The therapeutic potential of insulin-mimetic vanadium complexes

Expert Opinion on Investigational Drugs

Volumn 12, Issue 7, 2003, Pages 1189-1203

  Sakurai, Hiromu ^a   Yasui, Hiroyuki ^a   Adachi, Yusuke ^a  

^a KYOTO PHARMACEUTICAL UNIVERSITY   (Japan)

Author keywords

Adipocytes; Blood circulation monitoring EPR; Blood glucose; Coordination mode; Diabetes mellitus; Insulin mimetic activity; Structure activity relationship; Vanadyl(IV) complexes

Indexed keywords

CADMIUM; CARDIAC GLYCOSIDE; COORDINATION COMPOUND; FATTY ACID; GLUCOSE; GLUCOSE TRANSPORTER 4; GLUTAMIC ACID GAMMA HYDROXAMIC ACID; INSULIN RECEPTOR SUBSTRATE 1; LIGAND; MANGANESE; MERCURY; NAGLIVAN; OUABAIN; OXOVANADIUM; PHOSPHATIDYLINOSITOL 3 KINASE; PHOSPHOPROTEIN PHOSPHATASE; PICOLINE DERIVATIVE; SELENIUM; SYNTHETIC INSULIN; TRANSITION ELEMENT; TUMOR NECROSIS FACTOR ALPHA; TUNGSTEN; UNCLASSIFIED DRUG; UNINDEXED DRUG; VANADATE SODIUM; VANADIC ACID; VANADIUM; VANADIUM DERIVATIVE; VANADYL DERIVATIVE; VANADYL SULFATE; ZINC;

COMPLEX FORMATION; COMPLICATION; DIABETES MELLITUS; DISEASE SEVERITY; DOSE RESPONSE; DRUG ACTIVITY; DRUG BIOAVAILABILITY; DRUG DISTRIBUTION; DRUG EFFECT; DRUG HALF LIFE; DRUG OXIDATION; DRUG RESEARCH; DRUG USE; ELECTRON SPIN RESONANCE; GLUCOSE BLOOD LEVEL; HUMAN; INSULIN DEPENDENT DIABETES MELLITUS; LIFESTYLE; NON INSULIN DEPENDENT DIABETES MELLITUS; NONHUMAN; PAIN; REVIEW; STRUCTURE ACTIVITY RELATION; WORLD HEALTH ORGANIZATION;

EID: 0037768816     PISSN: 13543784     EISSN: None     Source Type: Journal    
DOI: 10.1517/13543784.12.7.1189     Document Type: Review

References (74)

1. BANTING FG, BEST CH: The internal secretion of the pancreas. J. Lab. Clin. Med. (1922) 7:251-266.
2. LYONNET B, MARTZ X, MARTIN E: L'emploi thérapeutique des derives du vanadium. Presse Med. (1899) 1(32):191-192.
3. MEYEROVITCH J, FARFEL Z, SACK J, SHECHTER Y: Oral administration of vanadate normalizes blood glucose levels in streptozotocin-treated rats. J. Biol. Chem. (1987) 262(14):6658-6662.
4. PEDERSON RA, RAMANADHAM S, BUCHAN AMJ, MCNEILL JH: Long-term effects of vanadyl treatment on streptozotocin-induced diabetes in rat. Diabetes (1989) 38(11):1390-1395.
5. THOMPSON KH, MCNEILL JH, ORVIG C: Vanadium complexes as insulin mimics. Chem Rev. (1999) 99(9):2561-2571.
6. THOMPSON KH, ORVIG C: Design of vanadium compounds as insulin enhancing agents. J. Chem. Soc. Dalton Trans. (2000) 99(17):2885-2892.
7. SAKURAI H: A new concept: The use of vanadium complexes in the treatment of diabetic mellitus. Chem. Rec. (2002) 2(4):237-248.
8. SAKURAI H, KOJIMA Y, YOSHIKAWA Y, KAWABE K, YASUI H: Antidiabetic vanadium (IV) and zinc(II) complexes. Coord. Chem. Rev. (2002) 226(1-2):187-198.
9. WHO: Diabetes mellitus; Report of a WHO study group. WHO Technical Report Series. (1985) 727:91-113.
10. CHASTEEN ND: The biochemistry of vanadium. Struc. Bonding (1983) 53:105-138.
11. KUSTIN K, MACARA IG: The new biochemistry of vanadium. Comments Inorg. Chem. (1982) 2(1-2):1-22.
12. REHDER D: Inorganic consideration on the function of vanadium in biological systems. In: Vanadium and its Roles in Life. Metal Ions in Biological Systems (Volume 31). H Siegel, A Siegel (Eds), Marcel Dekker, New York (1995):143.
13. STERN A, YIN X, TSANG SS, DAVISON A, MOON J: Vanadium as a modulator of cellular regulatory cascades and oncogene expressions. Biochem. Cell Biol. (1993) 71(3-4):103-112.
14. HOPKINS LL Jr, MOHR HE: The biological essentiality of vanadium. In: Newer Trace Elements. W Mertz, WE Cornatze (Eds), Marcel Dekker, New York (1971):195-213.
15. NIELSEN FH, OLLERICH DA: Studies on vanadium deficiency in chicks. Fed. Proc. (1973) 32(3):929.
16. BUTLER A, CARTEN JN, SIMPSON MT: Vanadium in proteins and enzymes. In: Handbook on Metalloproteins. I Bertini, A Sigel, H Sigel (Eds), Marcel Dekker, New York (2001):153-179.
17. WEVER R, HEMRIKA W: Chapter 12. In: Vanadium in the Environment, Part One: Chemistry and Biochemistry. JO Nriagu (Ed.), John Wiley & Sons, New York (1998).
18. SAKURAI H, TSUCHIYA K, NUKATSUKA M et al.: Insulin-mimetic action of vanadyl complexes. J. Clin. Biochem. Nutr. (1990) 8(3):193-200.
19. THOMPSON KH, TSUKADA Y, XU Z, BATEII M, MCNEILL JH, ORVIG C: Influence of chelation and oxidation state on vanadium bioavailability, and their effects on tissue concentrations of zinc, copper, and iron. Biol. Trace Elem. Res. (2002) 86(1):31-44.
20. HUDSON FTG: Vanadium: Toxicology and Biochemical Significance. Elsevier, New York (1964):140.
21. NIELSEN FH: Importance of making dietary recommendations for elements designated as nutritionally beneficial, pharmacologically beneficial, or conditionally essential. J. Trace Elem. Exp. Med. (2000) 13(1):113-129.
22. BRICHARD SM, HENQUIN JC: The role of vanadium in the management of diabetes. Trends Pharmacol. Sci. (1995) 16(8):265-270.
23. +)-ATPase inhibitor found in ATP derived from muscle. J. Biol. Chem. (1977) 252(21 ):7421-7423.
24. SAKURAI H, NISHIDA M, KOYAMA M, TAKADA J: Occurrence of vanadium ions in serum albumins. Biochim. Biophys. Acta (1987) 924(3):562-563.
25. SAKURAI H, NISHIDA M, KIDA K, KOYAMA M, TAKADA J: Determination and characterization of vanadium ion in serum albumins. Inorg. Chim. Acta (1987) 138(2):149-153.
26. FANTUS IG, LAI DR, TANG S: Modulation of insulin action by vanadate: evidence of a role for phosphotyrosine phosphatase activity to alter cellular signaling. Mol. Cell. Biochem. (1995) 153(1&2 ):103-112.
27. TSIANI E, BOGDANOVIC E, SORISKY A, NAGY L, FANTUS IG: Tyrosine phosphatase inhibitors, vanadate and pervanadate, stimulate glucose transport and GLUT translocation in muscle cells by a mechanism independent of phosphatidylinositol 3-kinase and protein kinase C. Diabetes (1998) 47(11):1676-1686.
28. SHAFRIR E, SPIELMAN S, NACHLIEL I, KHAMAISI M, BAR-ON H, ZIV E: Treatment of diabetes with vanadium salts: general overview and amelioration of nutritionally induced diabetes in the Psammomys obesus gerbil. Diabetes Metab. Res. (2001) 17(1):55-66.
29. SAKURAI H, SHIMOMURA S, FUKUZAWA K, ISHIZU K: Detection of oxovanadium(IV) and characterization of its ligand environment in subcellular fractions of the liver of rats treated with pentavalent vanadium(V). Biochem. Biophys. Res. Commun. (1980) 96(1):293-298.
30. SAKURAI H, TSUCHIYA K, NUKATSUKA M, SOFUE M, KAWADA J: Insulin-like effect of vanadyl ion on streptozotocin-induced diabetic rats. J. Endocrinol. (1990) 126(3):451-459.
31. NAKAI M, WATANABE H, FUJIWARA C et al.: Mechanism on insulin-like action of vanadyl sulfate: Studies on interaction between rat adipocytes and vanadium compounds. Biol. Chem. Bud. (1995) 18(5):719-725.
32. SAKURAI H, HAMADA Y, SHIMOMURA S, YAMASHITA S, ISHIZU K: Cysteine methyl ester-oxovanadium(IV) complex, preparation and characterization. Inorg. Chim. Acta (1980) 46(6):L119-L120.
33. SAKURAI H, TAIRA Z, SAKAI N: Crystal structure of an L-cysteine methyl ester-vanadyl(IV) complex. Inorg. Chim. Acta (1988) 151(2):85-86.
34. PEARSON RG: Hard and soft acids and bases. J. Am. Chem. Soc. (1963) 85(22):3533-3539.
35. CAM MC, CROS GH, SERRANO JJ, LAZARO R, MCNEILL JH: In vivo antidiabetic actions of naglivan, an organic vanadyl compound in streptozotocin-induced diabetes. Diab. Res. Clin. Pract. (1993) 20(2):89-91.
36. WATANABE H, NAKAI M, KOMAZAWA K, SAKURAI H: A new orally active insulin mimetic vanadyl complex: Bis(pyrrolidine-N-carbodithioato)oxovanadium(IV). J. Med Chem. (1994) 37(7):876-877.
37. SAKURAI H, WATANABE H, TAMURA H, YASUI H, MATSUSHITA R, TAKADA J: Insulin-mimetic vanadyl-dithiocarbamate complexes. Inorg. Chim. Acta (1998) 283(1):175-183.
38. 2) coordination mode. Chem. Lett. (1999) (9 ):913-914.
39. 2) coordination mode; in vitro and in vivo evaluation in rats. J. Inorg. Biochem. (2000) 80(1-2):99-105.
40. 2) coordination mode. J. Inorg. Biochem. (2001) 85(2-3):179-186.
41. MCNEILL JH, YUEN VG, HOVEYDA HR, ORVIG C: Bis(maltolato)oxovanadium(IV) is a potent insulin mimetic. J. Med. Chem. (1992) 35(8):1489-1491.
42. YUEN VG, ORVIG C, MCNEILL JH: Glucose-lowering effects of a new organic vanadium complex, bis(maltolato)oxovanadium(IV). Can. J. Physiol. Pharmacol. (1993) 71(3-4):263-269.
43. YUEN VG, ORVIG C, THOMPSON KH, MCNEILL JH: Improvement in cardiac dysfunction in streptozotocin-induced diabetic rats following chronic oral administration of bis(maltolato)oxovanadium(IV). Can. J. Physiol. Pharmacol. (1993) 71(3-4):270-276.
44. DIKANOV SA, LIBOIRON BD, THOMPSON KH et al.: In vivo electron-echo envelope modulation (ESEEM) spectroscopy: First observation of vanadyl coordination to phosphate in bone. J. Am. Chem. Soc. (1999) 121(47):11004-11005.
45. 4) coordination mode. J. Mol. Inorg. Chem. (2001) 6(2 ):128-132.
46. KATOH A, TANIGUCHI K, OKUDA H et al.: Synthesis of new vanadyl complexes of hydroxyazine-type heterocycles and their insulin-mimetic activities. Chem. Lett. (2000) (8):866-867.
47. 2O)]. Chem. Lett. (1998) (1):9-10.
48. KAWABE K, TADOKORO M, ICHIMURA A, KOJIMA Y, TAKINOT, SAKURAI H: Stereospecific and structure-dependent insulin-mimetic oxovanadium(IV) complexes with N, N'- ethylenebis(amino acids). J. Am. Chem. Soc. (1999) 121(34):7937-7938.
49. KAWABE K, SUEKUNI T, INADA T et al.: Syntheses, structures, and insulin-like activities of oxovanadium(IV) complexes with tetra- and penta-dentate histidine derivatives. Chem. Lett. (1998) (11):1155-1156.
50. SAKURAI H, TAMURA A, FUGONO J, YASUI H, KISS T: New Antidiabetic vanadyl-pyridone complexes: Effect of equivalent transformation of coordinating atom in the ligand. Coord. Chem. Rev. (2003) (In press).
51. GOLDWASER I, LI J, GERSHONOV E et al.: L-Glutamic acid γ-monohydroxamate, a potentiator of vanadium-evoked glucose metabolism in vitro and in vivo. J. Biol. Chem. (1999) 274(37 ):26617-26624.
52. SAKURAI H, FUJII K, WATANABE H, TAMURA H: Orally active and long-term acting insulin-mimetic vanadyl complex: Bis(picolinato)oxovanadium(IV). Biochem. Biophys. Res. Commun. (1995) 214(3):1095-1101.
53. SAKURAI H, TAMURA A, TAKINO T, OZUTSUMI K, KAWABE K, KOJIMA Y: Interaction of vanadyl complexes with biological systems: Structure-insulinomimetic activity relationship of vanadyl-picolinate complexes. Inorg. React. Mech. (2000) 2(1-2):69-77.
54. FUJIMOTO S, FUJII K, YASUI H, MATSUSHITA R, TAKADA J, SAKURAI H: Long-term acting and orally active vanadyl-methylpicolinate complex with hypoglycemic activity in streptozotocin-induced diabetic rats. J. Clin. Biochem. Nutr. (1997) 23(2):113-129.
55. 2) coordination mode, and evaluation of its effect on uptake of D-glucose by Ehrlich ascites. J. Pharm. Pharmacol. (1999) 51(2):119-124.
56. TAKINO T, YASUI H, YOSHITANE A et al.: A new halogenated antidiabetic vanadyl complex, bis(5-iodopicolinato) oxovanadium(IV): in vitro and in vivo insulinomimetic evaluations and metallokinetic analysis. J. Biol. Inorg. Chem. (2001) 6(2):133-142.
57. y mice with daily oral administration of bis(6-methylpicolinato) oxovanadium(IV) complex. Chem. Pharm. Bull. (1999) 47(11):1668-1670.
58. y mice. J. Inorg. Biochem. (2002) 88(1):108-112.
59. WOO L, YUEN V, THOMPSON KH, MCNEILL JH, ORVIG C: Vanadyl-biguanide complexes as potential synergistic insulin mimics. J. Inorg. Biochem. (1999) 76(3-4):251-257.
60. INOHARA T, KAWABE K, SAKURAI H: Insulin-like action of vanadyl-porphyrin complexes. 52th Kinki Branch Conference of Pharmaceutical Society of Japan, Osaka, Japan (2002):160 (Abstract).
61. 48V-labeled compounds in rats. J. Appl. Physiol. (1998) 84(2 ): 569-575.
62. KISS E, GARRIBBA E, MICERA G, KISS T, SAKURAI H: Ternary complex formation between VO(IV)-picolinic acid or VO(IV)-6-methylpicolinic acid and small blood serum bioligands. J. Inorg. Biochem. (2000) 78(2):97-108.
63. KISS T, KISS E, GARRIBBA E, SAKURAI H: Speciation of insulin-mimetic VO(IV)-containing drugs in blood serum. J. Inorg. Biochem. (2000) 80(1-2):65-73.
64. FUKUI K, OHYA-NISHIGUCHI H, NAKAI M, SAKURAI H, KAMADA H: Detection of vanadyl-nitrogen interaction in organs of the vanadyl-treated rat: Electron spin echo envelope modulation study. FEBS Lett. (1995) 368(1):31-35.
65. FUKUI K, FUJISAWA Y, OHYANISHIGUCHI H, KAMADA H, SAKURAI H: In vivo coordination structural changes of a potent insulin-mimetic agent, bis(picolinato) oxovanadium(IV), studied by electron spin-echo envelope modulation spectroscopy. J. Inorg. Biochem. 77(3-4):215-224 (1999).
66. YASUI H, TAMURA A, TAKINOT, SAKURAI H: Structure-dependent metallokinetics of Antidiabetic vanadyl-picolinate complexes in rats: Studies on solution structure, insulinomimetic activity, and metallokinetics. J. Inorg. Biochem. (2002) 91(1):327-338.
67. FUGONO J, YASUI H, SAKURAI H: Pharmacokinetic study on gastrointestinal absorption of insulinomimetic vanadyl complexes in rats by ESR spectroscopy. J. Pharm. Pharmacol. (2001) 53(9):1247-1255.
68. REHDER D, PESSOA JC, GERALDES CF et al.: In vitro study of the insulin-mimetic behavior of vanadium (IV, V) coordination compounds. J. Biol. Inorg. Chem. (2002) 7(4-5):384-396.
69. CRANS DC: Chemistry and insulin-like properties of vanadium(IV) and vanadium(IV) compounds. J. Inorg. Biochem. (2000) 80(1-2):123-131.
70. CUSI K, CUKIER S, DEFRONZO RA et al.: Vanadyl sulfate improves hepatic and muscle insulin sensitivity in Type 2 diabetes. J. Clin. Endocrinol. Metab. (2001) 86(3):1410-1417.
71. FUGONO J, YASUI H, SAKURAI H: Enteric-coating capsulation of insulinomimetic vanadyl sulfate enhances bioavailability of vanadyl species in rats. J. Pharm. Pharmacol. (2002) 54(5):611-615.
72. GOLDFINE AB, SIMONSON DC, FOLLI F, PATTI ME, KAHN CR: Metabolic effects of sodium metavanadate in humans with insulin-dependent and noninsulin-dependent diabetes mellitus in vivo and in vitro studies. J. Clin. Endocrinol. Metab. (1995) 80(11):3311-3320.
73. DUNAI N, SAMINATHAN G: Insulin-like effects of bis-salicylidine ethylenediiminato oxovanadium(IV) complex on carbohydrate metabolism. J. Clin. Biochem. Nutr. (1997) 22(1):31-39.
74. REUL BA, AMIN SS, BUCHED JP et al.: Effect of vanadium complexes with organic ligands on glucose metabolism: A comparison study in diabetic rats. Br. J. Pharmacol. (1999) 126(2):467-477.