Copyright (c) 2019 AJC
This work is licensed under a Creative Commons Attribution 4.0 International License.
DNA/BSA Binding, Molecular Docking, Nuclease Activity and Cytotoxicity Studies of Hydrazide Based Schiff Base Complexes
Corresponding Author(s) : Andy Ramu
Asian Journal of Chemistry,
Vol. 31 No. 12 (2019): Vol 31 Issue 12
Abstract
A new series of hydrazide based Schiff base metal Cu(II)/Zn(II) complexes of the type [Cu(L1-L4)2] and [Zn(L1-L4)2] has been synthesized and characterized by various analytical and spectral techniques. The proposed geometry of metal complexes, square planar for Cu2+ ion and tetrahedral for Zn2+ ion was confirmed by the spectral and analytical results. DNA interaction with metal complexes was explored by spectral and molecular docking analysis. The results obtained indicates that Cu(II)/Zn(II) complexes interaction with DNA via an intercalative binding mode and its respective intrinsic binding constant (Kb) was found in the order of 7 > 8 > 5 > 6 > 3 > 4 > 1 > 2. Further, similar interactions of these metal complexes with BSA were found in the same order of binding constant. Furthermore, the complexes showed moderate cleavage ability with pUC19 DNA. Cytotoxicity studies confirmed the biological importance of the Schiff base complexes.
Keywords
Download Citation
Endnote/Zotero/Mendeley (RIS)BibTeX
- K.L. Haas and K.J. Franz, Chem. Rev., 109, 4921 (2010); https://doi.org/10.1021/cr900134a.
- N. Arshad, P. Ali Channar, A. Saeed, S.I. Farooqi, A. Javeed, F. Ali Larik, W. Ahmad Abbasi and U. Flörke, J. Saudi Chem. Soc., 22, 1003 (2018); https://doi.org/10.1016/j.jscs.2018.05.002.
- P. Subbaraj, A. Ramu, N. Raman and J. Dharmaraja, J. Coord. Chem., 67, 2747 (2014); https://doi.org/10.1080/00958972.2014.950256.
- L.H. Abdel-Rahman, R.M. El-Khatib, L.A.E. Nassr and A.M. Abu-Dief, Arab. J. Chem., 10, S1835 (2017); https://doi.org/10.1016/j.arabjc.2013.07.010.
- L.H. Abdel-Rahman, A.M. Abu-Dief, E.F. Newair and S.K. Hamdan, J. Photochem. Photobiol. B, 160, 18 (2016); https://doi.org/10.1016/j.jphotobiol.2016.03.040.
- R.F. Brissos, A. Caubet and P. Gamez, Eur. J. Inorg. Chem., 2633 (2015); https://doi.org/10.1002/ejic.201500175.
- R. Gomathi, A. Ramu and A. Murugan, Bioinorg. Chem. Appl., 2014, Article ID 215392 (2014); https://doi.org/10.1155/2014/215392.
- A.S. Abu Surrah and M. Kettunen, Curr. Med. Chem., 13, 1337 (2006); https://doi.org/10.2174/092986706776872970.
- M. Mohamed Subarkhan, R.N. Prabhu, R. Raj Kumar and R. Ramesh, RSC Advances, 6, 25082 (2016); https://doi.org/10.1039/C5RA26071J.
- W.H. Ang and P.J. Dyson, Eur. J. Med. Chem., 4003 (2006); https://doi.org/10.1002/ejic.200600723.
- S. Kathiresan, S. Mugesh, J. Annaraj and M. Murugan, New J. Chem., 41, 1267 (2017); https://doi.org/10.1039/C6NJ03501A.
- A.A. Alothman, E.S. Al-Farraj, W.A. Al-Onazi, Z.M. Almarhoon and A.M. Al-Mohaimeed, Arab. J. Chem., (2019); https://doi.org/10.1016/j.arabjc.2019.02.003.
- F. Mohammadtabar, B. Shafaatian, A. Soleymanpour, S.A. Rezvani and B. Notash, Transition Met. Chem., 41, 475 (2016); https://doi.org/10.1007/s11243-016-0043-6.
- T. Thirunavukkarasu, H.A. Sparkes, V.G. Gnanasoundari and K. Natarajan, Appl. Organomet. Chem., 32, 4403 (2018); https://doi.org/10.1002/aoc.4403.
- R. Fekri, M. Salehi, A. Asadi and M. Kubicki, Inorg. Chim. Acta, 484, 245 (2019); https://doi.org/10.1016/j.ica.2018.09.022.
- A. Kamal, G. Bharath Kumar, V. Lakshma Nayak, V.S. Reddy, A.B. Shaik, R. Rajender and M. Kashi Reddy, MedChemComm, 6, 606 (2015); https://doi.org/10.1039/C4MD00400K.
- E. Kupeli, N. Erdemoglu, E. Yesilada and B. Sener, J. Ethnopharmacol., 89, 265 (2003); https://doi.org/10.1016/j.jep.2003.09.005.
- H.H. Al-Rasheed, E.N. Sholkamy, M. Al Alshaikh, M.R.H. Siddiqui, A.S. Al-Obaidi and A. El-Faham, J. Chem., 2018, Article ID 8507567 (2018); https://doi.org/10.1155/2018/8507567.
- P. Subbaraj, A. Ramu, N. Raman and J. Dharmaraja, J. Saudi Chem. Soc., 19, 207 (2015); https://doi.org/10.1016/j.jscs.2014.05.002.
- K. Kiranmai, Y. Prashanthi and N.J.P. Subhashini, J. Chem. Pharm. Res., 2, 375 (2010).
- L. Ruiz-Azuara and M. E. Bravo-Gomez, Curr. Med. Chem., 17, 3606 (2010); https://doi.org/10.2174/092986710793213751.
- B.L. Vallee and D.S. Auld, Biochemistry, 29, 5647 (1990); https://doi.org/10.1021/bi00476a001.
- Y. Li, Z. Yang, M. Zhou, J. He, X. Wang, Y. Wu and Z. Wang, J. Mol. Struct., 1130, 818 (2017); https://doi.org/10.1016/j.molstruc.2016.10.092.
- T. Todorovic, S. Grubisic, M. Pregelj, M. Jagodiè, S. Misirlic-Denèic, M. Dulovic, I. Markovic, O. Klisuric, A. Malesevic, D. Mitic, K. Andelkovic and N. Filipovic, Eur. J. Inorg. Chem., 2015, 3921 (2015); https://doi.org/10.1002/ejic.201500349.
- T. Ito, S. Thyagarajan, K.D. Karlin and S.E. Rokita, Chem. Commun., 4812 (2005); https://doi.org/10.1039/b509690a.
- D.S. Goodman, J. Am. Chem. Soc., 80, 3802 (1958); https://doi.org/10.1021/ja01547a091.
- E.L. Gelamo, C.H.T.P. Silva, H. Imasato and M. Tabak, Biochim. Biophys. Acta, 1594, 84 (2002); https://doi.org/10.1016/S0167-4838(01)00287-4.
- M. Xu, Z.R. Ma, L. Huang, F.J. Chen and Z.Z. Zeng, Spectrochim. Acta A: Mol. Biomol. Spectrosc., 78, 503 (2011); https://doi.org/10.1016/j.saa.2010.11.018.
- M. Sedighipoor, A.H. Kianfar, W.A. Kamil Mahmood and M.H. Azarian, Polyhedron, 129, 1 (2017); https://doi.org/10.1016/j.poly.2017.03.027.
- M. Jiang, Y.-T. Li, Z.-Y. Wu, Z.-Q. Liu and C.-W. Yan, J. Inorg. Biochem., 103, 833 (2009); https://doi.org/10.1016/j.jinorgbio.2009.02.007.
- A.P. Vieira, C.A. Wegermann and A.M. Da Costa Ferreira, New J. Chem., 42, 13169 (2018); https://doi.org/10.1039/C7NJ04799A.
- S. Sujarani and A. Ramu, J. Mol. Struct., 1079, 353 (2015); https://doi.org/10.1016/j.molstruc.2014.08.041.
- S. Sujarani and A. Ramu, J. Mol. Struct., 1059, 299 (2014); https://doi.org/10.1016/j.molstruc.2013.11.038.
- P. Nithya, S. Helena, J. Simpson, M. Ilanchelian, A. Muthusankar and S. Govindarajan, J. Photochem. Photobiol. B, 165, 220 (2016); https://doi.org/10.1016/j.jphotobiol.2016.10.024.
- M. Sakthi and A. Ramu, J. Mol. Struct., 1149, 727 (2017); https://doi.org/10.1016/j.molstruc.2017.08.040.
- L.H. Abdel-Rahman, M.S.S. Adam, A.M. Abu-Dief, H. Moustafa, M.T. Basha, A.S. Aboraia, B.S. Al-Farhan and H. El-Sayed Ahmed, Appl. Organomet. Chem., 32, e4527 (2018); https://doi.org/10.1002/aoc.4527.
- T. Sarkar, S. Banerjee, S. Mukherjee and A. Hussain, Dalton Trans., 45, 6424 (2016); https://doi.org/10.1039/C5DT04775G.
- 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.
- N.B. Gopal Reddy, P.M. Krishna, S.S. Shantha Kumar, Y.P. Patil and M. Nethaji, J. Mol. Struct., 1137, 543 (2017); https://doi.org/10.1016/j.molstruc.2017.02.009.
- M.C. Mandewale, B. Thorat, Y. Nivid, R. Jadhav, A. Nagarsekar and R. Yamgar, J. Saudi Chem. Soc., 22, 218 (2018); https://doi.org/10.1016/j.jscs.2016.04.003.
- S.Y. Ebrahimipour, I. Sheikhshoaie, M. Mohamadi, S. Suarez, R. Baggio, M. Khaleghi, M. Torkzadeh-Mahani and A. Mostafavi, Spectrochim. Acta A Mol. Biomol. Spectrosc., 142, 410 (2015); https://doi.org/10.1016/j.saa.2015.01.088.
- U.L. Kala, S. Suma, M.R.P. Kurup, S. Krishnan and R.P. John, Polyhedron, 26, 1427 (2007); https://doi.org/10.1016/j.poly.2006.11.035.
- S.T. Chew, K.M. Lo, S.K. Sinniah, K.S. Sim and K.W. Tan, RSC Adv., 4, 61232 (2014); https://doi.org/10.1039/C4RA11716F.
- C. Gokce and R. Gup, Appl. Organomet. Chem., 27, 263 (2013); https://doi.org/10.1002/aoc.2955.
- M. Kumar, S. Roy, M.S.H. Faizi, S. Kumar, M.K. Singh, S. Kishor, S.C. Peter and R.P. John, J. Mol. Struct., 1128, 195 (2017); https://doi.org/10.1016/j.molstruc.2016.08.004.
- C.J. Dhanaraj and M.S. Nair, J. Saudi Chem. Soc., 18, 479 (2014); https://doi.org/10.1016/j.jscs.2011.10.006.
- M.C. linescu, M.L. Fiastru, D. Bala, C. Mihailciuc, T.N. Pýrjol and B. Jurca, J. Saudi Chem. Soc., (2019) (in press); https://doi.org/10.1016/j.jscs.2019.02.006.
- K. Nagashri, J. Joseph and C.J. Dhanaraj, Arab. J. Chem., 9, 548 (2016); https://doi.org/10.1016/j.arabjc.2011.06.027.
- S. Yadav, I. Yousuf, M. Usman, M. Ahmad, F. Arjmand and S. Tabassum, RSC Adv., 5, 50673 (2015); https://doi.org/10.1039/C5RA06953J.
- N. Raman, R. Mahalakshmi, T. Arun, S. Packianathan and R. Rajkumar, J. Photochem. Photobiol. B, 138, 211 (2014); https://doi.org/10.1016/j.jphotobiol.2014.05.018.
- S. Kathiresan, T. Anand, S. Mugesh and J. Annaraj, J. Photochem. Photobiol. B, 148, 290 (2015); https://doi.org/10.1016/j.jphotobiol.2015.04.016.
- S. Kathiresan, S. Mugesh, M. Murugan, F. Ahamed and J. Annaraj, RSC Adv., 6, 1810 (2016); https://doi.org/10.1039/C5RA20607C.
- V.M. Manikandamathavan, T. Weyhermuller, R.P. Parameswari, M. Sathishkumar, V. Subramanian and B.U. Nair, Dalton Trans., 43, 13018 (2014); https://doi.org/10.1039/C4DT01378F.
- L. Li, Q. Guo, J. Dong, T. Xu and J. Li, J. Photochem. Photobiol. B, 125, 56 (2013); https://doi.org/10.1016/j.jphotobiol.2013.05.007.
- S. Banerjee, S. Mondal, W. Chakraborty, S. Sen, R. Gachhui, R.J. Butcher, A.M.Z. Slawin, C. Mandal and S. Mitra, Polyhedron, 28, 2785 (2009); https://doi.org/10.1016/j.poly.2009.05.071.
- P. Kavitha, M. Rama Chary, B.V.V.A. Singavarapu and K. Laxma Reddy, J. Saudi Chem. Soc., 20, 69 (2016); https://doi.org/10.1016/j.jscs.2013.03.005.
- M.S. Nair, D. Arish and R.S. Joseyphus, J. Saudi Chem. Soc., 16, 83 (2012); https://doi.org/10.1016/j.jscs.2010.11.002.
- N. Raman, S. Sobha and L. Mitu, Monatsh. Chem., 143, 1019 (2012); https://doi.org/10.1007/s00706-011-0699-8.
- S.S. Sreejith, N. Mohan and M.R.P. Kurup, Polyhedron, 135, 278 (2017); https://doi.org/10.1016/j.poly.2017.07.015.
- D. Senthil Raja, E. Ramachandran, N.S.P. Bhuvanesh and K. Natarajan, Eur. J. Med. Chem., 64, 148 (2013); https://doi.org/10.1016/j.ejmech.2013.03.040.
- P. Krishnamoorthy, P. Sathyadevi, R.R. Butorac, A.H. Cowley, N.S.P. Bhuvanesh and N. Dharmaraj, Dalton Trans., 41, 4423 (2012); https://doi.org/10.1039/c2dt11938b.
- M. Das, B. Kumar Kundu, R. Tiwari, P. Mandal, D. Nayak, R. Ganguly and S. Mukhopadhyay, Inorg. Chim. Acta, 469, 111 (2018); https://doi.org/10.1016/j.ica.2017.09.013.
- K. Hu, F. Li, Z. Zhang and F. Liang, New J. Chem., 41, 2062 (2017); https://doi.org/10.1039/C6NJ02483A.
- P. Vijayan, P. Viswanathamurthi, K. Velmurugan, R. Nandhakumar, M.D. Balakumaran, P.T. Kalaichelvan and J.G. Malecki, RSC Adv., 5, 103321 (2015); https://doi.org/10.1039/C5RA18568H.
References
K.L. Haas and K.J. Franz, Chem. Rev., 109, 4921 (2010); https://doi.org/10.1021/cr900134a.
N. Arshad, P. Ali Channar, A. Saeed, S.I. Farooqi, A. Javeed, F. Ali Larik, W. Ahmad Abbasi and U. Flörke, J. Saudi Chem. Soc., 22, 1003 (2018); https://doi.org/10.1016/j.jscs.2018.05.002.
P. Subbaraj, A. Ramu, N. Raman and J. Dharmaraja, J. Coord. Chem., 67, 2747 (2014); https://doi.org/10.1080/00958972.2014.950256.
L.H. Abdel-Rahman, R.M. El-Khatib, L.A.E. Nassr and A.M. Abu-Dief, Arab. J. Chem., 10, S1835 (2017); https://doi.org/10.1016/j.arabjc.2013.07.010.
L.H. Abdel-Rahman, A.M. Abu-Dief, E.F. Newair and S.K. Hamdan, J. Photochem. Photobiol. B, 160, 18 (2016); https://doi.org/10.1016/j.jphotobiol.2016.03.040.
R.F. Brissos, A. Caubet and P. Gamez, Eur. J. Inorg. Chem., 2633 (2015); https://doi.org/10.1002/ejic.201500175.
R. Gomathi, A. Ramu and A. Murugan, Bioinorg. Chem. Appl., 2014, Article ID 215392 (2014); https://doi.org/10.1155/2014/215392.
A.S. Abu Surrah and M. Kettunen, Curr. Med. Chem., 13, 1337 (2006); https://doi.org/10.2174/092986706776872970.
M. Mohamed Subarkhan, R.N. Prabhu, R. Raj Kumar and R. Ramesh, RSC Advances, 6, 25082 (2016); https://doi.org/10.1039/C5RA26071J.
W.H. Ang and P.J. Dyson, Eur. J. Med. Chem., 4003 (2006); https://doi.org/10.1002/ejic.200600723.
S. Kathiresan, S. Mugesh, J. Annaraj and M. Murugan, New J. Chem., 41, 1267 (2017); https://doi.org/10.1039/C6NJ03501A.
A.A. Alothman, E.S. Al-Farraj, W.A. Al-Onazi, Z.M. Almarhoon and A.M. Al-Mohaimeed, Arab. J. Chem., (2019); https://doi.org/10.1016/j.arabjc.2019.02.003.
F. Mohammadtabar, B. Shafaatian, A. Soleymanpour, S.A. Rezvani and B. Notash, Transition Met. Chem., 41, 475 (2016); https://doi.org/10.1007/s11243-016-0043-6.
T. Thirunavukkarasu, H.A. Sparkes, V.G. Gnanasoundari and K. Natarajan, Appl. Organomet. Chem., 32, 4403 (2018); https://doi.org/10.1002/aoc.4403.
R. Fekri, M. Salehi, A. Asadi and M. Kubicki, Inorg. Chim. Acta, 484, 245 (2019); https://doi.org/10.1016/j.ica.2018.09.022.
A. Kamal, G. Bharath Kumar, V. Lakshma Nayak, V.S. Reddy, A.B. Shaik, R. Rajender and M. Kashi Reddy, MedChemComm, 6, 606 (2015); https://doi.org/10.1039/C4MD00400K.
E. Kupeli, N. Erdemoglu, E. Yesilada and B. Sener, J. Ethnopharmacol., 89, 265 (2003); https://doi.org/10.1016/j.jep.2003.09.005.
H.H. Al-Rasheed, E.N. Sholkamy, M. Al Alshaikh, M.R.H. Siddiqui, A.S. Al-Obaidi and A. El-Faham, J. Chem., 2018, Article ID 8507567 (2018); https://doi.org/10.1155/2018/8507567.
P. Subbaraj, A. Ramu, N. Raman and J. Dharmaraja, J. Saudi Chem. Soc., 19, 207 (2015); https://doi.org/10.1016/j.jscs.2014.05.002.
K. Kiranmai, Y. Prashanthi and N.J.P. Subhashini, J. Chem. Pharm. Res., 2, 375 (2010).
L. Ruiz-Azuara and M. E. Bravo-Gomez, Curr. Med. Chem., 17, 3606 (2010); https://doi.org/10.2174/092986710793213751.
B.L. Vallee and D.S. Auld, Biochemistry, 29, 5647 (1990); https://doi.org/10.1021/bi00476a001.
Y. Li, Z. Yang, M. Zhou, J. He, X. Wang, Y. Wu and Z. Wang, J. Mol. Struct., 1130, 818 (2017); https://doi.org/10.1016/j.molstruc.2016.10.092.
T. Todorovic, S. Grubisic, M. Pregelj, M. Jagodiè, S. Misirlic-Denèic, M. Dulovic, I. Markovic, O. Klisuric, A. Malesevic, D. Mitic, K. Andelkovic and N. Filipovic, Eur. J. Inorg. Chem., 2015, 3921 (2015); https://doi.org/10.1002/ejic.201500349.
T. Ito, S. Thyagarajan, K.D. Karlin and S.E. Rokita, Chem. Commun., 4812 (2005); https://doi.org/10.1039/b509690a.
D.S. Goodman, J. Am. Chem. Soc., 80, 3802 (1958); https://doi.org/10.1021/ja01547a091.
E.L. Gelamo, C.H.T.P. Silva, H. Imasato and M. Tabak, Biochim. Biophys. Acta, 1594, 84 (2002); https://doi.org/10.1016/S0167-4838(01)00287-4.
M. Xu, Z.R. Ma, L. Huang, F.J. Chen and Z.Z. Zeng, Spectrochim. Acta A: Mol. Biomol. Spectrosc., 78, 503 (2011); https://doi.org/10.1016/j.saa.2010.11.018.
M. Sedighipoor, A.H. Kianfar, W.A. Kamil Mahmood and M.H. Azarian, Polyhedron, 129, 1 (2017); https://doi.org/10.1016/j.poly.2017.03.027.
M. Jiang, Y.-T. Li, Z.-Y. Wu, Z.-Q. Liu and C.-W. Yan, J. Inorg. Biochem., 103, 833 (2009); https://doi.org/10.1016/j.jinorgbio.2009.02.007.
A.P. Vieira, C.A. Wegermann and A.M. Da Costa Ferreira, New J. Chem., 42, 13169 (2018); https://doi.org/10.1039/C7NJ04799A.
S. Sujarani and A. Ramu, J. Mol. Struct., 1079, 353 (2015); https://doi.org/10.1016/j.molstruc.2014.08.041.
S. Sujarani and A. Ramu, J. Mol. Struct., 1059, 299 (2014); https://doi.org/10.1016/j.molstruc.2013.11.038.
P. Nithya, S. Helena, J. Simpson, M. Ilanchelian, A. Muthusankar and S. Govindarajan, J. Photochem. Photobiol. B, 165, 220 (2016); https://doi.org/10.1016/j.jphotobiol.2016.10.024.
M. Sakthi and A. Ramu, J. Mol. Struct., 1149, 727 (2017); https://doi.org/10.1016/j.molstruc.2017.08.040.
L.H. Abdel-Rahman, M.S.S. Adam, A.M. Abu-Dief, H. Moustafa, M.T. Basha, A.S. Aboraia, B.S. Al-Farhan and H. El-Sayed Ahmed, Appl. Organomet. Chem., 32, e4527 (2018); https://doi.org/10.1002/aoc.4527.
T. Sarkar, S. Banerjee, S. Mukherjee and A. Hussain, Dalton Trans., 45, 6424 (2016); https://doi.org/10.1039/C5DT04775G.
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.
N.B. Gopal Reddy, P.M. Krishna, S.S. Shantha Kumar, Y.P. Patil and M. Nethaji, J. Mol. Struct., 1137, 543 (2017); https://doi.org/10.1016/j.molstruc.2017.02.009.
M.C. Mandewale, B. Thorat, Y. Nivid, R. Jadhav, A. Nagarsekar and R. Yamgar, J. Saudi Chem. Soc., 22, 218 (2018); https://doi.org/10.1016/j.jscs.2016.04.003.
S.Y. Ebrahimipour, I. Sheikhshoaie, M. Mohamadi, S. Suarez, R. Baggio, M. Khaleghi, M. Torkzadeh-Mahani and A. Mostafavi, Spectrochim. Acta A Mol. Biomol. Spectrosc., 142, 410 (2015); https://doi.org/10.1016/j.saa.2015.01.088.
U.L. Kala, S. Suma, M.R.P. Kurup, S. Krishnan and R.P. John, Polyhedron, 26, 1427 (2007); https://doi.org/10.1016/j.poly.2006.11.035.
S.T. Chew, K.M. Lo, S.K. Sinniah, K.S. Sim and K.W. Tan, RSC Adv., 4, 61232 (2014); https://doi.org/10.1039/C4RA11716F.
C. Gokce and R. Gup, Appl. Organomet. Chem., 27, 263 (2013); https://doi.org/10.1002/aoc.2955.
M. Kumar, S. Roy, M.S.H. Faizi, S. Kumar, M.K. Singh, S. Kishor, S.C. Peter and R.P. John, J. Mol. Struct., 1128, 195 (2017); https://doi.org/10.1016/j.molstruc.2016.08.004.
C.J. Dhanaraj and M.S. Nair, J. Saudi Chem. Soc., 18, 479 (2014); https://doi.org/10.1016/j.jscs.2011.10.006.
M.C. linescu, M.L. Fiastru, D. Bala, C. Mihailciuc, T.N. Pýrjol and B. Jurca, J. Saudi Chem. Soc., (2019) (in press); https://doi.org/10.1016/j.jscs.2019.02.006.
K. Nagashri, J. Joseph and C.J. Dhanaraj, Arab. J. Chem., 9, 548 (2016); https://doi.org/10.1016/j.arabjc.2011.06.027.
S. Yadav, I. Yousuf, M. Usman, M. Ahmad, F. Arjmand and S. Tabassum, RSC Adv., 5, 50673 (2015); https://doi.org/10.1039/C5RA06953J.
N. Raman, R. Mahalakshmi, T. Arun, S. Packianathan and R. Rajkumar, J. Photochem. Photobiol. B, 138, 211 (2014); https://doi.org/10.1016/j.jphotobiol.2014.05.018.
S. Kathiresan, T. Anand, S. Mugesh and J. Annaraj, J. Photochem. Photobiol. B, 148, 290 (2015); https://doi.org/10.1016/j.jphotobiol.2015.04.016.
S. Kathiresan, S. Mugesh, M. Murugan, F. Ahamed and J. Annaraj, RSC Adv., 6, 1810 (2016); https://doi.org/10.1039/C5RA20607C.
V.M. Manikandamathavan, T. Weyhermuller, R.P. Parameswari, M. Sathishkumar, V. Subramanian and B.U. Nair, Dalton Trans., 43, 13018 (2014); https://doi.org/10.1039/C4DT01378F.
L. Li, Q. Guo, J. Dong, T. Xu and J. Li, J. Photochem. Photobiol. B, 125, 56 (2013); https://doi.org/10.1016/j.jphotobiol.2013.05.007.
S. Banerjee, S. Mondal, W. Chakraborty, S. Sen, R. Gachhui, R.J. Butcher, A.M.Z. Slawin, C. Mandal and S. Mitra, Polyhedron, 28, 2785 (2009); https://doi.org/10.1016/j.poly.2009.05.071.
P. Kavitha, M. Rama Chary, B.V.V.A. Singavarapu and K. Laxma Reddy, J. Saudi Chem. Soc., 20, 69 (2016); https://doi.org/10.1016/j.jscs.2013.03.005.
M.S. Nair, D. Arish and R.S. Joseyphus, J. Saudi Chem. Soc., 16, 83 (2012); https://doi.org/10.1016/j.jscs.2010.11.002.
N. Raman, S. Sobha and L. Mitu, Monatsh. Chem., 143, 1019 (2012); https://doi.org/10.1007/s00706-011-0699-8.
S.S. Sreejith, N. Mohan and M.R.P. Kurup, Polyhedron, 135, 278 (2017); https://doi.org/10.1016/j.poly.2017.07.015.
D. Senthil Raja, E. Ramachandran, N.S.P. Bhuvanesh and K. Natarajan, Eur. J. Med. Chem., 64, 148 (2013); https://doi.org/10.1016/j.ejmech.2013.03.040.
P. Krishnamoorthy, P. Sathyadevi, R.R. Butorac, A.H. Cowley, N.S.P. Bhuvanesh and N. Dharmaraj, Dalton Trans., 41, 4423 (2012); https://doi.org/10.1039/c2dt11938b.
M. Das, B. Kumar Kundu, R. Tiwari, P. Mandal, D. Nayak, R. Ganguly and S. Mukhopadhyay, Inorg. Chim. Acta, 469, 111 (2018); https://doi.org/10.1016/j.ica.2017.09.013.
K. Hu, F. Li, Z. Zhang and F. Liang, New J. Chem., 41, 2062 (2017); https://doi.org/10.1039/C6NJ02483A.
P. Vijayan, P. Viswanathamurthi, K. Velmurugan, R. Nandhakumar, M.D. Balakumaran, P.T. Kalaichelvan and J.G. Malecki, RSC Adv., 5, 103321 (2015); https://doi.org/10.1039/C5RA18568H.