Probing the inhibitor-binding site of aldose reductase with site-directed mutagenesis

European Journal of Biochemistry

Volumn 256, Issue 2, 1998, Pages 310-316

  Hohman, Thomas C ^a   El Kabbani, Ossama ^b   Malamas, Michael S ^a   Lai, Kehdih ^a   Putilina, Tatiana ^c   McGowan, Michelle H ^c   Wane, Yi Qun ^c   Carper, Deborah A ^c  

^a PFIZER INC   (United States)

^b MONASH UNIVERSITY   (Australia)

^c NATIONAL EYE INSTITUTE   (United States)

Author keywords

Diabetes; Enzyme inhibition; Human aldose reductase; Polyol pathway; Site directed mutagenesis

Indexed keywords

6 FLUORO 1 (5 TRIFLUOROMETHYL 2 BENZOTHIAZOLYL)SPIRO[ISOQUINOLINE 4,3' PYRROLIDINE] 1,2',3,5' TETRONE; 6 FLUORO 2 METHYLSPIRO[ISOQUINOLINE 4,3' PYRROLIDINE] 1,2',3,5' TETRONE; ALDEHYDE REDUCTASE; ENZYME INHIBITOR; IMIRESTAT; MINALRESTAT; PONALRESTAT; SORBINIL; TOLRESTAT; UNCLASSIFIED DRUG; ZENARESTAT; ZOPOLRESTAT;

ARTICLE; CRYSTAL STRUCTURE; DISSOCIATION CONSTANT; ENZYME ACTIVE SITE; ENZYME BINDING; ENZYME INHIBITION; ESCHERICHIA COLI; GENE CONSTRUCT; HUMAN; IN VITRO STUDY; MOLECULAR MODEL; PLASMID; PRIORITY JOURNAL; PROTEIN EXPRESSION; SITE DIRECTED MUTAGENESIS; SPECTROPHOTOMETRY;

ANIMALIA; ESCHERICHIA COLI;

EID: 0031719890     PISSN: 00142956     EISSN: None     Source Type: Journal    
DOI: 10.1046/j.1432-1327.1998.2560310.x     Document Type: Article

References (32)

1. Gonzalez, R., Barneu, P., Aguayo, J., Chen, H. M. & Chylack, L. T. Jr (1984) Direct measurement of polyol pathway activity in the ocular lens. Diabetes 33, 196-199.
2. Kinoshita, J. H. & Nishimura, C. (1988) The involvement of aldose reductase in diabetic complications. Diabetes Metab. Rev. 4, 323-337.
3. Kirchain, W. R. & Rendell, M. S. (1990) Aldose reductase inhibitors, Pharmacotherapy 10, 326-336.
4. Cameron, N. E., Cotter, M. A., Dines, K. C., Maxfield, E. K., Carey, E. & Mirrlees, D. J. (1994) Aldose reductase inhibition, nerve perfusion, oxygenation and function in streptozotocin-diabetic rats: dose-response considerations and independence from a myoinositol mechanism, Diabetologia 37, 651-663.
5. Greene, D., Arezzo, J., Brown, M. & The Zenarestat Study Group (1996) Dose related effects of the aldose reductase inhibitor Zenarestat on nerve sorbitol levels, nerve conduction velocity and nerve fiber density in human diabetic neuropathy, Diabetes 45, 5A.
6. Hohman, T. C. Bochenek, W. J., Meng, X., Neefe, L., Beg, M. & The ARI-509 Development Team (1997) Rapid improvement of nerve conduction velocity in diabetic patients treated with a potent aldose reductase inhibitor, J. Periph. Nerv. Syst. 2, 272.
7. Yamaoka, T., Matsuura, Y., Yamashita, K., Tanimoto, T. & Nishimura, C. (1992) Site-directed mutagenesis of His-42, His-188, and Lys-263 of human aldose reductase, Biochem. Riophys. Res. Commun. 183, 327-333.
8. Pelrash, J. M, Harter, T. M., Devine, C. S., Olins, P. O., Bhatnagar, A., Liu, S. Q. & Srivastava, S. K. (1992) Involvement of cysteine residues in catalysis and inhibition of human aldose reductase. Site-directed mutagenesis of Cys-80, -298 and -303, J. Biol. Chem. 267, 24833-24840.
9. Bhatnagar, A., Liu, S. Q., Ueno, N., Chakrabarti, B. & Srivastava, S. K. (1994) Human placental aldose reductase: role of Cys-298 in substrate and inhibitor binding. Biochim. Biophys. Acta 1205, 207-214.
10. +/ NADPH and alrestatin-like inhibitors, Biochemistry 33, 7157-7165.
11. Carper, D. A., Hohman, T. C. & Old, S. E. (1995) Residues affecting the catalysis and inhibition of rat lens aldose reductase, Biochim. Biophys. Acta 1246, 67-73.
12. Wilson, D. K., Tarle, I., Petrash, J. M. & Quiocho, F. A. (1993) Refined 1.8 Å structure of human aldose reductase complexed with the potent inhibitor Zopolrestat, Proc. Natl Acad. Sci. USA 90, 9847-9851.
13. Harrison, D. H., Bohren, K. M., Ringe, D., Petsko, G. A. & Gabbay, K. H. (1994) An anion hinding site in human aldose reductase: mechanistic implications for the binding of citrate, cacodylate, and glucose 6-phosphate, Biochemistry 33, 2011-2020.
14. Kador, P. F., Lee, Y. S., Rodriguez, L., Sato, S., Bartoszko-Malik, A., Abdel-Ghany, Y. S. & Miller, D. D. (1995) Identification of an aldose reductase inhibitor site by affinity labeling, Bioorg. Med. Chem. 3, 1313-1324.
15. Constantino, L., Rastelli, G., Vescovini, K., Cignarella, G., Vianello, P., Del Corso, A., Capiello, M., Mura, U. & Barlocco, D. (1996) Synthesis, activity, und molecular modeling of a new series of tricyclic pyridazinones as selective aldose reductase inhibitors, J. Med. Chem. 39, 4396-4405.
16. Urzhumtsev, A., Tete-Favier, F., Mitschler, A., Barbanton, J., Barath, P., Urzhumtseva, L., Biellmann, J.-F., Podjamy, A. D. & Moras, D. (1997) A 'specificity' pocket inferred from the crystal structures of the complexes of aldose reductase with the pharmaceutically important inhibitors Tolrestat and Sorbinil, Structure 5, 601-612.
17. Wilson, D. K., Bohren, K. M., Gabbay, K. H. & Quiocho, F. A. (1992) An unlikely sugar substrate site in the 1.6.1 Å structure of human aldose reductase holoenzyme implicated in diabetic complications. Science 257, 81-84.
18. El-Kabbani, O., Carper, D. A., McGowan, M. H. & Ginell, S. L. (1996) Crystal structure of porcine aldehyde reductase at 2.0 Å resolution: modeling an inhibitor in the active site of the enzyme, Protein Peptide Lett. 3, 427-434.
19. Brunger, A. T., Krukowski, A. & Erickson, J. (1990) Slow-cooling protocol for cristallographic refinement by simulated annealing, Acta Crytallogr. A46, 585-593.
20. Carper, D., Sato, S., Old, S., Chung, S. & Kador, P. F. (1990) In vitro expression of human placental aldose reductase in Escherichia coli, in Enzymology and molecular biology of carbonyl metabolism 3 (Weiner, H., Wermuth, B. & Crabb, D. W., eds) pp. 129-138, Plenum, New York.
21. Jones, D. H. & Howard, B. H. (1990) A rapid method for site-specific mutagenesis and directional subcloning by using the polymerase chain reaction to generate recombinant circles, Biotechniques 8, 178-183.
22. Grundmann, U., Bohn, H., Obermeier, R. & Amann, E. (1990) Cloning and prokaryotic expression of a biologically active human placental aldose reductase, DNA Cell Biol. 9, 149-157.
23. Bradford, M. M. (1976) A rapid and sensitive method for the quantitation of microgram quantities of protein utilizing the principle of protein-dye binding, Anal. Biochem. 72, 248-254.
24. Grimshaw, C. E., Shahbaz, M. & Putney, C. G. (1990) Mechanistic basis for nonlinear kinetics of aldehyde reduction catalyzed by aldose reductase, Biochemistry 29, 9947-9955.
25. Armitage, P. & Berry, G. (1987) Sampling, in Statistical methods in medical research, pp. 91, Blackwell Scientific Publications, London, England.
26. Carroll, R. J. & Ruppert, D. (1988) Transformation and weighting regression, Chapman and Hall, New York NY.
27. Kubiseski, T. J. & Flynn, T. G. (1995) Studies on human aldose reductase, J. Biol. Chem. 270, 16911-16917.
28. Tarle, I., Borhani, D. W., Wilson, D. K., Quiocho, F. A. & Petrash, J. M. (1993) Probing the active site of human aldose reductase. Site directed mutagenesis of Asp-43, Tyr-48, Lys-77, and His-110, J. Biol. Chem. 268, 25687-25693.
29. Grimshaw, C. E., Bohren, K. M., Lai, C.-J. & Gabbay, K. H. (1995) Human aldose reductase: rate constants for a mechanism including interconversion of ternary complexes by recombinant wild-type enzyme, Biochemistry 34, 14356-14365.
30. Bohren, K. M., Page, J. L., Shankar, R., Henry, S. P. & Gabbay, K. H. (1991) Expression of human aldose and aldehyde reductases, J. Biol. Chem. 266, 24031-24037.
31. Tsai, M.-D. & Yan, H. (1991) Mechanism of adenylate kinase: site-directed mutagenesis versus X-ray and NMR, Biochemistry 30, 6806-6818.
32. Bohren, K. M., Grimshaw, C. E., Lai, C.-J., Harrison, D. H., Ringe, D., Petsko, G. A. & Gabbay, K. H. (1994) Tyrosine-48 is the proton donor and histidine-110 directs substrate stereochemical selectivity in the reduction reaction of human aldose reductase: enzyme kinetics and the crystal structure of the Y48H mutant enzyme, Biochemistry 33, 2021-2032.