Effectiveness of novel imidazole-dioxolane heme oxygenase inhibitors in renal proximal tubule epithelial cells

Journal of Pharmacology and Experimental Therapeutics

Volumn 323, Issue 3, 2007, Pages 763-770

  Kinobe, Robert T ^a   Ji, Yanbin ^a   Vlahakis, Jason Z ^a   Motterlini, Roberto ^b   Brien, James F ^a   Szarek, Walter A ^a   Nakatsu, Kanji ^a  

^a QUEEN S UNIVERSITY   (Canada)

^b NORTHWICK PARK INSTITUTE FOR MEDICAL RESEARCH   (United Kingdom)

Author keywords

[No Author keywords available]

Indexed keywords

1,3 DIOXOLANE DERIVATIVE; 2 [2 (4 CHLOROPHENYL)ETHYL] 2 [(1H IMIDAZOL 1 YL)METHYL] 4 [[(4 AMINOPHENYL)THIO]METHYL] 1,3 DIOXOLANE; 2 [2 (4 CHLOROPHENYL)ETHYL] 2 [(1H IMIDAZOL 1 YL)METHYL] 4 METHYL 1,3 DIOXOLANE; 3 (4,5 DIMETHYL 2 THIAZOLYL) 2,5 DIPHENYLTETRAZOLIUM BROMIDE; ADENOVIRUS VECTOR; CARBON MONOXIDE; CASPASE 3; CHROMIUM MESOPORPHYRIN CHLORIDE; COMPLEMENTARY DNA; GLIOTOXIN; GUANYLATE CYCLASE; HEME OXYGENASE 1; HEME OXYGENASE 2; HEME OXYGENASE INHIBITOR; HEMIN; IMIDAZOLE DERIVATIVE; METALLOPORPHYRIN; NITRIC OXIDE SYNTHASE; QC 1; QC 13; TUMOR NECROSIS FACTOR ALPHA; UNCLASSIFIED DRUG;

ANIMAL CELL; APOPTOSIS; ARTICLE; CELL CULTURE; CELL VIABILITY; CONTROLLED STUDY; CYTOTOXICITY; DRUG EFFICACY; DRUG STRUCTURE; ENZYME ACTIVATION; ENZYME ACTIVITY; ENZYME INHIBITION; GENETIC TRANSFECTION; KIDNEY PROXIMAL TUBULE; KIDNEY TUBULE EPITHELIUM; NONHUMAN; PRIORITY JOURNAL; PROTEIN EXPRESSION; RENAL PROTECTION;

ANIMALS; APOPTOSIS; BLOTTING, WESTERN; CARBON MONOXIDE; CELL LINE; CELL SURVIVAL; DIOXOLANES; ELECTROPHORESIS, POLYACRYLAMIDE GEL; ENZYME INHIBITORS; EPITHELIAL CELLS; HEME OXYGENASE (DECYCLIZING); IMIDAZOLES; KIDNEY TUBULES, PROXIMAL; SWINE; TRANSFECTION;

EID: 36348957425     PISSN: 00223565     EISSN: 15210103     Source Type: Journal    
DOI: 10.1124/jpet.107.119800     Document Type: Article

References (39)

1. Abraham NG and Kappas A (2005) Heme oxygenase and the cardiovascular-renal system. Free Radic Biol Med 39:1-25.
2. Akaike T, Sato K, Ijiri S, Miyamoto Y, Kohno M, Ando M, and Maeda H (1992) Bactericidal activity of alkyl peroxyl radicals generated by heme-iron-catalyzed decomposition of organic peroxides. Arch Biochem Biophys 294:55-63.
3. Balogun E, Foresti R, Green CJ, and Motterlini R (2003) Changes in temperature modulate heme oxygenase-1 induction by curcumin in renal epithelial cells. Biochem Biophys Res Commun 308:950-955.
4. Braggins PE, Trakshel GM, Kutty RK, and Maines MD (1986) Characterisation of two heme oxygenase isoforms in rat spleen: comparison with the hematin-induced and constitutive isoforms of the liver. Biochem Biophys Res Commun 141:528-533.
5. Brouard S, Berberat PO, Tobiasch E, Seldon MP, Bach FH, and Soares MP (2002) Heme oxygenase-1-derived carbon monoxide requires activation of transcription factor NF-κB to protect endothelial cells from tumor necrosis factor-α-mediated apoptosis. J Biol Chem 277:17950-17961.
6. Brouard S, Otterbein LE, Anrather J, Tobiasch E, Bach FH, Choi AM, and Soares MP (2000) Carbon monoxide generated by heme oxygenase 1 suppresses endothelial cell apoptosis. J Exp Med 192:1015-1026.
7. Clark JE, Foresti R, Green CJ, and Motterlini R (2000a) Dynamics of haem oxygenase-1 expression and bilirubin production in cellular protection against oxidative stress. Biochem J 348:615-619.
8. Clark JE, Foresti R, Sarathchandra P, Kaur H, Green CJ, and Motterlini R (2000b) Heme oxygenase-1-derived bilirubin ameliorates postischemic myocardial dysfunction. Am J Physiol Heart Circ Physiol 278:H643-H651.
9. Clark JE, Naughton P, Shurey S, Green CJ, Johnson TR, Mann BE, Foresti R, and Motterlini R (2003) Cardioprotective actions by a water-soluble carbon monoxide-releasing molecule. Circ Res 93:2-8.
10. Doré S, Takahashi M, Ferris CD, Hester LD, Guastella D, and Snyder SH (1999) Bilirubin, formed by activation of heme oxygenase-2, protects neurons against oxidative stress injury. Proc Natl Acad Sci U S A 96:2445-2450.
11. Foresti R, Clark JE, Green CJ, and Motterlini R (1997) Thiol compounds interact with nitric oxide in regulating heme oxygenase-1 induction in endothelial cells. Involvement of superoxide and peroxynitrite anions. J Biol Chem 272:18411-18417.
12. Foresti R, Sarathchandra P, Clark JE, Green CJ, and Motterlini R (1999) Peroxynitrite induces haem oxygenase-1 in vascular endothelial cells: a link to apoptosis. Biochem J 337:729-736.
13. Hall TJ and Heckel C (1990) Lack of effect of verapamil and MDL 646, a cytoprotective PGE1 analogue on cyclosporin A nephrotoxicity in vitro. Res Commun Chem Pathol Pharmacol 67:293-296.
14. 1 cells. J Pharmacol Exp Ther 290:923-928.
15. Kim Y, Zhuang H, Koehler RC, and Doré S (2005) Distinct protective mechanisms of HO-1 and HO-2 against hydroperoxide-induced cytotoxicity. Free Radic Biol Med 38:85-92.
16. Kinobe RT, Vlahakis JZ, Vreman HJ, Stevenson DK, Brien JF, Szarek WA, and Nakatsu K (2006) Selectivity of imidazole-dioxolane compounds for in vitro inhibition of microsomal haem oxygenase isoforms. Br J Pharmacol 147:307-315.
17. Laemmli UK (1970) Cleavage of structural proteins during assembly of the head of the bacteriophage T4. Nature 277:680-685.
18. Lee T and Chau L (2002) Heme oxygenase-1 mediates the anti-inflammatory effect of interleukin-10 in mice. Nat Med 8:240-246.
19. Liang M, Croatt AJ, and Nath KA (2000) Mechanisms underlying induction of heme oxygenase-1 by nitric oxide in renal tubular epithelial cells. Am J Physiol 279: F728-F735.
20. Liu XM, Chapman GB, Peyton KJ, Schafer AI, and Durante W (2002) Carbon monoxide inhibits apoptosis in vascular smooth muscle cells. Cardiovasc Res 55:396-405.
21. Maines M (1997) The heme oxygenase system: a regulator of second messenger gases. Annu Rev Pharmacol Toxicol 37:517-554.
22. Maines M (1988) Heme oxygenase: function, multiplicity, regulatory mechanisms, and clinical applications. FASEB J 2:2557-2568.
23. Marks GS, McLaughlin BE, Vreman HJ, Stevenson DK, Nakatsu K, Brien JF, and Pang SC (1997) Heme oxygenase activity and immunohistochemical localization in bovine pulmonary artery and vein. J Cardiovasc Pharmacol 30:1-6.
24. Motterlini R, Mann BE, and Foresti R (2005) Therapeutic applications of carbon monoxide-releasing molecules. Expert Opin Investig Drugs 14:1305-1318.
25. Nagothu KK, Bhatt R, Kaushal GP, and Portilla D (2005) Fibrate prevents cisplatininduced proximal tubule cell death. Kidney Int 68:2680-2693.
26. Nath KA (2006) Heme oxygenase-1: a provenance for cytoprotective pathways in the kidney and other tissues. Kidney Int 70:432-443.
27. Nath KA, Vercellotti GM, Grande JP, Miyoshi H, Paya CV, Manivel JC, Haggard JJ, Croatt AJ, Payne WD, and Alam J (2001) Heme protein-induced chronic renal inflammation: suppressive effect of induced heme oxygenase-1. Kidney Int 59:106-117.
28. Parfenova P, Basuroy S, Bhattacharya S, Tcheranova D, Qu Y, Regan RF, and Leffler CW (2006) Glutamate induces oxidative stress and apoptosis in cerebral vascular endothelial cells: contributions of HO-1 and HO-2 to cytoprotection. Am J Physiol Cell Physiol 290:C1399-C1410.
29. Polte T, Hemmerle A, Bernd G, Grosser G, Abate A, and Schröder H (2002) Atrial natriuretic peptide reduces cyclosporin toxicity in renal cells: role of cGMP and heme oxygenase-1. Free Radic Biol Med 32:56-63.
30. Ramos KS, Lin H, and McGrath JJ (1989) Modulation of cyclic guanosine monophosphate levels in cultured aortic smooth muscle cells by carbon monoxide. Biochem Pharmacol 38:1368-1370.
31. Shiraishi F, Curtis LM, Truong L, Poss K, Visner GA, Madsen K, Nick HS, and Agarwal A (2000) Heme oxygenase-1 gene ablation or expression modulates cisplatin-induced renal tubular apoptosis. Am J Physiol Renal Physiol 278:F726-F736.
32. Stocker R, McDonaugh AF, Glazer AN, and Ames BN (1990) Antioxidant activities of bile pigments: biliverdin and bilirubin. Methods Enzymol 186:301-309.
33. Tayem Y, Johnson TR, Mann BE, Green CJ, and Motterlini R (2006) Protection against cisplatin-induced nephrotoxicity by a carbon monoxide-releasing molecule. Am J Physiol Renal Physiol 290:F789-F794.
34. Tenhunen R, Marver HS, and Schmid R (1969) Heme oxygenase: characterisation of the enzyme. J Biol Chem 244:6388-6394.
35. Utz J and Ullirich V (1991) Carbon monoxide relaxes ileal smooth muscle through activation of guanylate cyclase. Biochem Pharmacol 41:1195-1201.
36. Vlahakis JZ, Kinobe RT, Bowers RJ, Brien JF, Nakatsu K, and Szarek WA (2005) Synthesis and evaluation of azalanstat analogues as heme oxygenase inhibitors. Bioorg Med Chem Lett 15:1457-1461.
37. Vlahakis JZ, Kinobe RT, Bowers RJ, Brien JF, Nakatsu K, and Szarek WA (2006) Imidazole-dioxolane compounds as isozyme-selective heme oxygenase inhibitors. J Med Chem 49:4437-4441.
38. Vreman HJ and Stevenson DK (1999) Detection of heme oxygenase activity by measurement of CO, in Current Protocols in Toxicology (Maines MD, Costa LG, Reed DJ, Sassa S, and Sipes IG eds) pp 9.2.1-9.2.10, John Wiley and Sons, New York.
39. Zhou Z, Zhao A, Goping G, and Hirszel P (2000) Gliotoxin-induced cytotoxicity proceeds via apoptosis and is mediated by caspases and reactive oxygen species in LLC-PK1 cells. Toxicol Sci 54:194-202.