Copyright (c) 2018 AJC
This work is licensed under a Creative Commons Attribution 4.0 International License.
Synthesis, Characterization, Antimicrobial and Anticancer Activities of 14-Membered Macrocyclic Schiff Base Metal Complexes
Corresponding Author(s) : A. Kulandaisamy
Asian Journal of Chemistry,
Vol. 30 No. 6 (2018): Vol 30 Issue 6
Abstract
New cationic 14-membered macrocyclic Schiff base metal complexes have been synthesized by condensation of benzalidene-curcuminyl-4-iminoantipyrine and 2,6-diaminopyridine. Structural characterization of the compounds was done using elemental analysis, molar conductivity, magnetic susceptibility, Mass, SEM, XRD, 1H NMR, UV-visible, IR and EPR spectra. X-ray diffraction patterns suggested that the size of Schiff base is reduced due to chelation by the metal ion. Different morphologies of synthesized compounds were identified by SEM images. Magnetic moment values, UV-visible and IR spectral studies confirms the square planar geometry of chelates. However [VOL]Cl2 exists in octahedral geometry. Electron spin resonance spectra parameters of [CuL]Cl2 and [VOL]Cl2 complexes were well coinciding with proposed geometries. The in vitro biocidal activities of the compounds were done against some bacterial and fungal strains by disc diffusion method. Anticancer activity of Schiff base and copper complex were carried out by MTT method which reveals that the inhibition against the growth of breast cancer cell line culture for chelate is higher than Schiff base.
Keywords
Download Citation
Endnote/Zotero/Mendeley (RIS)BibTeX
- S.K. Bharti, G. Nath, R. Tilak and S.K. Singh, Eur. J. Med. Chem., 45, 651 (2010); https://doi.org/10.1016/j.ejmech.2009.11.008.
- P. Panneerselvam, B.A. Rather, D. Ravi Sankar Reddy and N. Ramesh Kumar, Eur. J. Med. Chem., 44, 2328 (2009); https://doi.org/10.1016/j.ejmech.2008.04.010.
- S.T. Ha, L.K. Ong, J.P.W. Wong, G.-Y. Yeap, H.-C. Lin, S.-T. Ong and T.-M. Koh, Phase Transit., 82, 387 (2009); https://doi.org/10.1080/01411590902957449.
- A. Kulandaisamy and A. Palanimurugan, J. Chem. Pharm. Res., 7, 111 (2015).
- P.R. Inamdar and A. Sheela, Int. J. Biol. Macromol., 76, 269 (2015); https://doi.org/10.1016/j.ijbiomac.2015.02.027.
- B. Balaji, B. Balakrishnan, S. Perumalla, A.A. Karande and A.R. Chakravarty, Eur. J. Med. Chem., 85, 458 (2014); https://doi.org/10.1016/j.ejmech.2014.07.098.
- J.M. Peng, J.C. Lin, Z.Y. Chen, M.C. Wei, Y.X. Fu, S.S. Lu, D.S. Yu and W. Zhao, Mater. Sci. Eng. C, 71, 10 (2017); https://doi.org/10.1016/j.msec.2016.09.070.
- M. Iqbal, S.D. Sharma, Y. Okazaki, M. Fujisawa and S. Okada, Basic Clin. Pharmacol. Toxicol., 92, 33 (2003); https://doi.org/10.1034/j.1600-0773.2003.920106.x.
- A. Gubendran, M.P. Kesavan, S. Ayyanaar, J.D. Raja, P. Athappan and J. Rajesh, Appl. Organomet. Chem., 31, e3708 (2017); https://doi.org/10.1002/aoc.3708.
- D. Mahendiran, R.S. Kumar, V. Viswanathan, D. Velmurugan and A.K. Rahiman, Dalton Trans., 45, 7794 (2016); https://doi.org/10.1039/C5DT03831F.
- R.J. Anto, G. Kuttan, K.V.D. Babu, K.N. Rajasekharan and R. Kuttan, Pharm. Pharmacol. Commun., 4, 103 (1998); https://doi.org/10.1111/j.2042-7158.1998.tb00515.x.
- B.B. Aggarwal, A. Kumar and A.C. Bharti, Anticancer Res., 23, 363 (2003).
- R.J. Anto, G. Kuttan, K.V. Dinesh Babu, K.N. Rajasekharan and R. Kuttan, Int. J. Pharm., 131, 1 (1996); https://doi.org/10.1016/0378-5173(95)04254-7.
- K.S. Kumar, V.K. Chityala, N.J.P. Subhashini, Y. Prashanthi and Shivaraj, ISRN Inorg. Chem., 7, 562082 (2013); https://doi.org/10.1155/2013/562082.
- T. Mehmood and A. Mukhtar, Modern Chem. Applications, 5, 1 (2017); https://doi.org/10.11648/j.mc.20170501.11.
- R. Kurtaran, L.T. Yildirim, A.D. Azaz, H. Namli and O. Atakol, J. Inorg. Biochem., 99, 1937 (2005); https://doi.org/10.1016/j.jinorgbio.2005.05.016.
- A.S. Gaballa, M.S. Asker, A.S. Barakat and S.M. Teleb, Spectrochim. Acta A Mol. Biomol. Spectrosc., 67, 114 (2007); https://doi.org/10.1016/j.saa.2006.06.031.
- J. Lv, T. Liu, S. Cai, X. Wang, L. Liu and Y. Wang, J. Inorg. Biochem., 100, 1888 (2006); https://doi.org/10.1016/j.jinorgbio.2006.07.014.
- L.K.W. Henri, J. Tagenine and B.M. Gupta, Indian J. Chem., 40A, 999 (2001).
- K.N. Kumar and R. Ramesh, Spectrochim. Acta A Mol. Biomol. Spectrosc., 60, 2913 (2004); https://doi.org/10.1016/j.saa.2004.02.011.
- M. Sirajuddin, Nooruddin, S. Ali, V. McKee, S.Z. Khan and K. Malook, Spectrochim. Acta A Mol. Biomol. Spectrosc., 134, 244 (2015); https://doi.org/10.1016/j.saa.2014.06.099.
- R.S. Joseyphus and M. Sivasankaran Nair, Arab. J. Chem., 3, 195 (2010); https://doi.org/10.1016/j.arabjc.2010.05.001.
- F.S. Kamounah, S.R. Salman and A.A.K. Mahmoud, Spectrosc. Lett., 31, 1557 (1998); https://doi.org/10.1080/00387019808001660.
- R. Herzfeld and P. Nagy, Spectrosc. Lett., 32, 57 (1999); https://doi.org/10.1080/00387019909349967.
- T. Masuda, K. Hidaka, A. Shinohara, T. Maekawa, Y. Takeda and H. Yamaguchi, J. Agric. Food Chem., 47, 71 (1999); https://doi.org/10.1021/jf9805348.
- E.C.S. Chan, M.J. Pelczar Jr. and N.R. Krieg, Microbiology, McGrawHill, New York, edn 5 (1988).
- A.K. Ghosh, M. Mitra, A. Fathima, H. Yadav, A. Roy Choudhury, B.U. Nair and R. Ghosh, Polyhedron, 107, 1 (2016); https://doi.org/10.1016/j.poly.2016.01.015.
- M.L. Kuo, T.S. Huang and J.K. Lin, Biochim. Biophys. Acta, 1317, 95 (1996); https://doi.org/10.1016/S0925-4439(96)00032-4.
- A. Mazumder, K. Raghavan, J. Weinstein, K.W. Kohn and Y. Pommier, Biochem. Pharmacol., 49, 1165 (1995); https://doi.org/10.1016/0006-2952(95)98514-A.
- H.P.T. Ammon and M.A. Wahl, Planta Med., 57, 1 (1991); https://doi.org/10.1055/s-2006-960004.
- A. Kulandaisamy and M. Thomas, Pol. J. Chem., 82, 469 (2008).
- S. Daniel, L.J. Limson, A. Dairam, M.G. Watkins and S. Daya, J. Inorg. Biochem., 98, 266 (2004); https://doi.org/10.1016/j.jinorgbio.2003.10.014.
- R. Motterlini, R. Foresti, R. Bassi and C.J. Green, Free Radic. Biol. Med., 28, 1303 (2000); https://doi.org/10.1016/S0891-5849(00)00294-X.
- R.C. Maurya, D.D. Mishra, P.K. Trivedi and A. Gupta, Synth. React. Inorg. Met.-Org. Chem., 24, 17 (1994); https://doi.org/10.1080/00945719408000091.
- M.K.M. Nair and P.K. Radhakrishnan, Synth. React. Inorg. Met.-Org. Chem., 26, 529 (1996); https://doi.org/10.1080/00945719608005122.
- K. Nakamoto, Infrared and Raman Spectra of Inorganic and Coordination Compounds, Wiley Interscience, New York, edn 3, p. 296 (1977).
- V. Prakash and M.S. Suresh, Res. J. Pharm. Biol. Chem. Sci., 4, 1536 (2013).
- N. Raman, S. Thalamuthu and S. Banerjee, J. Chil. Chem. Soc., 53, 1439 (2008); https://doi.org/10.4067/S0717-97072008000100025.
- J. Joseph, K. Nagashri and G.A.B. Rani, J. Saudi Chem. Soc., 17, 285 (2013); https://doi.org/10.1016/j.jscs.2011.04.007.
- R.S. Joseyphus and M.S. Nair, Mycobiology, 36, 93 (2008); https://doi.org/10.4489/MYCO.2008.36.2.093.
- Z. Tohidiyan, I. Sheikhshoaie and M. Khaleghi, Int. J. Nanodimens., 7, 127 (2016).
- N. Shahabadi, S. Mohammadi and R. Alizadeh, Bioinorg. Chem. Appl., Article ID 429241 (2011); https://doi.org/10.1155/2011/429241.
- C.J. Dhanaraj and M.S. Nair, J. Coord. Chem., 62, 4018 (2009); https://doi.org/10.1080/00958970903191142.
- N. Farrell, Coord. Chem. Rev., 232, 1 (2004); https://doi.org/10.1016/S0010-8545(02)00100-5.
- Y. Anjaneyulu and R.P. Rao, Synth. React. Inorg. Met.-Org. Nano-Met. Chem., 16, 257 (1986); https://doi.org/10.1080/00945718608057530.
- N. Dharmaraj, P. Viswanathamurthi and K. Natarajan, Transition Met. Chem., 26, 105 (2001); https://doi.org/10.1023/A:1007132408648.
- N. Raman, R. Jeyamurugan and J. Joseph, J. Iran. Chem. Res., 3, 83 (2010)
References
S.K. Bharti, G. Nath, R. Tilak and S.K. Singh, Eur. J. Med. Chem., 45, 651 (2010); https://doi.org/10.1016/j.ejmech.2009.11.008.
P. Panneerselvam, B.A. Rather, D. Ravi Sankar Reddy and N. Ramesh Kumar, Eur. J. Med. Chem., 44, 2328 (2009); https://doi.org/10.1016/j.ejmech.2008.04.010.
S.T. Ha, L.K. Ong, J.P.W. Wong, G.-Y. Yeap, H.-C. Lin, S.-T. Ong and T.-M. Koh, Phase Transit., 82, 387 (2009); https://doi.org/10.1080/01411590902957449.
A. Kulandaisamy and A. Palanimurugan, J. Chem. Pharm. Res., 7, 111 (2015).
P.R. Inamdar and A. Sheela, Int. J. Biol. Macromol., 76, 269 (2015); https://doi.org/10.1016/j.ijbiomac.2015.02.027.
B. Balaji, B. Balakrishnan, S. Perumalla, A.A. Karande and A.R. Chakravarty, Eur. J. Med. Chem., 85, 458 (2014); https://doi.org/10.1016/j.ejmech.2014.07.098.
J.M. Peng, J.C. Lin, Z.Y. Chen, M.C. Wei, Y.X. Fu, S.S. Lu, D.S. Yu and W. Zhao, Mater. Sci. Eng. C, 71, 10 (2017); https://doi.org/10.1016/j.msec.2016.09.070.
M. Iqbal, S.D. Sharma, Y. Okazaki, M. Fujisawa and S. Okada, Basic Clin. Pharmacol. Toxicol., 92, 33 (2003); https://doi.org/10.1034/j.1600-0773.2003.920106.x.
A. Gubendran, M.P. Kesavan, S. Ayyanaar, J.D. Raja, P. Athappan and J. Rajesh, Appl. Organomet. Chem., 31, e3708 (2017); https://doi.org/10.1002/aoc.3708.
D. Mahendiran, R.S. Kumar, V. Viswanathan, D. Velmurugan and A.K. Rahiman, Dalton Trans., 45, 7794 (2016); https://doi.org/10.1039/C5DT03831F.
R.J. Anto, G. Kuttan, K.V.D. Babu, K.N. Rajasekharan and R. Kuttan, Pharm. Pharmacol. Commun., 4, 103 (1998); https://doi.org/10.1111/j.2042-7158.1998.tb00515.x.
B.B. Aggarwal, A. Kumar and A.C. Bharti, Anticancer Res., 23, 363 (2003).
R.J. Anto, G. Kuttan, K.V. Dinesh Babu, K.N. Rajasekharan and R. Kuttan, Int. J. Pharm., 131, 1 (1996); https://doi.org/10.1016/0378-5173(95)04254-7.
K.S. Kumar, V.K. Chityala, N.J.P. Subhashini, Y. Prashanthi and Shivaraj, ISRN Inorg. Chem., 7, 562082 (2013); https://doi.org/10.1155/2013/562082.
T. Mehmood and A. Mukhtar, Modern Chem. Applications, 5, 1 (2017); https://doi.org/10.11648/j.mc.20170501.11.
R. Kurtaran, L.T. Yildirim, A.D. Azaz, H. Namli and O. Atakol, J. Inorg. Biochem., 99, 1937 (2005); https://doi.org/10.1016/j.jinorgbio.2005.05.016.
A.S. Gaballa, M.S. Asker, A.S. Barakat and S.M. Teleb, Spectrochim. Acta A Mol. Biomol. Spectrosc., 67, 114 (2007); https://doi.org/10.1016/j.saa.2006.06.031.
J. Lv, T. Liu, S. Cai, X. Wang, L. Liu and Y. Wang, J. Inorg. Biochem., 100, 1888 (2006); https://doi.org/10.1016/j.jinorgbio.2006.07.014.
L.K.W. Henri, J. Tagenine and B.M. Gupta, Indian J. Chem., 40A, 999 (2001).
K.N. Kumar and R. Ramesh, Spectrochim. Acta A Mol. Biomol. Spectrosc., 60, 2913 (2004); https://doi.org/10.1016/j.saa.2004.02.011.
M. Sirajuddin, Nooruddin, S. Ali, V. McKee, S.Z. Khan and K. Malook, Spectrochim. Acta A Mol. Biomol. Spectrosc., 134, 244 (2015); https://doi.org/10.1016/j.saa.2014.06.099.
R.S. Joseyphus and M. Sivasankaran Nair, Arab. J. Chem., 3, 195 (2010); https://doi.org/10.1016/j.arabjc.2010.05.001.
F.S. Kamounah, S.R. Salman and A.A.K. Mahmoud, Spectrosc. Lett., 31, 1557 (1998); https://doi.org/10.1080/00387019808001660.
R. Herzfeld and P. Nagy, Spectrosc. Lett., 32, 57 (1999); https://doi.org/10.1080/00387019909349967.
T. Masuda, K. Hidaka, A. Shinohara, T. Maekawa, Y. Takeda and H. Yamaguchi, J. Agric. Food Chem., 47, 71 (1999); https://doi.org/10.1021/jf9805348.
E.C.S. Chan, M.J. Pelczar Jr. and N.R. Krieg, Microbiology, McGrawHill, New York, edn 5 (1988).
A.K. Ghosh, M. Mitra, A. Fathima, H. Yadav, A. Roy Choudhury, B.U. Nair and R. Ghosh, Polyhedron, 107, 1 (2016); https://doi.org/10.1016/j.poly.2016.01.015.
M.L. Kuo, T.S. Huang and J.K. Lin, Biochim. Biophys. Acta, 1317, 95 (1996); https://doi.org/10.1016/S0925-4439(96)00032-4.
A. Mazumder, K. Raghavan, J. Weinstein, K.W. Kohn and Y. Pommier, Biochem. Pharmacol., 49, 1165 (1995); https://doi.org/10.1016/0006-2952(95)98514-A.
H.P.T. Ammon and M.A. Wahl, Planta Med., 57, 1 (1991); https://doi.org/10.1055/s-2006-960004.
A. Kulandaisamy and M. Thomas, Pol. J. Chem., 82, 469 (2008).
S. Daniel, L.J. Limson, A. Dairam, M.G. Watkins and S. Daya, J. Inorg. Biochem., 98, 266 (2004); https://doi.org/10.1016/j.jinorgbio.2003.10.014.
R. Motterlini, R. Foresti, R. Bassi and C.J. Green, Free Radic. Biol. Med., 28, 1303 (2000); https://doi.org/10.1016/S0891-5849(00)00294-X.
R.C. Maurya, D.D. Mishra, P.K. Trivedi and A. Gupta, Synth. React. Inorg. Met.-Org. Chem., 24, 17 (1994); https://doi.org/10.1080/00945719408000091.
M.K.M. Nair and P.K. Radhakrishnan, Synth. React. Inorg. Met.-Org. Chem., 26, 529 (1996); https://doi.org/10.1080/00945719608005122.
K. Nakamoto, Infrared and Raman Spectra of Inorganic and Coordination Compounds, Wiley Interscience, New York, edn 3, p. 296 (1977).
V. Prakash and M.S. Suresh, Res. J. Pharm. Biol. Chem. Sci., 4, 1536 (2013).
N. Raman, S. Thalamuthu and S. Banerjee, J. Chil. Chem. Soc., 53, 1439 (2008); https://doi.org/10.4067/S0717-97072008000100025.
J. Joseph, K. Nagashri and G.A.B. Rani, J. Saudi Chem. Soc., 17, 285 (2013); https://doi.org/10.1016/j.jscs.2011.04.007.
R.S. Joseyphus and M.S. Nair, Mycobiology, 36, 93 (2008); https://doi.org/10.4489/MYCO.2008.36.2.093.
Z. Tohidiyan, I. Sheikhshoaie and M. Khaleghi, Int. J. Nanodimens., 7, 127 (2016).
N. Shahabadi, S. Mohammadi and R. Alizadeh, Bioinorg. Chem. Appl., Article ID 429241 (2011); https://doi.org/10.1155/2011/429241.
C.J. Dhanaraj and M.S. Nair, J. Coord. Chem., 62, 4018 (2009); https://doi.org/10.1080/00958970903191142.
N. Farrell, Coord. Chem. Rev., 232, 1 (2004); https://doi.org/10.1016/S0010-8545(02)00100-5.
Y. Anjaneyulu and R.P. Rao, Synth. React. Inorg. Met.-Org. Nano-Met. Chem., 16, 257 (1986); https://doi.org/10.1080/00945718608057530.
N. Dharmaraj, P. Viswanathamurthi and K. Natarajan, Transition Met. Chem., 26, 105 (2001); https://doi.org/10.1023/A:1007132408648.
N. Raman, R. Jeyamurugan and J. Joseph, J. Iran. Chem. Res., 3, 83 (2010)