Inhibition of human placenta glutathione transferase P1-1 by the antibiotic calvatic acid and its diazocyanide analogue evidence for multiple catalytic intermediates

European Journal of Biochemistry

Volumn 245, Issue 3, 1997, Pages 663-667

  Antonini, Giovanni ^a,b   Pitari, Giuseppina ^a   Caccuri, Anna Maria ^c   Ricci, Giorgio ^c   Boschi, Donatella ^d   Fruttero, Roberta ^d   Gasco, Alberto ^d   Ascenzi, Paolo ^b,e  

^a UNIVERSITY OF L'AQUILA   (Italy)

^b SAPIENZA UNIVERSITY OF ROME   (Italy)

^c UNIVERSITY OF ROME TOR VERGATA   (Italy)

^d UNIVERSITY OF TURIN   (Italy)

^e ROMA TRE UNIVERSITY   (Italy)

Author keywords

calvatic acid; cysteine oxidation; enzyme inhibition; human placenta glutathione transferase; kinetics

Indexed keywords

ANTIBIOTIC AGENT; CALVATIC ACID; GLUTATHIONE TRANSFERASE; UNCLASSIFIED DRUG;

ARTICLE; ENZYME LOCALIZATION; ENZYME MECHANISM; HUMAN; INHIBITION KINETICS; MOLECULAR DYNAMICS; MOLECULAR INTERACTION; OXIDATION; PLACENTA; PRIORITY JOURNAL;

EID: 0031006947     PISSN: 00142956     EISSN: None     Source Type: Journal    
DOI: 10.1111/j.1432-1033.1997.00663.x     Document Type: Article

References (32)

1. Antonini, E., Ascenzi, P., Bolognesi, M., Menegatti, E. & Guarneri, M. (1983) Transient removal of proflavine inhibition of bovine β-trypsin by the bovine basic pancreatic trypsin inhibitor (Kunitz): a case for 'chronosteric effects', J. Biol. Chem. 258, 4676-4678.
2. Armstrong, R. N. (1991) Glutathione S-transferase: reaction mechanism, structure, and function, Chem. Res. Toxicol. 4, 131-140.
3. Armstrong, R. N. (1994) Glutathione S-transferase: structure and mechanism of an archetypical detoxication enzyme, Adv. Enzymol. Relat. Areas Mol. Biol. 69, 1-44.
4. Caccuri, A. M., Polizio, F., Piemonte, F., Tagliatesta, P., Federici, G. & Desideri, A. (1992) Investigation of the active site of human placenta glutathione transferase π by means of a spin-labeled glutathione analogue, Biochim. Biophys. Acta 1122, 265-268.
5. Caccuri, A. M., Ricci, G., Desideri, A., Buffa, M., Fruttero, R., Gasco, A. & Ascenzi, P. (1994) Inhibition of human placenta glutathione transferase PI-1 by calvatic acid, Biochem. Mol. Biol. Int. 32, 819-829.
6. Caccuri, A. M., Ascenzi, P., Antonini, G., Parker, M. W., Oakley, A. J., Chiessi, E., Nuccetelli, M., Battistoni, A., Bellizia, A. & Ricci, G. (1996) Structural flexibility modulates the activity of human glutathione transferase PI-1: influence of a poor co-substrate on dynamics and kinetics of human glutalhione transferase, J. Biol. Chem. 271, 16193-16198.
7. Calvino, R., Fruttero, R., Gasco, A., Miglietta, A. & Gabriel, L. (1986) Chemical and biological studies on calvatic acid and its analogs, J. Antibiot. (Tokyo) 39, 864-868.
8. Cleland, W. W. (1964) Dithiothreitol, a new protective reagent for SH groups, Biochemistry 3, 480-482.
9. Coles, B. & Ketterer, B. (1990) The role of glutathione transferases in chemical carcinogenesis, Crit. Rev. Biochem. Mol. Biol. 25, 47-70.
10. Ellman, G. L. (1959) Tissue sulfhydryl groups, Arch. Biochem. Biophys. 82, 70-77.
11. Gadoni, E., Miglietta, A., Olivero, A. & Gabriel, L. (1989) Phenylazoxycyanide damages microtubular protein more than its reference antibiotic, calvatic acid, Biochem. Pharmacol. 38, 1121-1124.
12. Gasco, A., Serafino, A., Mortarini, V., Bianco, M. A. & Scurti, J. C. (1974) An antibacterial and antifungal compound from Calvatia lilacina, Tetrahedron Lett. 38, 3431-3432.
13. Habig, W. H., Pabst, M. J. & Jakoby, W. B. (1974) Glutathione S-transferases: the first enzymatic step in mercapturic acid formation, J. Biol. Chem. 249, 7130-7139.
14. Haverkate, F., Tempel, A. & Pluijgers, C. W. (1971) Interaction of benzenediazocyanides with fungal spores and its relation to their stability in light, Recl. Trav. Chim. 90, 641-653.
15. Henry, E. R. & Hofrichter, J. (1992) Singular value decomposition: application to analysis of experimental data, Methods Enzymol. 210, 129-192.
16. Lo Bello, M., Battistoni, A., Mazzetti, A. P., Board, P. G., Muramatsu, M., Federici, G. & Ricci, G. (1995) Site-directed mutagenesis of human glutathione transferase PI-1: spectral, kinetic, and structural properties of Cys-47 and Lys-54 mutants, J. Biol. Chem. 270, 1249-1253.
17. Lowry, O. H., Rosebrough, N. J., Farr, A. L. & Randall, R. J. (1951) Protein measurement with the folin phenol reagent, J. Biol. Chem. 193, 265-275.
18. Mannervik, B. (1985) The isoenzymes of glutathione transferase, Adv. Enzymol. Relat. Areas Mol. Biol. 57, 357-417.
19. Mannervik, B. & Danielson, U. H. (1988) Glutathione transferases: structure and catalytic activity, CRC Crit. Rev. Biochem. 23, 283-337.
20. Mannervik, B., Alin, P., Guthenberg, C., Jensson, H., Tahir, M. K., Warholm, M. & Jörnvall, H. (1985) Identification of three classes of cytosolic glutathione transferase common to several mammalian species: correlation between structural data and enzymatic properties, Proc. Natl Acad. Sci. USA 82, 7202-7206.
21. Mannervik, B., Awasthi, Y. C., Board, P. G., Hayes, J. D., Di Ilio, C., Ketterer, B., Listowsky, I., Morgenstern, R., Muramatsu, M., Pearson, W. R., Pickett, C. B., Sato, K., Widersten, M. & Wolf, R. (1992) Nomenclature for human glutathione transferases, Biochem. J. 282, 305-306.
22. Meyer, D. J. & Thomas, M. (1995) Characterization of rat spleen prostaglandin H D-isomerase as a sigma-class GSH transferase, Biochem. J. 311, 739-742.
23. Meyer, D. J., Coles, B., Pemble, S. E., Gilmore, K. S., Fraser, G. M. & Ketterer, B. (1991) Theta, a new class of glutathione transferases purified from rat and man, Biochem. J. 274, 409-414.
24. O'Brien, M. L. & Tew, K. D. (1996) Glutathione and related enzymes in multidrug resistance, Eur. J. Cancer 32A, 967-978.
25. Reinemer, P., Dirr, H. W., Ladenstein, R., Huber, R., Lo Bello, M., Federici, G. & Parker, M. W. (1992) Three-dimensional structure of class π glutathione S-transferase from human placenta in complex with S-hexylglutathione at 2.8 Å resolution, J. Mol. Biol. 227, 214-226.
26. Ricci, G., Del Boccio, G., Pennelli, A., Aceto, A., Whitehead, E. P. & Federici, G. (1989) Nonequivalence of the two subunits of horse erythrocyte glutathione transferase in their reaction with sulfhydryl reagents, J. Biol. Chem. 264, 5462-5467.
27. Ricci, G., Del Boccio, G., Pennelli, A., Lo Bello, M., Petruzzelli, R., Caccuri, A. M., Barra, D. & Federici, G. (1991) Redox forms of human placenta glutathione transferase, J. Biol. Chem. 266, 21409-21415.
28. Ricci, G., Caccuri, A. M., Lo Bello, M., Rosato, N., Mei, G., Nicotra, M., Chiessi, E., Mazzetti, A. P. & Federici, G. (1996) Structural flexibility modulates the activity of human glutathione transferase PI-1: role of helix 2 flexibility in the catalytic mechanism, J. Biol. Chem. 271, 16187-16192.
29. 1 adrenoreceptors, Bioorg. Med. Chem. 3, 173-178.
30. Umezawa, H., Takeuchi, T., Iinuma, H., Ito, M., Ishizuka, M., Kurakata, Y., Umeda, Y. Nakanishi, Y. Nakamura, T., Obayashi, A. & Tanabe, O. (1975) A new antibiotic, calvatic acid, J. Antibiol. (Tokyo) 28, 87-90.
31. Waxman, D. J. (1990) Glutathione S-transferases: role in alkylating agent resistance and possible target for modulation chemoterapy, Cancer Res. 50, 6449-6454.
32. Wilce, M. C. J. & Parker, M. W. (1994) Structure and function of glutathione S-transferase, Biochim. Biophys. Acta 1205, 1-18.