Potent isozyme-selective inhibition of human glutathione S-transferase A1-1 by a novel glutathione S-conjugate

Amino Acids

Volumn 29, Issue 3, 2005, Pages 255-261

  Cacciatore, I ^a   Caccuri, A M ^b   Cocco, A ^a   De Maria, F ^b   Di Stefano, A ^a   Luisi, G ^a   Pinnen, F ^a   Ricci, G ^b   Sozio, P ^a   Turella, P ^b  

^a UNIVERSITY OF CHIETI   (Italy)

^b UNIVERSITY OF ROME TOR VERGATA   (Italy)

Author keywords

Glutamyl transpeptidase; Glutathione; Glutathione S conjugate; Glutathione S transferase inhibitors; Pseudopeptide

Indexed keywords

ANTINEOPLASTIC AGENT; CYSTEINYLGLYCINE; GAMMA GLUTAMYL(9 FLUORENYLMETHYL)CYSTEINYL GLYCINE; GAMMA GLUTAMYLTRANSFERASE; GAMMA(GAMMA OXA)GLUTAMYL(9 FLUORENYLMETHYL)CYSTEINYL GLYCINE; GLUTATHIONE TRANSFERASE; GLUTATHIONE TRANSFERASE A1; GLUTATHIONE TRANSFERASE INHIBITOR; ISOENZYME; PEPTIDE; PSEUDOPEPTIDE; TRANSFERASE INHIBITOR; UNCLASSIFIED DRUG;

ARTICLE; BIOLOGICAL ACTIVITY; CONJUGATE; DETOXIFICATION; DRUG INHIBITION; DRUG STRUCTURE; DRUG SYNTHESIS; GLUTATHIONE METABOLISM; IC 50; PEPTIDE SYNTHESIS; PRIORITY JOURNAL; STEREOCHEMISTRY; TUMOR RESISTANCE;

DRUG EVALUATION, PRECLINICAL; ENZYME INHIBITORS; FLUORENES; GLUTATHIONE; GLUTATHIONE S-TRANSFERASE PI; GLUTATHIONE TRANSFERASE; HUMANS; ISOENZYMES; MOLECULAR STRUCTURE; STRUCTURE-ACTIVITY RELATIONSHIP;

EID: 28644443832     PISSN: 09394451     EISSN: None     Source Type: Journal    
DOI: 10.1007/s00726-005-0232-7     Document Type: Article

References (26)

1. AE Adang J Brussee DJ Meyer B Coles B Ketterer A van der Gen GJ Mulder 1988 Substrate specificity of rat liver glutathione S-transferase isoenzymes for a series of glutathione analogues, modified at the gamma-glutamyl moiety. Biochem J 255 721 724
2. M Bodanszky MA Bednarek 1982 Derivatives of S-9-fluorenylmethyl-L- cysteine. Int J Pept Protein Res 20 434 437
3. MG Bolton OM Colvin J Hilton 1991 Specificity of isozymes of murine hepatic glutathione S-transferase for the conjugation of glutathione with L-phenylalanine mustard. Cancer Res 51 2410 2415
4. D Burg GJ Mulder 2002 Glutathione conjugates and their synthetic derivatives as inhibitors of glutathione-dependent enzymes involved in cancer and drug resistance. Drug Metab Rev 34 821 863
5. I Cacciatore AM Caccuri A Di Stefano G Luisi M Nalli F Pinnen G Ricci P Sozio 2003 Synthesis and activity of novel glutathione analogues containing an urethane backbone linkage. Il Farmaco 58 787 793
6. A Calcagni S Duprè G Lucente G Luisi F Pinnen D Rossi 1995 Synthesis and activity of the glutathione analogue γ-(L-γ- azaglutamyl)-L-cysteinyl-glycine. Int J Pept Protein Res 46 434 439
7. A Calcagni S Duprè G Lucente G Luisi F Pinnen D Rossi A Spirito 1996 Synthesis and activity of the glutathione analogue γ-(L-γ- oxaglutamyl)-L-cysteinyl-glycine. Arch Pharm Pharm Med Chem 329 498 502
8. W Davies Jr Z Ronai KD Tew 2001 Cellular thiols and reactive oxygen species in drug-induced apoptosis. J Pharmacol Exp Ther 296 1 6
9. HA Dirven B van Ommen PJ van Bladeren 1994 Involvement of human glutathione S-transferase isoenzymes in the conjugation of cyclophosphamide metabolites with glutathione. Cancer Res 54 6215 6220
10. N Fotouhi-Ardakani A Woo M Lewandowska R Schecter G Batist 1998 Identification of the Yc1 glutathione S-transferase mRNA as the overexpressed species in a nitrogen mustard-resistant rat mammary carcinoma cell line. J Biochem Mol Toxicol 12 11 17
11. G Han M Tamaki VJ Hruby 2001 Fast, efficient and selective deprotection of the tert-butoxycarbonyl (Boc) group using HCl/dioxane (4∈M). J Peptide Res 58 338 341
12. JD Hayes JU Flanagan IR Jowsey 2005 Glutathione transferases. Annu Rev Pharmacol Toxicol 45 51 88
13. RT Koehler HO Villar KE Bauer DL Higgins 1997 Ligand-based protein alignment and isozyme specificity of glutathione S-transferase inhibitors. Proteins: Structure, Function, and Genetics 28 202 216
14. M Lang O Pelkonen 1999 Metabolism of xenobiotics and chemical carcinogenesis. IARC Sc Publ 148 13 22
15. AD Lewis ID Hickson CN Robson AL Harris JD Hayes SA Griffiths MM Manson AE Hall JE Moss CR Wolf 1988 Amplification and increased expression of alpha class glutathione S-transferase-encoding genes associated with resistance to nitrogen mustards. Proc Natl Acad Sci USA Cell Biol 85 8511 8515
16. M Lo Bello A Battistoni AP Mazzetti PG Board M Muramatsu G Federici G Ricci 1995 Site-directed mutagenesis of human glutathione transferase P1-1. Spectral, kinetic, and structural properties of Cys-47 and Lys-54 mutants. J Biol Chem 270 1249 1253
17. 2. Tetrahedron Lett 34 2391 2392
18. F Morel WA Schulz H Sies 1994 Gene structure and regulation of expression of human glutathione S-transferases alpha. Biol Chem Hoppe Seyler 375 641 649
19. AS Morgan PJ Ciaccio KD Tew LM Kauvar 1996 Isozyme-specific glutathione S-transferase inhibitors potenziate drug sensitivity in cultured human tumor cell lines. Cancer Chemother Pharmacol 37 363 370
20. AJ Oakley M Lo Bello A Battistoni G Ricci J Rossjohn HO Villar MW Parker 1997 The structures of human glutathione transferase P1-1 in complex with glutathione and various inhibitors at high resolution. J Mol Biol 274 84 100
21. ML O'Brien KD Tew 1996 Glutathione and related enzymes in multidrug resistance. Eur J Cancer 32 A 967 978
22. M Paglialunga Paradisi A Mollica I Cacciatore A Di Stefano F Pinnen AM Caccuri G Ricci S Duprè A Spirito G Lucente 2003 Proline-glutamate chimeras in isopeptides. Synthesis and biological evaluation of conformationally restricted glutathione analogues. Bioorg Med Chem 11 1677 1683
23. A Pompella A Visvikis A Paolicchi V De Tata AF Casini 2003 The changing faces of glutathione, a cellular protagonist. Biochem Pharmacol 66 1499 1503 and references therein
24. AE Salinas MG Wong 1999 Glutathione S-transferases - A Review. Curr Med Chem 6 279 309
25. M Schultz S Dutta KD Tew 1997 Inhibitors of glutathione S-transferases as therapeutic agents. Adv Drug Deliver Rev 26 91 104
26. MCJ Wilce MW Parker 1994 Structure and function of glutathione S-transferases. Biochim Biophys Acta 1205 1 18