Copyright (c) 2016 AJC
This work is licensed under a Creative Commons Attribution 4.0 International License.
Synthesis, Characterization and Biological Activity of Zn(II) Complexes with Dibasic Tridentate ONS-Donor Ligand
Corresponding Author(s) : G. Rajagopal
Asian Journal of Chemistry,
Vol. 28 No. 11 (2016): Vol 28 Issue 11
Abstract
A new kind of zinc(II) complexes 1 and 2 with new Schiff base ligand (L) have been synthesized and characterized by 1H NMR, X-ray crystallography, IR and UV-visible spectroscopic studies. The trigonality index t of 0.63 for complex 2 indicates that the coordination geometry around zinc is intermediate between trigonal bipyramidal and square pyramidal geometries and is better described as trigonal bipyramidal distorted square based pyramid (TBDSBP) with zinc displaced above the N(2), N(4), O(1) and S(1) coordination plane and towards the elongated apical N(1) atom. The newly synthesized Schiff base ligand (L) and its Zn(II) complexes 1-2 were assayed for in vitro antibacterial activity against two Gram-positive bacteria strains (Stapholococcus aureus, Pseudomonas aeruginosa) and Gram-negative bacteria E. coli. The cancer cell line studies of the effect of the ligand (L) and its Zn(II) complexes 1-2 on a MCF-7 cancer cell line by an MTT assay indicates that the ligand (L) exhibits higher activity towards the metal complexes 1 and 2 when compared with cyclophosphamide as reference drug.
Keywords
Download Citation
Endnote/Zotero/Mendeley (RIS)BibTeX
- D.X. West, J.K. Swearingen, J. Valdes-Martinez, S. Hernandez-Ortega, A.K. El-Sawaf, F. van Meurs, A. Castiñeiras, I. Garcia and E. Bermejo, Polyhedron, 18, 2919 (1999); doi:10.1016/S0277-5387(99)00210-7.
- P. Tarasconi, S. Capacchi, G. Pelosi, M. Cornia, R. Albertini, A. Bonati, P. Dall Aglio, P. Lunghi and S. Pinelli, Bioorg. Med. Chem., 8, 157 (2000); doi:10.1016/S0968-0896(99)00260-6.
- S.E. Ghazy, M.A. Kabil, A.A. El-Asmy and Y.A. Sherief, Anal. Lett., 29, 1215 (1996); doi:10.1080/00032719608001470.
- A.R. Cowley, J.R. Dilworth, P.S. Donnelly, A.D. Gee and J.M. Heslop, Dalton Trans., 2404 (2004); doi:10.1039/B406429A.
- S. Chandra, P. Shikha and K. Yatender, Bioinorg. Chem. Appl., Article ID 851316 (2009); doi:10.1155/2009/851316.
- R. Kothari and B. Sharma, J. Chem. Chem. Sci., 1, 158 (2011).
- U. Kumar and S. Chandra, J. Saudi Chem. Soc., 15, 19 (2011); doi:10.1016/j.jscs.2010.08.003.
- S. Chandra, L.K. Gupta and S. Agrawal, Transition Met. Chem., 32, 558 (2007); doi:10.1007/s11243-007-0201-y.
- S. Chandra and Ruchi, Spectrochim. Acta A, 103, 338 (2013); doi:10.1016/j.saa.2012.10.065.
- S. Chandra, S. Bargujar, R. Nirwal and N. Yadav, Spectrochim. Acta A, 106, 91 (2013); doi:10.1016/j.saa.2012.12.014.
- (a) S. Ramakrishnan, V. Rajendiran, M. Palaniandavar, V.S. Periasamy, B.S. Srinag, H. Krishnamurthy and M.A. Akbarsha, Inorg. Chem., 48, 1309 (2009); doi:10.1021/ic801144x; (b) S. Ramakrishnan, D. Shakthipriya, E. Suresh, V.S. Periasamy, M.A. Akbarsha and M. Palaniandavar, Inorg. Chem., 50, 6458 (2011); doi:10.1021/ic1024185.
- (a) H.H. Thorp, Chem. Biol., 5, R125 (1998); doi:10.1016/S1074-5521(98)90166-1; (b) H. Vahrenkamp, Dalton Trans., 42, 4751 (2007); doi:10.1039/b712138e; (c) A.I. Anzellotti and N.P. Farrell, Chem. Soc. Rev., 37, 1629 (2008); doi:10.1039/b617121b.
- S. Emami, S.J. Hosseinimehr, S.M. Taghdisi and S. Akhlaghpoor, Bioorg. Med. Chem. Lett., 17, 45 (2007); doi:10.1016/j.bmcl.2006.09.097.
- Q. Huang, Z. Pan, P. Wang, Z. Chen, X. Zhang and H. Xu, Bioorg. Med. Chem. Lett., 16, 3030 (2006); doi:10.1016/j.bmcl.2005.02.094.
- (a) A. Nakayama, M. Hiromura, Y. Adachi and H.J. Sakurai, Biol. Inorg. Chem., 13, 675 (2008); doi:10.1007/s00775-008-0352-0; (b) H. Sakurai, Y. Yoshikawa and H. Yasui, Chem. Soc. Rev., 37, 2383 (2008); doi:10.1039/b710347f.
- M.T. Kaczmarek, R. Jastrzab, E. Holderna-Kedzia and W. Radecka-Paryzek, Inorg. Chim. Acta, 362, 3127 (2009); doi:10.1016/j.ica.2009.02.012.
- M.M. Ali, E. Frei, J. Straub, A. Breuer and M. Wiessler, Toxicology, 179, 85 (2002); doi:10.1016/S0300-483X(02)00322-0.
- Q. Jiang, J. Zhu, Y. Zhang, N. Xiao and Z. Guo, Biometals, 22, 297 (2009); doi:10.1007/s10534-008-9166-3.
- (a) S. Mathan Kumar, K. Dhahagani, J. Rajesh, K. Nehru, J. Annaraj, G. Chakkaravarthi and G. Rajagopal, Polyhedron, 59, 58 (2013); doi:10.1016/j.poly.2013.04.048; (b) K. Dhahagani, S. Mathan Kumar, G. Chakkaravarthi, K. Anitha, J. Rajesh, A. Ramu and G. Rajagopal, Spectrochim. Acta A, 117, 87 (2014); doi:10.1016/j.saa.2013.07.101; (c) K.K. Raja, D. Easwaramoorthy, S.K. Rani, J. Rajesh, Y. Jorapur, S. Thambidurai, P. Athappan and G. Rajagopal, J. Mol. Catal. Chem., 303, 52 (2009); doi:10.1016/j.molcata.2008.12.021; (d) G. Puthilibai, S. Vasudhevan, S. Kutti Rani and G. Rajagopal, Spectrochim. Acta A, 72, 796 (2009); doi:10.1016/j.saa.2008.11.019.
- (a) J. Rajesh, A. Gubendran, G. Rajagopal and P.R. Athappan, J. Mol. Struct., 1010, 169 (2012); doi:10.1016/j.molstruc.2011.12.002; (b) J. Rajesh, M. Rajasekaran, G. Rajagopal and P.R. Athappan, Spectrochim. Acta A, 97, 223 (2012); doi:10.1016/j.saa.2012.05.006; (c) A. Gubendran, J. Rajesh, K. Anitha and P.R. Athappan, J. Mol. Struct., 1075, 419 (2014); doi:10.1016/j.molstruc.2014.06.079.
- G. Kumar, D. Kumar, S. Devi, R. Johari and C.P. Singh, Eur. J. Med. Chem., 45, 3056 (2010); doi:10.1016/j.ejmech.2010.03.036.
- T. Mosmann, J. Immunol. Methods, 65, 55 (1983); doi:10.1016/0022-1759(83)90303-4.
- A.W. Addison, T.N. Rao, J. Reedijk, J. van Rijn and G.C. Verschoor, J. Chem. Soc., Dalton Trans., 158, 1349 (1984); doi:10.1039/DT9840001349.
- Y. Hayashi, R. Matsuda, K. Ito, W. Nishimura, K. Imai and M. Maeda, Anal. Sci., 21, 167 (2005); doi:10.2116/analsci.21.167.
- E.B. Seena and M.R.P. Kurup, Spectrochim. Acta A, 69, 726 (2008); doi:10.1016/j.saa.2007.05.025.
- C.B. Castellani, G. Gatti and R. Millini, Inorg. Chem., 23, 4004 (1984); doi:10.1021/ic00192a032.
- N.J. Ray and B.J. Hathaway, Acta Crystallogr., 34, 3224 (1978); doi:10.1107/S0567740878010547.
- R.P. John, A. Sreekanth, V. Rajakannan, T.A. Ajith and M.R.P. Kurup, Polyhedron, 23, 2549 (2004); doi:10.1016/j.poly.2004.09.004.
- C. Zhang and C. Janiak, J. Chem. Crystallogr., 31, 29 (2001); doi:10.1023/A:1013774502147.
- E.B. Seena, M.R. Prathapachandra Kurup and E. Suresh, J. Chem. Crystallogr., 38, 93 (2008); doi:10.1007/s10870-007-9268-8.
- T. Bal-Demirci, Polyhedron, 27, 440 (2008); doi:10.1016/j.poly.2007.10.001.
- S. Güveli, N. Özdemir, T. Bal-Demirci, B. Ülküseven, M. Dinçer and Ö. Andaç, Polyhedron, 29, 2393 (2010); doi:10.1016/j.poly.2010.05.004.
- R. Prabhakaran, R. Sivasamy, J. Angayarkanni, R. Huang, P. Kalaivani, R. Karvembu, F. Dallemer and K. Natarajan, Inorg. Chim. Acta, 374, 647 (2011); doi:10.1016/j.ica.2011.03.020.
- T.A. Gerber, A. Abrahams, P. Mayer and E. Hosten, J. Coord. Chem., 56, 1397 (2003); doi:10.1080/00958970510001641691.
- J.R. Dilworth, Coord. Chem. Rev., 21, 29 (1976); doi:10.1016/S0010-8545(00)82050-0.
- S.G. Teoh, S.H. Ang, S.B. Teo, H.K. Fun, K.L. Khew and C.W. Ong, J. Chem. Soc., Dalton Trans., 465 (1997); doi:10.1039/a605679b.
- S.K. Jain, B.S. Garg and Y.K. Bhoon, Spectrochim. Acta A, 42, 959 (1986); doi:10.1016/0584-8539(86)80003-4.
- M.E. Hossain, M.N. Alam, J. Begum, M. Akbar Ali, M. Nazimuddin, F.E. Smith and R.C. Hynes, Inorg. Chim. Acta, 249, 207 (1996); doi:10.1016/0020-1693(96)05098-0.
- D. Gambino, Min-Rev. J. Med. Chem., 4, 1 (2004); doi:10.2174/1389557043487529.
- S. Singh, N. Bharti, F. Naqvi and A. Azam, Eur. J. Med. Chem., 39, 459 (2004); doi:10.1016/j.ejmech.2004.02.003.
- X.Y. Qiu, S.Z. Li, A.R. Shi, Q. Li and B. Zhai, Chin. J. Struct. Chem., 31, 555 (2012).
References
D.X. West, J.K. Swearingen, J. Valdes-Martinez, S. Hernandez-Ortega, A.K. El-Sawaf, F. van Meurs, A. Castiñeiras, I. Garcia and E. Bermejo, Polyhedron, 18, 2919 (1999); doi:10.1016/S0277-5387(99)00210-7.
P. Tarasconi, S. Capacchi, G. Pelosi, M. Cornia, R. Albertini, A. Bonati, P. Dall Aglio, P. Lunghi and S. Pinelli, Bioorg. Med. Chem., 8, 157 (2000); doi:10.1016/S0968-0896(99)00260-6.
S.E. Ghazy, M.A. Kabil, A.A. El-Asmy and Y.A. Sherief, Anal. Lett., 29, 1215 (1996); doi:10.1080/00032719608001470.
A.R. Cowley, J.R. Dilworth, P.S. Donnelly, A.D. Gee and J.M. Heslop, Dalton Trans., 2404 (2004); doi:10.1039/B406429A.
S. Chandra, P. Shikha and K. Yatender, Bioinorg. Chem. Appl., Article ID 851316 (2009); doi:10.1155/2009/851316.
R. Kothari and B. Sharma, J. Chem. Chem. Sci., 1, 158 (2011).
U. Kumar and S. Chandra, J. Saudi Chem. Soc., 15, 19 (2011); doi:10.1016/j.jscs.2010.08.003.
S. Chandra, L.K. Gupta and S. Agrawal, Transition Met. Chem., 32, 558 (2007); doi:10.1007/s11243-007-0201-y.
S. Chandra and Ruchi, Spectrochim. Acta A, 103, 338 (2013); doi:10.1016/j.saa.2012.10.065.
S. Chandra, S. Bargujar, R. Nirwal and N. Yadav, Spectrochim. Acta A, 106, 91 (2013); doi:10.1016/j.saa.2012.12.014.
(a) S. Ramakrishnan, V. Rajendiran, M. Palaniandavar, V.S. Periasamy, B.S. Srinag, H. Krishnamurthy and M.A. Akbarsha, Inorg. Chem., 48, 1309 (2009); doi:10.1021/ic801144x; (b) S. Ramakrishnan, D. Shakthipriya, E. Suresh, V.S. Periasamy, M.A. Akbarsha and M. Palaniandavar, Inorg. Chem., 50, 6458 (2011); doi:10.1021/ic1024185.
(a) H.H. Thorp, Chem. Biol., 5, R125 (1998); doi:10.1016/S1074-5521(98)90166-1; (b) H. Vahrenkamp, Dalton Trans., 42, 4751 (2007); doi:10.1039/b712138e; (c) A.I. Anzellotti and N.P. Farrell, Chem. Soc. Rev., 37, 1629 (2008); doi:10.1039/b617121b.
S. Emami, S.J. Hosseinimehr, S.M. Taghdisi and S. Akhlaghpoor, Bioorg. Med. Chem. Lett., 17, 45 (2007); doi:10.1016/j.bmcl.2006.09.097.
Q. Huang, Z. Pan, P. Wang, Z. Chen, X. Zhang and H. Xu, Bioorg. Med. Chem. Lett., 16, 3030 (2006); doi:10.1016/j.bmcl.2005.02.094.
(a) A. Nakayama, M. Hiromura, Y. Adachi and H.J. Sakurai, Biol. Inorg. Chem., 13, 675 (2008); doi:10.1007/s00775-008-0352-0; (b) H. Sakurai, Y. Yoshikawa and H. Yasui, Chem. Soc. Rev., 37, 2383 (2008); doi:10.1039/b710347f.
M.T. Kaczmarek, R. Jastrzab, E. Holderna-Kedzia and W. Radecka-Paryzek, Inorg. Chim. Acta, 362, 3127 (2009); doi:10.1016/j.ica.2009.02.012.
M.M. Ali, E. Frei, J. Straub, A. Breuer and M. Wiessler, Toxicology, 179, 85 (2002); doi:10.1016/S0300-483X(02)00322-0.
Q. Jiang, J. Zhu, Y. Zhang, N. Xiao and Z. Guo, Biometals, 22, 297 (2009); doi:10.1007/s10534-008-9166-3.
(a) S. Mathan Kumar, K. Dhahagani, J. Rajesh, K. Nehru, J. Annaraj, G. Chakkaravarthi and G. Rajagopal, Polyhedron, 59, 58 (2013); doi:10.1016/j.poly.2013.04.048; (b) K. Dhahagani, S. Mathan Kumar, G. Chakkaravarthi, K. Anitha, J. Rajesh, A. Ramu and G. Rajagopal, Spectrochim. Acta A, 117, 87 (2014); doi:10.1016/j.saa.2013.07.101; (c) K.K. Raja, D. Easwaramoorthy, S.K. Rani, J. Rajesh, Y. Jorapur, S. Thambidurai, P. Athappan and G. Rajagopal, J. Mol. Catal. Chem., 303, 52 (2009); doi:10.1016/j.molcata.2008.12.021; (d) G. Puthilibai, S. Vasudhevan, S. Kutti Rani and G. Rajagopal, Spectrochim. Acta A, 72, 796 (2009); doi:10.1016/j.saa.2008.11.019.
(a) J. Rajesh, A. Gubendran, G. Rajagopal and P.R. Athappan, J. Mol. Struct., 1010, 169 (2012); doi:10.1016/j.molstruc.2011.12.002; (b) J. Rajesh, M. Rajasekaran, G. Rajagopal and P.R. Athappan, Spectrochim. Acta A, 97, 223 (2012); doi:10.1016/j.saa.2012.05.006; (c) A. Gubendran, J. Rajesh, K. Anitha and P.R. Athappan, J. Mol. Struct., 1075, 419 (2014); doi:10.1016/j.molstruc.2014.06.079.
G. Kumar, D. Kumar, S. Devi, R. Johari and C.P. Singh, Eur. J. Med. Chem., 45, 3056 (2010); doi:10.1016/j.ejmech.2010.03.036.
T. Mosmann, J. Immunol. Methods, 65, 55 (1983); doi:10.1016/0022-1759(83)90303-4.
A.W. Addison, T.N. Rao, J. Reedijk, J. van Rijn and G.C. Verschoor, J. Chem. Soc., Dalton Trans., 158, 1349 (1984); doi:10.1039/DT9840001349.
Y. Hayashi, R. Matsuda, K. Ito, W. Nishimura, K. Imai and M. Maeda, Anal. Sci., 21, 167 (2005); doi:10.2116/analsci.21.167.
E.B. Seena and M.R.P. Kurup, Spectrochim. Acta A, 69, 726 (2008); doi:10.1016/j.saa.2007.05.025.
C.B. Castellani, G. Gatti and R. Millini, Inorg. Chem., 23, 4004 (1984); doi:10.1021/ic00192a032.
N.J. Ray and B.J. Hathaway, Acta Crystallogr., 34, 3224 (1978); doi:10.1107/S0567740878010547.
R.P. John, A. Sreekanth, V. Rajakannan, T.A. Ajith and M.R.P. Kurup, Polyhedron, 23, 2549 (2004); doi:10.1016/j.poly.2004.09.004.
C. Zhang and C. Janiak, J. Chem. Crystallogr., 31, 29 (2001); doi:10.1023/A:1013774502147.
E.B. Seena, M.R. Prathapachandra Kurup and E. Suresh, J. Chem. Crystallogr., 38, 93 (2008); doi:10.1007/s10870-007-9268-8.
T. Bal-Demirci, Polyhedron, 27, 440 (2008); doi:10.1016/j.poly.2007.10.001.
S. Güveli, N. Özdemir, T. Bal-Demirci, B. Ülküseven, M. Dinçer and Ö. Andaç, Polyhedron, 29, 2393 (2010); doi:10.1016/j.poly.2010.05.004.
R. Prabhakaran, R. Sivasamy, J. Angayarkanni, R. Huang, P. Kalaivani, R. Karvembu, F. Dallemer and K. Natarajan, Inorg. Chim. Acta, 374, 647 (2011); doi:10.1016/j.ica.2011.03.020.
T.A. Gerber, A. Abrahams, P. Mayer and E. Hosten, J. Coord. Chem., 56, 1397 (2003); doi:10.1080/00958970510001641691.
J.R. Dilworth, Coord. Chem. Rev., 21, 29 (1976); doi:10.1016/S0010-8545(00)82050-0.
S.G. Teoh, S.H. Ang, S.B. Teo, H.K. Fun, K.L. Khew and C.W. Ong, J. Chem. Soc., Dalton Trans., 465 (1997); doi:10.1039/a605679b.
S.K. Jain, B.S. Garg and Y.K. Bhoon, Spectrochim. Acta A, 42, 959 (1986); doi:10.1016/0584-8539(86)80003-4.
M.E. Hossain, M.N. Alam, J. Begum, M. Akbar Ali, M. Nazimuddin, F.E. Smith and R.C. Hynes, Inorg. Chim. Acta, 249, 207 (1996); doi:10.1016/0020-1693(96)05098-0.
D. Gambino, Min-Rev. J. Med. Chem., 4, 1 (2004); doi:10.2174/1389557043487529.
S. Singh, N. Bharti, F. Naqvi and A. Azam, Eur. J. Med. Chem., 39, 459 (2004); doi:10.1016/j.ejmech.2004.02.003.
X.Y. Qiu, S.Z. Li, A.R. Shi, Q. Li and B. Zhai, Chin. J. Struct. Chem., 31, 555 (2012).