Computational, antimicrobial, DNA binding and anticancer activities of pyrimidine incorporated ligand and its copper(II) and zinc(II) complexes(II) complexes
Main Article Content
Abstract
In this research article, the synthesis, structural characterization, and biological, DNA binding and anticancer properties of pyrimidine incorporated Schiff base ligand L and its [CuL2](ClO4)2 (1) and [ZnL2](ClO4)2 (2) complexes are reported. The isolated complexes 1 and 2 have significant antibacterial and antifungal properties, greater than those of ligand L. The interaction between protein and L were analyzed by an in silico method. The intercalative binding of the prepared compounds was proved from electronic absorption, fluorometric, cyclic voltammetric and viscometric methods. The calculated binding parameters such as, Kb (2.65×103, L; 7.74×103, 1 and 2.99×103, 2); Ksv (3.30×103, L; 4.31×103, 1 and 3.89×103, 2), and Kapp (2.15×105, L; 3.30×105, 1 and 2.82×105, 2) indicted that complex 1 has better interaction ability than L and complex 2. The in vitro anticancer properties of L, and complexes 1 and 2 against human cancer (MCF-7, HeLa and HEp-2) and normal (NHDF) cell lines were determined by the MTT assay method. The obtained results designated that complexes 1 and 2 exhibited substantial anticancer activity against the cancer cell lines, better than that of L.
Downloads
Metrics
Article Details
Authors retain copyright and grant the journal right of first publication with the work simultaneously licensed under a Creative Commons Attribution license 4.0 that allows others to share the work with an acknowledgement of the work's authorship and initial publication in this journal.
References
R. C. Reynolds, A. Tiwari, J. E. Harwell, D. G. Gordon, B. D. Garrett, K. S. Gilbert, S. M. Schmid, W. R. Waud, R. F. Struck, J. Med. Chem. 43 (2000) 1484 (https://doi.org/10.1021/jm990417j)
S. A. F. Rostom, H. M. A. Ashour, H. A. Abdel Razik, Arch. Pharm. 342 (2009) 299 (https://doi.org/10.1002/ardp.200800223)
H. Parveen, F. Hayat, A. Salahuddin, A. Salahuddin, A. Azam, Eur. J. Med. Chem. 45 (2010) 3497 (https://doi.org/10.1016/j.ejmech.2010.04.023)
C. Sirichaiwat, C. Intaraudom, S. Kamchonwongpaisan, J. Vanichtanankul, Y. Thebtaranonth, Y. Yuthavong, J. Med. Chem. 47 (2004) 345 (https://doi.org/10.1021/jm0303352)
S. Kamchonwongpaisan, R. Quarrell, N. Charoensetakul, R. Ponsinet, T. Vilaivan, J. Vanichtanankul, B. Tarnchompoo, W. Sirawaraporn, G. Lowe, Y. Yuthavong, J. Med. Chem. 47 (2004) 673 (https://doi.org/10.1021/jm030165t)
D. W. Boykin, A. Kumar, M. Baji, G. Xiao, W. D. Wilson, B. C. Bender, D. R. McCurdy, J. E. Hall, R. R. Tidwell, Eur. J. Med. Chem. 32 (1998) 965 (https://doi.org/10.1016/s0223-5234(97)89640-7)
S. F. Chowdhury, V. B. Villamor, R. H. Guerrero, I. Leal, R. Brun, S. L. Croft, J. M. Goodman, L. Maes, L. M. Ruiz-Perez, D. G. Pacanowska, I. H. Gilbert, J. Med. Chem. 42 (1999) 4300 (https://doi.org/10.1021/jm981130)
M. S. S. Palanki, P. E. Erdman, L. M. G. Fung, G. I. Shevlin, R. W. Sullivan, M. E. Goldman, L. J. Ransone, B. L. Bennett, A. M. Manning, M. J. Suto, J. Med. Chem. 43 (2000) 3995 (https://doi.org/10.1021/jm0001626)
P. Bravo, D. Diliddo, G. Resnati, Tetrahedron 50 (1994) 8827 (https://doi.org/10.1016/s0040-4020(01)85356-4)
J. C. Jung, E. B. Watkins, M. A. Avery, Tetrahedron 58 (2002) 3639 (https://doi.org/10.1016/S0040-4020(02)00306-X)
K. L. Kees, J. J. Fitzgerald, K. E. Steiner, J. F. Mattes, B. Mihan, T. Tosi, D. Mondoro, M. L. McCaleb, J. Med. Chem. 39 (1996) 3920 (https://doi.org/10.1021/jm960444z)
G. T. Payne, D. C. Deecher, D. M. Soderlund, Pestic Biochem. Physiol. 60 (1998) 177 (https://doi.org/10.1006/pest.1998.2350)
S. G. Kucukguzel, S. Rollas, H. Erdeniz, M. Kiranz, A. C. Ekinci, A. Vidin, Eur. J. Med. Chem. 35 (2000) 761 (https://doi.org/10.1016/s0223-5234(00)90179-x)
M. Burotto, E. E. Manasanch, J. Wilkerson, T. Fojo, Oncologist 20 (2015) 400 (https://doi.org/10.1634/theoncologist.2014-0154)
M. S. El-Shahawi, M. S. Al-Jahdali, A. S. Bashammakh, A. A. Al-Sibaai, H. M. Nassef, Spectrochim. Acta, A 113 (2013) 459 (https://doi.org/10.1016/j.saa.2013.04.090)
A. H. Osman, Transition Met. Chem. 31 (2006) 35 (https://doi.org/10.1007/s11243-005-6265-7)
A. H. Osman, M. S. Saleh, S. M. Mahmoud, Synth. React. Inorg. Met. - Org. Chem. 34 (2004) 1069 (https://doi.org/10.1081/sim-120039258)
P. R. Inamdar, A. Sheela, Int. J. Biol. Macromol. 76 (2015) 269 (https://doi.org/10.1016/j.ijbiomac.2015.02.027)
B. Balaji, B. Balakrishnan, S. Perumalla, A. A. Karande, A. R. Chakravarty, Eur. J. Med. Chem. 85 (2014) 458 (https://doi.org/10.1016/j.ejmech.2014.07.098)
A. Sheela, S. M. Roopan, R. Vijayrahavan, Eur. J. Med. Chem. 43 (2008) 2206 (https://doi.org/10.1016/j.ejmech.2008.01.002)
M. Sankarganesh, J. Rajesh, G. G. Vinoth Kumar, M. Vadivel, L. Mitu, R. Senthil Kumar, J. Dhaveethu Raja, J. Saudi Chem. Soc. 22 (2018) 416 (https://doi.org/10.1016/j.jscs.2017.08.007)
J. W. Liang, Y. Wang, K. J. Du, G. Y. Li, R. L. Guan, L. N. Ji, H. Chao, J. Inorg. Biochem. 141 (2014) 17 (https://doi.org/10.1016/j.jinorgbio.2014.08.006)
S. Yasmin, S. Rabi, F. B. Biswas, T. G. Roy, F. Olbrich, D. Rehder, J. Inclusion Phenom. Macrocyclic Chem. 87 (2017) 239 (https://doi.org/10.1007/s10847-017-0693-9)
Gaussian 09, Revision A.02, Gaussian, Inc., Wallingford CT, 2009
N. Revathi, M. Sankarganesh, J. Rajesh, J. Dhaveethu Raja, J. Fluoresc. 27 (2017) 1801 (https://doi.org/10.1007/s10895-017-2118-y)
R. Arunkumara, G. Sharmilaa, P. Elumalaia, K. Senthilkumara, S. Banudevia, D. N. Gunadharinia, C. S. Bensona, P. Daisyb, J. Arunakarana, Phytomedicine 19 (2012) 912 (http://dx.doi.org/10.1016/j.phymed.2012.04.000)
M. Sankarganesh, P. Adwin Jose, J. Dhaveethu Raja, M. P. Kesavan, M. Vadivel, J. Rajesh, R. Jeyamurugan, R. Senthil Kumar, S. Karthikeyan, J. Photochem. Photobiol., B 176 (2017) 44 (https://doi.org/10.1016/j.jphotobiol.2017.09.013)
A. Gubendran, M. P. Kesavan, S. Ayyanaar, J. Dhaveethu Raja, P. Athappan, J. Rajesh, Appl. Organomet. Chem. 31 (2017) e3708 (https://doi.org/10.1002/aoc.3708)
S. Chandra, L. K. Gupta, Spectrochim. Acta, Part A 60 (2004) 1563 (https://doi.org/10.1016/¬j.saa.2004.01.015)
R. M. Silverstein, G. C. Bassler, T. C. Morrill, Spectrometric Identification of Organic Compounds, 4th ed., Wiley, New York, 1981
A. B. P. Lever, Inorganic Electronic Spectroscopy, Elsevier, Amsterdam, 1984
C. Ballhausen, Ligand field theory, McGraw Hill, New York, 1962
M. B. Halli, R. B. Sumathi, M. Kinni, Spectrochim. Acta, Part A 99 (2012) 46 (https://doi.org/10.1016/j.saa.2012.08.089)
N. Raman, A. Sakthivel, J. Dhaveethu Raja, K. Rajasekaran, Russ. J. Inorg. Chem. 53 (2008) 213 (https://doi.org/10.1134/s0036023608020113)
N. Raman, L. Mitu, A. Sakthivel, M. S. S. Pandi, J. Iran. Chem. Soc. 6 (2009) 738 (https://doi.org/10.1007/bf03246164)
N. Raman, J. Dhaveethu Raja, A. Saktivel, J. Chem. Sci. 119 (2007) 303 (https://doi.org/10.1007/s12039-007-0041-5)
R. L. Dutta, A. Syamal, Elements of Magnetochemistry, Affiliated East-West Press, New Delhi, 1993
B. J. Hathaway, D. E. Billing, Coord. Chem. Rev. 5 (1970) 143 (https://doi.org/10.1016/s0010-8545(00)80135-6)
H. Montgomery, E. C. Lingefetter, Acta Crystallogr. 20 (1966) 728 (https://doi.org/10.1107/s0365110x66001750)
A. M. F. Benial, V. Ramakrishnan, R. Murugesan Spectrochim. Acta, A 56 (2000) 2775 (https://doi.org/10.1016/s1386-1425(00)00322-x)
N. Raman, S. S. A. Fathima, J. Dhaveethu Raja, J. Serb. Chem. Soc. 73 (2008) 1063 (https://doi.org/10.2298/jsc0811063r)
P. Daisy, S. Suveena, V. Lilly Sr., J. Chem. Pharm. Res. 3 (3) (2011) 557 (http://www.jocpr.com/articles/molecular-docking-of-medicinal-compound-lupeol-with-autolysin-and-potential-drug-target-of-uti.pdf)
P. Daisy, P. Vijayalakshmi, C. Selvaraj S. K. Singh, K. Saipriya, Indian J. Pharm. Sci. 74 (2012) 217 (https://doi.org/10.4103/0250-474x.106063)
P. Adwin Jose, J. Dhaveethu Raja, M. Sankarganesh, J. Rajesh, J. Photochem. Photobiol., B 178 (2018) 143 (https://doi.org/10.1016/j.jphotobiol.2017.11.005)
S. M. Kumar, M. P. Kesavan, G. G. Vinoth Kumar, M. Sankarganesh, G. Chakkaravarthi, G. Rajagopal, J Rajesh, J. Mol. Struct. 1153 (2018) 1 (https://doi.org/10.1016/j.molstruc.2017.09.070).