Chemistry and insulin-mimetic properties of Bis(acetylacetonate)oxovanadium(IV) and derivatives

Inorganic Chemistry

Volumn 39, Issue 3, 2000, Pages 406-416

  Amin, Sean S ^a   Cryer, Kirk ^a   Zhang, Boyan ^a   Dutta, Subodh K ^a   Eaton, Sandra S ^b   Anderson, Oren P ^a   Miller, Susie M ^a   Reul, Benedicte A ^c   Brichard, Sonia M ^c   Crans, Debbie C ^a  

^a Immunology and Pathology   (United States)

^b UNIVERSITY OF DENVER   (United States)

^c UNIVERSITÉ CATHOLIQUE DE LOUVAIN   (Belgium)

Author keywords

[No Author keywords available]

Indexed keywords

BIS(ACETYLACETONATE)OXOVANADIUM; BIS(ACETYLACETONATE)OXOVANADIUM(IV); GLUCOSE; INSULIN; ORGANOMETALLIC COMPOUND; OXOVANADIUM IV; STREPTOZOCIN; UNCLASSIFIED DRUG; VANADIC ACID; VANADIUM DERIVATIVE; VANADIUM OXIDE(3 ETHYL 2,4 PENTANEDIONATE); VANADIUM OXIDE(3 METHYL 2,4 PENTANEDIONATE);

ANIMAL; ANIMAL MODEL; ARTICLE; CHEMICAL REACTION; CHEMICAL STRUCTURE; COMPUTER SIMULATION; CONTROLLED STUDY; DIABETES MELLITUS; DISEASE MODEL; DOSE TIME EFFECT RELATION; DRUG ACTIVITY; DRUG STRUCTURE; DRUG SYNTHESIS; ELECTRON SPIN RESONANCE; EXPERIMENTAL DIABETES MELLITUS; GLUCOSE BLOOD LEVEL; HYDROLYSIS; INSULIN LIKE ACTIVITY; MALE; MOLECULAR MIMICRY; NONHUMAN; NUCLEAR MAGNETIC RESONANCE; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; PH; RAT; RAT STRAIN; REACTION ANALYSIS; STRUCTURE ACTIVITY RELATION; STRUCTURE ANALYSIS; TEMPERATURE DEPENDENCE; X RAY CRYSTALLOGRAPHY;

ANIMALS; BLOOD GLUCOSE; CRYSTALLOGRAPHY, X-RAY; DIABETES MELLITUS, EXPERIMENTAL; DISEASE MODELS, ANIMAL; ELECTRON SPIN RESONANCE SPECTROSCOPY; INSULIN; MAGNETIC RESONANCE SPECTROSCOPY; MALE; MOLECULAR MIMICRY; MOLECULAR STRUCTURE; ORGANOMETALLIC COMPOUNDS; RATS; RATS, WISTAR; STREPTOZOCIN; STRUCTURE-ACTIVITY RELATIONSHIP; VANADATES;

EID: 0034614871     PISSN: 00201669     EISSN: None     Source Type: Journal    
DOI: 10.1021/ic9905897     Document Type: Article

References (72)

1. Abbreviations: acac = 2,4-pentanedionato; Me-acac = 3-methyl-2,4-pentanedionato; Et-acac = 3-ethyl-2,4-pentanedionato; pb = 1-phenyl-1,3-butanedionate; acen = N,N′-ethylenebis(acetylacetoneiminato); R-acac = 3-alkyl-2,4-pentanedionato.
2. Shechter, Y.; Karlish, S. J. D. Nature 1980, 284, 556-558.
3. Heyliger, C. E.; Tahiliani, A. G.; McNeill, J. H. Science 1985, 227, 1474-1477.
4. Srivastava, A. K.; Chiasson, J.-L. Mol. Cell. Biochem. 1995, 153.
5. Cohen, N.; Halberstam, M.; Shlimovich, P.; Chang, C. J.; Shamoon, H.; Rossetti, L. J. Clin. Invest. 1995, 95, 2501-2509.
6. Goldfine, A. B.; Simonson, D. C.; Folli, F.; Patti, M.-E.; Kahn, C. R. Mol. Cell. Biochem. 1995, 153, 217-231.
7. Goldfine, A. B.; Simonson, D. C.; Folli, F.; Patti, M.-E.; Kahn, C. R. J. Clin. Endocrinol. Metab. 1995, 80, 3311-3320.
8. Posner, B. I.; Shaver, A.; Fantus, I. G. In New Antidiabetic Drugs; Bailey, C. J., Flatt, P. R., Eds.; Smith-Gordon: London, 1990; Chapter 8, pp 107-118.
9. Posner, B. I.; Faure, R.; Burgess, J. W.; Bevan, A. P.; Lachance, D.; Zhang-Sun, G.; Fantus, I. G.; Ng, J. B.; Hall, D. A.; Lum, B. S.; Shaver, A. J. Biol. Chem. 1994, 269, 4596-4604.
10. Shaver, A.; Hall, D. A.; Ng, J. B.; Lebuis, A.-M.; Hynes, R. C.; Posner, B. I. Inorg. Chim. Acta 1995, 229, 253-260.
11. Shaver, A.; Ng, J. B.; Hall, D. A.; Soo Lum, B.; Posner, B. I. Inorg. Chem. 1993, 32, 3109-3113.
12. Kadota, S.; Fantus, I. G.; Deragon, G.; Guyda, H. J.; Hersh, B.; Posner, B. I. Biochem. Biophys. Res. Commun. 1987, 147, 259-266.
13. McNeill, J. H.; Yuen, V. G.; Hoveyda, H. R.; Orvig, C. J. Med. Chem. 1992, 35, 1489-1491.
14. Caravan, P.; Gelmini, L.; Glover, N.; Herring, F. G.; Li, H.; McNeill, J. H.; Rettig, S. J.; Setyawati, I. A.; Shuter, E.; Sun, Y.; Tracey, A. S.; Yuen, V. G.; Orvig, C. J. Am. Chem. Soc. 1995, 117, 12759-12770.
15. Kinetek Pharmaceutical. Inc., Press Release Dec 18, 1998, via NewsEdge Corporation.
16. Li, J.; Elberg, G.; Crans, D. C.; Shechter, Y. Biochemistry 1996, 35, 8314-8318.
17. Reul, B. A.; Amin, S. S.; Buchet, J. P.; Ongemba, L. N.; Crans, D. C.; Brichard, S. M. Br. J. Pharmacol. 1999, 126, 467-477.
18. Morgan, G. T.; Moss, H. W. J. Chem. Soc. 1914, 103, 78-90.
19. Kaneda, K.; Jitsukawa, K.; Itoh, T.; Teranishi, S. J. Org. Chem. 1980, 45, 3004-3009.
20. Hirao, T. Chem. Rev. 1997, 97, 2707-2724.
21. Wender, P. A.; Rice, K. D.; Schnute, M. E. J. Am. Chem. Soc. 1997, 119, 7897-7898.
22. Taguchi, H.; Isobe, K.; Nakamura, Y.; Kawaguchi, S. Chem. Lett. 1975, 757-760.
23. Selbin, J.; Manning, H. R.; Cessac, G. J. Inorg. Nucl. Chem. 1963, 25, 1253-1258.
24. Atherton, N. M.; Gibbon, P. J.; Shohoji, M. C. B. J. Chem. Soc., Dalton Trans. 1982, 2289-2290.
25. Dodge, R. P.; Templeton, D. H.; Zalkin, A. J. Chem. Phys. 1961, 35, 55-67.
26. Al-Niaimi, N. S.; Al-Karaghouli, A. R.; Aliwi, S. M.; Jalhoom, M. G. J. Inorg. Nucl. Chem. 1974, 36, 283-288.
27. Pandya, B. J.; Bhattacharya, P. K. Indian J. Chem. 1986, 25A, 776-778.
28. Hon, P.-K.; Belford, R. L.; Pfluger, C. E. J. Chem. Phys. 1965, 43, 1323-1333.
29. Caira, M. R.; Haigh, J. M.; Nassimbeni, L. R. Inorg. Nucl. Chem. Lett. 1972, 8, 109-112.
30. Isobe, K.; Nakamura, Y.; Kawaguchi, S. J. Inorg. Nucl. Chem. 1978, 40, 607-611.
31. Caira, M. R.; Haigh, J. M.; Nassimbeni, L. R. J. Inorg. Nucl. Chem. 1972, 34, 3171-3176.
32. Carlin, R. L.; Walker, F. A. J. Am. Chem. Soc. 1965, 87, 2128-2133.
33. Nath, P. K.; Dash, K. C. Indian J. Chem. 1986, 25A, 968-969.
34. Frausto da Silva, J. J. R.; Wooton, R. J. Chem. Soc., Dalton Trans. 1969, 421-422.
35. Van Willigen, H. Chem. Phys. Lett. 1979, 65, 490-492.
36. Kirste, B.; van Willigen, H. J. Phys. Chem. 1982, 86, 2743-2749.
37. Hanson, G. R.; Sun, Y.; Orvig, C. Inorg. Chem. 1996, 35, 6507-6512.
38. Linert, W.; Herlinger, E.; Margl, P.; Boca, R. J. Coord. Chem. 1993, 28, 1-16.
39. Caira, M. R.; Nassimbeni, L. R.; Scott, J. L.; Wildervanck, A. F. J. Chem. Crystallogr. 1996, 26, 117-122.
40. Sheldrick, G. M. SADBS (a Program for Siemens Area Detection Absorption Correction), to be published.
41. Sheldrick, G. M. SHELXTL; Siemens: Madison, WI, 1996; Vol. 5.
42. Eaton, S. S.; Eaton, G. R. Anal. Chem. 1977, 49, 1277-1278.
43. Swartz, H. M.; Bolton, J. R.; Borg, D. C. Biological Applications of Electron Spin Resonance; Wiley-Interscience: New York, 1972.
44. Chasteen, N. D. In Biological Magnetic Resonance; Berliner, L., Reuben, J., Eds.; Plenum Press: New York, 1981; Vol. 3, pp 53-119.
45. Wilson, R.; Kivelson, D. J. Chem. Phys. 1966, 44, 154-168.
46. Drago, R. S. Physical Methods for Chemists, 2nd ed.; Saunders College Publishing: Orlando, 1992.
47. 2+.
48. Francavilla, J.; Chasteen, N. D. Inorg. Chem. 1975, 14, 2860-2862.
49. Atherton, N. M. In Principles of Electron Spin Resonance; Atherton, N. M., Ed.; Ellis Horwood/PTR Prentice Hall: New York, 1993; pp 114-122.
50. Chasteen, N. D.; Hanna, M. W. J. Phys. Chem. 1972, 76, 3951-3958.
51. 2 in the presence of excess ligand (1 mM for Hacac, 50 mM for HMe-acac, and 50 mM for HEt-acac) are 0.043, 0.050, and 0.043 at ca. 820 nm for acac, Me-acac, and Et-acac, respectively, and 0.015, 0.016, and 0.018 at ca. 570 nm.
52. Becker, D. J.; Ongemba, L.-N.; Henquin, J.-C. Eur. J. Pharmacol. 1994, 260, 169-175.
53. Rowe, R. A.; Jones, M. M. Inorg. Synth. 1957, 5, 114-115.
54. Selbin, J. Coord. Chem. Rev. 1966, 1, 293-314.
55. Bruins, D.; Weaver, D. L. Inorg. Chem. 1970, 9, 130-135.
56. 2+ (or a chloride derivative thereof) were left in solution. The solutions for administration to the rats were obtained by addition of NaCl after sonication. On the basis of the studies describing the interaction of salts with vanadium compounds, addition of NaCl before or during sonication would have resulted in administration of a different species mixture and may yield very different results.
57. Ballhausen, C. J.; Gray, H. B. Inorg. Chem. 1962, 1, 111-122.
58. Crans, D. C.; Mahroof-Tahir, M.; Keramidas, A. D. Mol. Cell. Biochem. 1995, 153, 17-24.
59. Jiang, F.; Anderson, O. P.; Miller, S. M.; Chen, J.; Mahroof-Tahir, M.; Crans, D. C. Inorg. Chem. 1998, 37, 5439-5451.
60. Crans, D. C.; Keramidas, A. D.; Amin, S. S.; Anderson, O. P.; Miller, S. M. J. Chem. Soc., Dalton Trans. 1997, 2799-2812.
61. Schmidt, H.; Bashirpoor, M.; Rehder, D. J. Chem. Soc., Dalton Trans. 1996, 3865-3870.
62. Cornman, C. R.; Kampf, J.; Lah, M. S.; Pecoraro, V. L. Inorg. Chem. 1992, 31, 2035-2043.
63. Taguchi, H.; Isobe, K.; Nakamura, Y.; Kawaguchi, S. Bull. Chem. Soc. Jpn. 1978, 51, 2030-2035.
64. Selbin, J. Chem. Rev. 1965, 65, 153-175.
65. Selbin, J.; Holmes, L. H., Jr.; McGlynn, S. P. J. Inorg. Nucl. Chem. 1963, 25, 1359-1369.
66. Zeltmann, A. H.; Morgan, L. O. Inorg. Chem. 1971, 10, 2739-2745.
67. McPherson, G. L.; Freedman, M. R. Inorg. Chem. 1976, 15, 2299-2301.
68. Jezierski, A.; Raynor, J. B. J. Chem. Soc., Dalton Trans. 1981, 1-7.
69. Chakravorti, N. C.; Sarkar, A. R. J. Fluorine Chem. 1976, 81, 421-428.
70. Sakurai, H.; Fujii, K.; Watanabe, H.; Tamura, H. Biochem. Biophys. Res. Commun. 1995, 214, 1095-1101.
71. Watanabe, H.; Nakai, M.; Komazawa, K.; Sakurai, H. J. Med. Chem. 1994, 37, 876-877.
72. Tracey, A. S.; Crans, D. C. ACS Symp. Ser. 1998, 711.