Copyright (c) 2024 S. Syed Ali Fathima, M. Mohamed Sahul Meeran
This work is licensed under a Creative Commons Attribution 4.0 International License.
Synthesis, Characterization, Biological and in silico ADMET Studies of Mixed Ligand Transition Metal Complexes Based on Novel Schiff Base and 1,10-Phenanthroline
Corresponding Author(s) : S. Syed Ali Fathima
Asian Journal of Chemistry,
Vol. 37 No. 1 (2025): Vol 37 Issue 1, 2025
Abstract
The main objective of this work is to mitigate the challenges associated with the use of platinum-based chemotherapy drugs through investigating chemotherapeutic compounds based on mixed ligand transition metal complexes. Thus, Cu(II), Co(II), Ni(II) and Zn(II) complexes were synthesized from novel Schiff base compound derived from 2-amino-3-hydroxypyridine and 5-chloro-2-nitrobenzaldehyde and the co-ligand 1,10-phenanthroline. The spectral investigations were conducted to characterize the synthesized compounds and revealed that they possess an octahedral structure. The interactions of synthesized compounds with calf thymus DNA (ct-DNA) demonstrated that the binding takes place through an intercalation. Comparatively to Schiff base ligand, the synthesized transition metal complexes proved to be better anti-pathogenic agent when tested against bacteria. The prepared compounds possess more the biological capability, according to in silico ADMET study, which may attributed to the presence of two N-heterocyclic ligands. The computational screening of biological activities related to cancer activity using PASS software propose the drug-like nature of the compounds.
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- U. Ndagi, N. Mhlongo and M.E. Soliman, Drug Des. Devel. Ther., 11, 599 (2017); https://doi.org/10.2147/DDDT.S119488
- R.L. Lucaciu, A.C. Hangan, B. Sevastre and L.S. Oprean, Molecules. 27, 6485 (2022);https://doi.org/10.3390/molecules27196485
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- N.J. Wheate, S. Walker, G.E. Craig and R. Oun, Dalton Trans., 39, 8113 (2010); https://doi.org/10.1039/c0dt00292e
- S. Rottenberg, C. Disler and P. Perego, Nat. Rev. Cancer, 21, 37 (2021); https://doi.org/10.1038/s41568-020-00308-y
- S.J. Tan, Y.K. Yan, P.P.F. Lee and K.H. Lim, Future Med. Chem., 2, 1591 (2010); https://doi.org/10.4155/fmc.10.234
- C. Marzano, M. Pellei, F. Tisato and C. Santini, Anticancer. Agents Med. Chem., 9, 185 (2009); https://doi.org/10.2174/187152009787313837
- I. Romero-Canelon and P.J. Sadler, Inorg. Chem., 52, 12276 (2013); https://doi.org/10.1021/ic400835n
- I.A. Khan, M.V. Kulkarni, M. Gopal, M.S. Shahabuddin and C.M. Sun, Bioorg. Med. Chem. Lett., 15, 3584 (2005); https://doi.org/10.1016/j.bmcl.2005.05.063
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- R.K. Mohapatra, P.K. Das, M.K. Pradhan, M.M. El-Ajaily, D. Das, H.F. Salem, U. Mahanta, G. Badhei, P.K. Parhi, A.A. Maihub and M.K. E-Zahan, Comments Inorg. Chem., 39, 127 (2019); https://doi.org/10.1080/02603594.2019.1594204
- S. Pullen and G.H. Clever, Acc. Chem. Res., 51, 3052 (2018); https://doi.org/10.1021/acs.accounts.8b00415
- S.K. Singh, S. Joshi A.R. Singh J.K. Saxena and D.S. Pandey, Inorg. Chem., 46, 10869 (2007); https://doi.org/10.1021/ic700885m
- Y. Li, G. Zhang and M. Tao, J. Photochem. Photobiol. B, 138, 109 (2014); https://doi.org/10.1016/j.jphotobiol.2014.05.011
- A.K. Sadana, Y. Mirza, K.R. Aneja and O. Prakash, Eur. J. Med. Chem., 38, 533 (2003); https://doi.org/10.1016/s0223-5234(03)00061-8
- M. Chauhan, K. Banerjee and F. Arjmand, Inorg. Chem., 46, 3072 (2007); https://doi.org/10.1021/ic061753a
- N. Udilova, A.V. Kozlov, W. Bieberschulte, K. Frei, K. Ehrenberger and H. Nohl, Biochem. Pharm., 65, 59 (2003); https://doi.org/10.1016/S0006-2952(02)01452-1
- M. Sonmez, M. Celebi and I. Berber, Eur. J. Med. Chem., 45, 1935 (2010); https://doi.org/10.1016/j.ejmech.2010.01.035
- A.M. Dar, M.A. Khan, S. Mir and M.A. Gatoo, Pharm. Anal. Acta, 7, 464 (2016); https://doi.org/10.4172/2153-2435.1000464
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- A. Lagunin, D. Filimonov and V. Poroikov, Curr. Pharm. Des., 16, 1703 (2010); https://doi.org/10.2174/138161210791164063
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- A.Z. El-Sonbati, M.A. Diab, A.A. El-Bindary, M.I. Abou-Dobara and H.A. Seyam, Spectrochim. Acta A Mol. Biomol. Spectrosc., 104, 213 (2013); https://doi.org/10.1016/j.saa.2012.11.024
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- S. Nakamura, R. Nagao, R. Takahashi and T. Noguchi, Biochemistry, 53, 3131 (2014); https://doi.org/10.1021/bi500237y
- C.X. Wang, Y.H. Yang and G.W. Yang, J. Appl. Phys., 97, 066104 (2005); https://doi.org/10.1063/1.1863415
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- G.G. Mohamed, Spectrochim. Acta A Mol. Biomol. Spectrosc., 64, 188 (2006); https://doi.org/10.1016/j.saa.2005.05.044
- M. Almasi, M. Vilkova and J. Bednarcik, Inorg. Chim. Acta, 515, 120064 (2021); https://doi.org/10.1016/j.ica.2020.120064
- I. El Heda, J. Massoudi, R. Dhahri, E. Dhahri, F. Bahri, K. khirouni and B.F.O. Costa, J. Alloys Compd., 931, 167479 (2023); https://doi.org/10.1016/j.jallcom.2022.167479
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- K. Dyrek and M. Che, Chem. Rev., 97, 305 (1997); https://doi.org/10.1021/cr950259d
- A. Das, K. Bhattacharya, L.K. Das, S. Giri and A. Ghosh, Dalton Trans., 47, 9385 (2018); https://doi.org/10.1039/C8DT01400K
- J. Ammeter, G. Rist and H.H. Gunthard, J. Chem. Phys., 57, 3852 (1972); https://doi.org/10.1063/1.1678855
- A.K. Patel, R.N. Jadeja, R.J. Butcher, M.K. Kesharwani, J. Kastner and M. Muddassir, Polyhedron, 195, 114969 (2021); https://doi.org/10.1016/j.poly.2020.114969
- N.K. Modukuru, K.J. Snow, B.S. Perrin Jr., A. Bhambhani, M. Duff and C.V. Kumar, J. Photochem. Photobiol. Chem., 177, 43 (2006); https://doi.org/10.1016/j.jphotochem.2005.05.010
- N. Kumar, R. Kaushal and P. Awasthi, J. Mol. Struct., 1288, 135751 (2023); https://doi.org/10.1016/j.molstruc.2023.135751
- M.A. Olusegun, D. Reddy and D. Jaganyi, Int. J. Chem. Kinet., 52, 884 (2020); https://doi.org/10.1002/kin.21407
- M. Tripathi, R. Syed, A. Stalin, A. Malik, R. Pande and A.K. Asatkar, J. Lumin., 36, 1277 (2021); https://doi.org/10.1002/bio.4054
- R.R. Joshi and K.N. Ganesh, Biochem. Biophys. Res. Commun., 182, 588 (1992); https://doi.org/10.1016/0006-291X(92)91773-J
- A.A. Adeleke, M.S. Islam, K. Olofinsan, V.F. Salau, C. Mocktar and B. Omondi, New J. Chem., 45, 17827 (2021); https://doi.org/10.1039/D1NJ03231C
- Y.T. Hussein and Y.H. Azeez, J. Biomol. Struct. Dyn., 41, 1168 (2023); https://doi.org/10.1080/07391102.2021.2017350
References
U. Ndagi, N. Mhlongo and M.E. Soliman, Drug Des. Devel. Ther., 11, 599 (2017); https://doi.org/10.2147/DDDT.S119488
R.L. Lucaciu, A.C. Hangan, B. Sevastre and L.S. Oprean, Molecules. 27, 6485 (2022);https://doi.org/10.3390/molecules27196485
U. Anand, A. Dey, A.K.S. Chandel, R. Sanyal, A. Mishra, D.K. Pandey, V. De Falco, A. Upadhyay, R. Kandimalla, A. Chaudhary, J.K. Dhanjal, S. Dewanjee, J. Vallamkondu and J.M. Pérez de la Lastra, Genes Dis., 10, 1367 (2023); https://doi.org/10.1016/j.gendis.2022.02.007
N.J. Wheate, S. Walker, G.E. Craig and R. Oun, Dalton Trans., 39, 8113 (2010); https://doi.org/10.1039/c0dt00292e
S. Rottenberg, C. Disler and P. Perego, Nat. Rev. Cancer, 21, 37 (2021); https://doi.org/10.1038/s41568-020-00308-y
S.J. Tan, Y.K. Yan, P.P.F. Lee and K.H. Lim, Future Med. Chem., 2, 1591 (2010); https://doi.org/10.4155/fmc.10.234
C. Marzano, M. Pellei, F. Tisato and C. Santini, Anticancer. Agents Med. Chem., 9, 185 (2009); https://doi.org/10.2174/187152009787313837
I. Romero-Canelon and P.J. Sadler, Inorg. Chem., 52, 12276 (2013); https://doi.org/10.1021/ic400835n
I.A. Khan, M.V. Kulkarni, M. Gopal, M.S. Shahabuddin and C.M. Sun, Bioorg. Med. Chem. Lett., 15, 3584 (2005); https://doi.org/10.1016/j.bmcl.2005.05.063
D. HaMai, S.C. Bondy, A. Becaria and A. Campbell, Curr. Top. Med. Chem., 1, 541 (2001); https://doi.org/10.2174/1568026013394796
R.K. Mohapatra, P.K. Das, M.K. Pradhan, M.M. El-Ajaily, D. Das, H.F. Salem, U. Mahanta, G. Badhei, P.K. Parhi, A.A. Maihub and M.K. E-Zahan, Comments Inorg. Chem., 39, 127 (2019); https://doi.org/10.1080/02603594.2019.1594204
S. Pullen and G.H. Clever, Acc. Chem. Res., 51, 3052 (2018); https://doi.org/10.1021/acs.accounts.8b00415
S.K. Singh, S. Joshi A.R. Singh J.K. Saxena and D.S. Pandey, Inorg. Chem., 46, 10869 (2007); https://doi.org/10.1021/ic700885m
Y. Li, G. Zhang and M. Tao, J. Photochem. Photobiol. B, 138, 109 (2014); https://doi.org/10.1016/j.jphotobiol.2014.05.011
A.K. Sadana, Y. Mirza, K.R. Aneja and O. Prakash, Eur. J. Med. Chem., 38, 533 (2003); https://doi.org/10.1016/s0223-5234(03)00061-8
M. Chauhan, K. Banerjee and F. Arjmand, Inorg. Chem., 46, 3072 (2007); https://doi.org/10.1021/ic061753a
N. Udilova, A.V. Kozlov, W. Bieberschulte, K. Frei, K. Ehrenberger and H. Nohl, Biochem. Pharm., 65, 59 (2003); https://doi.org/10.1016/S0006-2952(02)01452-1
M. Sonmez, M. Celebi and I. Berber, Eur. J. Med. Chem., 45, 1935 (2010); https://doi.org/10.1016/j.ejmech.2010.01.035
A.M. Dar, M.A. Khan, S. Mir and M.A. Gatoo, Pharm. Anal. Acta, 7, 464 (2016); https://doi.org/10.4172/2153-2435.1000464
E. Oruc, S. Rollas, F. Kandemirili, N. Shvets and A.S. Dimoglo, J. Med. Chem., 47, 6760 (2004); https://doi.org/10.1021/jm0495632
A. Lagunin, D. Filimonov and V. Poroikov, Curr. Pharm. Des., 16, 1703 (2010); https://doi.org/10.2174/138161210791164063
M.D. Segall, A.P. Beresford, J.M.R. Gola, D. Hawksley and M.H. Tarbit, Expert. Opin. Drug. Metab. Toxicol., 2, 325 (2006); https://doi.org/10.1517/17425255.2.2.325
B. Mathew, J. Suresh, S. Anbazhagan and S. Dev, Biomed. Aging. Pathol., 4, 327 (2014); https://doi.org/10.1016/j.biomag.2014.07.011
T. Sander, J. Freyss, M.V. Korff, J.R. Reich and C. Rufener, J. Chem. Inf. Model., 49, 232 (2009); https://doi.org/10.1021/ci800305f
F. Liu and B.-S. Fang, Chin. J. Biotechnol., 23, 133 (2007); https://doi.org/10.1016/S1872-2075(07)60012-0
A.Z. El-Sonbati, M.A. Diab, A.A. El-Bindary, M.I. Abou-Dobara and H.A. Seyam, Spectrochim. Acta A Mol. Biomol. Spectrosc., 104, 213 (2013); https://doi.org/10.1016/j.saa.2012.11.024
O. Ozdemir, J. Photochem. Photobiol. Chem., 392, 112356 (2020); https://doi.org/10.1016/j.jphotochem.2020.112356
S. Nakamura, R. Nagao, R. Takahashi and T. Noguchi, Biochemistry, 53, 3131 (2014); https://doi.org/10.1021/bi500237y
C.X. Wang, Y.H. Yang and G.W. Yang, J. Appl. Phys., 97, 066104 (2005); https://doi.org/10.1063/1.1863415
A.Z. El-Sonbati, W.H. Mahmoud, G.G. Mohamed, M.A. Diab, S.M. Morgan and S.Y. Abbas, Appl. Organomet. Chem., 33, 5048 (2019); https://doi.org/10.1002/aoc.5048
M.I. Khan, A. Khan, I. Hussain, M.A. Khan, S. Gul, M. Iqbal, Inayat-Ur-Rahman and F. Khuda, Inorg. Chem. Commun., 35, 104 (2013); https://doi.org/10.1016/j.inoche.2013.06.014
G.G. Mohamed, Spectrochim. Acta A Mol. Biomol. Spectrosc., 64, 188 (2006); https://doi.org/10.1016/j.saa.2005.05.044
M. Almasi, M. Vilkova and J. Bednarcik, Inorg. Chim. Acta, 515, 120064 (2021); https://doi.org/10.1016/j.ica.2020.120064
I. El Heda, J. Massoudi, R. Dhahri, E. Dhahri, F. Bahri, K. khirouni and B.F.O. Costa, J. Alloys Compd., 931, 167479 (2023); https://doi.org/10.1016/j.jallcom.2022.167479
M. Almasi, M. Vilkova and J. Bednarcik, Inorg. Chim. Acta, 515, 120064 (2021); https://doi.org/10.1016/j.ica.2020.120064
D.K. Mishra, U.K. Singha, A. Das, S. Dutta, P. Kar, A. Chakraborty, A. Sen and B. Sinha, J. Coord. Chem., 71, 2165 (2018); https://doi.org/10.1080/00958972.2018.1476687
K. Dyrek and M. Che, Chem. Rev., 97, 305 (1997); https://doi.org/10.1021/cr950259d
A. Das, K. Bhattacharya, L.K. Das, S. Giri and A. Ghosh, Dalton Trans., 47, 9385 (2018); https://doi.org/10.1039/C8DT01400K
J. Ammeter, G. Rist and H.H. Gunthard, J. Chem. Phys., 57, 3852 (1972); https://doi.org/10.1063/1.1678855
A.K. Patel, R.N. Jadeja, R.J. Butcher, M.K. Kesharwani, J. Kastner and M. Muddassir, Polyhedron, 195, 114969 (2021); https://doi.org/10.1016/j.poly.2020.114969
N.K. Modukuru, K.J. Snow, B.S. Perrin Jr., A. Bhambhani, M. Duff and C.V. Kumar, J. Photochem. Photobiol. Chem., 177, 43 (2006); https://doi.org/10.1016/j.jphotochem.2005.05.010
N. Kumar, R. Kaushal and P. Awasthi, J. Mol. Struct., 1288, 135751 (2023); https://doi.org/10.1016/j.molstruc.2023.135751
M.A. Olusegun, D. Reddy and D. Jaganyi, Int. J. Chem. Kinet., 52, 884 (2020); https://doi.org/10.1002/kin.21407
M. Tripathi, R. Syed, A. Stalin, A. Malik, R. Pande and A.K. Asatkar, J. Lumin., 36, 1277 (2021); https://doi.org/10.1002/bio.4054
R.R. Joshi and K.N. Ganesh, Biochem. Biophys. Res. Commun., 182, 588 (1992); https://doi.org/10.1016/0006-291X(92)91773-J
A.A. Adeleke, M.S. Islam, K. Olofinsan, V.F. Salau, C. Mocktar and B. Omondi, New J. Chem., 45, 17827 (2021); https://doi.org/10.1039/D1NJ03231C
Y.T. Hussein and Y.H. Azeez, J. Biomol. Struct. Dyn., 41, 1168 (2023); https://doi.org/10.1080/07391102.2021.2017350