Transition-state analogs as inhibitors of human and malarial hypoxanthine-guanine phosphoribosyltransferases

Nature Structural Biology

Volumn 6, Issue 6, 1999, Pages 582-587

  Li, Caroline M ^a   Tyler, Peter C ^b   Furneaux, Richard H ^b   Kicska, Gregory ^a   Xu, Yiming ^c   Grubmeyer, Charles ^c   Girvin, Mark E ^a   Schramm, Vern L ^a  

^a ALBERT EINSTEIN COLLEGE OF MEDICINE   (United States)

^b CALLAGHAN INNOVATION   (New Zealand)

^c TEMPLE UNIVERSITY SCHOOL OF MEDICINE   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

HYDROGEN; HYPOXANTHINE PHOSPHORIBOSYLTRANSFERASE; NUCLEOTIDE; PROTON; TRANSFERASE INHIBITOR;

ARTICLE; BINDING AFFINITY; DRUG MECHANISM; DRUG SYNTHESIS; ENZYME INHIBITION; ENZYME STRUCTURE; HUMAN; MICHAELIS CONSTANT; NONHUMAN; PLASMODIUM; PRIORITY JOURNAL; PROTOZOON; SPECIES DIFFERENCE;

5'-GUANYLIC ACID; ANIMALS; BINDING SITES; CATALYSIS; DIPHOSPHATES; DRUG DESIGN; ENZYME INHIBITORS; HUMANS; HYDROGEN BONDING; HYPOXANTHINE; HYPOXANTHINE PHOSPHORIBOSYLTRANSFERASE; INOSINE MONOPHOSPHATE; KINETICS; MAGNESIUM COMPOUNDS; NUCLEAR MAGNETIC RESONANCE, BIOMOLECULAR; PHOSPHORIBOSYL PYROPHOSPHATE; PHOSPHORYLATION; PLASMODIUM FALCIPARUM; PROTEIN BINDING; PROTONS; PYRIMIDINONES; PYRROLES;

PROTOZOA;

EID: 0033017467     PISSN: 10728368     EISSN: None     Source Type: Journal    
DOI: 10.1038/9367     Document Type: Article

References (34)

1. Berens, R.L., Krug, E.C. & Marc, J.J. in Biochemistry of parasitic organisms and its molecular foundations (eds Marr, J.J. & Muller, M.) 89-117 (Academic Press. London; 1995).
2. Berrnan, P.A., Human, L. & Freese, J.A. Xanthine oxidase inhibits growth of Plasmodium falciparum in human erythrocytes in vitro. J. Clin. Invest. 88, 1848-1855 (1991).
3. Nchinda, T.C. Malaria: a reemerging disease in Africa. Emerg. Infect. Dis. 4, 398-403 (1998).
4. Jadhav, A.L, Townsend, L.B. & Nelson, J.A. Inhibition of hypoxanthine-guanine phosphoribosyltransferase. Biochem. Pharmacol. 28, 1057-1062 (1979).
5. Bennett, L.L. et al. Inhibition of utilization of hypoxanthine and guanine in cells treated with the carbocyclic analog of adenosine. Phosphates of carbocyclic nucleoside analogs as inhibitors of hypoxanthine (guanine) phosphoribosyltransferase. Mol. Pharmacol. 27, 666-675 (1985).
6. Eakin, A.E., Guerra, A., Focia, P.J., Torres-Martinez, J. & Craig, S.P. Hypoxanthine phosphoribosyltransferase from Trypanosoma cruzi as a target for structure-based inhibitor design: crystallization and inhibition studies with purine analogs. Antimicrob. Agents Chemother. 41, 1686-1692 (1997).
7. Somoza, J.R. et al. Rational design of novel antimicrobials blocking purine salvage in a parasitic protozoan. Biochemistry 37, 5344-5348 (1998).
8. Queen, S.A., Vander Jagt, D.L. & Reyes, P. In vitro susceptibilities of Plasmodium falciparum to compounds which inhibit nucleotide metabolism. Antimicrob. Agents Chemother. 34, 1393-1398 (1990).
9. Tao, W., Grubmeyer, C. & Blanchard, J.S. Transition state structure of Salmonella typhimurium orotate phosphoribosyltransferase. Biochemistry 35, 14-21 (1996).
10. Schramm, V.L. Enzymatic N-riboside scission in RNA and RNA precursors. Curr. Opin. Chem. Biol. 1, 323-331 (1997).
11. Miles, R.W., Tyler, P.C., Furneaux, R.H., Bagdassarian, C.K. & Schramm, V.L. One-third-the-sites transition state inhibitors for purine nucleoside phosphorylase. Biochemistry 37, 8615-8621 (1998).
12. Focia, P.J., Craig, S.P. & Eakin, A.E. Approaching the transition state in the crystal structure of a phosphoribosyltransferase. Biochemistry 37, 17120-17127 (1998).
13. Shi, W. et al. The 2.0 Å structure of human hypoxanthine-guanine phosphoribosyltransferase in complex with a transition-state analog inhibitor. Nature Struct. Biol. 6, (1999).
14. Xu, Y. & Grubmeyer, C. Catalysis in human hypoxanthine-guanine phosphoribosyltransferase: Asp-137 aas as a general acid/base. Biochemistry 37. 4114-4124 (1998).
15. Xu, Y., Eads, J.C, Sacchettini, J.C. & Grubmeyer, C. Kinetic mechanism of human hypoxanthine-guanine phosphoribosyltransferase: rapid phosphoribosyl transfer chemistry. Biochemistry 36, 3700-3712 (1997).
16. Morrison, J.F. & Walsh, C.T. The behavior and significance of slow-binding enzyme inhibitors. Adv. Enzymol. 61, 201-301 (1988).
17. Cleland, W.W. & Kreevoy, M.M. Low-barrier hydrogen bonds and enzymic catalysis. Science 264, 1887-1890 (1994).
18. Shan, S-O. & Herschlag, D. The change in hydrogen bond strength accompanying charge rearrangement: implications for enzymatic catalysis. Proc. Natl. Acad. Sci. USA 93, 14474-14479 (1996).
19. Gerlt, J.A. & Gassman, P.G. An explanation for rapid enzyme-catalyzed proton abstraction from carbon acids: importance of late transition states in concerted mechanisms. J. Am. Chem. Soc. 115, 11552-11568 (1993).
20. 1SN NMR studies with peptidyl trifluoromethyl ketones. Biochemistry 35, 15941-15948 (1996).
21. Kahyaoglu, K.A. et al. Low barrier hydrogen bond is absent in the ground state but is present in a transition-state complex in the prolyl oligopeptidase family of serine proteases. J. Biol. Chem. 272, 25547-25554 (1997).
22. Zhao, Q., Abeygunawardana, C., Gittis, A.G. & Mildvan, A.S. Hydrogen bonding at the active site of delta 5,3-ketosteroid isomerase. Biochemistry 36, 14616-14626 (1997).
23. Eigen, M. Proton transfer, acid-base catalysis, and enzymatic hydrolysis. Part I: Elementary processes. Angew. Chem. Int. Edn. Engl. 33, 1-72 (1964).
24. Horenstein, B.A., Zabinski, R.F. & Schramm, V.L. A new class of C-nucleoside analogs. 1-(S)-aryl-1,4-dideoxy-1,4-imino-D-ribitols, transition state analog inhibitors of nucleoside hydrolase. Tetrahedr. Lett. 34, 7213-7216 (1993).
25. Furneaux, R.H., Limberg, G., Tyler, P.C. & Schramm, V.L. Synthesis of transition state inhibitors for N-riboside hydrolases and transferases. Tetrahedron 53, 2915-2930 (1997).
26. Lim, M-I., Ren, W-Y, Otter, B.A. & Kline, R.S. Synthesis of 9-deazaguanosine and other new pyrrolo[3,2-d]pyrimidine C-nucleosides. J. Org. Chem. 48, 780-788 (1983).
27. Bennett, L.W., Comber, R.N. & Secrist, J.A. Differences in the metabolism and metabolic effects of the carbocyclic adenosine analogs, neplanocin A and aristeromycin. Mol. Pharmacol. 29, 383-390 (1986).
28. Merkler, D.J. & Schramm, V.L. A preparative method for the enzymatic 5′-monophosphorylation of nucleosides. Anal. Biochem. 167, 148-153 (1987).
29. Brennard, J., Konecki, D.S. & Caskey, C.T. Expression of human and Chinese hamster hypoxanthine-guanine phosphoribosyltransferase cDNA recombinants in cultured Lesch-Nyhan and Chinese hamster fibroblasts. J. Biol. Chem. 258, 9593-9598 (1983).
30. Eads, J.C., Scapin, G., Xu, Y., Grubmeyer, C. & Sacchettini, J.C. The crystal structure of human hypoxanthine-guanine phosphoribosyltransferase with bound GMP. Cell 78, 325-334 (1994).
31. Schramm, V.L. Comparison of initial velocity and binding data for allosteric adenosine monophosphate nucleosidase. J. Biol. Chem. 251, 3417-3424 (1976).
32. Plateau, P. & Guéron, M. Exchangeable proton NMR without base-line distortion, using new strong-pulse sequences. J. Am. Chem. Soc. 104, 7310-7311 (1982).
33. Bax, A., Griffey, R.H. & Hawkins, B.L. Correlation of proton and nitrogen-15 chemical shifts by multiple quantum NMR. J. Magn. Reson. 55, 301-315 (1983).
34. Horenstein, B.A. & Schramm, V.L. Correlation of the molecular electrostatic potential surface of an enzymatic transition state with novel transition state inhibitors. Biochemistry 32, 9917-9925 (1993).