Hypoxanthine phosphoribosyltransferase from Trypanosoma cruzi as a target for structure-based inhibitor design: Crystallization and inhibition studies with purine analogs

Antimicrobial Agents and Chemotherapy

Volumn 41, Issue 8, 1997, Pages 1686-1692

  Eakin, Ann E ^a   Guerra, Astrid ^b   Focia, Pamela J ^c   Torres Martinez, Jan ^a   Craig III, Sydney P ^a  

^a UNIVERSITY OF NORTH CAROLINA   (United States)

^b UNIVERSITY OF PUERTO RICO SCHOOL OF MEDICINE   (Puerto Rico)

^c UNIVERSITY OF CALIFORNIA   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

6 SULFINYLPURINE; 6 THIOCYANOPURINE; ACICLOVIR; ALLOPURINOL; ANTIPROTOZOAL AGENT; ENZYME INHIBITOR; FORMYCIN B; GUANINE; GUANOSINE PHOSPHATE; HYPOXANTHINE; HYPOXANTHINE PHOSPHORIBOSYLTRANSFERASE; INOSINE PHOSPHATE; PURINE DERIVATIVE; UNCLASSIFIED DRUG;

ANTIPROTOZOAL ACTIVITY; ARTICLE; CHAGAS DISEASE; CONTROLLED STUDY; CRYSTALLIZATION; DRUG DESIGN; DRUG SCREENING; DRUG STRUCTURE; ENZYME ACTIVITY; ENZYME INHIBITION; ESCHERICHIA COLI; HUMAN; NONHUMAN; PRIORITY JOURNAL; TRYPANOSOMA CRUZI; X RAY DIFFRACTION;

EID: 0030789250     PISSN: 00664804     EISSN: None     Source Type: Journal    
DOI: 10.1128/aac.41.8.1686     Document Type: Article

References (34)

1. Allen, T. E., and B. Ullman. 1994. Molecular characterization and overexpression of the hypoxanthine-guanine phosphoribosyltransferase gene from Trypanosoma cruzi. Mol. Biochem. Parasitol. 65:233-245.
2. Appelt, K., R. J. Bacquet, C. A. Bartlett, et al. 1991. Design of enzyme inhibitors using iterative protein crystallographic analysis. J. Med. Chem. 34:1925-1934.
3. Berens, R. L., E. C. Krug, and J. J. Marr. 1995. Purine and pyrimidine metabolism, p. 89-117. In J. J. Marr and M. Müller (ed.), Biochemistry and molecular biology of parasites. Academic Press, Inc., San Diego, Calif.
4. Craig, S. P., III, L. Yuan, D. A. Kuntz, J. H. McKerrow, and C. C. Wang, 1991. High level expression in Escherichia coli of soluble, enzymatically active schistosomal hypoxanthine-guanine phosphoribosyltransferase and trypanosomal ornithine decarboxylase. Proc. Natl. Acad. Sci. USA 88:2500-2504.
5. Craig, S. P., III, and A. E. Eakin. 1997. Purine salvage enzymes as targets for structure based inhibitor design. Parasitol. Today 13:238-241.
6. Craig, S. P., III, C. Castro, A. E. Eakin, and M. Castaneda. 1990. Trypanosoma (Schizotrypanum) cruzi: repetitive DNA sequence evolution in three geographically distinct isolates. Comp. Biochem. Physiol. B Comp. Biochem. 95:657-662.
7. De Castro, S. L. 1993. The challenge of Chagas' disease chemotherapy: an update of drugs assayed against Trypanosoma cruzi. Acta Trop. 53:83-98.
8. De Clercq, E. 1995. Toward improved anti-HIV chemotherapy: therapeutic strategies for intervention with HIV infections. J. Med. Chem. 38:2491-2517.
9. Dixon, M. 1953. Determination of enzyme inhibition constants. Biochem. J. 55:170-171.
10. Eads, J. C., G. Scapin, Y. Xu, C. Grubmeyer, and J. C. Sacchettini. 1994. The crystal structure of human hypoxanthine-guanine phosphoribosyltransferase with bound GMP. Cell 78:325-334.
11. Eakin, A. E., R. Nieves-Alicea, R. Tosado-Acevedo, M. S. Chin, C. C. Wang, and S. P. Craig III. 1995. Comparative complementation selection in bacteria enables screening for lead compounds targeted to a purine salvage enzyme of parasites. Antimicrob. Agents Chemother. 39:620-625.
12. Gallerano, R. H., J. J. Marr, and R. R. Sosa. 1990. Therapeutic efficacy of allopurinol in patients with chronic Chagas' disease. Am. J. Trop. Med. Hyg. 43:159-166.
13. Garcia-Zapata, M. T. A., P. B. McGreevy and P. D. Marsden. 1991. American trypanosomiasis, p. 628-637. In G. T. Strickland (ed.), Hunter's tropical medicine, 7th ed. The W. B. Saunders Co., Philadelphia, Pa.
14. Giacomello, A., and C. Salerno. 1978. Human hypoxanthine-guanine phosphorihosyltransferase: steady stale kinetics of the forward and reverse reactions. J. Biol. Chem. 253:6038-6044.
15. Gutteridge, W. E., and M. J. Davies. 1982. Properties of the purine phosphoribosyltransferases of Trypanosoma cruzi. FEMS Microbiol. Lett. 13:207-212.
16. Gutteridge, W. E., and M. Gaborak. 1979. A re-examination of purine and pyrimidine synthesis in the three main forms of Trypanosoma cruzi. Int. J. Biochem. 10:415-422.
17. Hammond, D. J., and W. E. Gutteridge. 1984 Purine and pyrimidine metabolism in the Trypanosomatidae. Mol. Biochem. Parasitol. 13:243-261.
18. Hartwick, R. A., A. M. Krstulovic, and P. R. Brown. 1979 Identification and quantitation of nucleosides, bases and other UV-absorbing compounds in serum, using reversrd-phase HPLC. II. Evaluation of human sera. J. Chromatogr. 186:659-676.
19. Jadhav, A. L., L. B. Townsend, and J. A. Nelson. 1979. Inhibition of hypoxanthine-guanine phosphoribosyltransferase. Biochem. Pharmacol. 28:1057-1062.
20. Jancarik, J., and S. H. Kim. 1991. Sparse matrix sampling: a screening method for crystallization of proteins. J. Appl. Crystallogr. 24:409-411.
21. Jochimsen, B., P. Nygaard, and T. Vestergaard. 1975. Location on the chromosome of Escherichia call of genes governing purine metabolism. Mol. Gen. Genet. 143:85-91.
22. Marr, J. J. 1991. Purine analogs as chemotherapeutic agents in leishmaniasis and American trypanosomiasis. J. Lab. Clin. Med. 118:111-119.
23. Marr, J. J., and R. L. Berens. 1983. Pyrazolopyrimidine metabolism in the pathogenic Trypanosomatidae. Mol. Biochem. Parasitol. 7:339-356.
24. Marr, J. J., R. L. Berens, S. W. LaFon, and D. J. Nelson. 1981. Purine metabolism in T. cruzi. Mol. Biochem. Parasitol. 3:187-196.
25. Otwinowski, Z. 1993. DENZO, p. 56-62 In Proceedings of the CCP4 Study Weekend: Data Collection and Processing. SERC Daresbury Laboratory, Warrington, England.
26. Schramm, V. L., B. A. Horenstein, and P. C. Kline. 1994. Transition state analysis and inhibitor design for enzymatic reactions. J. Biol. Chem. 269: 18259-18262.
27. Segel, I. H. 1975. Enzyme inhibition, p. 118-120. In Enzyme kinetics. John Wiley & Sons, Inc., New York, N.Y.
28. Somoza, J. R., M. S. Chin, P. J. Focia, C. C. Wang, and R. J. Fletterick. 1996. Crystal structure of the hypoxanthine-guanine-xanthine phosphoribosyl-transferase from the protozoan parasite Tritrichomonas foetus. Biochemistry 35:7032-7040.
29. Ullman, B., and D. Carter. 1995. Hypoxanthine-guanine phosphoribosyl-transferase as a therapeutic target in protozoal infections. Infect. Agents Dis. 4:29-40.
30. Varney, M. D., G. P. Marzoni, C. L. Palmer, et al. 1992. Crystal-structure-based design and synthesis of benz[cd]indole-containing inhibitors of thymidylate synthetase. J. Med. Chem. 35:663-676.
31. Wolfendon, R. 1969. Transition state analogs for enzyme catalysis. Nature 223:704-705.
32. Yuan, L., S. P. Craig III, J. H. McKerrow, and C. C. Wang. 1990. The hypoxanthine-guanine phosphoribosyltransferase of Schistosoma mansoni. J. Biol. Chem. 265:13528-13532.
33. Yuan, L., S. P. Craig III, J. H. McKerrow, and C. C. Wang. 1992. Steady-state kinetics of the schislosomal hypoxanthine-guanine phosphoribosyl-transferase. Biochemistry 31:806-810.
34. Yuan, L., C. S. C. Wu, S. P. Craig III, A. F. Liu, J. H. McKerrow, and C. C. Wang. 1993. Comparing human and schistosomal hypoxanthine-guanine phosphoribosyltransferases by circular dichroism. Biochim. Biophys. Acta 1162:10-16.