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Synthesis, Characterization, DNA Synergy and Molecular Docking Studies of Novel 1,10-Phenanthroline Derived Mixed Ligand Metal(II) Complexes
Corresponding Author(s) : S. SYED ALI FATHIMA
Asian Journal of Chemistry,
Vol. 35 No. 10 (2023): Vol 35 Issue 10, 2023
Abstract
The effect of tumour and all its related costs, both human and commercial factor is driving the exploration for novel curative medicines.
Although platinum-based anticancer drugs have shown considerable success, their use is complicated by a number of drawbacks. Therefore, this study is mainly designed for transition metal complex based chemotherapeutic agents to reduce the obstacles for platinum-based anticancer agents presently used. Herein, novel mixed ligand-metal(II) complexes derived from 9-anthraldehyde, 2-aminophenol, metal chlorides and 1,10-phenanthroline (co-ligand) were synthesized and characterized using several spectral techniques, which revealed that they possess an octahedral structure. The interaction of calf thymus DNA (CT-DNA) with synthesized compounds confirmed that the compounds are binded with DNA via intercalation. The mode of interaction was affirmed by the docking simulations, where the synthesized compounds were docked with EGFR protein and 1B-DNA through intercalation. The biological screening results revealed that the synthesized complexes exhibited superior anti-pathogenic screening properties compared to ligands. The proliferation resistance against cancer cells and free radical scavenger studies of prepared compounds indicated that the presence of heterocyclic ligand is an important factor for boosting the anticancer potential and radical scavenger skill.
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- T. Ashraf, B. Ali, H. Qayyum, M.S. Haroone and G. Shabbir, Inorg. Chem. Commun., 150, 110449 (2023); https://doi.org/10.1016/j.inoche.2023.110449
- A.M. Florea and D. Busselberg, Cancers, 3, 1351 (2011); https://doi.org/10.3390/cancers3011351
- M.A. Fuertes, C. Alonso and J.M. Perez, Chem. Rev., 103, 645 (2003); https://doi.org/10.1021/cr020010d
- N. Shahid, N. Sami, M. Shakir and M. Aatif, J. Saudi Chem. Soc., 23, 315 (2019); https://doi.org/10.1016/j.jscs.2018.08.004
- R. Anjum, D. Palanimuthu, D.S. Kalinowski, W. Lewis, K.C. Park, Z. Kovacevic, I.U. Khan and D.R. Richardson, Inorg. Chem., 58, 13709 (2019); https://doi.org/10.1021/acs.inorgchem.9b01281
- C. Santini, M. Pellei, V. Gandin, M. Porchia, F. Tisato and C. Marzano, Chem. Rev., 114, 815 (2014); https://doi.org/10.1021/cr400135x
- S.B. Chanu, S. Banerjee and M. Roy, Eur. J. Med. Chem., 125, 816 (2017); https://doi.org/10.1016/j.ejmech.2016.09.090
- L. Ruiz-Azuara and M.E. Bravo-Gomez, Curr. Med. Chem., 17, 3606 (2010); https://doi.org/10.2174/092986710793213751
- R. Lugano, M. Ramachandran and A. Dimberg, Cell Mol. Life Sci., 77, 1745 (2020); https://doi.org/10.1007/s00018-019-03351-7
- M.M. Eatock, A. Schatzlein and S.B. Kaye, Cancer Treat. Rev., 26, 191 (2000); https://doi.org/10.1053/ctrv.1999.0158
- H. Xie and Y.J. Kang, Curr. Med. Chem., 16, 1304 (2009); https://doi.org/10.2174/092986709787846622
- A. Gupte and R.J. Mumper, Cancer Treat. Rev., 35, 32 (2009); https://doi.org/10.1016/j.ctrv.2008.07.004
- F. Tisato, C. Marzano, M. Porchia, M. Pellei and C. Santini, Med. Res. Rev., 30, 708 (2010); https://doi.org/10.1002/med.20174
- K.L. Haas and K.J. Franz, Chem. Rev., 109, 4921 (2009); https://doi.org/10.1021/cr900134a
- M. Chikira, C.H. Ng and M. Palaniandavar, Int. J. Mol. Sci., 16, 22754 (2015); https://doi.org/10.3390/ijms160922754
- 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.2010.06.016
- 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
- F. Liu and B. Fang, Chinese J. Biotechnol., 23, 133 (2007); https://doi.org/10.1016/S1872-2075(07)60012-0
- H. Chen, J.A. Parkinson, R.E. Morris and P.J. Sadler, J. Am. Chem. Soc., 125, 173 (2003); https://doi.org/10.1021/ja027719m
- R.S. Kumar and S. Arunachalam, Polyhedron, 26, 3255 (2007); https://doi.org/10.1016/j.poly.2007.03.001
- C. Justin Dhanaraj and J. Johnson, Spectrochim. Acta A Mol. Biomol. Spectrosc., 118, 624 (2014); https://doi.org/10.1016/j.saa.2013.09.007
- A.R. Silva, M.M.A. Freitas, C. Freire, B. de Castro, J.L. Figueiredo, Langmuir, 18, 8017 (2002); https://doi.org/10.1021/la025833c
- D.X. West, A.A. Nassar, F.A. El-Saied and M.I. Ayad, Transition Met. Chem., 23, 321 (1998); https://doi.org/10.1023/A:1006957325074
- K.R. Wilson, D.J. Cannon-Smith, O.C. Birdsong, S.J. Archibald, B.P. Burke and T.J. Hubin, Polyhedron, 114, 118 (2016); https://doi.org/10.1016/j.poly.2015.11.014
- G.B. Bagihalli, P.G. Avaji, S.A. Patil and P.S. Badami, Eur. J. Med. Chem., 43, 2639 (2008); https://doi.org/10.1016/j.ejmech.2008.02.013
- M. Manimohan, S. Pugalmani, K. Ravichandran and M.A. Sithique, RSC Adv., 10, 18259 (2020); https://doi.org/10.1039/D0RA01724H
- G. Garcia-Friaza, A. Fernandez-Betello, J.M. Perez, M.J. Prieto and V. Moreno, J. Inorg. Biochem, 100, 1368 (2006); https://doi.org/10.1016/j.jinorgbio.2006.03.011
- K. Dyrek and M. Che, Chem. Rev., 97, 305 (1997); https://doi.org/10.1021/cr950259d
- K. Satyanarayana and M.N.A. Rao, Eur. J. Med. Chem., 30, 641 (1995); https://doi.org/10.1016/0223-5234(96)88280-8
- N. Raman, S.F.S. Ali and D.J. Raja, J. Serbian Chem. Soc., 73, 1063 (2008); https://doi.org/10.2298/JSC0811063R
- R.J. Dudley and B.J. Hathaway, J. Chem. Soc. A, 0, 2794 (1970); https://doi.org/10.1039/J19700002794
- P. Pakravan and S. Masoudian, Iran. J. Pharm. Res., 14, 111 (2015).
- E.T. Knittl, A.A. Abou-Hussein and W. Linert, Monatsh. Chem., 149, 431 (2018); https://doi.org/10.1007/s00706-017-2075-9
- R. Antony, S. Theodore David Manickam, K. Karuppasamy, P. Kollu, P.V. Chandrasekar and S. Balakumar, RSC Adv., 4, 42816 (2014); https://doi.org/10.1039/C4RA08303B
- Z.H. Chohan, M. Arif and M. Sarfraz, Appl. Organomet. Chem., 21, 294 (2007); https://doi.org/10.1002/aoc.1200
- B.J. Pages, D.L. Ang, E.P. Wright and J.R. Aldrich-Wright, Dalton Trans., 44, 3505 (2015); https://doi.org/10.1039/C4DT02700K
- V. Rajendiran, M. Murali, E. Suresh, S. Sinha, K. Somasundaram, M. Palaniandavar, Dalton Trans., 148 (2008); https://doi.org/10.1039/B710578A
- S.A. Tysoe, R.J. Morgan, A.D. Baker and T.C. Strekas, J. Phys. Chem., 97, 1707 (1993); https://doi.org/10.1021/j100110a038
- Clinical and Laboratory Standards Institute, Performance Standards for Antimicrobial Susceptibility Testing, Clinical and Laboratory Standards Institute (CLSI), USA, edn. 31, (2021).
- Z.C. Liu, B.D. Wang, B. Li, Q. Wang, Z.-Y. Yang, T.-R. Li and Y. Li, Eur. J. Med. Chem., 45, 5353 (2010); https://doi.org/10.1016/j.ejmech.2010.08.060
- H.H. Harris, A. Levina, C.T. Dillon, I. Mulyani, B. Lai, Z. Cai and P.A. Lay, J. Biol. Inorg. Chem., 10, 105 (2005); https://doi.org/10.1007/s00775-004-0617-1
- S. Satyanarayana, J.C. Dabrowiak and J.B. Chaires, Biochemistry, 32, 2573 (1993); https://doi.org/10.1021/bi00061a015
- A. Tarushi, E. Polatoglou, J. Kljun, I. Turel, G. Psomas and D.P. Kessissoglou, Dalton Trans., 40, 9461 (2011); https://doi.org/10.1039/c1dt10870k
- A.R. Silva, M.M.A. Freitas, C. Freire, B. de Castro and J.L. Figueiredo, Langmuir, 18, 8017 (2002); https://doi.org/10.1021/la025833c
- M. Shakir, S. Hanif, M.A. Sherwani, O. Mohammad and S.I. Al-Resayes, J. Mol. Struct., 1092, 143 (2015); https://doi.org/10.1016/j.molstruc.2015.03.012
- M. Vasconcellos-Dias, C.D. Nunes, P.D. Vaz, P. Ferreira and M.J. Calhorda, Eur. J. Inorg. Chem., 18, 2917 (2007); https://doi.org/10.1002/ejic.200700091
References
T. Ashraf, B. Ali, H. Qayyum, M.S. Haroone and G. Shabbir, Inorg. Chem. Commun., 150, 110449 (2023); https://doi.org/10.1016/j.inoche.2023.110449
A.M. Florea and D. Busselberg, Cancers, 3, 1351 (2011); https://doi.org/10.3390/cancers3011351
M.A. Fuertes, C. Alonso and J.M. Perez, Chem. Rev., 103, 645 (2003); https://doi.org/10.1021/cr020010d
N. Shahid, N. Sami, M. Shakir and M. Aatif, J. Saudi Chem. Soc., 23, 315 (2019); https://doi.org/10.1016/j.jscs.2018.08.004
R. Anjum, D. Palanimuthu, D.S. Kalinowski, W. Lewis, K.C. Park, Z. Kovacevic, I.U. Khan and D.R. Richardson, Inorg. Chem., 58, 13709 (2019); https://doi.org/10.1021/acs.inorgchem.9b01281
C. Santini, M. Pellei, V. Gandin, M. Porchia, F. Tisato and C. Marzano, Chem. Rev., 114, 815 (2014); https://doi.org/10.1021/cr400135x
S.B. Chanu, S. Banerjee and M. Roy, Eur. J. Med. Chem., 125, 816 (2017); https://doi.org/10.1016/j.ejmech.2016.09.090
L. Ruiz-Azuara and M.E. Bravo-Gomez, Curr. Med. Chem., 17, 3606 (2010); https://doi.org/10.2174/092986710793213751
R. Lugano, M. Ramachandran and A. Dimberg, Cell Mol. Life Sci., 77, 1745 (2020); https://doi.org/10.1007/s00018-019-03351-7
M.M. Eatock, A. Schatzlein and S.B. Kaye, Cancer Treat. Rev., 26, 191 (2000); https://doi.org/10.1053/ctrv.1999.0158
H. Xie and Y.J. Kang, Curr. Med. Chem., 16, 1304 (2009); https://doi.org/10.2174/092986709787846622
A. Gupte and R.J. Mumper, Cancer Treat. Rev., 35, 32 (2009); https://doi.org/10.1016/j.ctrv.2008.07.004
F. Tisato, C. Marzano, M. Porchia, M. Pellei and C. Santini, Med. Res. Rev., 30, 708 (2010); https://doi.org/10.1002/med.20174
K.L. Haas and K.J. Franz, Chem. Rev., 109, 4921 (2009); https://doi.org/10.1021/cr900134a
M. Chikira, C.H. Ng and M. Palaniandavar, Int. J. Mol. Sci., 16, 22754 (2015); https://doi.org/10.3390/ijms160922754
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.2010.06.016
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
F. Liu and B. Fang, Chinese J. Biotechnol., 23, 133 (2007); https://doi.org/10.1016/S1872-2075(07)60012-0
H. Chen, J.A. Parkinson, R.E. Morris and P.J. Sadler, J. Am. Chem. Soc., 125, 173 (2003); https://doi.org/10.1021/ja027719m
R.S. Kumar and S. Arunachalam, Polyhedron, 26, 3255 (2007); https://doi.org/10.1016/j.poly.2007.03.001
C. Justin Dhanaraj and J. Johnson, Spectrochim. Acta A Mol. Biomol. Spectrosc., 118, 624 (2014); https://doi.org/10.1016/j.saa.2013.09.007
A.R. Silva, M.M.A. Freitas, C. Freire, B. de Castro, J.L. Figueiredo, Langmuir, 18, 8017 (2002); https://doi.org/10.1021/la025833c
D.X. West, A.A. Nassar, F.A. El-Saied and M.I. Ayad, Transition Met. Chem., 23, 321 (1998); https://doi.org/10.1023/A:1006957325074
K.R. Wilson, D.J. Cannon-Smith, O.C. Birdsong, S.J. Archibald, B.P. Burke and T.J. Hubin, Polyhedron, 114, 118 (2016); https://doi.org/10.1016/j.poly.2015.11.014
G.B. Bagihalli, P.G. Avaji, S.A. Patil and P.S. Badami, Eur. J. Med. Chem., 43, 2639 (2008); https://doi.org/10.1016/j.ejmech.2008.02.013
M. Manimohan, S. Pugalmani, K. Ravichandran and M.A. Sithique, RSC Adv., 10, 18259 (2020); https://doi.org/10.1039/D0RA01724H
G. Garcia-Friaza, A. Fernandez-Betello, J.M. Perez, M.J. Prieto and V. Moreno, J. Inorg. Biochem, 100, 1368 (2006); https://doi.org/10.1016/j.jinorgbio.2006.03.011
K. Dyrek and M. Che, Chem. Rev., 97, 305 (1997); https://doi.org/10.1021/cr950259d
K. Satyanarayana and M.N.A. Rao, Eur. J. Med. Chem., 30, 641 (1995); https://doi.org/10.1016/0223-5234(96)88280-8
N. Raman, S.F.S. Ali and D.J. Raja, J. Serbian Chem. Soc., 73, 1063 (2008); https://doi.org/10.2298/JSC0811063R
R.J. Dudley and B.J. Hathaway, J. Chem. Soc. A, 0, 2794 (1970); https://doi.org/10.1039/J19700002794
P. Pakravan and S. Masoudian, Iran. J. Pharm. Res., 14, 111 (2015).
E.T. Knittl, A.A. Abou-Hussein and W. Linert, Monatsh. Chem., 149, 431 (2018); https://doi.org/10.1007/s00706-017-2075-9
R. Antony, S. Theodore David Manickam, K. Karuppasamy, P. Kollu, P.V. Chandrasekar and S. Balakumar, RSC Adv., 4, 42816 (2014); https://doi.org/10.1039/C4RA08303B
Z.H. Chohan, M. Arif and M. Sarfraz, Appl. Organomet. Chem., 21, 294 (2007); https://doi.org/10.1002/aoc.1200
B.J. Pages, D.L. Ang, E.P. Wright and J.R. Aldrich-Wright, Dalton Trans., 44, 3505 (2015); https://doi.org/10.1039/C4DT02700K
V. Rajendiran, M. Murali, E. Suresh, S. Sinha, K. Somasundaram, M. Palaniandavar, Dalton Trans., 148 (2008); https://doi.org/10.1039/B710578A
S.A. Tysoe, R.J. Morgan, A.D. Baker and T.C. Strekas, J. Phys. Chem., 97, 1707 (1993); https://doi.org/10.1021/j100110a038
Clinical and Laboratory Standards Institute, Performance Standards for Antimicrobial Susceptibility Testing, Clinical and Laboratory Standards Institute (CLSI), USA, edn. 31, (2021).
Z.C. Liu, B.D. Wang, B. Li, Q. Wang, Z.-Y. Yang, T.-R. Li and Y. Li, Eur. J. Med. Chem., 45, 5353 (2010); https://doi.org/10.1016/j.ejmech.2010.08.060
H.H. Harris, A. Levina, C.T. Dillon, I. Mulyani, B. Lai, Z. Cai and P.A. Lay, J. Biol. Inorg. Chem., 10, 105 (2005); https://doi.org/10.1007/s00775-004-0617-1
S. Satyanarayana, J.C. Dabrowiak and J.B. Chaires, Biochemistry, 32, 2573 (1993); https://doi.org/10.1021/bi00061a015
A. Tarushi, E. Polatoglou, J. Kljun, I. Turel, G. Psomas and D.P. Kessissoglou, Dalton Trans., 40, 9461 (2011); https://doi.org/10.1039/c1dt10870k
A.R. Silva, M.M.A. Freitas, C. Freire, B. de Castro and J.L. Figueiredo, Langmuir, 18, 8017 (2002); https://doi.org/10.1021/la025833c
M. Shakir, S. Hanif, M.A. Sherwani, O. Mohammad and S.I. Al-Resayes, J. Mol. Struct., 1092, 143 (2015); https://doi.org/10.1016/j.molstruc.2015.03.012
M. Vasconcellos-Dias, C.D. Nunes, P.D. Vaz, P. Ferreira and M.J. Calhorda, Eur. J. Inorg. Chem., 18, 2917 (2007); https://doi.org/10.1002/ejic.200700091