Small-molecular inhibitors of Ca2+-induced mitochondrial permeability transition (MPT) derived from muscle relaxant dantrolene

Bioorganic and Medicinal Chemistry

Volumn 20, Issue 21, 2012, Pages 6384-6393

  Murasawa, Shinpei ^a   Iuchi, Katsuya ^b,c,d   Sato, Shinichi ^a,e   Noguchi Yachide, Tomomi ^a   Sodeoka, Mikiko ^b,c   Yokomatsu, Tsutomu ^f   Dodo, Kosuke ^b,c   Hashimoto, Yuichi ^a   Aoyama, Hiroshi ^f  

^a UNIVERSITY OF TOKYO   (Japan)

^b JAPAN SCIENCE AND TECHNOLOGY AGENCY   (Japan)

^c RIKEN   (Japan)

^d NIPPON MEDICAL SCHOOL   (Japan)

^e GAKUSHUIN UNIVERSITY   (Japan)

^f TOKYO UNIVERSITY OF PHARMACY AND LIFE SCIENCES   (Japan)

Author keywords

Cyclophilin A; Cyclophilin D; Dantrolene; Ischemia reperfusion; Mitochondrial permeability transition (MPT); Mitochondrial swelling

Indexed keywords

1 [[5 (3,5 DICHLOROPHENYL)FURFURYLIDENE]AMINO] 3 METHYLIMIDAZOLIDINE 2,4 DIONE; 3 (3 AMINOBENZYL) 1 [[5 (3 CHLOROPHENYL)FURFURYLIDENE]AMINO]IMIDAZOLIDINE 2,4 DIONE; 3 (3 AMINOBENZYL) 1 [[5 (3,5 DICHLOROPHENYL)FURFURYLIDENE]AMINO]IMIDAZOLIDINE 2,4 DIONE; 5 (3 CHLOROPHENYL) N (2,4 DIOXO 3 METHYLIMIDAZOLIDIN 1 YL) 2 FURAMIDE; 5 (3,5 DICHLOROPHENYL) N [2,4 DIOXO 3 [(PYRIDIN 3 YL)METHYL]IMIDAZOLIDIN 1 YL] 2 FURAMIDE; CALCIUM ION; DANTROLENE; N [3 (3 AMINOBENZYL) 2,4 DIOXOIMIDAZOLIDIN 1 YL] 5 (3 BROMOPHENYL) 2 FURAMIDE; N [3 (3 AMINOBENZYL) 2,4 DIOXOIMIDAZOLIDIN 1 YL] 5 (3 CHLOROPHENYL) 2 FURAMIDE; N [3 (3 AMINOBENZYL) 2,4 DIOXOIMIDAZOLIDIN 1 YL] 5 (3,5 DICHLOROPHENYL) 2 FURAMIDE; N [3 (3 AMINOBENZYL) 2,4 DIOXOIMIDAZOLIDIN 1 YL] 5 (4 CHLOROPHENYL) 2 FURAMIDE; N [3 (3 AMINOBENZYL) 2,4 DIOXOIMIDAZOLIDIN 1 YL] 5 [3 (TRIFLUOROMETHYL)PHENYL] 2 FURAMIDE; N [3 (3 AMINOBENZYL) 2,4 DIOXOIMIDAZOLIDIN 1 YL] 5 PHENYL 2 FURAMIDE; N [3 (4 AMINOBENZYL) 2,4 DIOXOIMIDAZOLIDIN 1 YL] 5 (3,5 DICHLOROPHENYL) 2 FURAMIDE; SMALL MOLECULE TRANSPORT AGENT; UNCLASSIFIED DRUG;

ARTICLE; CELL STRAIN HL 60; CHEMICAL MODIFICATION; CRYSTAL STRUCTURE; DRUG POTENCY; DRUG STRUCTURE; DRUG SYNTHESIS; HUMAN; HUMAN CELL; ISCHEMIA; MITOCHONDRIAL PERMEABILITY; MITOCHONDRION SWELLING; MOLECULAR WEIGHT; REACTION ANALYSIS; REPERFUSION INJURY; STRUCTURE ACTIVITY RELATION; VASCULAR DISEASE;

CALCIUM; CRYSTALLOGRAPHY, X-RAY; CYCLOSPORINE; CYCLOSPORINS; DANTROLENE; DOSE-RESPONSE RELATIONSHIP, DRUG; HL-60 CELLS; HUMANS; MITOCHONDRIA; MITOCHONDRIAL MEMBRANE TRANSPORT PROTEINS; MODELS, MOLECULAR; MOLECULAR STRUCTURE; MOLECULAR WEIGHT; MUSCLE RELAXATION; SMALL MOLECULE LIBRARIES; STRUCTURE-ACTIVITY RELATIONSHIP; TUMOR CELLS, CULTURED;

EID: 84867571036     PISSN: 09680896     EISSN: 14643391     Source Type: Journal    
DOI: 10.1016/j.bmc.2012.08.062     Document Type: Article

References (37)

1. Y. Tsujimoto, T. Nakagawa, and S. Shimizu Biochim. Biophys. Acta 1757 2006 1297
2. Y. Tsujimoto, and S. Shimizu Apoptosis 12 2007 835
3. J.J. Lemasters, T.P. Theruvath, Z. Zhong, and A-.L. Nieminen Biochim. Biophys. Acta 1787 2009 1395
4. P.G. Sullivan, A.G. Rabchevsky, P.C. Waldmeier, and J.E. Springer J. Neurosci. Res. 79 2005 231
5. A.T. Mazzeo, A. Beat, A. Singh, and M.R. Bullock Exp. Neurol. 218 2009 363
6. H.M. Honda, and P. Ping Cardiovasc. Drugs Ther. 20 2006 425
7. L. Gomez, H. Thibault, A. Gharib, J.-M. Dumont, G. Vuagniaux, P. Scalfaro, G. Derumeaux, and M. Ovize1 Am. J. Physiol. Heart Circ. Physiol. 293 2007 H1654
8. I.G. Stavrovskaya, M.V. Narayanan, W. Zhang, B.F. Krasnikov, J. Heemskerk, S.S. Young, J.P. Blass, A.M. Brown, M.F. Beal, R.M. Friedlander, and B.S. Kristal J. Exp. Med. 200 2004 211
9. N.R. Sims, and H. Muyderman Biochim. Biophys. Acta 1802 2010 80
10. M.M. Osman, D. Lulic, L. Glover, C.E. Stahl, T. Lau, H. van Loveren, and C.V. Borlongan Neuropeptides 45 2011 359
11. A. Tanveer, S. Virji, L. Andreeva, N.F. Totty, J.J. Hsuan, J.M. Ward, and M. Crompton Eur. J. Biochem. 238 1996 166
12. L.J. Kieffer, T.W. Seng, W. Li, D.G. Osterman, R.E. Handschumacher, and R.M. Bayney J. Biol. Chem. 268 1993 12303
13. Y. Shiga, H. Onodera, Y. Matsuo, and K. Kogure Brain Res. 595 1992 145
14. S. Matsumoto, H. Friberg, M. Ferrand-Drake, and T. Wieloch J. Cereb. Blood Flow Metab. 19 1999 736
15. T. Yoshimoto, and B.K. Siesjö Brain Res. 839 1999 283
16. D.J. Hausenloy, M.R. Duchen, and D.M. Yellon Cardiovas. Res. 60 2003 617
17. W.M. Bennett, A. DeMattos, M.M. Meyer, T. Andoh, and J.M. Barry Kidney Int. 50 1996 1089
18. M. Hauben Pharmacotherapy 16 1996 576
19. J.M. Gijtenbeek, M.J. van den Bent, and C.J. Vecht J. Neurol. 246 1999 339
20. B.D.N. Kahan Engl. J. Med. 321 1989 1725
21. H.R. Snyder Jr., C.S. Davis, R.K. Bickerton, and R.P. Halliday J. Med. Chem. 10 1967 807
22. A. Ward, M.O. Chaffman, and E.M. Sorkin Drugs 32 1986 130
23. T. Yano, R. Nakayama, T. Imaizumi, H. Terasaki, and K. Ushijima Resuscitation 50 2001 117
24. F. Li, T. Hayashi, G. Jin, K. Deguchi, S. Nagotani, I. Nagano, M. Shoji, P.H. Chan, and K. Abe Brain Res. 1048 2005 59
25. M. Acikel, M.E. Buyukokuroglu, F. Erdogan, H. Aksoy, E. Bozkurt, and H. Senocak Int. J. Cardiol. 98 2005 389
26. B.R. Fruen, J.R. Mickelson, and C.F. Louis J. Biol. Chem. 272 1997 26965
27. I. Thomson, R.M. Shepherd, R. Fraser, and C.J. Kenyon J. Steroid Biochem. Mol. Biol. 38 1991 703
28. S. Chen, X. Zhao, J. Tan, H. Lu, Z. Qi, Q. Huang, X. Zeng, M. Zhang, S. Jiang, and L. Yu Eur. J. Pharmacol. 565 2007 54
29. K.O. Ellis, and F.L. Wessels Naunyn-Schmiedeberg's Arch. Pharmacol. 301 1978 237
30. S. Daum, M. Schumann, S. Mathea, T. Aumüller, M.A. Balsley, S.L. Constant, B.F. de Lacroix, F. Kruska, M. Braun, and C. Schiene-Fischer Biochemistry 48 2009 6268
31. K. Kajitani, M. Fujihashi, Y. Kobayashi, S. Shimizu, Y. Tsujimoto, and K. Miki Proteins 70 2008 1635
32. F.J. Brown, P.R. Bernstein, L.A. Cronk, D.L. Dosset, K.C. Hebbel, T.P. Maduskuie Jr., H.S. Shapiro, E.P. Vacek, Y.K. Yee, A.K. Willard, R.D. Krell, and D.W. Snyder J. Med. Chem. 32 1989 807
33. M. Kunishima, C. Kawachi, F. Iwasaki, K. Terao, and S. Tani Tetrahedron Lett. 40 1999 5327
34. T. Hosoya, H. Aoyama, T. Ikemoto, Y. Kihara, T. Hiramatsu, M. Endo, and M. Suzuki Bioorg. Med. Chem. 11 2003 663
35. G. Beutner, V.K. Sharma, D.R. Giovannucci, D.I. Yule, and S.S. Sheu J. Biol. Chem. 276 2001 21482
36. D. Ma, S. Yu, L. Chen, R. Chen, K. Yu, L. Zhang, Z. Chen, D. Zhong, Z. Gong, R. Wang, H. Jiang, and G. Pei ChemMedChem 2 2007 187
37. I.A. Trounce, Y.L. Kim, A.S. Jun, and D.C. Wallace Methods Enzymol. 264 1996 484