Oxidovanadium(IV) schiff base complex derived from vitamin B6: Synthesis, characterization, and insulin enhancing properties

Inorganic Chemistry

Volumn 50, Issue 10, 2011, Pages 4349-4361

  Mukherjee, Tirtha ^a   Costa Pessoa, Joao ^b   Kumar, Amit ^b   Sarkar, Asit R ^a  

^a UNIVERSITY OF KALYANI   (India)

^b INSTITUTO SUPERIOR TÉCNICO   (Portugal)

Author keywords

[No Author keywords available]

Indexed keywords

ADRENALIN; FATTY ACID; GLUCOSE; INSULIN; METHYLAMINE; PYRIDOXAL; SCHIFF BASE; VANADIUM; VANADIUM DERIVATIVE;

ADIPOCYTE; ANIMAL; ARTICLE; CELL CULTURE; CHEMICAL STRUCTURE; CHEMISTRY; CONFORMATION; CYTOLOGY; DRUG EFFECT; ELECTRON SPIN RESONANCE; ISOLATION AND PURIFICATION; METABOLISM; RAT; SPECTROSCOPY; SYNTHESIS; X RAY CRYSTALLOGRAPHY; X RAY DIFFRACTION;

ADIPOCYTES; ANIMALS; CELLS, CULTURED; CRYSTALLOGRAPHY, X-RAY; ELECTRON SPIN RESONANCE SPECTROSCOPY; EPINEPHRINE; FATTY ACIDS, NONESTERIFIED; GLUCOSE; INSULIN; METHYLAMINES; MODELS, MOLECULAR; MOLECULAR CONFORMATION; PYRIDOXAL; RATS; SCHIFF BASES; SPECTRUM ANALYSIS; VANADIUM; VANADIUM COMPOUNDS; X-RAY DIFFRACTION;

EID: 79955808759     PISSN: 00201669     EISSN: None     Source Type: Journal    
DOI: 10.1021/ic102412s     Document Type: Article

References (127)

1. Crans, D. C.; Smee, J. J.; Gaidamauskas, E.; Yang, L. Chem. Rev. 2004, 104, 849-902
2. Rehder, D. Bioinorganic Vanadium Chemistry; John Wiley & Sons: New York, U.S.A., 2008; p 1-213.
3. Thompson, K. H.; Orvig, C. Coord. Chem. Rev. 2001, 219-221, 1033-1053
4. Shechter, Y.; Goldwaser, I.; Mironchik, M.; Fridkin, M.; Gefel, D. Coord. Chem. Rev. 2003, 237, 3-11
5. Thompson, K. H.; Orvig, C. J. Inorg. Biochem. 2006, 100, 1925-1935
6. Saltiel, A. R.; Kahn, C. R. Nature 2001, 414, 799-806
7. Thompson, K. H.; McNeill, J. H.; Orvig, C. Chem. Rev. 1999, 99, 2561-2572
8. Crans, D. C. Vanadium Compounds: Chemistry, Biochemistry, and Therapeutic Applications; Tracey, A. S., Ed.; American Chemical Society: Washington, DC, U.S.A., 1998; pp 259-269, 278-296, 308-368.
9. Li, M.; Smee, J. J.; Ding, W.; Crans, D. C. J. Inorg. Biochem. 2009, 103, 585-589
10. Xie, M.; Li, L.; Yang, X.; Liu, W.; Yan, S.; Niu, Y.; Meng, Z. Eur. J. Med. Chem. 2010, 45, 2327-2335
11. Orvig, C.; Thompson, K. H.; Liboiron, B. D.; McNeill J. H. Yuen, V. G. J. Inorg. Biochem. 2003, 96, 14-14
12. Thompson, K. H.; Orvig, C. Dalton Trans. 2006, 761-764
13. Thompson, K. H.; Lichter, J.; LeBel, C.; Scaife, M. C.; McNeill, J. H.; Orvig, C. J. Inorg. Biochem. 2009, 103, 554-558
14. Kawabe, K.; Yoshikawa, Y.; Adachi, Y.; Sakurai, H. Life Sci. 2006, 78, 2860-2866
15. Sekar, N.; Li, J.; Shechter, Y. Crit. Rev. Biochem. Mol. Biol. 1996, 31, 339-359
16. Fantus, I. G.; Tsiani, E. Mol. Cell. Biochem. 1998, 182, 109-119
17. Molero, J. C.; Martinez, C.; Andres, A.; Satrustegui, J.; Carrascosa, J. M. FEBS Lett. 1998, 425, 298-304
18. Mohammad, A.; Sharma, V.; McNeill, J. H. Mol. Cell. Biochem. 2002, 233, 139-143
19. Scior, T.; Mack, H. G.; García, J. A.; Koch, W. Drug Des. Dev. Ther. 2009, 2, 221-231
20. Evangelou, A. M. Crit. Rev. Oncol. Hematol. 2002, 42, 249-265
21. Kostova, I. Anti-Cancer Agents Med. Chem. 2009, 8, 827-842
22. Noblía, P.; Vieites, M.; Parajón-Costa, B. S.; Baran, E. J.; Cerecetto, H.; Draper., P.; González, M.; Piro, O. E.; Castellano, E. E.; Azqueta, A.; López de Ceráin, A.; Monge-Vega, A.; Gambino, D. J. Inorg. Biochem. 2005, 99, 443-451
23. Abdelhamid, G.; Anwar-Mohamed, A.; Badary, O.; Moustafa, A.; El-Kadi, A. Cell. Biol. Toxicol. 2010, 26, 421-434
24. DCruz, O. J.; Uckun, F. M. Expert Opin. Invest. Drugs 2002, 11, 1829-1836
25. Papaioannou, A.; Manos, M.; Karkabounas, S.; Liasko, R.; Evangelou, A. M.; Correia, I.; Kalfakakou, V.; Costa Pessoa, J.; Kabanos, T. A. J. Inorg. Biochem. 2004, 98, 959-968
26. Chatterjee, M.; Bishaye, A. Vanadium - A New Tool for Cancer Prevention. In Vanadium in the Environment; Nriagu, J. O., Ed.; John Wiley & Sons: New York, U.S.A., 1998; Vol. 31, pp 347-390. (Pubitemid 128049993)
27. Mishra, A. P.; Soni, M. Met. Based Drugs 2008, 2008, 875410
28. Muhammad, N.; Ali, S.; Shahzadi, S.; Khan, A. Russ. J. Coord. Chem. 2008, 34, 448-453
29. Dong, Y.; Narla, R. K.; Sudbeck, E.; Uckun, F. M. J. Inorg. Biochem. 2000, 78, 321-330
30. Cohen, P. P. Biochem. J. 1939, 33, 1478-1487
31. Yanofsky, C.; Reissig, J. L. J. Biol. Chem. 1953, 202, 567-577
32. Prior, F. G. R. Med. Hypotheses 1985, 16, 421-428
33. Eto, I.; Krumdieck, C. L. Adv. Exp. Med. Biol. 1986, 206, 313-330
34. Herbert, V. Nutritional Factors in the Induction and Maintenance of Malignancy; Butterworth, C. E.; Hutchinson, M. L., Eds.; Academic Press: New York, U.S.A., 1983; pp 273-287.
35. Herbert, V. Adv. Exp. Med. Biol. 1986, 206, 293-311
36. Bender, D. A. Nutritional Biochemistry of the Vitamins; Bender, D. A., Ed.; Cambridge University Press: New York, U.S.A., 1992; pp 223-268.
37. Bender, D. A.; Bowden, J. F.; Coulsen, W. F.; Dewji, M. R.; Sutton, J.; Symes, E. K. Current Topics in Nutrition and Disease: Clinical and Physiological Applications of Vitamin B6; Leklem, J. E.; Reynolds, R. D., Ed.; Alan R. Liss: New York, U.S.A., 1988; pp 45-49.
38. Richardson, D. R.; Tran, E.; Ponka, P. Blood 1995, 86, 4295-4306
39. Metzler, D. E.; Longenecker, J. B.; Snell, E. E. J. Am. Chem. Soc. 1953, 75, 2786-2787
40. Metzler, D. E.; Olivard, J.; Snell, E. E. J. Am. Chem. Soc. 1954, 76, 644-648
41. Abbott, E. H.; Martell, A. E. J. Am. Chem. Soc. 1970, 92, 5845-5851
42. Martell, A. E.; Eidson, A. F. Bioinorg. Chem. 1975, 4, 277-289
43. Capasso, S.; Giordano, F.; Mattia, C.; Mazzarella, L.; Ripamonti, A. J. Chem. Soc., Dalton Trans. 1974, 2228-2233
44. Costa Pessoa, J.; Cavaco, I.; Correia, I.; Duarte, M. T.; Gillard, R. D.; Henriques, R. T.; Higes, F. J.; Madeira, C.; Tomaz, I. Inorg. Chim. Acta 1999, 293, 1-11
45. Correia, I.; Costa Pessoa, J.; Duarte, M. T.; Henriques, R. T.; Piedade, M. F. M.; Veiros, L. F.; Jakusch, T.; Kiss, T.; Dörnyei, A.; Castro, M. M. C. A.; Geraldes, C. F. G. C.; Avecilla, F. Chem.-Eur. J. 2004, 10, 2301-2317
46. Sundaravel, K.; Suresh, E.; Palaniandavar, M. Inorg. Chim. Acta 2009, 362, 199-207
47. Correia, I.; Dornyei, A.; Avecilla, F.; Kiss, T.; Costa Pessoa, J. Eur. J. Inorg. Chem. 2006, 656-662
48. Correia, I.; Dornyei, A.; Jakusch, T.; Avecilla, F.; Kiss, T.; Costa Pessoa, J. Eur. J. Inorg. Chem. 2006, 2819-2830
49. Adão, P.; Maurya, M. R.; Kumar, U.; Avecilla, F.; Henriques, R. T.; Kusnetsov, M. L.; Costa Pessoa, J.; Correia, I. Pure Appl. Chem. 2009, 81, 1279-1296
50. Hamana, K.; Niitsu, M.; Samejima, K. Can. J. Bot. 1998, 76, 130-133
51. Hamana, K.; Matsuzaki, S. J. Biochem. 1982, 91, 1321-1328
52. Prakash, N. J.; Bowlin, T. L.; Davis, G. F.; Sunkara, P. S.; Sjoerdsma, A. Anticancer Res. 1988, 8, 563-568
53. Sunkara, P. S.; Zwolshen, J. H.; Prakash, N. J.; Bowlin, T. L. Adv. Exp. Med. Biol. 1988, 250, 707-716
54. Kawabe, K.; Suekuni, T.; Inada, T.; Yamato, K.; Tadokoro, M.; Kojima, Y.; Fujisawa, Y.; Sakurai, H. Chem. Lett. 1998, 27, 1155-1156
55. Sakurai, H.; Yoshikawa, Y.; Yasui, H. Chem. Soc. Rev. 2008, 37, 2383-2392
56. Sakurai, H.; Kojima, Y.; Yoshikawa, Y.; Kawabe, K.; Yasui, H. Coord. Chem. Rev. 2002, 226, 187-198
57. Crans, D. C. J. Inorg. Biochem. 2000, 80, 123-131
58. Sakurai, H.; Yoshikawa, Y.; Yasui, H. Chem. Soc. Rev. 2008, 37, 2383-2392
59. Vogel, A. I. A text-book of quantitative inorganic analysis, including elementary instrumental analysis; Longman: London, U.K., 1962; pp 808-809, 790-791.
60. Rockenbauer, A.; Korecz, L. Appl. Magn. Reson. 1996, 10, 29-43
61. SAINT-Plus, Version 6.45; Bruker AXS Inc.: Madison, WI, 2003.
62. Sheldrick, G. M. SADABS; Bruker AXS Inc.: Madison, WI, 1997.
63. Altomare, A.; Cascarano, G.; Giacovazzo, C.; Guagliardi, A.; Burla, M. C.; Polidori, G.; Camalli, M. J. Appl. Crystallogr. 1994, 27, 435
64. Sheldrick, G. M. SHELXTL NT, Version 5.1, Program for Solution and Refinement of Crystal Structures; University of Göttingen: Göttingen, Germany, 1997.
65. Farrugia, L. J. J. Appl. Crystallogr. 1999, 32, 837-838
66. Frisch, M. J.; Trucks, G. W.; Schlegel, H. B.; Scuseria, G. E.; Robb, M. A.; Cheeseman, J. R.; Montgomery, J. A.; Vreven, Jr., T.; Kudin, K. N.; Burant, J. C.; Millam, J. M.; Iyengar, S. S.; Tomasi, J.; Barone, V.; Mennucci, B.; Cossi, M.; Scalmani, G.; Rega, N.; Petersson, G. A.; Nakatsuji, H.; Hada, M.; Ehara, M.; Toyota, K.; Fukuda, R.; Hasegawa, J.; Ishida, M.; Nakajima, T.; Honda, Y.; Kitao, O.; Nakai, H.; Klene, M.; Li, X.; Knox, J. E.; Hratchian, H. P.; Cross, J. B.; Adamo, C.; Jaramillo, J.; Gomperts, R.; Stratmann, R. E.; Yazyev, O.; Austin, A. J.; Cammi, R.; Pomelli, C.; Ochterski, J. W.; Ayala, P. Y.; Morokuma, K.; Voth, G. A.; Salvador, P.; Dannenberg, J. J.; Zakrzewski, V. G.; Dapprich, S.; Daniels, A. D.; Strain, M. C.; Farkas, O.; Malick, D. K.; Rabuck, A. D.; Raghavachari, K.; Foresman, J. B.; Ortiz, J. V.; Cui, Q.; Baboul, A. G.; Clifford, S.; Cioslowski, J.; Stefanov, B. B.; Liu, G.; Liashenko, A.; Piskorz, P.; Komaromi, I.; Martin, R. L.; Fox, D. J.; Keith, T.; Al-Laham, M. A.; Peng, C. Y.; Nanayakkara, A.; Challacombe, M.; Gill, P. M. W.; Johnson, B.; Chen, W.; Wong, M. W.; Gonzalez, C.; Pople, J. A. Gaussian 03, Revision A.1; Gaussian, Inc.: Pittsburgh, PA, 2003.
67. Becke, A. D. Phys. Rev. A 1988, 38, 3098-3100
68. Lee, C.; Yang, W.; Parr, R. G. Phys. Rev. B 1988, 37, 785-789
69. Ditchfield, R.; Hehre, W. J.; Pople, J. A. J. Chem. Phys. 1971, 54, 724-728
70. Liu, T.; Gu, J.; Tan, X. J.; Zhu, W. L.; Luo, X. M.; Jiang, H. L.; Ji, R. Y.; Chen, K. X.; Silman, I.; Sussman, J. L. J. Phys. Chem. A 2001, 105, 5431-5437
71. Yang, W.; Mortier, W. J. J. Am. Chem. Soc. 1986, 108, 5708-5711
72. Adamo, C.; Barone, V. J. Chem. Phys. 1998, 108, 664-675
73. Burke, K.; Perdew, J. P.; Wang, Y. Electronic Density Functional Theory: Recent Progress and New Directions; Dobson, J. F.; Vignale, G.; Das, M. P., Eds.; Plenum Press: New York, U.S.A., 1998.
74. Perdew, J. P. Electronic Structure of Solids 91; Ziesche, P.; Eschrig, H., Eds.; Akademie Verlag: Berlin, Germany, 1991. p 11.
75. Perdew, J. P.; Chevary, J. A.; Vosko, S. H.; Jackson, K. A.; Pederson, M. R.; Singh, D. J.; Fiolhais, C. Phys. Rev. B 1992, 46, 6671-6687
76. Perdew, J. P.; Chevary, J. A.; Vosko, S. H.; Jackson, K. A.; Pederson, M. R.; Singh, D. J.; Fiolhais, C. Phys. Rev. B 1993, 48, 11638-11645
77. Perdew, J. P.; Burke, K.; Wang, Y. Phys. Rev. B 1996, 54, 16533-16539
78. Lee, C.; Yang, W.; Parr, R. G. Phys. Rev. B 1988, 37, 785-789
79. Becke, A. D. J. Chem. Phys. 1992, 97, 9173-9177
80. Perdew, J. P. Phys. Rev. B 1986, 33, 8822-8824
81. Wachters, A. J. H. J. Chem. Phys. 1970, 52, 1033-1034
82. Hay, P. J. J. Chem. Phys. 1977, 66, 4377-4384
83. McLean, A. D.; Chandler, G. S. J. Chem. Phys. 1980, 72, 5639-5648
84. Krishnan, R.; Binkley, J. S.; Seeger, R.; Pople, J. A. J. Chem. Phys. 1980, 72, 650-654
85. Raghavachari, K.; Trucks, G. W. J. Chem. Phys. 1989, 91, 1062-1065
86. Skripnikov, L. Chemissian, version 2.000; 2005-2010; http://www. chemissian.com.
87. Adachi, Y.; Sakurai, H. Chem. Pharm. Bull. 2004, 52, 428-443
88. Itaya, K.; Ui, M. J. Lipid Res. 1965, 6, 16-20
89. Yang, W. T.; Mortier, W. J. J. Am. Chem. Soc. 1986, 108, 5708-5711
90. Kostova, I.; Trendafilova, N.; Mihaylov, T. Chem. Phys. 2005, 314, 73-84
91. Kostova, I.; Trendafilova, N.; Momekov, G. J. Inorg. Biochem. 2005, 99, 477-487
92. Macrae, C. F.; Edgington, P. R.; McCabe, P.; Pidcock, E.; Shields, G. P.; Taylor, R.; Towler, M.; Van de Streek, J. J. Appl. Crystallogr. 2006, 39, 453-457
93. Yuan, C.; Lu, L.; Gao, X.; Wu, Y.; Guo, M.; Li, Y.; Fu, X.; Zhu, M. J. Biol. Inorg. Chem. 2009, 14, 841-851
94. Maurya, M. R.; Kumar, A.; Ebel, M.; Rehder, D. Inorg. Chem. 2006, 45, 5924-5937
95. Amin, S. S.; Cryer, K.; Zhang, B.; Dutta, S. K.; Eaton, S. S.; Anderson, O. P.; Miller, S. M.; Reul, B. A.; Brichard, S. M.; Crans, D. C. Inorg. Chem. 2000, 39, 406-416
96. Boas, L. V.; Costa Pessoa, J. Comprehensive Coordination Chemistry; Wilkinson, G.; Gillard, R. D.; McCleverty, J. A., Eds.; Oxford: Oxford, U.K., 1987; Vol. 3, pp 453-583 and refs therein.
97. Crans, D. C.; Smee, J. J. Comprehensive Coordination Chemistry II; McCleverty, J. A.; Meyer, T. J., Eds.; Elsevier: Amsterdam, The Netherlands, 2004; Vol. 4, pp 176-239.
98. Cornman, C. R.; Kampf, J.; Lah, M. S.; Pecoraro, V. L. Inorg. Chem. 1992, 31, 2035-2043
99. Gätjens, J.; Meier, B.; Kiss, T.; Nagy, E. M.; Buglyó, P.; Sakurai, H.; Kawabe, K.; Rehder, D. Chem.-Eur. J. 2003, 9, 4924-4935
100. Smith, T. S.; Root, C. A.; Kampf, J. W.; Rasmussen, P. G.; Pecoraro, V. L. J. Am. Chem. Soc. 2000, 122, 767-775
101. Seifert, H. J.; Uebach, J. Z. Anorg. Allg. Chem. 1981, 479, 32-40
102. Baruah, B.; Das, S.; Chakravorty, A. Inorg. Chem. 2002, 41, 4502-4508
103. Turel, I.; Golobič, A.; Klavžar, A.; Pihlar, B.; Buglyó, P.; Tolis, E.; Rehder, D.; Sepčić, K. J. Inorg. Biochem. 2003, 95, 199-207
104. Sokolowski, A.; Adam, B.; Weyhermüller, T.; Kikuchi, A.; Hildenbrand, K.; Schnepf, R.; Hildebrandt, P.; Bill, E.; Wieghardt, K. Inorg. Chem. 1997, 36, 3702-3710
105. Mohan, M.; Holmes, S. M.; Butcher, R. J.; Jasinski, J. P.; Carrano, C. J. Inor Chem. 1992, 31, 2029-2034
106. Zhang, Y.; Holm, R. H. Inorg. Chem. 1990, 29, 911-917
107. Crans, D. C. Pure Appl. Chem. 2005, 77, 1497-1527
108. Noguera, M.; Ríos-Font, R.; Rodríguez-Santiago, L.; Solans-Monfort, X.; Oliva, A.; Bertran, J.; Sodupe, M. Theor. Chem. Acc. 2009, 123, 105-111
109. Kawabe, K.; Tadokoro, M.; Ichimura, A.; Kojima, Y.; Takino, T.; Sakurai, H. J. Am. Chem. Soc. 1999, 121, 7937-7938
110. Wüthrich, K. Helv. Chim. Acta 1965, 48, 1012-1017
111. Chasteen, N. D. Biological Magnetic Resonance; Reuben, J., Ed.; Plenum: New York, U.S.A., 1981; p 53.
112. Costa Pessoa, J.; Calhorda, M. J.; Cavaco, I.; Costa, P. J.; Correia, I.; Costa, D.; Vilas-Boas, L. F.; Félix, V.; Gillard, R. D.; Henriques, R. T.; Wiggins, R. Dalton Trans. 2004, 2855-2866
113. Rehder, D. Bioinorganic Vanadium Chemistry; John Wiley & Sons: New York, U.S.A., 2008; pp 67-74.
114. Munzarová, M. T. L.; Kaupp, M. J. Phys. Chem. B 2001, 105, 12644-12652
115. Saladino, A. C.; Larsen, S. C. J. Phys. Chem. A 2003, 107, 1872-1878
116. Neese, F. J. Chem. Phys. 2003, 118, 3939-3948
117. Costa Pessoa, J.; Calhorda, M. J.; Cavaco, I.; Correia, I.; Duarte, M. T.; Felix, V.; Henriques, R. T.; Piedade, M. F. M.; Tomaz, T. J. Chem. Soc., Dalton Trans. 2002, 4407-4415
118. Micera, G.; Garribba, E. Dalton Trans. 2009, 1914-1918
119. Gorelsky, S.; Micera, G.; Garribba, E. Chem.-Eur. J. 2010, 16, 8167-8180
120. Lodyga-Chruscinska, E.; Micera, G.; Garribba, E. Inorg. Chem. 2011, 50, 883-899
121. Costa Pessoa, J.; Boas, L. V.; Gillard, R. D.; Lancashire, R. J. Polyhedron 1988, 7, 1245-1262
122. BioDataFit, version 1.02, Data Fit for Biologists; Chang Bioscience Inc.: Castro Valley, CA, 2008; (http//www.changbioscience.com/stat/ec50.html).
123. Costa Pessoa, J.; Tomaz, I. Curr. Med. Chem. 2010, 17, 3701-3738
124. Sakurai, H.; Watanabe, H.; Tamura, H.; Yasui, H.; Matsushita, R.; Takada, J. Inorg. Chim. Acta 1998, 283, 175-183
125. Karmaker, S.; Saha, T. K.; Yoshikawa, Y.; Yasui, H.; Sakurai, H. J. Inorg. Biochem. 2006, 100, 1535-1546
126. Kawabe, K.; Sasagawa, T.; Yoshikawa, Y.; Ichimura, A.; Kumekawa, K.; Yanagihara, N.; Takino, T.; Sakurai, H.; Kojima, Y. J. Biol. Inorg. Chem. 2003, 8, 893-906
127. Nakai, M.; Obata, M.; Sekiguchi, F.; Kato, M.; Shiro, M.; Ichimura, A.; Kinoshita, I.; Mikuriya, M.; Inohara, T.; Kawabe, K.; Sakurai, H.; Orvig, C.; Yano, S. J. Inorg. Biochem. 2004, 98, 105-112