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Biological Screening Studies of DNA Relate Metal Complexes from Benzylidene-4-imino-2,3-dimethyl-1-phenyl-3-pyrazolin-5-one and 2-aminothiazole
Corresponding Author(s) : A. Kulandaisamy
Asian Journal of Chemistry,
Vol. 30 No. 3 (2018): Vol 30 Issue 3
Abstract
Novel terdentate cationic complexes of Cu(II), Ni(II), Co(II), Mn(II) and Zn(II) ion have been prepared using a Schiff base derived from benzylidene-4-imino-2,3-dimethyl-1-phenyl-3-pyrazolin-5-one and 2-aminothiazole. The structural features of metal-chelates have been confirmed by micro-analytical data, FAB-Mass spectra, powder XRD, SEM, FTIR, UV-visible, 1H NMR, EPR, CV and thermal analysis techniques. The analytical data of the complexes correspond well with the general formula [ML2]Cl2. The high conductance data of metal chelates supports their 1:2 electrolytic nature. The magnetic susceptibility and electronic absorption spectra of the complexes indicate that all the metal-chelates exhibit octahedral geometry around the central metal ion. Powder XRD data and SEM images persist that the complexes are nano size grain with polycrystalline structure. DNA interaction studies of [CuL2]Cl2 complex have been done by electronic spectral and cyclic voltammetric measurements which revealed that the binding occurs through intercalation between complex and DNA interaction of [CuL2]Cl2 complex with CT-DNA leads to hypochromism. The MIC values against the growth of microorganisms are lower for metal chelates than the ligand. This is mainly due to lipophilicity of metal ion in complexes.
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- J.S. Kumaran, S. Priya, J. Muthukumaran, N. Jayachandramani and S. Mahalakshmi, J. Chem. Pharm. Res., 5, 56 (2013).
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P. Deshmukh, P.K. Soni, A. Kankoriya, A.K. Halve and R. Dixit, Int. J. Pharm. Sci. Rev. Res., 34, 26, 162 (2015).
J.S. Kumaran, S. Priya and J. Gowsika, Res. J. Pharm. Biol. Chem. Sci., 4, 279 (2013).
M.N. Al-Jibouri, F.R. Hafith and A.M. Rasheed, Eur. Chem. Bull., 3, 559 (2014); https://doi.org/10.17628/ecb.2014.3.559-562.
M. Noroozifar, M. Khorasani-Motlagh and P.A. Fard, Eur. J. Med. Chem., 45, 5438 (2010); https://doi.org/10.1016/j.ejmech.2010.09.004.
P. Goel, D. Kumar and S. Chandra, J. Chem. Biol. Phys. Sci., 4, 1946 (2014).
T. Ahmad, F. Kandil and C. Moustaph, AASCIT Commun., 2, 127 (2015).
H.L. Siddiqui, A. Iqbal, S. Ahmad and G.W. Weaver, Molecules, 11, 206 (2006); https://doi.org/10.3390/11020206.
A.-N.M.A. Alaghaz and H.A. Bayoumi, Int. J. Electrochem. Sci., 8, 11860 (2013).
L.H. Abdel-Rahman, R.M. El-Khatib, L.A.E. Nassr, A.M. Abu-Dief, F.E. Lashin, Spectrochim Acta A: Mol. Biomol. Spectrosc., 111, 266 (2013); https://doi.org/10.1016/j.saa.2013.03.061.
T. Arun, R. Subramanian and N. Raman, J. Photochem. Photobiol. B, 154, 67 (2016); https://doi.org/10.1016/j.jphotobiol.2015.11.011.
X. Zhou, L. Shao, Z. Jin, J.-B. Liu, H. Dai, J.-X. Fang, Heteroatom Chem., 18, 55 (2007); https://doi.org/10.1002/hc.20256.
A.M. Nalawade, R.A. Nalawade, S.M. Patange and D.R. Tase, Int. J. Eng. Sci. Invention, 2, 2319 (2013).
W. Al Zoubi, Int. J. Org. Chem., 3, 73 (2013); https://doi.org/10.4236/ijoc.2013.33A008.
A.M. Abu-Dief and I.M.A. Mohamed, Beni-Suef Univ. J. Basic Appl. Sci., 4, 119 (2015); https://doi.org/10.1016/j.bjbas.2015.05.004.
M.A. Neelakantan, M. Esakkiammal, S.S. Mariappan, J. Dharmaraja and T. Jeyakumar, Indian J. Pharm. Sci., 72, 216 (2016); https://doi.org/10.4103/0250-474X.65015.
N. Revathi, M. Sankarganesh, J. Rajesh and J.D. Raja, J. Fluoresc., 27, 1801 (2017); https://doi.org/10.1007/s10895-017-2118-y.
F.C. Jiang and C.Y. Cheng, Yao Xue Xue Bao, 41, 727 (2006).
A.M. Katsori, M. Chatzopoulou, C. Kontogiorgis, A. Patsilinakos, K. Dimas, T. Trangas and D. Hadjipavlou-Litina, Eur. J. Med. Chem., 46, 2722 (2011); https://doi.org/10.1016/j.ejmech.2011.03.060.
J. Lal, S.K. Gupta, D. Thavaselvam and D.D. Agarwal, Eur. J. Med. Chem., 64, 579 (2013); https://doi.org/10.1016/j.ejmech.2013.03.012.
J.E. Dickeson and L.A. Summers, Aust. J. Chem., 23, 1023 (1970); https://doi.org/10.1071/CH9701023.
D.D. Perrin, W.L.F. Armarego and D.R. Perrin, Purification of Laboratory Chemicals, Oxford, UK: Pergamon Press (1980).
R.J. Angellici, Synthesis and Techniques in Inorganic Chemistry, W.B. Saunders Company (1969).
E.C.S. Chan, M.J. Pelczar Jr. and N.R. Krieg, Microbiology, Tata McGrawHill Education Pvt. Ltd., edn 5, pp. 87-688 (1998).
N. Raman, R. Jeyamurugan, A. Sakthivel and L. Mitu, Spectrochim. Acta A Mol. Biomol. Spectrosc., 75, 88 (2010); https://doi.org/10.1016/j.saa.2009.09.047.
E.K. Barefield, G.M. Freeman and D.G. Van Derveer, Inorg. Chem., 25, 552 (1986); https://doi.org/10.1021/ic00224a033.
N. DeVries and J. Reedijk, Inorg. Chem., 30, 3700 (1991); https://doi.org/10.1021/ic00019a026.
N. Raman and R. Jeyamurugan, J. Coord. Chem., 62, 2375 (2009); https://doi.org/10.1080/00958970902825195.
N. Raman, R. Jeyamurugan, S. Sudharsan, K. Karuppasamy and L. Mitu, Arab. J. Chem., 6, 235 (2013); https://doi.org/10.1016/j.arabjc.2012.04.010.
E.I. Solomon, J.W. Hare and H.B. Gray, Proc. Natl. Acad. Sci. USA, 73, 1389 (1976); https://doi.org/10.1073/pnas.73.5.1389.
N. Kitajima, ed: A.G. Sykes, Advances in Inorganic Chemistry, Academic Press, New Yor (1992).
R.K. Ray and G.B. Kauffman, Inorg. Chim. Acta, 173, 207 (1990); https://doi.org/10.1016/S0020-1693(00)80215-7.
N. Raman and R. Jeyamurugan, J. Coord. Chem., 62, 2375 (2009); https://doi.org/10.1080/00958970902825195.
J.K. Barton, A.T. Danishefsky and J.M. Goldberg, J. Am. Chem. Soc., 106, 2172 (1984); https://doi.org/10.1021/ja00319a043.
C.J. Dhanaraj and M.S. Nair, J. Coord. Chem., 62, 4018 (2009); https://doi.org/10.1080/00958970903191142.
A. Thakar, K. Joshi, K. Pandya and A. Pancholi, E-J. Chem., 8, 1750 (2011); https://doi.org/10.1155/2011/282061.
N. Raman, R. Jeyamurugan, R.U. Rani, T. Baskaran and L. Mitu, J. Coord. Chem., 63, 1629 (2010); https://doi.org/10.1080/00958972.2010.485643.
V. Prakash and M.S. Suresh, Res. J. Pharm. Biol. Chem. Sci., 4, 1536 (2013).
N. Dharmaraj, P. Viswanathamurthi and K. Natarajan, Transition Met. Chem., 26, 105 (2001); https://doi.org/10.1023/A:1007132408648.
M.M. Ali, M. Jesmin, M.S. Salahuddin, M.R. Habib and J.A. Khanam, Int. J. Biol. Chem. Sci., 2, 292 (2008); https://doi.org/10.4314/ijbcs.v2i3.39748.
Z. Tohidiyan, I. Sheikhshoaie and M. Khaleghi, Int. J. Nanodimens., 7, 127 (2016); https://doi.org/10.7508/IJND.2016.02.004.
N. Raman, A. Kulandaisamy and K. Jeyasubramanian, Synth. React. Inorg. Met.-Org. Chem., 32, 1583 (2002); https://doi.org/10.1081/SIM-120015081.
L.H. Abdel-Rahman, R.M. El-Khatib, L.A.E. Nassr and A.M. Abu-Dief, Arab. J. Chem., 10, 1835 (2017); https://doi.org/10.1016/j.arabjc.2013.07.010.
N. Raman, A. Kulandaisamy and K. Jeyasubramanian, Synth. React. Inorg. Met.-Org. Chem., 31, 1249 (2001); https://doi.org/10.1081/SIM-100106862.
N. Raman, R. Jeyamurugan and J. Joseph, J. Iranian Chem. Res., 3, 83 (2010).