Three new complexes with formula [VOL2]·xH2O [(1) HL: N,N-dimethylbiguanide, x = 0.5; (2) HL: 1-phenylbiguanide, x = 0; (3) HL: 1-(o-tolyl)biguanide, x = 0.5] were synthesised and characterised. The IR and UV–Vis spectral data indicate that these biguanide derivatives act as bidentate chelating anionic ligands and generate VO(II) complexes with a square–pyramidal stereochemistry. The thermal analysis (TG, DTA) elucidated the composition and also the number and nature of the water molecules.
1. McNeill, JH, Yuen, VG, Hoveyda, HR, Orvig, C 1992 Bis(maltolato)-oxovanadium(IV) is a potent insulin mimic. J Med Chem 35:1489–1491 .
2. Yuen, VG, Caravan, P, Gelmini, L, Glover, N, McNeill, JH, Setyawati, IA, Zhou, Y, Orvig, C 1997 Glucose-lowering properties of vanadium compounds: comparison of coordination complexes with maltol or kojic acid as ligands. J Inorg Biochem 68:109–116 .
3. Sakurai, H, Fujii, K, Watanabe, H, Tamura, H 1995 Orally active and long-term acting insulin-mimetic vanadyl complex: bis(picolinato)oxovanadium(iv). Biochem Biophys Res Commun 214:1095–1101 .
4. Sakurai, H, Sano, H, Takino, T, Yasui, H 2000 An orally active antidiabetic vanadyl complex, bis(1-oxy-2-pyridinethiolato)oxovanadium(IV), with VO(S2O2) coordination mode; in vitro and in vivo evaluations in rats. J Inorg Biochem 80:99–105 .
5. Peters, KG, Davis, MG, Howard, BW, Pokross, M, Hastogi, V, Diven, C, Greis, KD, Eby-Wilkens, E, Mayer, M, Evodokimov, A, Soper, S, Gebbauffe, F 2003 Mechanism of insulin sensitization by BMOV (bis maltolato oxovanadium); unliganded vanadium (VO) as the active component. J Inorg Biochem 96:321–330 .
6. Sakurai, H, Katoh, A, 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 .
7. Zhang, Y, Yang, XD, Wang, K, Crans, DC 2006 The permeability and cytotoxicity of insulin-mimetic vanadium (III, IV, V)-dipicolinate complexes. J Inorg Biochem 100:80–87 .
8. Rehder, D 2008 The trigonal-bipyramidal NO4 ligand set in biologically relevant vanadium compounds and their inorganic models. J Inorg Biochem 102:1152–1158 .
9. Kaliva, M, Gabriel, C, Raptopoulou, CP, Terzis, A, Salifoglou, A 2008 pH-specific synthesis, isolation, spectroscopic and structural characterization of a new dimeric assembly of dinuclear vanadium(V)–citrate–peroxo species from aqueous solutions. Inorg Chim Acta 361:2631–2640 .
10. Sheela, A, Roopan, SM, Vijayaraghavan, R 2008 New diketone based vanadium complexes as insulin mimetics. Eur J Med Chem 43:2206–2210 .
11. Nilsson, J, Degerman, E, Haukka, M, Lisensky, GC, Garribba, E, Yoshikawa, Y, Sakurai, H, Enyedy, EA, Kiss, T, Esbak, H, Rehder, D, Nordlander, E 2009 Bis- and tris(pyridyl)amine-oxidovanadium complexes: characteristics and insulin-mimetic potential. Dalton Trans 38:7902–7911 .
12. Parajón-Costa, BS, Baran, EJ 2011 Vibrational spectra of bis(maltolato)oxovanadium(IV): a potent insulin mimetic agent. Spectrochim Acta A Mol Biomol Spectrosc 78:133–135 .
13. Willsky, GR, Chi, L-H M Godzala III Kostyniak, PJ, Smee, JJ, Trujillo, AM, Alfano, JA, Ding, W, Hu, Z, Crans, DC 2011 Anti-diabetic effects of a series of vanadium dipicolinate complexes in rats with streptozotocin-induced diabetes. Coord Chem Rev 255:2258–2269 .
14. Xie, M-J, Niu, Y-F, Yang, X-D, Liu, W-P, Li, L, Gao, L-H, Yan, S-P, Meng, Z-H 2010 Effect of the chloro-substitution on lowering diabetic hyperglycemia of vanadium complexes with their permeability and citotoxicity. Eur J Med Chem 45:6077–6084 .
15. Wei, Y, Zhang, C, Zhao, P, Yang, X, Wang, K 2011 A new salicylic acid-derivatized kojic acid vanadyl complex: synthesis, characterization and anti-diabetic therapeutic potential. J Inorg Biochem 105:1081–1085 .
16. Passadouro, M, Metelo, AM, Melão, AS, Pedro, JR, Faneca, H, Carvalho, E, Margarida, M, Castro, CA 2010 Study of the antidiabetic capacity of the VO(dmpp)2 complex. J Inorg Biochem 104:987–992 .
17. Cransa, DC, Trujillo, AM, Pharazyna, PS, Cohenc, MD 2011 How environment affects drug activity: localization, compartmentalization and reactions of a vanadium insulin-enhancing compound, dipicolinatooxovanadium(V). Coord Chem Rev 255:2178–2192 .
18. Poucheret, P, Verma, S, Grynpas, MD, McNeill, JH 1998 Vanadium and diabetes. Mol Cell Biochem 188:73–80 .
19. Bailey, CJ, Turner, RC 1996 Metformin. N Engl J Med 334:574–579 .
20. Woo, LC, Yuen, VG, Thompson, KH, McNeill, JH, Orvig, C 1999 Vanadyl-biguanide complexes as potential synergistic insulin mimics. J Inorg Biochem 76 3–4 251–257 .
21. Pignard, P 1962 Spectrophotometric determination of N,N-dimethylbiguanide in blood and urine. Ann Biol Clin 20:325–333.
22. Siest, G, Roos, F, Gabou, JJ 1963 Dosage du N–N-dimethyl biguanide (glucophage) par le diacetyle en milieu alcalin. Bull Soc Pharm Nancy 58:29–38.
23. Kanaze, FI, Kokkalou, E, Niopas, I, Georgarakis, M, Stergiou, A, Bikiaris, D 2006 Thermal analysis study of flavonoid solid dispersions having enhanced solubility. J Therm Anal Calorim 83:283–290 .
24. Nakamoto, K 1986 Infrared and Raman spectra of inorganic and coordination compounds Wiley New York.
25. Lever, ABP 1986 Inorganic electronic spectroscopy Elsevier Amsterdam.
26. Shukla S , Mishra AP. Non-isothermal degradation-based solid state kinetics studyof copper (II) schiff base complex, at different heating rates. J Therm Anal Calorim. 2011. doi: .
27. Olar, R, Badea, M, Marinescu, D 2010 Thermal study of some new Ni(II) and Cu(II) complexes with ligands derived from N,N-dimethylbiguanide as potential antimicrobials. J Therm Anal Calorim 99:893–898 .
28. Olar, R, Badea, M, Grecu, MN, Marinescu, D, Lazar, V, Balotescu, C 2008 Thermal behavior, spectroscopic and biological characterization of copper(II) complexes with N,N-dimethylbiguanide. J Therm Anal Calorim 92:239–243 .
29. Olar, R, Badea, M, Cristurean, E, Parnau, C, Marinescu, D 2006 Thermal behaviour of new N,N-dimethylbiguanide complexes having selective and effective antibacterial activity. J Therm Anal Calorim 84:53–58 .
30. Olar, R, Badea, M, Cristurean, E, Lazar, V, Cernat, R, Balotescu, C 2005 Thermal behavior, spectroscopic and biological characterization of Co(II), Zn(II), Pd(II) and Pt(II) complexes with N,N-dimethylbiguanide. J Therm Anal Calorim 80:451–455 .
31. Olar, R, Badea, M, Marinescu, D, Iorgulescu, E, Stoleriu, S 2005 Ni(II) complexes with ligands resulted in condensation of N,N-dimethylbiguanide and pentane-2,4-dione. Synthesis, thermal behaviour and spectroscopic characterization. J Therm Anal Calorim 80:363–367 .
32. Valmalette, JC, Gavarri, JR 1998 High efficiency thermochromic VO2(R) resulting from the irreversible transformation of VO2(B). Mater Sci Eng B54:168–173 .
33. Babykutty, PV, Prabhakaran, CP, Anantaraman, R, Nair, CGR 1974 Electronic and infrared spectra of biguanide complexes of 3d-transition metals. J Inorg Nucl Chem 36:3685–3688 .