Synthesis, characterization, X-ray crystal structure, DFT calculation and antibacterial activities of new vanadium(IV, V) complexes containing chelidamic acid and novel thiourea derivatives

Journal of Inorganic Biochemistry

Volumn 147, Issue , 2015, Pages 54-64

  Farzanfar, Javad ^a   Ghasemi, Khaled ^a   Rezvani, Ali Reza ^a   Delarami, Hojat Samareh ^a   Ebrahimi, Ali ^a   Hosseinpoor, Hona ^a   Eskandari, Amir ^a   Rudbari, Hadi Amiri ^b   Bruno, Giuseppe ^c  

^a UNIVERSITY OF SISTAN AND BALUCHESTAN   (Iran)

^b UNIVERSITY OF ISFAHAN   (Iran)

^c UNIVERSITY OF MESSINA   (Italy)

Author keywords

4 hydroxy 2,6 pyridine dicarboxylic acid; Antibacterial activity; N,N dimethylbiguanide; Oxo vanadium(IV, V) complex; Thiourea

Indexed keywords

CHELIDAMIC ACID DERIVATIVE; ISOTHIOCYANIC ACID DERIVATIVE; LIGAND; METAL COMPLEX; METFORMIN; PYRIDINE DERIVATIVE; THIOUREA DERIVATIVE; UNCLASSIFIED DRUG; VANADIUM DERIVATIVE; ANTIINFECTIVE AGENT; CHELIDAMIC ACID; COORDINATION COMPOUND; PYRIDONE DERIVATIVE; THIOUREA; VANADIUM;

ABSORPTION SPECTROSCOPY; ANTIBACTERIAL ACTIVITY; ARTICLE; BACTERIUM CULTURE; BIOLOGICAL ACTIVITY; COMPLEX FORMATION; CRYSTAL STRUCTURE; DENSITY FUNCTIONAL THEORY; DRUG SYNTHESIS; ENTEROCOCCUS FAECALIS; ESCHERICHIA COLI; GEOMETRY; GRAM NEGATIVE BACTERIUM; GRAM POSITIVE BACTERIUM; INFRARED SPECTROSCOPY; MINIMUM INHIBITORY CONCENTRATION; NONHUMAN; PROTON NUCLEAR MAGNETIC RESONANCE; PSEUDOMONAS AERUGINOSA; SOLID STATE; STAPHYLOCOCCUS AUREUS; ULTRAVIOLET SPECTROSCOPY; X RAY DIFFRACTION; BACTERIUM; CHEMISTRY; DRUG EFFECTS; SYNTHESIS;

BACTERIA (MICROORGANISMS); NEGIBACTERIA; POSIBACTERIA;

ANTI-BACTERIAL AGENTS; BACTERIA; COORDINATION COMPLEXES; PYRIDONES; THIOUREA; VANADIUM;

EID: 84930868650     PISSN: 01620134     EISSN: 18733344     Source Type: Journal    
DOI: 10.1016/j.jinorgbio.2015.02.007     Document Type: Article

References (68)

1. A. Khalaj, M. Nakhjiri, A.S. Negahbani, M. Samadizadeh, L. Firoozpour, S. Rajabalian, N. Samadi, M.A. Faramarzi, N. Adibpour, A. Shafiee, and A. Foroumadi Eur. J. Med. Chem. 46 2011 65 70
2. M.S. Karthikeyan, D.J. Prasad, B. Poojary, K.S. Bhat, B.S. Holla, and N.S. Kumari Bioorg. Med. Chem. 14 2006 7482 7489
3. X.S. Cui, C. Jing, K.Y. Chai, J.S. Lee, and Z.S. Quan Med. Chem. Res. 18 2009 49 58
4. J. Chen, X.Y. Sun, K.Y. Chai, J.S. Lee, M.S. Song, and Z.S. Quan Bioorg. Med. Chem. 15 2007 6775 6781
5. X.J. Chen, F. Niyonsaba, H. Ushio, D. Okuda, I. Nagaoka, S. Ikeda, K. Okumura, and H. Ogawa J. Dermatol. Sci. 40 2005 123 132
6. W. Yang, H. Liu, M. Li, F. Wang, W. Zhou, and J. Fan J. Inorg. Biochem. 116 2012 97 105
7. U. El-Ayaan J. Mol. Struct. 998 2011 11 19
8. H. Arslan, N. Duran, G. Borekci, C.K. Ozer, and C. Akbay Molecules 14 2009 519 527
9. Z. Zhong, R. Xing, S. Liu, L. Wang, S. Caia, and P. Li Carbohydr. Res. 343 2008 566 570
10. M.Kh. Rauf, I. Din, A. Badshah, M. Gielen, M. Ebihara, D.D. Vos, and S. Ahmed J. Inorg. Biochem. 103 2009 1135 1144
11. S.A. Khan, N. Singh, and K. Saleem Eur. J. Med. Chem. 43 2008 2272 2277
12. G. Binzet, H. Arslan, U. Flörke, N. Külcü, and N. Duran J. Coord. Chem. 59 2006 1395 1406
13. S. Cunha, F.C. Macedo Jr., G.A.N. Costa, M.T. Rodrigues Jr., R.B.V. Verde, L.C.D.S. Neta, I. Vencato, C. Lariucci, and F.P. Sa Monatsh. Chem. 138 2007 511 516
14. A.A. Isab, S. Nawaz, M. Saleem, M. Altaf, M. Monim-ul-Mehboob, S. Ahmad, and H.S. Evans Polyhedron 29 2010 1251 1256
15. A. Saeed, U. Shaheen, A. Hameed, and S.Z. Haider Naqvi J. Fluor. Chem. 130 2009 1028 1034
16. G.S. Kurt, F. Sevgi, and B. Mercimek Chem. Pap. 63 2009 548 553
17. E. RodrÍguez-Fernández, E. GarcÍa, M.R. Hermosa, A. Jiménez-Sánchez, M.M. Sánchez, E. Monte, and J.J. Criado J. Inorg. Biochem. 75 1999 181 188
18. Z. Weiqun, Y. Wen, X. Liqun, and C. Xianchen J. Inorg. Biochem. 99 2005 1314 1319
19. R.D. Campo, J.J. Criado, R. Gheorghe, F.J. Gonzalez, M.R. Hermosa, F. Sanz, J.L. Manzano, E. Monte, and E. Rodriguez-Fernandez J. Inorg. Biochem. 98 2004 1307 1314
20. F. Bilek, T. Krizova, and M. Lehocky Colloids Surf. B: Biointerfaces 88 2011 440 447
21. R.D. Campo, J.J. Criado, E. Garcia, M.R. Hermosa, A. Jimenez-Sanchez, J.L. Manzano, E. Monte, E. Rodriguez-Fernandez, and F. Sanz J. Inorg. Biochem. 89 2002 74 82
22. H. Pluempe, and W. Pulls Chem. Abstr. 74 1971 1251154n
23. H.M. Faidallah, K.A. Khan, and A.M. Asiri J. Fluor. Chem. 132 2011 131 137
24. H.M. Faidallah, K.A. Khan, and A.M. Asiri J. Fluor. Chem. 132 2011 870 877
25. S. Karakus, and S. Rollas Farmaco 57 2002 577 581
26. S.B. Tsogoeva, M.J. Hateley, D.A. Yalalov, K. Meindl, C. Weckbecker, and K. Huthmacher Bioorg. Med. Chem. 13 2005 5680 5685
27. O.J. DCruz, Y. Dong, and F.M. Uckun Biochem. Biophys. Res. Commun. 302 2003 253 264
28. T.K. Venkatachalam, E.A. Sudbeck, and F.M. Uckun Tetrahedron Lett. 42 2001 6629 6632
29. I.J. Kang, L.W. Wang, C.C. Lee, Y.C. Lee, Y.S. Chao, T.A. Hsu, and J.H. Chern Bioorg. Med. Chem. Lett. 19 2009 1950 1955
30. W. Hermindez, E. Spodine, L. Beyer, U. Schrtider, R. Richter, J. Ferreira, and M. Pavani Bioinorg. Chem. Appl. 3 2005 3 4
31. W. Hermindez, E. Spodine, J.C. Mufioz, L. Beyer, U. Schrtider, R. Richter, J. Ferreira, and M. Pavani Bioinorg. Chem. Appl. 1 2003 3 4
32. E. Rodríguez-Fernández, J.L. Manzano, J.J. Benito, R. Hermosa, E. Monte, and J.J. Criado J. Inorg. Biochem. 99 2005 1558 1572
33. M.K. Rauf, I.A. Badshah, M. Gielen, M. Ebihara, D. de Vos, and S. Ahmed J. Inorg. Biochem. 103 2009 1135 1144
34. H.J. Zhang, X. Qin, K. Liu, D.D. Zhu, X.M. Wang, and H.L. Zhu Bioorg. Med. Chem. 19 2011 5708 5715
35. I.C. Mendes, M.A. Soares, R.G. dos Santos, C. Pinheiro, and H. Beraldo Eur. J. Med. Chem. 44 2009 1870 1877
36. F.H. Nielsen FASEB J. 5 1991 2661 2667
37. M. Anke, H. Illing-Gunther, and U. Schafer Biomed. Res. Trace Elem. 16 2005 208 214
38. G. Müller, H. Benkhai, R. Matthes, B. Finke, W. Friedrichs, N. Geist, W. Langel, and A. Kramer Biomaterials 35 2014 5261 5277
39. I.O. Adriazola, A.E. doAmaral, J.C. Amorim, B.L. Correia, C.L.O. Petkowicz, A.L.R. Mercê, and G.R. Noleto J. Inorg. Biochem. 132 2014 45 51
40. Z.H. Chohan, S.H. Sumrra, M.H. Youssoufi, and T.B. Hadda Eur. J. Med. Chem. 45 2010 2739 2747
41. T. Rosu, E. Pahontu, M. Reka-Stefana, D.C. Ilies, R. Georgescu, S. Shova, and A. Gulea Polyhedron 31 2012 352 360
42. S.H. Sumrra, and Z.H. Chohan Spectrochim. Acta A Mol. Biomol. Spectrosc. 98 2012 53 61
43. D.C. Crans, M. Mahroof-Tahir, M.D. Johnson, P.C. Wilkins, L. Yang, K. Robbins, A. Johnson, J.A. Alfano, M.E. Godzala, L.T. Austin, and G.R. Willsky Inorg. Chim. Acta 356 2003 365 378
44. L. Yang, A. la Cour, O.P. Anderson, and D.C. Crans Inorg. Chem. 41 2002 6322 6331
45. T.G. Porter, and D.L. Martin Biochem. Pharmacol. 34 1985 4145 4150
46. I. Sánchez-Lombardo, E. Sánchez-Lara, A. Pérez-Benítez, Á. Mendoza, S. Bernès, and E. González-Vergara Eur. J. Inorg. Chem. 2014 4581 4588
47. G. Li, D.J. Che, Z.F. Li, Y. Zhu, and D.P. Zou New J. Chem. 26 2002 1629 1633
48. C.K. Ozer, H. Arslan, D. VanDerveer, and G. Binzet J. Coord. Chem. 62 2009 266 276
49. A.D. Becke Density-functional thermochemistry. III. The role of exact exchange J. Chem. Phys. 98 1993 5648 5652
50. C. Lee, W. Yang, and R.G. Parr Development of the Colle-salvetti correlation-energy formula into a functional of the electron density Phys. Rev. B 37 1988 785 789
51. M.J. Frisch, G.W. Trucks, H.B. Schlegel, G.E. Scuseria, M.A. Robb, J.R. Cheeseman, G. Scalmani, V. Barone, B. Mennucci, G.A. Petersson, H. Nakatsuji, M. Caricato, X. Li, H.P. Hratchian, A.F. Izmaylov, J. Bloino, G. Zheng, J.L. Sonnenberg, M. Hada, M. Ehara, K. Toyota, R. Fukuda, J. Hasegawa, M. Ishida, T. Nakajima, Y. Honda, O. Kitao, H. Nakai, T. Vreven, J.A. Montgomery, J.E. Peralta, F. Ogliaro, M. Bearpark, J.J. Heyd, E. Brothers, K.N. Kudin, V.N. Staroverov, R. Kobayashi, J. Normand, K. Raghavachari, A. Rendell, J.C. Burant, S.S. Iyengar, J. Tomasi, M. Cossi, N. Rega, J.M. Millam, M. Klene, J.E. Knox, J.B. Cross, V. Bakken, C. Adamo, J. Jaramillo, R. Gomperts, R.E. Stratmann, O. Yazyev, A.J. Austin, R. Cammi, C. Pomelli, J.W. Ochterski, R.L. Martin, K. Morokuma, V.G. Zakrzewski, G.A. Voth, P. Salvador, J.J. Dannenberg, S. Dapprich, A.D. Daniels, O. Farkas, J.B. Foresman, J.V. Ortiz, J. Cioslowski, and D.J. Fox Gaussian 09, Revision A.1 2009 Gaussian, Inc. Wallingford CT
52. E.D. Glendening, A.E. Reed, J.E. Carpenter, and F. Weinhold NBO 3.1 1990 Theoretical Chemistry Institute, University of Wisconsin Madison
53. G. Micera, and E. Garribba Int. J. Quantum Chem. 112 2012 2486 2498
54. G. Micera, V.L. Pecoraro, and E. Garribba Inorg. Chem. 48 2009 5790 5796
55. S. Gorelsky, G. Micera, and E. Garribba Chem. Eur. J. 16 2010 8167 8180
56. Bruker, SAINT and SMART 2009 Bruker AXS Inc. Madison, Wisconsin, USA
57. G.M. Sheldrick Acta Crystallogr. A: Found. Crystallogr. 64 2008 112 122
58. A.L. Spek Acta Crystallogr. D Biol. Crystallogr. 65 2009 148 155
59. L.J. Farrugia J. Appl. Crystallogr. 45 2012 849 854
60. C.F. Macrae, P.R. Edgington, P. McCabe, E. Pidcock, G.P. Shields, R. Taylor, M. Towler, and J.V.D. Streek J. Appl. Crystallogr. 39 2006 453 457
61. I. Wiegand, K. Hilpert, and R.E.W. Hancock Nat. Protoc. 3 2008 163 175
62. B.J.A. Jeragh, and A. El-Dissouky Transit. Met. Chem. 29 2004 579 585
63. K. Nakamoto Infrared and Raman Spectra of Inorganic and Coordination Compounds 1997 Wiley-Interscience New York
64. C.J. Ballhausen, and H.B. Gray Inorg. Chem. 1 1962 111 122
65. H.Y. Zhao, Y.H. Zhang, Y.H. Xing, Z.P. Li, Y.Z. Cao, M.F. Ge, X.Q. Zeng, and S.Y. Niu Inorg. Chim. Acta 362 2009 4110 4118
66. B.S. Parajón-Costa, O.E. Piro, R. Pis-Diez, E.E. Castellano, and A.C. González-Baro Polyhedron 25 2006 2920 2928
67. D.C. Crans, M. Mahroof-Tahir, M.D. Johnson, P.C. Wilkins, L. Yang, K. Robbins, A. Johnson, J.A. Alfano, M.E. Godzala, L.T. Austin, and G.R. Willsky Inorg. Chim. Acta 356 2003 365 378
68. A.W. Addison, T.N. Rao, J. Reedijk, J. van Rijn, and G.C. Verschoor J. Chem. Soc. Dalton Trans. 1984 1349