Mol. Pharmacol. 51:132-138.
39. Wang, L., A. Karlsson, E. S. J. Arner, and S. Eriksson. 1993. Substrate specificity of mitochondrial 2′-deoxyguanosine kinase. J. Biol. Chem. 268: 22847-22852.
40. Wang, L., U. Hellman, and S. Eriksson. 1996. Cloning and expression of human mitochondrial deoxyguanosine kinase cDNA. FEBS Lett. 390:39-43.
41. Worku, Y., and A. C. Newby. 1982. Nucleoside exchange catalyzed by the cytoplasmic 5′-nucleotidase. Biochem. J. 205:503-510.
42. Wu, T.-T., L. Coates, C. E. Aldrich, J. Summers, and W. S. Mason. 1990. In hepatocytes infected with duck hepatitis B virus, the template for viral RNA synthesis is amplified by an intracellular pathway. Virology 175:255-261.
43. Yamada, Y., H. Goto, and N. Ogasawara. 1982. Deoxyguanosine kinase from human placenta. Biochim. Biophys. Acta 709:265-272.
44. Zavada, V., V. Erban, D. Rezacova, and V. Vonka. 1976. Thymidine-kinase in cytomegalovirus infected cells. Arch. Virol. 52:333-339.