Copyright (c) 2021 AJC
This work is licensed under a Creative Commons Attribution 4.0 International License.
Study of Photophysico-chemical and Antimicrobial Photodynamic Properties of Visible Light Active Azometal(II) Complexes
Corresponding Author(s) : H.S. Bhojya Naik
Asian Journal of Chemistry,
Vol. 33 No. 8 (2021): Vol 33 Issue 8, 2021
Abstract
The Co(II) and Mn(II) complexes with octahedral geometries of the type [Co(L)2(H2O)2] and [Mn(L)2(H2O)2] were synthesized and characterized by elemental analysis, FT-IR, UV-visible spectra, powered XRD and photoluminescence. Both metal(II) complexes were prepared with 4-[(Z)-(8-hydroxyquinolin-5-yl)diazenyl]-1,5-dimethyl-2-phenyl-1,2-dihydro-3H-pyrazol-3-one. The complexes were evaluated for in vitro antimicrobial photodynamic activity against Gram-positive, Gram-negative bacteria and fungi. The cell inhibition rate was found to be 80-96%. in vitro Cytotoxic studies were performed for the synthesized complexes against human melanoma (A-375) and human primary glioblastoma (U-87) cell lines by MTT assay where Co(II) complex showed potential inhibitory efficiency with IC50 value of 115 μg/mL when compared to Mn(II) complex.
Keywords
Download Citation
Endnote/Zotero/Mendeley (RIS)BibTeX
- Á. Juarranz, P. Jaén, F. Sanz-Rodríguez, J. Cuevas and S. González, Clin. Transl. Oncol., 10, 148 (2008); https://doi.org/10.1007/s12094-008-0172-2
- R.R. Allison, H.C. Mota and C.H. Sibata, Photodiagn. Photodyn. Ther., 1, 263 (2004); https://doi.org/10.1016/S1572-1000(04)00084-5
- R.R. Allison and C.H. Sibata, Photodiagn. Photodyn. Ther., 7, 61 (2010); https://doi.org/10.1016/j.pdpdt.2010.02.001
- L. Cizeková, A. Grolmusová, Z. Ipóthová, Z. Barbieriková, V. Brezová, L. Hunáková, J. Imrich, L. Janovec, I. Dovinová and H. Paulíková, Bioorg. Med. Chem., 22, 4684 (2014); https://doi.org/10.1016/j.bmc.2014.07.013
- A. Gasparetto, T.F. Lapinski, S.R. Zamuner, S. Khouri, L.P. Alves, E. Munin and M.J. Salvador, J. Photochem. Photobiol. B, 99, 15 (2010); https://doi.org/10.1016/j.jphotobiol.2010.01.009
- N. Barbero, S. Visentin and G. Viscardi, J. Photochem. Photobiol. Chem., 299, 38 (2015); https://doi.org/10.1016/j.jphotochem.2014.11.002
- A.P. Castano, T.N. Demidova and M.R. Hamblin, Photodiagn. Photodyn. Ther., 1, 279 (2004); https://doi.org/10.1016/S1572-1000(05)00007-4
- M.S. Baptista and M. Wainwright, J. Med. Biol. Res., 44, 1 (2011); https://doi.org/10.1590/S0100-879X2010007500141
- M. Managa, E.K. Amuhaya and T. Nyokong, Spectrochim. Acta A Mol. Biomol. Spectrosc., 151, 867 (2015); https://doi.org/10.1016/j.saa.2015.06.088
- Y.D. Kim, J.H. Cho, C.R. Park, J.-H. Choi, C. Yoon and J.P. Kim, Dyes Pigments, 89, 1 (2011); https://doi.org/10.1016/j.dyepig.2010.07.008
- V. Kumar, M. Gohain, J.H. Van Tonder, B.C.B. Bezuindenhoudt, S. Ponra, O.M. Ntwaeaborwa and H.C. Swart, Opt. Mater., 50, 275 (2015); https://doi.org/10.1016/j.optmat.2015.11.009
- N.C. Warshakoon, J. Sheville, R.T. Bhatt, W. Ji, J.L. Mendez-Andino, K.M. Meyers, N. Kim, J.A. Wos, C. Mitchell, J.L. Paris, B.B. Pinney, O. Reizes and X.E. Hu, Bioorg. Med. Chem. Lett., 16, 5207 (2006); https://doi.org/10.1016/j.bmcl.2006.07.006
- R. Teran, R. Guevara, J. Mora, L. Dobronski, O. Barreiro-Costa, T. Beske, J. Pérez-Barrera, R. Araya-Maturana, P. Rojas-Silva, A. Poveda and J. Heredia-Moya, Molecules, 24, 2696 (2019); https://doi.org/10.3390/molecules24152696
- S. Kumar, S. Bawa and H. Gupta, Mini Rev. Med. Chem., 9, 1648 (2009); https://doi.org/10.2174/138955709791012247
- H.-R. Zhang, K.-B. Huang, Z.-F. Chen, Y.-C. Liu, Y.-N. Liu, T. Meng, Q.-P. Qin, B.-Q. Zou and H. Liang, MedChemComm, 7, 806, (2016); https://doi.org/10.1039/C6MD00073H
- M.C. Prabahkara and H.S. Bhojya Naik, Biometals, 21, 675 (2008); https://doi.org/10.1007/s10534-008-9152-9
- C.N. Sudhamani, H.S. Bhojya Naik and D. Girija, Synth. React. Inorg. Met.-Org. Nano-Met. Chem., 42, 518 (2012); https://doi.org/10.1080/15533174.2011.613439
- M.A. Gouda, H.F. Eldien, M.M. Girges and M.A. Berghot, J. Saudi Chem. Soc., 20, 151 (2016); https://doi.org/10.1016/j.jscs.2012.06.004
- C.H. Kim, E.S. Lee, S.M. Kang, E. de Josselin de Jong and B.-I. Kim, Photodiagn. Photodyn. Ther., 18, 279 (2017); https://doi.org/10.1016/j.pdpdt.2017.03.015
- A. Vt, P. Paramanantham, S.L. Sb, A. Sharan, M.H. Alsaedi, T.M.S. Dawoud, S. Asad and S. Busi, Photodiagn. Photodyn. Ther., 24, 300 (2018); https://doi.org/10.1016/j.pdpdt.2018.10.013
- C.N. Sudhamani, H.S. Bhojya Naik, K.R.S. Gowda, M. Giridhar, D. Girija and P.N.P. Kumar, Med. Chem. Res., 26, 1160 (2017); https://doi.org/10.1007/s00044-017-1831-z
- S. Ali, V. Singh, P. Jain and V. Tripathi, J. Saudi Chem. Soc., 23, 52 (2019); https://doi.org/10.1016/j.jscs.2018.04.005
- M. Zhu, J. Liu, J. Su, B. Meng, Y. Feng, B. Jia, T. Peng, Z. Qi and E. Gao, Appl. Organomet. Chem., 33, 4676 (2019); https://doi.org/10.1002/aoc.4676
- 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
- A. De, H.P. Ray, P. Jain, H. Kaur and N. Singh, J. Mol. Struct., 1199, 126901 (2020); https://doi.org/10.1016/j.molstruc.2019.126901
- A.Y. Al-Dawood, N.M. El -Metwaly and H.A. El-Ghamry, J. Mol. Liq., 220, 311 (2016); https://doi.org/10.1016/j.molliq.2016.04.079
- V.A. Mamedov, V.R. Galimullina, N.A. Zhukova, S.F. Kadyrova, E.V. Mironova, I.K. Rizvanov and S.K. Latypov, Tetrahedron Lett., 55, 4319 (2014); https://doi.org/10.1016/j.tetlet.2014.06.023
- A. Saylam, Z. Seferoglu and N. Ertan, J. Mol. Liq., 195, 267 (2014); https://doi.org/10.1016/j.molliq.2014.02.027
- G. Karpiñska, A.P. Mazurek and J.C. Dobrowolski, J. Mol. Struct. THEOCHEM, 961, 101 (2010); https://doi.org/10.1016/j.theochem.2010.09.006
- M. Manjunath, A.D. Kulkarni, G.B. Bagihalli, S. Malladi and S.A. Patil, J. Mol. Struct., 1127, 314 (2016); https://doi.org/10.1016/j.molstruc.2016.07.123
- N. Venugopal, G. Krishnamurthy, H.S. Bhojyanaik and P. Murali Krishna, J. Mol. Struct., 1183, 37 (2019); https://doi.org/10.1016/j.molstruc.2019.01.031
- M.A. Ayoub, J. Mol. Struct., 1173, 17 (2018); https://doi.org/10.1016/j.molstruc.2018.06.051
- S.A.F. Rostom, I.M. El-Ashmawy, H.A. Abd El Razik, M.H. Badr and H.M.A. Ashour, Bioorg. Med. Chem., 17, 882 (2009); https://doi.org/10.1016/j.bmc.2008.11.035
- X. Li, Y. Wu, D. Gu and F. Gan, Dyes Pigments, 86, 182 (2010); https://doi.org/10.1016/j.dyepig.2010.01.002
- M.K.B. Break, M. Ibrahim M. Tahir, K.A. Crouse and T.-J. Khoo, Bioinorg. Chem. Appl., 2013, 362513 (2013); https://doi.org/10.1155/2013/362513
- S.M. Pradeepa, H.S. Bhojya Naik, B.V. Kumar, K.I. Priyadarsini, A. Barik and M.C. Prabhakara, Spectrochim. Acta A Mol. Biomol. Spectrosc., 141, 34 (2015); https://doi.org/10.1016/j.saa.2015.01.019
- S.M. Pradeepa, H.S. Bhojya Naik, B.V. Kumar, K.I. Priyadarsini, A. Barik, T.R. Ravikumar Naik and M.C. Prabhakara, Spectrochim. Acta A Mol. Biomol. Spectrosc., 115, 12 (2013); https://doi.org/10.1016/j.saa.2013.06.009
- K. Andiappan, A. Sanmugam, E. Deivanayagam, K. Karuppasamy, H.-S. Kim and D. Vikraman, Sci. Rep., 8, 3054 (2018); https://doi.org/10.1038/s41598-018-21366-1
- T. Manjuraj, G. Krishnamurthy, Y.D. Bodke, H.S.B. Naik and H.S. Anil Kumar, J. Mol. Struct., 1171, 481 (2018); https://doi.org/10.1016/j.molstruc.2018.06.055
- M. Sennappan, P.M. Krishna, R. Ranganathan and P. Sivakami Sundari, J. Mol. Struct., 1179, 86 (2019); https://doi.org/10.1016/j.molstruc.2018.10.087
- N.K. Chaudhary and P. Mishra, Bioinorg. Chem. Appl., 2017, 6927675 (2017); https://doi.org/10.1155/2017/6927675
- O.A.M. Ali, S.M. El-Medani, D.A. Ahmed and D.A. Nassar, Spectrochim. Acta A Mol. Biomol. Spectrosc., 144, 99 (2015); https://doi.org/10.1016/j.saa.2015.02.078
- Z. Sun, S. Zhou, H. Qiu, Y. Gu and Y. Zhao, RSC Adv., 8, 17073 (2018); https://doi.org/10.1039/C8RA02557F
- L.M. Tokubo, P.L. Rosalen, J. de Cássia Orlandi Sardi, I.A. Freires, M. Fujimaki, J.E. Umeda, P.M. Barbosa, G.O. Tecchio, N. Hioka, C.F. de Freitas and R.S. Suga Terada, Photodiagn. Photodyn. Ther., 23, 94 (2018); https://doi.org/10.1016/j.pdpdt.2018.05.004
- C.M. Cassidy, R.F. Donnelly, J.S. Elborn, N.D. Magee and M.M. Tunney, J. Photochem. Photobiol. B, 106, 95 (2012); https://doi.org/10.1016/j.jphotobiol.2011.10.010
- S. Leonard, P. M. Gannett, Y. Rojanasakul, D. Schwegler-Berry, V. Castranova, V. Vallyathan and X. Shi, J. Inorg. Biochem., 70, 239 (1998); https://doi.org/10.1016/S0162-0134(98)10022-3
- A. Hanakova, K. Bogdanova, K. Tomankova, K. Pizova, J. Malohlava, S. Binder, R. Bajgar, K. Langova, M. Kolar, J. Mosinger and H. Kolarova, Microbiol. Res., 169, 163 (2014); https://doi.org/10.1016/j.micres.2013.07.005
- Z. Yaghobi, Z. Rashidi Ranjbar and S. Gharbi, Polyhedron, 164, 176 (2019); https://doi.org/10.1016/j.poly.2019.02.039
References
Á. Juarranz, P. Jaén, F. Sanz-Rodríguez, J. Cuevas and S. González, Clin. Transl. Oncol., 10, 148 (2008); https://doi.org/10.1007/s12094-008-0172-2
R.R. Allison, H.C. Mota and C.H. Sibata, Photodiagn. Photodyn. Ther., 1, 263 (2004); https://doi.org/10.1016/S1572-1000(04)00084-5
R.R. Allison and C.H. Sibata, Photodiagn. Photodyn. Ther., 7, 61 (2010); https://doi.org/10.1016/j.pdpdt.2010.02.001
L. Cizeková, A. Grolmusová, Z. Ipóthová, Z. Barbieriková, V. Brezová, L. Hunáková, J. Imrich, L. Janovec, I. Dovinová and H. Paulíková, Bioorg. Med. Chem., 22, 4684 (2014); https://doi.org/10.1016/j.bmc.2014.07.013
A. Gasparetto, T.F. Lapinski, S.R. Zamuner, S. Khouri, L.P. Alves, E. Munin and M.J. Salvador, J. Photochem. Photobiol. B, 99, 15 (2010); https://doi.org/10.1016/j.jphotobiol.2010.01.009
N. Barbero, S. Visentin and G. Viscardi, J. Photochem. Photobiol. Chem., 299, 38 (2015); https://doi.org/10.1016/j.jphotochem.2014.11.002
A.P. Castano, T.N. Demidova and M.R. Hamblin, Photodiagn. Photodyn. Ther., 1, 279 (2004); https://doi.org/10.1016/S1572-1000(05)00007-4
M.S. Baptista and M. Wainwright, J. Med. Biol. Res., 44, 1 (2011); https://doi.org/10.1590/S0100-879X2010007500141
M. Managa, E.K. Amuhaya and T. Nyokong, Spectrochim. Acta A Mol. Biomol. Spectrosc., 151, 867 (2015); https://doi.org/10.1016/j.saa.2015.06.088
Y.D. Kim, J.H. Cho, C.R. Park, J.-H. Choi, C. Yoon and J.P. Kim, Dyes Pigments, 89, 1 (2011); https://doi.org/10.1016/j.dyepig.2010.07.008
V. Kumar, M. Gohain, J.H. Van Tonder, B.C.B. Bezuindenhoudt, S. Ponra, O.M. Ntwaeaborwa and H.C. Swart, Opt. Mater., 50, 275 (2015); https://doi.org/10.1016/j.optmat.2015.11.009
N.C. Warshakoon, J. Sheville, R.T. Bhatt, W. Ji, J.L. Mendez-Andino, K.M. Meyers, N. Kim, J.A. Wos, C. Mitchell, J.L. Paris, B.B. Pinney, O. Reizes and X.E. Hu, Bioorg. Med. Chem. Lett., 16, 5207 (2006); https://doi.org/10.1016/j.bmcl.2006.07.006
R. Teran, R. Guevara, J. Mora, L. Dobronski, O. Barreiro-Costa, T. Beske, J. Pérez-Barrera, R. Araya-Maturana, P. Rojas-Silva, A. Poveda and J. Heredia-Moya, Molecules, 24, 2696 (2019); https://doi.org/10.3390/molecules24152696
S. Kumar, S. Bawa and H. Gupta, Mini Rev. Med. Chem., 9, 1648 (2009); https://doi.org/10.2174/138955709791012247
H.-R. Zhang, K.-B. Huang, Z.-F. Chen, Y.-C. Liu, Y.-N. Liu, T. Meng, Q.-P. Qin, B.-Q. Zou and H. Liang, MedChemComm, 7, 806, (2016); https://doi.org/10.1039/C6MD00073H
M.C. Prabahkara and H.S. Bhojya Naik, Biometals, 21, 675 (2008); https://doi.org/10.1007/s10534-008-9152-9
C.N. Sudhamani, H.S. Bhojya Naik and D. Girija, Synth. React. Inorg. Met.-Org. Nano-Met. Chem., 42, 518 (2012); https://doi.org/10.1080/15533174.2011.613439
M.A. Gouda, H.F. Eldien, M.M. Girges and M.A. Berghot, J. Saudi Chem. Soc., 20, 151 (2016); https://doi.org/10.1016/j.jscs.2012.06.004
C.H. Kim, E.S. Lee, S.M. Kang, E. de Josselin de Jong and B.-I. Kim, Photodiagn. Photodyn. Ther., 18, 279 (2017); https://doi.org/10.1016/j.pdpdt.2017.03.015
A. Vt, P. Paramanantham, S.L. Sb, A. Sharan, M.H. Alsaedi, T.M.S. Dawoud, S. Asad and S. Busi, Photodiagn. Photodyn. Ther., 24, 300 (2018); https://doi.org/10.1016/j.pdpdt.2018.10.013
C.N. Sudhamani, H.S. Bhojya Naik, K.R.S. Gowda, M. Giridhar, D. Girija and P.N.P. Kumar, Med. Chem. Res., 26, 1160 (2017); https://doi.org/10.1007/s00044-017-1831-z
S. Ali, V. Singh, P. Jain and V. Tripathi, J. Saudi Chem. Soc., 23, 52 (2019); https://doi.org/10.1016/j.jscs.2018.04.005
M. Zhu, J. Liu, J. Su, B. Meng, Y. Feng, B. Jia, T. Peng, Z. Qi and E. Gao, Appl. Organomet. Chem., 33, 4676 (2019); https://doi.org/10.1002/aoc.4676
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
A. De, H.P. Ray, P. Jain, H. Kaur and N. Singh, J. Mol. Struct., 1199, 126901 (2020); https://doi.org/10.1016/j.molstruc.2019.126901
A.Y. Al-Dawood, N.M. El -Metwaly and H.A. El-Ghamry, J. Mol. Liq., 220, 311 (2016); https://doi.org/10.1016/j.molliq.2016.04.079
V.A. Mamedov, V.R. Galimullina, N.A. Zhukova, S.F. Kadyrova, E.V. Mironova, I.K. Rizvanov and S.K. Latypov, Tetrahedron Lett., 55, 4319 (2014); https://doi.org/10.1016/j.tetlet.2014.06.023
A. Saylam, Z. Seferoglu and N. Ertan, J. Mol. Liq., 195, 267 (2014); https://doi.org/10.1016/j.molliq.2014.02.027
G. Karpiñska, A.P. Mazurek and J.C. Dobrowolski, J. Mol. Struct. THEOCHEM, 961, 101 (2010); https://doi.org/10.1016/j.theochem.2010.09.006
M. Manjunath, A.D. Kulkarni, G.B. Bagihalli, S. Malladi and S.A. Patil, J. Mol. Struct., 1127, 314 (2016); https://doi.org/10.1016/j.molstruc.2016.07.123
N. Venugopal, G. Krishnamurthy, H.S. Bhojyanaik and P. Murali Krishna, J. Mol. Struct., 1183, 37 (2019); https://doi.org/10.1016/j.molstruc.2019.01.031
M.A. Ayoub, J. Mol. Struct., 1173, 17 (2018); https://doi.org/10.1016/j.molstruc.2018.06.051
S.A.F. Rostom, I.M. El-Ashmawy, H.A. Abd El Razik, M.H. Badr and H.M.A. Ashour, Bioorg. Med. Chem., 17, 882 (2009); https://doi.org/10.1016/j.bmc.2008.11.035
X. Li, Y. Wu, D. Gu and F. Gan, Dyes Pigments, 86, 182 (2010); https://doi.org/10.1016/j.dyepig.2010.01.002
M.K.B. Break, M. Ibrahim M. Tahir, K.A. Crouse and T.-J. Khoo, Bioinorg. Chem. Appl., 2013, 362513 (2013); https://doi.org/10.1155/2013/362513
S.M. Pradeepa, H.S. Bhojya Naik, B.V. Kumar, K.I. Priyadarsini, A. Barik and M.C. Prabhakara, Spectrochim. Acta A Mol. Biomol. Spectrosc., 141, 34 (2015); https://doi.org/10.1016/j.saa.2015.01.019
S.M. Pradeepa, H.S. Bhojya Naik, B.V. Kumar, K.I. Priyadarsini, A. Barik, T.R. Ravikumar Naik and M.C. Prabhakara, Spectrochim. Acta A Mol. Biomol. Spectrosc., 115, 12 (2013); https://doi.org/10.1016/j.saa.2013.06.009
K. Andiappan, A. Sanmugam, E. Deivanayagam, K. Karuppasamy, H.-S. Kim and D. Vikraman, Sci. Rep., 8, 3054 (2018); https://doi.org/10.1038/s41598-018-21366-1
T. Manjuraj, G. Krishnamurthy, Y.D. Bodke, H.S.B. Naik and H.S. Anil Kumar, J. Mol. Struct., 1171, 481 (2018); https://doi.org/10.1016/j.molstruc.2018.06.055
M. Sennappan, P.M. Krishna, R. Ranganathan and P. Sivakami Sundari, J. Mol. Struct., 1179, 86 (2019); https://doi.org/10.1016/j.molstruc.2018.10.087
N.K. Chaudhary and P. Mishra, Bioinorg. Chem. Appl., 2017, 6927675 (2017); https://doi.org/10.1155/2017/6927675
O.A.M. Ali, S.M. El-Medani, D.A. Ahmed and D.A. Nassar, Spectrochim. Acta A Mol. Biomol. Spectrosc., 144, 99 (2015); https://doi.org/10.1016/j.saa.2015.02.078
Z. Sun, S. Zhou, H. Qiu, Y. Gu and Y. Zhao, RSC Adv., 8, 17073 (2018); https://doi.org/10.1039/C8RA02557F
L.M. Tokubo, P.L. Rosalen, J. de Cássia Orlandi Sardi, I.A. Freires, M. Fujimaki, J.E. Umeda, P.M. Barbosa, G.O. Tecchio, N. Hioka, C.F. de Freitas and R.S. Suga Terada, Photodiagn. Photodyn. Ther., 23, 94 (2018); https://doi.org/10.1016/j.pdpdt.2018.05.004
C.M. Cassidy, R.F. Donnelly, J.S. Elborn, N.D. Magee and M.M. Tunney, J. Photochem. Photobiol. B, 106, 95 (2012); https://doi.org/10.1016/j.jphotobiol.2011.10.010
S. Leonard, P. M. Gannett, Y. Rojanasakul, D. Schwegler-Berry, V. Castranova, V. Vallyathan and X. Shi, J. Inorg. Biochem., 70, 239 (1998); https://doi.org/10.1016/S0162-0134(98)10022-3
A. Hanakova, K. Bogdanova, K. Tomankova, K. Pizova, J. Malohlava, S. Binder, R. Bajgar, K. Langova, M. Kolar, J. Mosinger and H. Kolarova, Microbiol. Res., 169, 163 (2014); https://doi.org/10.1016/j.micres.2013.07.005
Z. Yaghobi, Z. Rashidi Ranjbar and S. Gharbi, Polyhedron, 164, 176 (2019); https://doi.org/10.1016/j.poly.2019.02.039