N-methylpurine DNA glycosylase and 8-oxoguanine DNA glycosylase metabolize the antiviral nucleoside 2-bromo-5,6-dichloro-1-(β-D-ribofuranosyl) benzimidazole

Drug Metabolism and Disposition

Volumn 34, Issue 6, 2006, Pages 1070-1077

  Lorenzi, Philip L ^a,c   Landowski, Christopher P ^a,d   Brancale, Andrea ^b   Song, Xueqin ^a   Townsend, Leroy B ^a   Drach, John C ^a   Amidon, Gordon L ^a  

^a UNIVERSITY OF MICHIGAN   (United States)

^b CARDIFF UNIVERSITY   (United Kingdom)

^c NATIONAL CANCER INSTITUTE   (United States)

^d UNIVERSITY OF BERN   (Switzerland)

Author keywords

[No Author keywords available]

Indexed keywords

2 BROMO 5,6 DICHLORO 1 (BETA DEXTRO RIBOFURANOSYL)BENZIMIDAZOLE; 2,5,6 TRICHLORO 1 (BETA DEXTRO RIBOFURANOSYL)BENZIMIDAZOLE; 8 OXOGUANINE DNA GLYCOSYLASE; ANTIVIRUS AGENT; ASPARAGINE; BENZIMIDAVIR; DNA GLYCOSYLTRANSFERASE; GUANOSINE; HISTIDINE; LYSINE; N METHYLPURINE DNA GLYCOSYLASE; PHENYLALANINE; SERINE; UNCLASSIFIED DRUG;

ARTICLE; CONTROLLED STUDY; DRUG BINDING SITE; DRUG METABOLISM; ENZYME ANALYSIS; HUMAN; HUMAN CELL; MOLECULAR DYNAMICS; PRIORITY JOURNAL;

ANTIVIRAL AGENTS; BENZIMIDAZOLES; CACO-2 CELLS; COMPUTER SIMULATION; DNA GLYCOSYLASES; GENE EXPRESSION PROFILING; HUMANS; INTESTINES; MICROSOMES, LIVER; MODELS, MOLECULAR; OLIGONUCLEOTIDE ARRAY SEQUENCE ANALYSIS; PROTEIN CONFORMATION; RIBONUCLEOSIDES; SUBCELLULAR FRACTIONS;

HUMAN HERPESVIRUS 5;

EID: 33646778183     PISSN: 00909556     EISSN: 1521009X     Source Type: Journal    
DOI: 10.1124/dmd.105.009209     Document Type: Article

References (43)

1. Bennett EM, Li C, Allan PW, Parker WB, and Ealick SE (2003) Structural basis for substrate specificity of Escherichia coli purine nucleoside phosphorylase. J Biol Chem 278:47110-47118.
2. Berendsen HJC, van der Spoel D, and van Drunen R (1995) GROMACS: a message-passing parallel molecular dynamics implementation. Comput Phys Commun 91:43-56.
3. Birnie GD, Kroeger H, and Heidelberger C (1963) Studies of fluorinated pyrimidines. XVIII. The degradation of 5-fluoro-2′-deoxyuridine and related compounds by nucleoside phosphorylase. Biochemistry 13:566-572.
4. Biron KK, Harvey RJ, Chamberlain SC, Good SS, Smith AA 3rd, Davis MG, Talarico CL, Miller WH, Ferris R, Dornsife RE, et al. (2002) Potent and selective inhibition of human cytomegalovirus replication by 1263W94, a benzimidazole L-riboside with a unique mode of action. Antimicrob Agents Chemother 46:2365-2372.
5. Bjoras M, Seeberg E, Luna L, Pearl LH, and Barrett TE (2002) Reciprocal "flipping" underlies substrate recognition and catalytic activation by the human 8-oxo-guanine DNA glycosylase. J Mol Biol 317:171-177.
6. Chulay J, Biron K, Wang L, Underwood M, Chamberlain S, Frick L, Good S, Davis M, Harvey R, Townsend L, et al. (1999) Development of novel benzimidazole riboside compounds for treatment of cytomegalovirus disease. Adv Exp Med Biol 458:129-134.
7. Dawson RMC (1960) Data for Biochemical Research. Clarendon Press, Oxford.
8. Dodson ML and Lloyd RS (2002) Mechanistic comparisons among base excision repair glycosylases. Free Radic Biol Med 32:678-682.
9. Erion MD, Stoeckler JD, Guida WC, Walter RL, and Ealick SE (1997) Purine nucleoside phosphorylase. 2. Catalytic mechanism. Biochemistry 36:11735-11748.
10. Good SS, Owens BS, Townsend LB, and Drach JC (1994) The disposition in rats and monkeys of 2-bromo-5,6-dichloro-1-(β-D-ribofuranosyl)benzimidazole (BDCRB) and its 2,5,6-trichloro congener (TCRB). Antiviral Res 23:103.
11. Hidalgo IJ, Raub TJ, and Borchardt RT (1989) Characterization of the human colon carcinoma cell line (Caco-2) as a model system for intestinal epithelial permeability. Gastroenterology 96:736-749.
12. Humphrey W, Dalke A, and Schulten K (1996) VMD - visual molecular dynamics. J Mol Graphics 14:33-38.
13. Jiang YL and Stivers JT (2001) Reconstructing the substrate for uracil DNA glycosylase: tracking the transmission of binding energy in catalysis. Biochemistry 40:7710-7719.
14. Kern ER, Hartline CB, Rybak RJ, Drach JC, Townsend LB, Biron KK, and Bidanset DJ (2004) Activities of benzimidazole D- and L-ribonucleosides in animal models of cytomegalovirus infections. Antimicrob Agents Chemother 48:1749-1755.
15. Kline PC and Schramm VL (1993) Purine nucleoside phosphorylase. Catalytic mechanism and transition-state analysis of the arsenolysis reaction. Biochemistry 32:13212-13219.
16. Kline PC and Schramm VL (1995) Pre-steady-state transition-state analysis of the hydrolytic reaction catalyzed by purine nucleoside phosphorylase. Biochemistry 34:1153-1162.
17. Koszalka GW, Johnson NW, Good SS, Boyd L, Chamberlain SC, Townsend LB, Drach JC, and Biron KK (2002) Preclinical and toxicology studies of 1263W94, a potent and selective inhibitor of human cytomegalovirus replication. Antimicrob Agents Chemother 46:2373-2380.
18. Krosky PM, Underwood MR, Turk SR, Feng KW, Jain RK, Ptak RG, Westerman AC, Biron KK, Townsend LB, and Drach JC (1998) Resistance of human cytomegalovirus to benzimidazole ribonucleosides maps to two open reading frames: UL89 and UL56. J Virol 72:4721-4728.
19. Lash AE, Tolstoshev CM, Wagner L, Schuler GD, Strausberg RL, Riggins GJ, and Altschul SF (2000) SAGEmap: a public gene expression resource. Genome Res 10:1051-1060.
20. Lau AY, Wyatt MD, Glassner BJ, Samson LD, and Ellenberger T (2000) Molecular basis for discriminating between normal and damaged bases by the human alkyladenine glycosylase, AAG. Proc Natl Acad Sci USA 97:13573-13578.
21. Lindahl E, Hess B, and van der Spoel D (2001) GROMACS 3.0: a package for molecular simulation and trajectory analysis. J Mol Mod 7:306-317.
22. Lorenzi PL, Landowski CP, Song X, Borysko KZ, Breitenbach JM, Kim JS, Hilfinger JM, Townsend LB, Drach JC, and Amidon GL (2005) Amino acid ester prodrugs of 2-bromo-5,6-dichloro-1-(β-D-ribofuranosyl)benzimidazole enhance metabolic stability in vitro and in vivo. J Pharmacol Exp Ther 343:883-890.
23. McCullough AK, Dodson ML, and Lloyd RS (1999) Initiation of base excision repair: glycosylase mechanisms and structures. Annu Rev Biochem 68:255-285.
24. Miao F, Bouziane M, and O'Connor TR (1998) Interaction of the recombinant human methylpurine-DNA glycosylase (MPG protein) with oligodeoxyribonucleotides containing either hypoxanthine or abasic sites. Nucleic Acids Res 26:4034-4041.
25. Nishioka K, Ohtsubo T, Oda H, Fujiwara T, Kang D, Sugimachi K, and Nakabeppu Y (1999) Expression and differential intracellular localization of two major forms of human 8-oxoguanine DNA glycosylase encoded by alternatively spliced OGG1 mRNAs. Mol Biol Cell 10:1637-1652.
26. Norman DP, Chung SJ, and Verdine GL (2003) Structural and biochemical exploration of a critical amino acid in human 8-oxoguanine glycosylase. Biochemistry 42:1564-1572.
27. O'Brien PJ and Ellenberger T (2003) Human alkyladenine DNA glycosylase uses acid-base catalysis for selective excision of damaged purines. Biochemistry 42:12418-12429.
28. O'Brien PJ and Ellenberger T (2004a) Dissecting the broad substrate specificity of human 3-methyladenine-DNA glycosylase. J Biol Chem 279:9750-9757.
29. O'Brien PJ and Ellenberger T (2004b) The Escherichia coli 3-methyladenine DNA glycosylase AlkA has a remarkably versatile active site. J Biol Chem 279:26876-26884.
30. Russo MT, De Luca G, Degan P, Parlanti E, Dogliotti E, Barnes DE, Lindahl T, Yang H, Miller JH, and Bignami M (2004) Accumulation of the oxidative base lesion 8-hydroxyguanine in DNA of tumor-prone mice defective in both the Myh and Ogg1 DNA glycosylases. Cancer Res 64:4411-4414.
31. Scheffczik H, Savva CG, Holzenburg A, Kolesnikova L, and Bogner E (2002) The terminase subunits pUL56 and pUL89 of human cytomegalovirus are DNA-metabolizing proteins with toroidal structure. Nucleic Acids Res 30:1695-1703.
32. Scholz B, Rechter S, Drach JC, Townsend LB, and Bogner E (2003) Identification of the ATP-binding site in the terminase subunit pUL56 of human cytomegalovirus. Nucleic Acids Res 31:1426-1433.
33. Slupphaug G, Mol CD, Kavli B, Arvai AS, Krokan HE, and Tainer JA (1996) A nucleotide-flipping mechanism from the structure of human uracil-DNA glycosylase bound to DNA. Nature (Lond) 384:87-92.
34. Sun D, Lennernas H, Welage LS, Barnett JL, Landowski CP, Foster D, Fleisher D, Lee KD, and Amidon GL (2002) Comparison of human duodenum and Caco-2 gene expression profiles for 12,000 gene sequences tags and correlation with permeability of 26 drugs. Pharm Res (NY) 19:1400-1416.
35. Townsend LB, Devivar RV, Turk SR, Nassiri MR, and Drach JC (1995) Design, synthesis and antiviral activity of certain 2,5,6-trihalo-1-(beta-D- ribofuranosyl)benzimidazoles. J Med Chem 38:4098-4105.
36. Townsend LB and Drach JC (1992) Benzimidazole ribonucleosides: design, synthesis, evaluation and mode of action. Fifth International Conference on Antiviral Research; 1992 Mar 8-13; Vancouver, BC, Canada, Abstracts 12, 105, 107, 108, 110. Antiviral Res (17 suppl 1):1-159.
37. Townsend LB, Gudmundsson KS, Daluge SM, Chen JJ, Zhu Z, Koszalka GW, Boyd L, Chamberlain SD, Freeman GA, Biron KK, et al. (1999) Studies designed to increase the stability and antiviral activity (HCMV) of the active benzimidazole nucleoside, TCRB. Nucleosides Nucleotides 18:509-519.
38. Underwood MR, Harvey RJ, Stanat SC, Hemphill ML, Miller T, Drach JC, Townsend LB, and Biron KK (1998) Inhibition of human cytomegalovirus DNA maturation by a benzimidazole ribonucleoside is mediated through the UL89 gene product. J Virol 72:717-725.
39. Williams JD, Chen JJ, Drach JC, and Townsend LB (2004a) Design, synthesis and antiviral activity of certain 3-substituted 2,5,6-trichloroindole nucleosides. J Med Chem 47:5753-5765.
40. Williams JD, Drach JC, and Townsend LB (2004b) Synthesis and antiviral evaluation of some novel tricyclic pyrazolo[3,4-b]indole nucleosides. Nucleosides Nucleotides Nucleic Acids 23:805-812.
41. Williams JD, Ptak RG, Drach JC, and Townsend LB (2004c) Synthesis, antiviral activity and mode of action of some 3-substituted 2,5,6- trichloroindole 2′- and 5′-deoxyribonucleosides. J Med Chem 47:5773-5782.
42. Xia L and O'Connor TR (2001) DNA glycosylase activity assay based on streptavidin paramagnetic bead substrate capture. Anal Biochem 298:322-326.
43. Zoltewicz JA, Clark DF, Sharpless TW, and Grahe G (1970) Kinetics and mechanism of the acid-catalyzed hydrolysis of some purine nucleosides. J Am Chem Soc 92:1741-1749.