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4-Aminoindane Derived Novel Schiff Base Metal Complexes: Synthesis, Characterization, DNA Binding and Molecular Docking Studies
Corresponding Author(s) : D. Sumalatha
Asian Journal of Chemistry,
Vol. 32 No. 3 (2020): Vol 32 Issue 3
Abstract
A novel Schiff base [SAL-L=2-((2,3-dihydro-1H-inden-4-ylimino)methyl phenol] was synthesized and used as ligand for the synthesis of Ni(II) and Co(II) complexes. The structural characterization of ligand and its Ni(II) and Co(II) complexes was determined using various spectroscopic methods. Based on spectral studies, a square planar and octahedral geometry have been proposed for Ni(II) and Co(II) complexes, respectively. DNA binding properties of these metal complexes with calf-thymus DNA in tris-hydrochloride buffer (pH 7.2) were investigated using UV-visible absorption studies. The binding constants were in the order of 105 M-1 suggested a good binding affinity towards CT-DNA. The synthesized ligand is docked on TSPO protein showing good binding energy and found to be a potent inhibitor of cancer.
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- A.M. Abu-Diefab and I.M.A. Mohameda, Beni-Suef Univ. J. Basic Appl. Sci., 4, 119 (2015); https://doi.org/10.1016/j.bjbas.2015.05.004
- M.N. Uddin and D.A. Chowdhury, Modern Chem., 2, 6 (2014); https://doi.org/10.11648/j.mc.20140202.11
- S. Kumar, D.N. Dhar and P.N. Saxena, J. Sci. Ind. Res., 68, 181 (2009).
- R.V. Heinzelmann, H.G. Kolloff, J.H. Hunter, C. Upjohn and M.I. Kalamazoo, J. Am. Chem. Soc., 70, 1386 (1948); https://doi.org/10.1021/ja01184a028
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- N.S.R.R.M.M. Koteswara Rao and M.G. Ram Reddy, BioMetals, 3, 19 (1990); https://doi.org/10.1007/BF01141172
- N. Pinterova, R.R. Horsley and T. Palenicek, Front. Psychiatry, 8, 236 (2017); https://doi.org/10.3389/fpsyt.2017.00236
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- B. Sreekanth, G. Krishnamurthy, H.S.B. Naik, M.C. Prabhakara and T.K. Vishnuvardhan, Synth. React. Inorg. Met.-Org. Nano-Met. Chem., 40, 955 (2010); https://doi.org/10.1080/15533174.2010.522665
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- B. Sreekanth and G. Krishnamurthy, J. Chem. Pharm. Res., 3, 407 (2011).
- D.S. Sigman, A. Mazumder and D.M. Perrin, Chem. Rev., 93, 2295 (1993); https://doi.org/10.1021/cr00022a011
- S. Routier, N. Cotelle, J.P. Catteau, J.-L. Bernier, M.J. Waring, J.-F. Riou and C. Bailly, Bioorg. Med. Chem., 4, 1185 (1996); https://doi.org/10.1016/0968-0896(96)00082-X
- M.R. Lokesh, G. Krishnamurthy, H.S. Bhojyanaik, N.D. Shashikumar, P. Murali Krishna and B. Sreekanth, Pharma Chem., 6, 192 (2014).
- N. Shahabadi, S. Kashanian and F. Darabi, Eur. J. Med. Chem., 45, 4239 (2010); https://doi.org/10.1016/j.ejmech.2010.06.020
- N. Raman, S. Sobha and L. Mitu, J. Saudi Chem. Soc., 17, 151 (2013); https://doi.org/10.1016/j.jscs.2011.03.003
- Ch.S. Aduri, V.R. Reddy and B. Sireesha, Pharma Chem., 9, 90 (2017).
- Ch.S. Aduri, V.R. Reddy and B. Sireesha, Asian J. Sci. Technol., 1, 4125 (2017).
- M. Bhargavi, S.K. Sivan and S.R. Potlapally, Comput. Biol. Chem., 68, 43 (2017); https://doi.org/10.1016/j.compbiolchem.2016.12.016
- A. Batarseh, C. Giatzakis and V. Papadopoulos, Biochemistry, 47, 12886 (2008); https://doi.org/10.1021/bi8012643
- J. Marmur, J. Mol. Biol., 3, 208 (1961); https://doi.org/10.1016/S0022-2836(61)80047-8
- M.E. Reichmann, S.A. Rice, C. Thomas and P. Doty, J. Am. Chem. Soc., 76, 3047 (1954); https://doi.org/10.1021/ja01640a067
- M. Sirajuddin, N. Uddin, S. Ali and M.N. Tahir, Spectrochim. Acta A Mol. Biomol. Spectrosc., 116, 111 (2013); https://doi.org/10.1016/j.saa.2013.06.096
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- G.M. Morris and M. Lim-Wilby, ed.: A. Kukol, Molecular Docking. In: Molecular Modeling of Proteins. Methods Molecular Biology™, Humana Press, vol 443 (2008).
- D.B. Kitchen, H. Decornez, J.R. Furr and J. Bajorath, Nat. Rev. Drug Discov., 3, 935 (2004); https://doi.org/10.1038/nrd1549
- R.K. Agarwal and S. Prasad, Bioinorg. Chem. Appl., 3, 271 (2005); https://doi.org/10.1155/BCA.2005.271
- S.M. Drawz and R.A. Bonomo, Clin. Microbiol. Rev., 23, 160 (2010); https://doi.org/10.1128/CMR.00037-09
References
A.M. Abu-Diefab and I.M.A. Mohameda, Beni-Suef Univ. J. Basic Appl. Sci., 4, 119 (2015); https://doi.org/10.1016/j.bjbas.2015.05.004
M.N. Uddin and D.A. Chowdhury, Modern Chem., 2, 6 (2014); https://doi.org/10.11648/j.mc.20140202.11
S. Kumar, D.N. Dhar and P.N. Saxena, J. Sci. Ind. Res., 68, 181 (2009).
R.V. Heinzelmann, H.G. Kolloff, J.H. Hunter, C. Upjohn and M.I. Kalamazoo, J. Am. Chem. Soc., 70, 1386 (1948); https://doi.org/10.1021/ja01184a028
P.D. Sainsbury, A.T. Kicman, R.P. Archer, L.A. King and R.A. Braithwaite, Drug Test. Anal., 3, 479 (2011); https://doi.org/10.1002/dta.318
W. Maruyama, M.B.H. Youdim and M. Naoi, Ann. N. Y. Acad. Sci., 939, 320 (2001); https://doi.org/10.1111/j.1749-6632.2001.tb03641.x
G.A. Rogers, S.M. Parsons, D.C. Anderson, L.M. Nilsson, B.A. Bahr, W.D. Kornreich, R. Kaufman, R.S. Jacobs and B. Kirtman, J. Med. Chem., 32, 1217 (1989); https://doi.org/10.1021/jm00126a013
N.S.R.R.M.M. Koteswara Rao and M.G. Ram Reddy, BioMetals, 3, 19 (1990); https://doi.org/10.1007/BF01141172
N. Pinterova, R.R. Horsley and T. Palenicek, Front. Psychiatry, 8, 236 (2017); https://doi.org/10.3389/fpsyt.2017.00236
A.A. Osowole and A.O. Daramola, Elixir Appl. Chem., 47, 8662 (2012).
A.A. Osowole, I. Ott and O.M. Ogunlana1, Int. J. Inorg. Chem., 2012, Article ID 206417 (2012); https://doi.org/10.1155/2012/206417
B. Sreekanth, G. Krishnamurthy, H.S.B. Naik, M.C. Prabhakara and T.K. Vishnuvardhan, Synth. React. Inorg. Met.-Org. Nano-Met. Chem., 40, 955 (2010); https://doi.org/10.1080/15533174.2010.522665
L. Singh, N. Tyagi, N.P. Dhaka and S.K. Sindhu, Asian J. Chem., 11, 503 (1999).
B. Sreekanth and G. Krishnamurthy, J. Chem. Pharm. Res., 3, 407 (2011).
D.S. Sigman, A. Mazumder and D.M. Perrin, Chem. Rev., 93, 2295 (1993); https://doi.org/10.1021/cr00022a011
S. Routier, N. Cotelle, J.P. Catteau, J.-L. Bernier, M.J. Waring, J.-F. Riou and C. Bailly, Bioorg. Med. Chem., 4, 1185 (1996); https://doi.org/10.1016/0968-0896(96)00082-X
M.R. Lokesh, G. Krishnamurthy, H.S. Bhojyanaik, N.D. Shashikumar, P. Murali Krishna and B. Sreekanth, Pharma Chem., 6, 192 (2014).
N. Shahabadi, S. Kashanian and F. Darabi, Eur. J. Med. Chem., 45, 4239 (2010); https://doi.org/10.1016/j.ejmech.2010.06.020
N. Raman, S. Sobha and L. Mitu, J. Saudi Chem. Soc., 17, 151 (2013); https://doi.org/10.1016/j.jscs.2011.03.003
Ch.S. Aduri, V.R. Reddy and B. Sireesha, Pharma Chem., 9, 90 (2017).
Ch.S. Aduri, V.R. Reddy and B. Sireesha, Asian J. Sci. Technol., 1, 4125 (2017).
M. Bhargavi, S.K. Sivan and S.R. Potlapally, Comput. Biol. Chem., 68, 43 (2017); https://doi.org/10.1016/j.compbiolchem.2016.12.016
A. Batarseh, C. Giatzakis and V. Papadopoulos, Biochemistry, 47, 12886 (2008); https://doi.org/10.1021/bi8012643
J. Marmur, J. Mol. Biol., 3, 208 (1961); https://doi.org/10.1016/S0022-2836(61)80047-8
M.E. Reichmann, S.A. Rice, C. Thomas and P. Doty, J. Am. Chem. Soc., 76, 3047 (1954); https://doi.org/10.1021/ja01640a067
M. Sirajuddin, N. Uddin, S. Ali and M.N. Tahir, Spectrochim. Acta A Mol. Biomol. Spectrosc., 116, 111 (2013); https://doi.org/10.1016/j.saa.2013.06.096
M. Tariq, N. Muhammad, M. Sirajuddin, S. Ali, N.A. Shah, N. Khalid, M.N. Tahir and M.R. Khan, J. Organomet. Chem., 723, 79 (2013); https://doi.org/10.1016/j.jorganchem.2012.09.011
S.S. Bhat, A.A. Kumbhar, H. Heptullah, A.A. Khan, V.V. Gobre, S.P. Gejji and V.G. Puranik, Inorg. Chem., 50, 545 (2011); https://doi.org/10.1021/ic101534n
N. Raman and S. Sobha, Spectrochim. Acta A Mol. Biomol. Spectrosc., 85, 223 (2012); https://doi.org/10.1016/j.saa.2011.09.065
G.M. Morris and M. Lim-Wilby, ed.: A. Kukol, Molecular Docking. In: Molecular Modeling of Proteins. Methods Molecular Biology™, Humana Press, vol 443 (2008).
D.B. Kitchen, H. Decornez, J.R. Furr and J. Bajorath, Nat. Rev. Drug Discov., 3, 935 (2004); https://doi.org/10.1038/nrd1549
R.K. Agarwal and S. Prasad, Bioinorg. Chem. Appl., 3, 271 (2005); https://doi.org/10.1155/BCA.2005.271
S.M. Drawz and R.A. Bonomo, Clin. Microbiol. Rev., 23, 160 (2010); https://doi.org/10.1128/CMR.00037-09