Synthesis, crystal structure, and insulin-like activity of dimeric vanadium complex derived from 4-bromo-N'-(2-hydroxy-5-methoxybenzylidene)benzohydrazide

References

• Scior, T.; Guevara-Garcia, J. A.; Melendez, F. J.; Abdallah, H. H.; Do, Q. T.; Bernad, P. Chimeric design, synthesis, and biological assays of a new nonpeptide insulin-mimetic vanadium compound to inhibit protein tyrosine phosphatase 1B. Drug Des. Dev. Ther. 2010, 4, 231–242.
   PubMed Web of Science ®Google Scholar
• Rivadeneira, J.; Barrio, D. A.; Arrambide, G.; Gambino, D.; Bruzzone, L.; Etcheverry, S. B. Biological effects of a complex of vanadium(V) with salicylaldehyde semicarbazone in osteoblasts in culture: Mechanism of action. J. Inorg. Biochem. 2009, 103, 633–642.
   PubMed Web of Science ®Google Scholar
• Guilherme, L. R.; Massabni, A. C.; Cuin, A.; Oliveira, L. A. A.; Castellano, E. E.; Heinrich, T. A.; Costa-Neto, C. M. Synthesis, characterization, crystal structure, and biological studies of vanadium complexes with glycolic acid. J. Coord. Chem. 2009, 62, 1561–1571.
   Web of Science ®Google Scholar
• Frank, P.; Carlson, E. J.; Carlson, R. M. K.; Hedman, B.; Hodgson, K. O. The uptake and fate of vanadyl ion in ascidian blood cells and a detailed hypothesis for the mechanism and location of biological vanadium reduction. A visible and X-ray absorption spectroscopic study. J. Inorg. Biochem. 2008, 102, 809–823.
   Web of Science ®Google Scholar
• Ashiq, U.; Ara, R.; Mahroof-Tahir, M.; Maqsood, Z. T.; Khan, K. M.; Khan, S. N.; Siddiqui, H.; Choudhary, M. I. Synthesis, spectroscopy, and biological properties of vanadium(IV) - Hydrazide complexes. Chem. Biodivers. 2008, 5, 82–92.
   PubMed Web of Science ®Google Scholar
• Mochizuki, M.; Kudo, E.; Kikuchi, M.; Takano, T.; Taniuchi, Y.; Kitamura, T.; Hondo, R.; Ueda, F. A basic study on the biological monitoring for vanadium-effects of vanadium on vero cells and the evaluation of intracellular vanadium contents. Biol. Trace Elem. Res. 2011, 142, 117–126.
   PubMed Web of Science ®Google Scholar
• Hu, Y. L.; Lee, C. C.; Ribbe, M. W. Vanadium nitrogenase: A two-hit wonder? Dalton Trans. 2012, 41, 1118–1127.
   PubMed Web of Science ®Google Scholar
• Crans, D. C.; Schoeberl, S.; Gaidamauskas, E.; Baruah, B.; Roess, D. A. Antidiabetic vanadium compound and membrane interfaces: interface-facilitated metal complex hydrolysis. J. Biol. Inorg. Chem. 2011, 16, 961–972.
   PubMed Web of Science ®Google Scholar
• Li, S. H.; McNeill, J. H. In vivo effects of vanadium on GLUT4 translocation in cardiac tissue of STZ-diabetic rats. Mol. Cell Biochem. 2001, 217, 121–129.
   PubMed Web of Science ®Google Scholar
• Hwang, S.-L.; Chang, H. W. Natural vanadium-containing Jeju ground water stimulates glucose uptake through the activation of AMP-activated protein kinase in L6 myotubes. Mol. Cell Biochem. 2012, 360, 401–409.
   PubMed Web of Science ®Google Scholar
• Sanna, D.; Micera, G.; Garribba, E. New developments in the comprehension of the biotransformation and transport of insulin-enhancing vanadium compounds in the blood serum. Inorg. Chem. 2010, 49, 174–187.
   PubMed Web of Science ®Google Scholar
• Delgado, T. C.; Tomaz, A. I.; Correia, I.; Pessoa, J. C.; Jones, J. G.; Geraldes, C. F. G. C.; Castro, M. M. C. A. Uptake and metabolic effects of insulin mimetic oxovanadium compounds in human erythrocytes. J. Inorg. Biochem. 2005, 99, 2328–2339.
   PubMed Web of Science ®Google Scholar
• Lu, B.; Ennis, D.; Lai, R.; Bogdanovic, E.; Nikolov, R.; Salamon, L.; Fantus, C.; Le-Tien, H.; Fantus, I. G. 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. 2001, 276, 35589–35598.
   PubMed Web of Science ®Google Scholar
• Cocco, M. T.; Onnis, V.; Ponticelli, G.; Meier, B.; Rehder, D.; Garribba, E.; Micera, G. Synthesis, characterisation and insulin-mimetic activity of oxovanadium(IV) complexes with amidrazone derivatives. J. Inorg. Biochem. 2007, 101, 19–29.
   PubMed Web of Science ®Google Scholar
• Pillai, S. L.; Subramanian, S. P.; Kandaswamy, M. A novel insulin mimetic vanadium-flavonol complex: Synthesis, characterization and in vivo evaluation in STZ-induced rats. Eur. J. Med. Chem. 2013, 63, 109–117.
   PubMed Web of Science ®Google Scholar
• Crans, D. C.; Trujillo, A. M.; Pharazyn, P. S.; Cohen, M. D. How environment affects drug activity: Localization, compartmentalization and reactions of a vanadium insulin-enhancing compound, dipicolinatooxovanadium(V). Coord. Chem. Rev. 2011, 255, 2178–2192.
   Web of Science ®Google Scholar
• Mendes, I. C.; Botion, L. M.; Ferreira, A. V. M.; Castellano, E. E.; Beraldo, H. Vanadium complexes with 2-pyridineformamide thiosemicarbazones: In vitro studies of insulin-like activity. Inorg. Chim. Acta 2009, 362, 414–420.
   Web of Science ®Google Scholar
• Nejo, A. A.; Kolawole, G. A.; Opoku, A. R.; Wolowska, J.; Obrien, P. Synthesis, characterization and preliminary insulin-enhancing studies of symmetrical tetradentate Schiff base complexes of oxovanadium(IV). Inorg. Chim. Acta 2009, 362, 3993–4001.
   Web of Science ®Google Scholar
• Altintop, M. D.; Ozdemir, A.; Turan-Zitouni, G.; Ilgin, S.; Atlik, O.; Iscan, G.; Kaplancikli, Z. A. Synthesis and biological evaluation of some hydrazone derivatives as new anticandidal and anticancer agents. Eur. J. Med. Chem. 2012, 58, 299–307.
   PubMed Web of Science ®Google Scholar
• Bruker, A. X. S. SAINT software reference manual; Bruker, Madison, WI, 1998.
   Google Scholar
• Sheldrick, G. M. SADABS, Siemens Area Detector Absorption Corrected Software; University of Göttingen, Germany, 1996.
   Google Scholar
• Sheldrick, G. M. A history of Shelxltl. Acta Crystallogr. 2008, A64, 112–122.
   Google Scholar
• Sarkar, A.; Pal, S. Some ternary complexes of oxovanadium(IV) with acetylacetone and N-(2-pyridyl)-N'-(salicylidene)hydrazine and its derivatives. Polyhedron 2006, 25, 1689–1694.
   Web of Science ®Google Scholar
• Geary, W. J. Use of conductivity measurements in organic solvents for characterisation of coordination compounds. Coord. Chem. Rev. 1971, 7, 81–122.
   Web of Science ®Google Scholar
• Maurya, M. R.; Khan, A. A.; Azam, A.; Ranjan, S.; Mondal, N.; Kumar, A.; Avecilla, F.; Pessoa, J. C. Vanadium complexes having [VIVO]2+ and [VVO2]+ cores with binucleating dibasic tetradentate ligands: Synthesis, characterization, catalytic and antiamoebic activities. Dalton Trans. 2010, 39, 1345–1360.
   PubMed Web of Science ®Google Scholar
• Kurup, M. R. P.; Seena, E. B.; Kuriakose, M. Synthesis, spectral and structural studies of oxovanadium(IV/V) complexes derived from 2-hydroxyacetophenone-3-hydroxy-2-naphthoylhydrazone: polymorphs of oxovanadium(V) complex [VOL(OCH3)]. Struct. Chem. 2010, 21, 599–605.
   Web of Science ®Google Scholar
• Zhao, X.; Chen, X.; Li, J.; Chen, J.; Sheng, G.; Niu, F.; Qu, D.; Huo, Y.; Zhu, H.; You, Z. Synthesis, structures and insulin-like activity of oxidovanadium(V) complexes with aroylhydrazones and ethylmaltol mixed-ligands. Polyhedron 2015, 97, 268–272.
   Web of Science ®Google Scholar
• Ye, Y.-T.; Niu, F.; Sun, Y.; Qu, D.; Zhao, X.-L.; Wang, J.; Xian, D.-M.; Jurg, H.; You, Z.-L. N’-(2-Hydroxy-5-methoxybenzylidene)-4-dimethylaminobenzohydrazide and its oxovanadium(V) complex: Syntheses, crystal structures, and urease inhibitory activity. Chinese J. Inorg. Chem. 2015, 31, 1019–1026.
   Web of Science ®Google Scholar