Overview and frontier for the development of metallopharmaceutics

Journal of Health Science

Volumn 56, Issue 2, 2010, Pages 129-143

  Sakurai, Hiromu ^a  

^a SUZUKA UNIVERSITY OF MEDICAL SCIENCE   (Japan)

Author keywords

Anticancer; Antidiabetes; Antioxidative; Chemotherapy; Inorganic compound; Metallopharmaceutics

Indexed keywords

ACETYLSALICYLATE COPPER; ARSENIC DERIVATIVE; ARSPHENAMINE; AURANOFIN; AUROTHIOGLUCOSE; CARBOXYETHYLGERMANIUM SESQUIOXIDE; CISPLATIN; COPPER COMPLEX; CYANOCOBALAMIN; EBSELEN; HISTAMINE; INSULIN; LITHIUM CARBONATE; METAL COMPLEX; METFORMIN; PLATINUM COMPLEX; POLAPREZINC; RUTHENIUM COMPLEX; SILVER DERIVATIVE; SUCRALFATE; SULFADIAZINE SILVER; SUPEROXIDE DISMUTASE; TETRATHIOMOLYBDIC ACID; UNINDEXED DRUG; VANADIC ACID; VANADIUM DERIVATIVE; VANADYL SULFATE; ZINC ACETATE; ZINC CHLORIDE; ZINC COMPLEX;

ANEMIA; ANTINEOPLASTIC ACTIVITY; ANTIOXIDANT ACTIVITY; BACTERIAL INFECTION; BRAIN ISCHEMIA; BURN; CLINICAL TRIAL; DERMATITIS; DIABETES MELLITUS; DRUG ABSORPTION; DRUG BINDING SITE; DRUG BIOAVAILABILITY; DRUG DESIGN; DRUG PROTEIN BINDING; DRUG RESEARCH; DRUG STRUCTURE; GLUCOSE INTOLERANCE; GROWTH DISORDER; HUMAN; HYPERGLYCEMIA; INSULIN RESISTANCE; MALIGNANT NEOPLASTIC DISEASE; MANIC DEPRESSIVE PSYCHOSIS; NON INSULIN DEPENDENT DIABETES MELLITUS; NONHUMAN; REVIEW; RHEUMATOID ARTHRITIS; STOMACH ULCER; STRUCTURE ANALYSIS; SYPHILIS; UNSPECIFIED SIDE EFFECT; WILSON DISEASE;

EID: 77953523701     PISSN: 13449702     EISSN: 13475207     Source Type: Journal    
DOI: 10.1248/jhs.56.129     Document Type: Review

References (59)

1. Clarkson, T. (1995) Health effects of metals: A role for evolution? Environ. Health Perspect., 103 (Suppl. 1), 9-12.
2. Lloyd, N. C., Morgan, H. W., Nicholson, B. K. and Ronimis, R. S. (2005) Substituted phenylarsonic acids; structures and spectroscopy. Angew. Chem. Int. Ed. Engl., 44, 941-944.
3. Bowman-James, K. (2005) Alfred Werner revisited: The coordination chemistry of anions. Acc. Chem. Res., 38, 671-678.
4. Lippert, B., Ed. (1991) Cisplatin, Chemistry and Biochemistry of a Leading Anticancer Drug, Wiley-VCH, Zurich.
5. Komeda, S. and Chikuma, M. (2005) Interactions of polynuclear platinum(II) complexes with DNA. In Metal Compounds in Cancer Chemotherapy (Perez, J. M., Fuertes, M. A. and Alonso, C., Eds.), Research Signpost, pp. 219-239.
6. Todd, R. C. and Lippard, S. J. (2009) Inhibition of transcription by platinum antitumor compounds. Metallomics, 1, 280-291.
7. Alderden, R. A., Hall, M. D. and Hambley, T. W. (2006) The discovery and development of cisplatin. J. Chem. Educ., 83, 728-734.
8. Levina, A., Mitra, A. and Lay, P. A. (2009) Recent developments in ruthenium anticancer drugs. Metal-lomics, 1, 458-470.
9. Brigelius, R., Spgttl, R., Bors, W., Lengfelder, E., Saran, A. and Weser, U. (1974) Superoxide dis-mutase activity of low molecular weight Cu2 plus-chelates studied by pulse radiolysis. FEBS Lett., 47, 72-75.
10. Muscoli, C., Cuzzocrea, S., Riley, D. P., Zweier, J. L., Thiemermann, C., Wang, Z. Q. and Salvemini, D. (2003) On the selectivity of superoxide dismu-tase mimetics and its importance in pharmacological studies. Br. J. Pharmacol., 140, 445-450.
11. +)-ATPase in-hibitor found in ATP derived from muscle. J. Biol. Chem., 252, 7421-7423.
12. Nielsen, F. H. (1998) Vanadium Compounds: Chemistry, Biochemistry, and Therapeutic Applications, ACS Symp. Ser. 711, (Tracer, A. S. and Crans, D. C., Eds.), American Chemical Society, Washington, D.C.
13. Sakurai, H. (2007) The discovery of vanadyl and zinc complexes for treating diabetes and metabolic syndromes. Expert Opinion on Drug Discoverey, 2, 873-887.
14. Sakurai, H., Yoshikawa, Y. and Yasui, H. (2008) Current state for the development of metallophar-maceutics and anti-diabetic metal complexes. Chem. Soc. Rev., 37, 2383-2392.
15. Barceloux, D. G. (1999) Vanadium. J. Toxicol. Clin. Toxicol., 37, 265-278.
16. Miller, J., McLachlan, A. D. and Klug, A. (1985) Repetitive zinc-binding domains in the protein tran-scription factor IIIA from Xenopus oocytes. EMBO J., 4, 1609-1614.
17. Maret, W. and Vallee, B. L. (1998) Thiolate lig-ands in metallothionein confer redox activity on zinc clusters. Proc. Natl. Acad. Sci. U.S.A., 95, 3483-3488.
18. Frederickson, C. J., Su, S. W., Silva, D. and Thompson, R. B. (2000) Importance of zinc in the central nervous system: the zinc-containing neuron. J. Nutr., 130, 1471S-1483S.
19. Sakurai, S., Kojima, Y., Yoshikawa, Y., Kawae, K. and Yasui, H. (2002) Antidiabetic vanadium(IV) and zinc(II) complexes. Coordination Chemistry Re-views, 26, 187-198.
20. James, M. M. and Charles, S. C. (1982) The mechanism of the insulin-like effects of ionic zinc. J. Biol. Chem., 257, 4362-4368
21. Shisheva, A., Gefel, D. and Shechter, Y. (1992) Insulinlike effects of zinc ion in vitro and in vivo. Preferential effects on desensitized adipocytes and in-duction of normoglycemia in streptozocin-induced rats. Diabetes, 41, 982-988.
22. Sakurai, H., Katoh, A. and Yoshikawa, Y. (2006) Chemistry and biochemistry of insulin-mimetic vanadium and zinc complexes. Trial for treatment of diabetes mellitus. Bull. Chem. Soc. Jpn., 79, 1645-1664.
23. Szilagyi, R. K. and Solomon, E. I. (2002) Electronic structure and its relation to function in copper proteins. Curr. Opin. Chem. Biol., 6, 250-258.
24. Nersissian, A. M. and Ship, E. L. (2002) Blue copper-binding domains. Adv. Protein Chem., 60, 271-340.
25. Solomon, E. I., Chen, P., Metz, M., Lee, S.-K. and Palmer, A. E. (2001) Oxygen binding, activation, and reduction to water by copper proteins. Angew. Chem. Int. Ed. Engl., 40, 4570-4590.
26. Brewer, G. J. (2009) Zinc and tetrathiomolybdate for the treatment of Wilson's disease and the potential efficacy of anticopper therapy in a wide variety of disease. Metallomics, 1, 199-206.
27. Pyatskowit, J. W. and Prohaska, J. R. (2008) Copper deficient rats and mice both develop anemia but only rats have lower plasma and brain iron levels. Comp. Biochem. Physiol. C Toxicol. Pharamacol., 147,316-323.
28. Thompson, K. H., McNeill, J. H. and Orvig, C. (1999) Vanadium Complexes as insulin mimetics. Chem. Rev., 99, 2561-2571.
29. Sakurai, H., Tsuchiya, K., Nukatsuka, M., Kawada, J., Ishikawa, S., Yoshida, H. and Komatsu, M. (1990) Insulin-mimetic action of vanadyl com-plexes. Journal of Clinical Biochemistry and Nutrition, 8, 193-200.
30. McNeill, J. H., Yuen, V. G., Hoveyda, H. R. and Orvig, C. (1992) Bis(maltolato)oxovanadium(IV) is a potent insulin mimetic. J. Med. Chem., 35, 1489-1491.
31. Sakurai, H., Fujii, K., Watanabe, H. and Tamura, H. (1995) Orally active and longterm acting insulin-mimetic vanadyl complex: Bis(picolinato)oxovanadium(IV). Biochem. Bio-phys. Res. Commun., 214, 1095-1101.
32. Adachi, Y., Yoshida, J., Kodera, Y., Katoh, A., Takada, J. and Sakurai, H.(2006) Bis(allixinato)oxovanadium(IV) complex is a potent antidiabetic agent: studies on structure-activity re-lationship for a series of hydroxypyrone-vanadium complexes. J. Med. Chem., 49, 3251-3256.
33. Cusi, K., Cukier, S., DeFronzo, R. A., Torres, M., Puchulu, F. M. and Redondo, J. C. (2001) Vanadyl sulfate improves hepatic and muscle insulin sensitivity in type 2 diabetes. J. Clin. Endocrinol. Metab., 86,1410-1417.
34. Thompson, K. H. and Orvig, C. (2006) Vanadium in diabetes: 100 years from Phase 0 to Phase I. J. Inorg. Biochem., 100, 1925-1935.
35. ′-1,3-propyl-bis(salicyladimine)]oxovanadium(IV). Eur. J. Med. Chem., 42, 817-822.
36. Shukla, R., Barve, V., Padhye, S. and Bhonde, R. (2004) Synthesis, structural propertiesand insulin-enhancing potential of bis(quercetinato)oxovanadium(IV)conjugate. Bioorg. Med. Chem. Lett., 14, 4961-4965.
37. Xie, M., Gao, L., Li, L., Li, W. and Yan, S. (2005) A new orally active antidiabetic vanadyl complex-bis(α-furancarboxylato)oxovanadium(IV). J. Inorg. Biochem., 99, 546-551.
38. Moller, D. E. (2001) New drugs target for type 2 diabetes and metabolic syndromes. Nature, 414, 821-827.
39. Herman, G., Bergman, A., Liu, F., Stevens, C., Wang, A., Zeng, W., Chen, L., Snyder, K., Hilliard, D., Tanen, M., Tanaka, W., Meehan, A., Lasseter, K., Dilzer, S., Blum, R. and Wagner, J. (2006) Pharmacokinetics and pharmacodynamic effects of the oral DPP-4 inhibitor sitagliptin in middle-aged obese subjects. J. Clin. Pharmacol., 46, 876-886.
40. Ripa, S. and Ripa, R. (1995) Zinc and diabetes mellitus. Minerva Med., 86, 415-421.
41. M. K., Rosenthal, M. J., Hong, S., Harris, D. M., Hwang, I., Yip, I., Goulb, M. S., Ament, M. E., Go, V. L.W. (2001) Synergistic antidiabetic activi-ties of zinc, cyclo (his-pro), and arachidonic acid. Metabolism, 50, 53-59.
42. Adachi, Y., Yoshida, J., Kodera, Y., Kiss, T., Enyedy, E. A., Yoshikawa, Y. and Sakurai, H. (2006) Oral ad-ministration of a zinc complex improves type 2 dia-betes and metabolic syndromes. Biochem. Biophys. Res. Commun., 351, 165-170.
43. Yoshikawa, Y., Adachi, Y. and Sakurai, H. (2007) A new type of orally active anti-diabetic Zn(II)-dithiocarbamate complex. Life Sci., 80, 759-766.
44. Lu, B., Ennis, D., Lai, R., Bogdanovic, E., Nikolov, R., Salamon, L., Fantus, C., Hoang, L. T. and Fantus, I. G. (2001) Enhanced sensitivity of insulin-resistant adipocytes to vanadate is associated with oxidative stress and decreased reduction of vanadate (+5) to vanadyl (+4). J. Biol. Chem., 276, 35589-35598.
45. Hiromura, M., Nakayama, A., Adachi, Y., Doi, M. and Sakurai, H. (2007) Action mechanism of bis(allixinato)oxovanadium(IV) as a novel potent insulin-mimetic complex: regulation of GLUT4 translocation and FoxO1 transcription factor. J. Biol. Inorg. Chem., 12, 1275-1287.
46. Hiromura, M., Adachi, Y., Machida, M., Hattori, M. and Sakurai, H. (2009) Glucose lowering activity by oral administration of bis(allixinato)oxidovanadium(IV) complex in streptozotocin-induced diabetic mice and gene expression profiling in their skeletal muscles. Metallomics, 1, 92-100.
47. Ho, E., Quan, N., Tsai, Y. H., Lai, W. and Bray, T. M. (2001) Dietary zinc supplementation inhibits NFkappaB activation and protects against chem-ically induced diabetes in CD1 mice. Exp. Biol. Med., 226, 103-111.
48. Hasse, H. and Maret, M. (2005) Protein Tyrosine Phosphatases as Targets of the Combined Insuli-nomimetic Effects of Zinc and Oxidants. BioMetals, 18,333-338.
49. Basuki, W., Hiromura, M. and Sakurai, H. (2007) Insulinomimetic Zn complex (Zn(opt)2) enhances insulin signaling pathway in 3T3-L1 adipocytes. J. Inorg. Biochem., 101, 692-699.
50. Nakayama, A., Hiromura, M., Adachi, Y. and Sakurai, H. (2008) Molecular mechanism of antidi-abetic zinc-allixin complexes: regulations of glu-cose utilization and lipid metabolism. J. Biol. Inorg. Chem., 13, 675-684.
51. Riley, D. P. and Schall, O. F. (2007) Structure-activity studies and the design of synthetic superox-ide dismutase (SOD) mimetics as therapeutics. Adv. Inorg. Chem., 59, 233-263.
52. Afonso, V., Champy, R., Mitrovic, D., Collin, P. and Lomri, A. (2007) Reactive oxygen species and superoxide dismutases: role in joint diseases. Joint Bone Spine, 74, 324-329.
53. Doggrell, S. A. (2002) Therapeutic potential of selective superoxide dismutase mimetics. Drugs of the Future, 27, 385-390.
54. Salvemini, D., Riley, D. P. and Cuzzocrea, S. (2002) SOD mimetics are coming of age. Nat. Rev. Drug Disc., 1, 367-374.
55. Fujimori, T., Yamada, S., Yasui, H., Sakurai, H., In, Y. and Ishida, T. (2005) Orally active antioxidative copper(II) aspirinate: synthesis, structure character-ization, superoxide scavenging activity, and in vitro and in vivo antioxidative evaluations. J. Biol. Inorg. Chem., 10, 831-841.
56. Fujimori, T., Yasui, H., Hiromura, M. and Sakurai, H. (2007) Suppressive effect of orally administered copper(II)-aspirinate (Cu2(asp)4) complex on the generation of reactive oxygen species in the skin of animals subjected to UVA exposure. Exp. Dermatol., 16, 746-752.
57. T., Geroe, D., Lin, L.-N., Loganathan, S., Hoppe-Tichy, T., Szabo, C., Karck, M., Sakurai, H. and Szabo, G. (2008) Improvement of aging-associated cardiovascular dysfunction by the orally administered copper(II)-aspirinate complex. Rejuvenation Res., 11, 945-956.
58. Masaki, H., Ochiai, Y., Okano, Y., Yagami, A., Akamatsu, H., Matsunaga, K., Sakurai, H. and Suzuki, K. (2007) A zinc(II)-glycine complex is an effective inducer of metallothionein and removes oxidative stress. J. Dermatol. Sci., 45, 73-75.
59. Ochiai, Y., Kaburagi, S., Okano, Y., Masaki, H., Ichihashi, M., Funasaka, Y. and Sakurai, H. (2008) A Zn(II)-glycine complex suppresses UVB-induced melanin production by stimulating metallothionein expression. Int. J. Cosmet. Sci., 30, 105-112.