Evaluation of insulin-mimetic activities of vanadyl and zinc(II) complexes from the viewpoint of heterocyclic bidentate ligands

Journal of Inorganic Biochemistry

Volumn 103, Issue 4, 2009, Pages 567-574

  Katoh, Akira ^a   Matsumura, Yuriko ^a   Yoshikawa, Yutaka ^b   Yasui, Hiroyuki ^b   Sakurai, Hiromu ^c  

^a SEIKEI UNIVERSITY   (Japan)

^b KYOTO PHARMACEUTICAL UNIVERSITY   (Japan)

^c SUZUKA UNIVERSITY OF MEDICAL SCIENCE   (Japan)

Author keywords

Heterocyclic compound; Insulin mimetic activity; The structure activity relationship; Vanadyl complex; Zinc(II) complex

Indexed keywords

1 PHENYLALKYL 3 HYDROXY 2(1H) PYRIDINETHIONE; 3 HYDROXY 2-METHYL 4(1H) PYRIDINETHIONES; 4 (4 CHLOROPHENYL)THIAZOLE; 4 METHYLTHIAZOLE 2 (3H) THIONE; 5 DIALKYLSULFONAMIDO; 5,7 BIS(DIALKYLSULFONAMIDO) 8 HYDROXYQUINOLINE; FATTY ACID; INSULIN; METAL ION; PYRIDINE DERIVATIVE; QUINOLINE DERIVATIVE; STREPTOZOCIN; SULFONE DERIVATIVE; THIAZOLE DERIVATIVE; UNCLASSIFIED DRUG; VANADYL SULFATE; ZINC COMPLEX;

ADIPOCYTE; ARTICLE; DIABETES MELLITUS; GLUCOSE BLOOD LEVEL; IC 50; IN VIVO STUDY; LIPID BILAYER; MOLECULAR WEIGHT; PARTITION COEFFICIENT;

ANIMALS; BIOMIMETICS; DIABETES MELLITUS, EXPERIMENTAL; HETEROCYCLIC COMPOUNDS; HYPOGLYCEMIC AGENTS; INSULIN; KINETICS; MICE; MICE, INBRED STRAINS; RATS; STRUCTURE-ACTIVITY RELATIONSHIP; VANADIUM; ZINC;

MUS; RATTUS;

EID: 62349093804     PISSN: 01620134     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.jinorgbio.2008.12.005     Document Type: Article

References (61)

1. WHO, Diabetes Mellitus, Reports of a WHO Study Group, WHO Technical Report Series, 1985, pp. 727-876.
2. Cohen N., Halberstam M., Shlimovich P., Chang C.J., Shamoon H., and Rosssetti L. J. Clin. Invest. 95 (1995) 2501-2509
3. Goldfine A.B., Patti M.-E., Zuberi L., Goldstein B.J., LeBlanc R., Landaker E.J., Jiang Z.Y., Willsky G.R., and Kahn C.R. Metabolism 49 (2000) 400-410
4. Thompson K.H., McNeill J.H., and Orvig C. Chem. Rev. 99 (1999) 2561-2572
5. Rehder D., Pessoa J.C., Geraldes C.F., Castro M.M., Kabanos T., Kiss T., Meier B., Micera G., Pettersson L., Rangel M., Salifoglou A., Turel I., and Wang D. J. Biol. Inorg. Chem. 7 (2002) 384-396
6. Sakurai H. Chem. Rec. 2 (2002) 237-248
7. Sakurai H., Tamura A., Fugono J., Yasui H., and Kiss T. Coord. Chem. Rev. 245 (2003) 31-37
8. Sakurai H., Yasui H., and Adachi Y. Expert Opin. Invest. Drugs 12 (2003) 1189-1203
9. Crans D.C. Pure Appl. Chem. 77 (2005) 1497-1527
10. Fugono J., Yasui H., and Sakurai H. J. Pharm. Pharmacol. 53 (2001) 1247-1255
11. Fugono J., Yasui H., and Sakurai H. J. Pharm. Pharmacol. 54 (2002) 611-616
12. Fugono J., Yasui H., and Sakurai H. J. Pharm. Pharmacol. 57 (2005) 665-669
13. Surg M.-H., Park C., Kim C.-J., Poo H., Soda K., and Ashiuchi M. Chem. Rec. 5 (2005) 352-366
14. Karmaker S., Saha T.K., Yoshikawa Y., Yasui H., and Sakurai H. J. Inorg. Biochem. 100 (2006) 1535-1546
15. Ohkanda J., and Katoh A. J. Synth. Org. Chem. Jpn. 55 (1997) 524-534
16. Ohkanda J., and Katoh A. Rev. Heteroatom. Chem. 18 (1998) 87-118
17. Ellis B.L., Duhme A.K., Hider R.C., Hossain M.B., Rizvi S., and van der Helm D. J. Med. Chem. 39 (1996) 3659-3670
18. Nelson W., Karpishin T.B., Rettig S.J., and Orvig C. Can. J. Chem. 66 (1988) 123-131
19. Farber M., Osiander H., and Severin T. J. Heterocycl. Chem. 31 (1994) 947-956
20. Katoh A., Taguchi K., Saito R., Fujisawa Y., Takino T., and Sakurai H. Heterocycles 60 (2003) 1147-1159
21. Ohkanda J., Tokumitsu T., Mitsuhashi K., and Katoh A. Bull. Chem. Soc. Jpn. 66 (1993) 841-847
22. Nakai M., Watanabe H., Fujisawa C., Kakegawa H., Satoh T., Takada J., Matsushita R., and Sakurai H. Biol. Pharm. Bull. 18 (1995) 719-725
23. Katoh A., Taguchi K., Okada H., Harata M., Fujisawa Y., Takino T., and Sakurai H. Chem. Lett. (2000) 866-867
24. Rai B.L., Dekhordi L.S., Khodr H., Jin Y., Liu Z., and Hider R.C. J. Med. Chem. 41 (1998) 3347-3359
25. Zhang Z., Rettig S.J., and Orvig C. Inorg. Chem. 30 (1991) 509-515
26. Katoh A., Tsukahara T., Saito R., Ghosh K.K., Yoshikawa Y., Kojima Y., Tamura A., and Sakurai H. Chem. Lett. 31 (2002) 114-115
27. Yamaguchi M., Wakasugi K., Saito R., Adachi Y., Yoshikawa Y., Sakurai H., and Katoh A. J. Inorg. Biochem. 100 (2006) 260-269
28. Hartung J., Schwarz M., Svoboda I., Fuess H., and Duarte M.T. Eur. J. Org. Chem. (1999) 1275-1290
29. M. Yamaguchi, The Doctor Thesis at Seikei University, 2008.
30. Pearce D.A., Jotterand N., Carrico I.S., and Imperiali B. J. Am. Chem. Soc. 123 (2001) 5160-5161
31. Yamaguchi M., Saito R., Adachi Y., Yoshikawa Y., Sakurai H., and Katoh A. Heterocycles 73 (2007) 603-615
32. Katoh A., Yamaguchi M., Saito R., Adachi Y., and Sakurai H. Chem. Lett. 33 (2004) 1274-1275
33. Sakurai H., Fujii K., Watanabe H., and Tamura H. Biochem. Biophys. Res. Commun. 214 (1995) 1095-1101
34. Sakurai H., Katoh A., and Yoshikawa Y. Bull. Chem. Soc. Jpn. 79 (2006) 1645-1664
35. Adachi Y., Yoshida J., Kodera Y., Katoh A., Yoshikawa Y., Kojima Y., and Sakurai H. J. Biol. Inorg. Chem. 9 (2004) 885-893
36. Adachi Y., Yoshida J., Kodera Y., and Sakurai H. Chem. Lett. 34 (2005) 656-657
37. Yoshikawa Y., Ueda E., Kawabe K., Miyake H., Sakurai H., and Kojima Y. Chem. Lett. 29 (2000) 874-875
38. Ueda E., Yoshikawa Y., Kishimoto N., Tadokoro M., Yanagihara N., and Sakurai H. Chem. Lett. 30 (2001) 1184-1185
39. Kojima Y., Yoshikawa Y., Ueda E., Kishimoto N., Tadokoro M., and Sakurai H. Bull. Chem. Soc. Jpn. 78 (2005) 451-455
40. Yoshikawa Y., Kondo M., Sakurai H., and Kojima Y. J. Inorg. Biochem. 99 (2005) 1497-1503
41. Yamane M., Adachi Y., Yoshikawa Y., and Sakurai H. Chem. Lett. 34 (2005) 1694-1695
42. Yamamoto S., Yoshikawa Y., Ueda E., Yamashita T., Kajiwara N., Sakurai H., and Kojima Y. Biomed. Res. Trace Elem. 15 (2004) 85-87
43. Sakurai H., Inohara T., Adachi Y., Kawabe K., Yasui H., and Takada J. Bioorg. Med. Chem. Lett. 14 (2004) 1093-1096
44. Saha T.K., Adachi Y., Yoshikawa Y., Yasui H., and Sakurai H. Chem. Lett. 34 (2005) 1350-1351
45. Saha T.K., Yoshikawa Y., Yasui H., and Sakurai H. Bull. Chem. Soc. Jpn. 79 (2006) 1191-1200
46. Noblía P., Vieites M., Torre M.H., Costa-Filho A.J., Cerecetto H., González M., Lavaggi M.L., Adachi Y., Sakurai H., and Gambio D. J. Inorg. Biochem. 100 (2006) 281-287
47. Sakurai H., Fujii K., Fujimoto S., Fjisawa Y., Takechi K., and Yasui H. In: Tracey A.S., and Crans D.C. (Eds). Vanadium Compounds - Chemistry, Biochemistry, and Therapeutic Applications. A CS Symposium Series 711 (1998), American Chemical Society, Washington, DC 344-352
48. Fujimoto S., Fujii K., Yasui H., Matsushita R., Takada J., and Sakurai H. J. Clin. Biochem. Nutr. 23 (1997) 113-129
49. Adachi Y., and Sakurai H. Chem. Pharm. Bull. 52 (2004) 428-433
50. Rangel M., Tamura A., Fukushima C., and Sakurai H. J. Biol. Inorg. Chem. 6 (2001) 128-132
51. Sakurai H., Tamura A., Takino T., Ozutsumi K., Kawabe K., and Kojima Y. Inorg. React. Mech. 2 (2000) 69-77
52. Takino T., Yasui H., Yoshitake A., Hamajima Y., Matsushita R., Takada J., and Sakurai H. J. Biol. Inorg. Chem. 6 (2001) 133-142
53. Tayama K., Adachi Y., Yasui H., and Sakurai H. Biomed. Res. Trace Elem. 16 (2005) 251-348
54. Sasagawa T., Yoshikawa Y., Kawabe K., Sakurai H., and Kojima Y. J. Inorg. Biochem. 88 (2002) 108-112
55. Sakurai H., and Yasui H. J. Trace Elem. Experi. Med. 16 (2003) 269-280
56. Adachi Y., Yoshida J., Kodera Y., Katoh A., Takada J., and Sakurai H. J. Med. Chem. 49 (2006) 3251-3256
57. Harris D.C., and Aisen P. In: Loehr T.M. (Ed). In Iron Carriers and Iron Proteins (1989), VCH Publishers, New York 239-352
58. Kaim W., and Schwederski B. Bioinorganic Chemistry: Inorganic Elements in the Chemistry of Life (1991), John Wiley & Sons, Inc., New York
59. Kiss T., Kiss E., Garribba E., and Sakurai H. J. Inorg. Biochem. 80 (2000) 65-73
60. Liboiron B.D., Thompson K.H., Hanson G.R., Lam E., Aebischer N., and Orvig C. J. Am. Chem. Soc. 127 (2005) 51045115
61. Kiss T., Jakusch T., Bouhsina S., Sakurai H., and Enyedy E.A. Eur. J. Inorg. Chem. (2006) 3607-3613