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This work is licensed under a Creative Commons Attribution 4.0 International License.
Synthesis, Characterization and Biological Activities of Some Metal Complexes Derived from Azo Dye Ligand 2-[2'-(5-Methyl thiazolyl)azo]-5-dimethylamino Benzoic Acid
Corresponding Author(s) : Khalid J. Al-Adilee
Asian Journal of Chemistry,
Vol. 30 No. 7 (2018): Vol 30 Issue 7
Abstract
In this paper we report the synthesis and identification of Ni(II), Cu(II) and Zn(II) complexes with new thiazole based azo dye 2-[2’-(5-methyl thiazolyl)azo]-5-dimethyl amino benzoic acid (5-MeTAMB) by the diazotization of 2-amino-5-methyl thiazole and coupling with 3-dimethyl amino benzoic acid in alkaline alcoholic solution. The structures of the azo dye ligand and its metal complexes were confirmed by various analytical techniques like by elemental analysis (C.H.N.S), UV-visible, FT-IR spectroscopic, mass spectroscopic, 1H NMR spectroscopic, SEM, XRD data and thermal studies (TGA & DSC). The magnetic moment value of metal complexes [ML2] M = Ni(II) and Cu(II) occurs in the range of high spin octahedral environment of azo ligand while Zn(II) complex show diamagnetic properties and octahedral structure. The analytical and spectral techniques show that the ligand coordinates as tridentate (N,N,O) donor molecule. The antibacterial and antifungal activity of the thiazolylazo ligand and its metal complexes have shown activity towards both bacterial and fungal strains. The biological activity was also conducted by cells cytotoxicity and viability of the ligand and Cu(II)-complex was screened for in vitro, antitumor activity against human breast cancer using MTT assay. The results shows that this type of compounds plays an important role in the rate of inhibition of the growth of cells of cancerous and natural lines and indicate undoubtedly the possibility of using them as antitumor drugs against breast cancer.
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L.-H. Ahlström, C.S. Eskilsson and E. Björklund, TrAC Trends Anal. Chem., 24, 49 (2005); https://doi.org/10.1016/j.trac.2004.09.004.
V.A. Lemos, E.S. Santos, M.S. Santos and R.T. Yamaki, Microchim. Acta, 158, 189 (2007); https://doi.org/10.1007/s00604-006-0704-9.
K. Bredereck, Dyes Pigments, 21, 23 (1993); https://doi.org/10.1016/0143-7208(93)85003-I.
G.M. Malik and S.K. Zadafiva, Der Chem. Sinica, 1, 15 (2010).
L.-H. Ahlström, C. Sparr Eskilsson and E. Björklund, Trends Analyt. Chem., 24, 49 (2005); https://doi.org/10.1016/j.trac.2004.09.004.
A. Khosravi, S. Moradian, K. Gharanjig and F.A. Taromi, Dyes Pigments, 69, 79 (2006); https://doi.org/10.1016/j.dyepig.2005.02.007.
A.A. Zuhair, K.J. Al-Adilee and T. Zianab, Int. Res. J. Pure Appl. Chem., 8, 33 (2015)
X. Fan, C. Zhu and G. Zhang, Analyst, 123, 109 (1998); https://doi.org/10.1039/a705268e.
K. Syrmanova, E. Negim, J. Kaldybekova and A.M. Tuleuov, Orient. J. Chem., 32, 01 (2016); https://doi.org/10.13005/ojc/320101.
U. Parimi and L. Pappu, Int. J. Pharm. Pharm. Sci., 4, 523 (1998).
G. Giorgioni, B. Accorroni, A. Di Stefano, G. Marucci, A. Siniscalchi and F. Claudi, Med. Chem. Res., 14, 57 (2005); https://doi.org/10.1007/s00044-005-0125-z.
T.D. Bradshaw, M.F. Stevens and A.D. Westwell, Curr. Med. Chem., 8, 203 (2001); https://doi.org/10.2174/0929867013373714.
P. Venkatesh and S.N. Pandeya, Int. J. Chem. Tech. Res., 1, 1354 (2002).
K.C. Keerthi, J. Keshavayya, T. Ragesh and S.K. Peethampar, Int. J. Pharm. Pharm. Sci., 5, 296 (2013).
M.R. Yazdanbakhsh, H. Yousefi, M. Mamaghani, E.O. Moradi, M. Rassa, H. Pouramir and M. Bagheri, J. Mol. Liq., 6, 21 (2012); https://doi.org/10.1016/j.molliq.2012.03.003.
M. Amir, S. Alamkhan and S.K. Peethampar, J. Indian Chem. Soc., 79, 280 (2002).
K.J. Al-Adilee and H.M. Hessoon, J. Chem. Pharm. Res., 7, 89 (2015).
K.J. Al-Adilee and S.H. Jawad, J. Global Pharma Technol., (In Press).
K.J. Al-Adilee and D.Y. Fanfon, J. Chem. Chem. Eng., 6, 1016 (2012); https://doi.org/10.17265/1934-7375/2012.11.011.
X. Fan, C. Zhu and G. Zhang, Analyst, 123, 109 (1998); https://doi.org/10.1039/a705268e.
G.P. Hildebrand and C.N. Reilley, Anal. Chem., 29, 258 (1957); https://doi.org/10.1021/ac60122a025.
K.J. Al-Adilee, H.A.H. Al-Shamsi and M.N. Dawood, Res. J. Pharm. Biol. Chem. Sci., 7, 2882 (2016).
K.J. Al-Adilee and S. Adnan, Orient. J. Chem., 33, 1815 (2017); https://doi.org/10.13005/ojc/330426.
A. Mostafa, N. El-Ghossein, G.B. Cieslinski and H.S. Bazzi, J. Mol. Struct., 1054-1055, 199 (2013); https://doi.org/10.1016/j.molstruc.2013.09.007.
K.J. Al-Adilee, Asian J. Chem., 24, 5419 (2012).
W.C. Vosburgh and G.R. Cooper, J. Am. Chem. Soc., 63, 437 (1941); https://doi.org/10.1021/ja01847a025.
E. Mercer, W. Peterson and B. Jordan, J. Inorg. Nucl. Chem., 34, 3290 (1972); https://doi.org/10.1016/0022-1902(72)80139-8.
K.J. Al-Adilee, A.K. Abass and A.M. Taher, J. Mol. Struct., 1108, 378 (2016); https://doi.org/10.1016/j.molstruc.2015.11.038.
S. Chandra, M. Tyagi and K. Sharma, J. Iran. Chem. Soc., 6, 310 (2009); https://doi.org/10.1007/BF03245839.
K.J. Al-Adilee and B.A. Hatem, J. Adv. Chem., 11, 3412 (2015); https://doi.org/10.24297/jac.v11i3.870.
K.J. Al-Adilee, K.A. Abedalrazaq and Z.M. Al-Hamdiny, Asian J. Chem., 25, 10475 (2013); https://doi.org/10.14233/ajchem.2013.15735.
V. Bankova, Chem. Cent. J., 1, 1 (2007); https://doi.org/10.1186/1752-153X-1-1.
H. Alshamsi, K. Al-Adilee and S.A. Jaber, Orient. J. Chem., 31, 809 (2015); https://doi.org/10.13005/ojc/310223.
M.B. Halli, K. Mallikarjun and S.S. Suryakant, J. Chem. Pharm. Res., 7, 1797 (2015).
H.A. Habeeb, K.J. Al-Adilee and S.A. Jaber, J. Chem. Mater. Res., 6, 69 (2014).
M.A. Neelakantan, S.S. Marriappan, J. Dharmaraja, T. Jeyakumar and K. Muthukumaran, Spectrochim. Acta Part A: Mol. Biomol. Spectrosc., 71, 628 (2008); https://doi.org/10.1016/j.saa.2008.01.023.
C. Anitha, S. Sumathi, P. Tharmaraj and C.D. Sheela, Int. J. Inorg. Chem., Article ID 493942 (2011); https://doi.org/10.1155/2011/493942.
K. Al-Adilee and H.A.K. Kyhoiesh, J. Mol. Struct., 1137, 160 (2017); https://doi.org/10.1016/j.molstruc.2017.01.054.
C.M. Harris and D.B. Kell, Biosensors, 1, 17 (1985); https://doi.org/10.1016/0265-928X(85)85005-7.
K. Mazumdar, N.K. Dutta, K.A. Kumar and S.G. Dastidar, Biol. Pharm. Bull., 28, 713 (2005); https://doi.org/10.1248/bpb.28.713.
Shamsuzzaman, A.M. Dar, H. Khanam and M.A. Gatoo, Arab. J. Chem., 7, 461 (2014); https://doi.org/10.1016/j.arabjc.2013.06.027.
W.-X. Cai, A.-L. Liu, Z.-M. Li, W.-L. Dong, X.-H. Liu and N.-B. Sun, Appl. Sci., 6, 8 (2016); https://doi.org/10.3390/app6010008.
S.L. Yan, M.-Y. Yang, Z.-H. Sun, L.-J. Min, C.X. Tan, J.-Q. Weng, H.-K. Wu and X.-H. Liu, Lett. Drug Des. Discov., 11, 940 (2014); https://doi.org/10.2174/1570180811666140423222141