European Journal of Chemistry

Synthesis, characterization, DNA-binding and biological activity of Zn(II) complexes of sulfadiazine with different amino acids

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Published: Jun 30, 2015
DOI: https://doi.org/10.5155/eurjchem.6.2.117-126.1172
Keywords:
Docking, Antifungal, Amino acid, Sulfadiazine, DNA-binding, Antibacterial activity
Section
Research Article
Issue
Vol. 6 No. 2 (2015): June 2015
Dates
Received 2014-10-19
Accepted 2015-01-18
Published 2015-06-30


Main Article Content

Ahmed Abdlmonem El-Henawy
Chemistry Department, Faculty of Science, Al-Azhar University, Cairo, 11884, Egypt
Ahmed Imam Hanafy
Chemistry Department, Faculty of Science, Al-Azhar University, Cairo, 11884, Egypt

Abstract

New Zn(II) complexes (ZnII-VS, ZnII-LS, ZnII-SS, ZnII-CS and ZnII-MS) of the sulfonamide antibiotic sulfadiazine with different amino acids were prepared and fully characterized by elemental analyses, thermal analysis and IR, UV/Vis and 1H NMR spectroscopy. The IR and 1H NMR spectral data show that the ligands behave in a dibasic bidentate fashion coordinating to zinc ion. Interactions of these complexes with DNA were investigated by spectrophotometric method. Moreover, the antibacterial and antifungal activities were evaluated for five ligands and their complexes. The computational study for prediction of absorption, distribution, metabolism, elimination and toxic factors (ADMET) properties were performed for the prepared ligands.


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El-Henawy, A. A.; Hanafy, A. I. Synthesis, Characterization, DNA-Binding and Biological Activity of Zn(II) Complexes of Sulfadiazine With Different Amino Acids. Eur. J. Chem. 2015, 6, 117-126.

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References

[1]. Song, Y. M.; Wu, Q.; Yang, P. J.; Luan, N. N.; Wang, L. F.; Liu, Y. M. J. Inorg. Biochem. 2006, 100, 1685-1691.
http://dx.doi.org/10.1016/j.jinorgbio.2006.06.001

[2]. Tan, C. P.; Liu, J.; Chen, L. M.; Shi, S.; Ji, L. N. J. Inorg. Biochem. 2008, 102, 1644-1653.
http://dx.doi.org/10.1016/j.jinorgbio.2008.03.005

[3]. Zuber, G.; Quada Jr J. C.; Hecht, S. M. J. Am. Chem. Soc. 1998, 120, 9368-9396.
http://dx.doi.org/10.1021/ja981937r

[4]. Hecht, S. M. J. Nat. Prod. 2000, 63, 158 -168.
http://dx.doi.org/10.1021/np990549f

[5]. Lerman, L. S. J. Mol. Biol. 1961, 3, 18-30.
http://dx.doi.org/10.1016/S0022-2836(61)80004-1

[6]. Jonathan, B. C. Biopolymers 1997, 44, 201-215.
http://dx.doi.org/10.1002/(SICI)1097-0282(1997)44:3<201::AID-BIP2>3.0.CO;2-Z

[7]. Alessio, E. Bioinorganic Medicinal Chemistry, Wiley-VCH, Weinheim, 2011.
http://dx.doi.org/10.1002/9783527633104

[8]. Keene, F. R.; Smith, J. A.; Collins, J. G. Coord. Chem. Rev. 2009, 253, 2021-2035.
http://dx.doi.org/10.1016/j.ccr.2009.01.004

[9]. Ott, I. Coord. Chem. Rev. 2009, 253, 1670-1681.
http://dx.doi.org/10.1016/j.ccr.2009.02.019

[10]. Thurston, D. E., Chemistry and Pharmacology of Anticancer Drugs, CRC Press, Boca Raton, FL, 2007.

[11]. Mederos, A.; Dominguez, S.; Hernandez-Molina, R.; Sanchiz, J.; Brito, F. Coord. Chem. Rev. 1999, 857, 193-195.

[12]. Hambley, T. W. Dalton Trans. 2007, 43, 4929-4937.
http://dx.doi.org/10.1039/b706075k

[13]. Han Ang, W.; Dyson, P. J. Eur. J. Inorg. Chem. 2006, 4003-4018.

[14]. Busto, N.; Valladolid, J.; Aliende, C.; Jalon, F. A.; Manzano, B. R.; Rodriguez, A. M.; Gaspar, J. F.; Martins, C.; Biver, T.; Espino, G., Leal, J. M.; Garcia, B. Chem. Asian J. 2012, 7, 788-801.
http://dx.doi.org/10.1002/asia.201100883

[15]. Al-Mogren, M. M.; Alaghaz, A. M. A.; Ebrahem, A. E. Spectrochim. Acta A 2013, 114, 695-707.
http://dx.doi.org/10.1016/j.saa.2013.05.079

[16]. Pothiraj, K.; Baskaran, T.; Raman, N. J. Coord. Chem. 2012, 65, 2110-2126.
http://dx.doi.org/10.1080/00958972.2012.690037

[17]. Holder, A. A. Annu. Rep. Prog. Chem. Sect. A: Inorg. Chem. 2012, 108, 350-368.
http://dx.doi.org/10.1039/c2ic90009b

[18]. Ronconi, L.; Sadler, P. J. Coord. Chem. Rev. 2007, 251, 1633-1648.
http://dx.doi.org/10.1016/j.ccr.2006.11.017

[19]. Schwietert, C. W.; McCue, J. P. Coord. Chem. Rev. 1999, 184, 67-89.
http://dx.doi.org/10.1016/S0010-8545(98)00205-7

[20]. Vaira, M. D.; Bazzicalupi, C.; Orioli, P.; Messori, L.; Bruni, B.; Zatta, P. Inorg. Chem. 2004, 43, 3795-3797.
http://dx.doi.org/10.1021/ic0494051

[21]. Li, Z. Q.; Wu, F. J.; Gong, Y.; Hu, C. W.; Zhang, Y. H.; Gan, M. Y. Chin. J. Chem. 2007, 25 1809-1814.
http://dx.doi.org/10.1002/cjoc.200790334

[22]. Sakurai, H.; Kojima, Y.; Yoshikawa, Y.; Kawabe, K.; Yasui, H. Coord. Chem. Rev. 2002, 226, 187-198.
http://dx.doi.org/10.1016/S0010-8545(01)00447-7

[23]. Zhou, Q.; Hambley, T. W.; Kennedy, B. J.; Lay, P. A.; Turner, P.; Warwick, B.; Biffin, J. R.; Regtop, H. L. Inorg. Chem. 2000, 39, 3742-3748.
http://dx.doi.org/10.1021/ic991477i

[24]. Kasuga, N. C.; Sekino, K.; Ishikawa, M.; Honda, A.; Yokoyama, M.; Nakano, S.; Shimada, N.; Koumo, C.; Nomiya, K. J. Inorg. Biochem. 2003, 96, 298-310.
http://dx.doi.org/10.1016/S0162-0134(03)00156-9

[25]. Travnicek, Z.; Krystof, V.; Sipl, M. J. Inorg. Biochem. 2006, 100, 214-225.
http://dx.doi.org/10.1016/j.jinorgbio.2005.07.006

[26]. Casas, J. S.; Castellano, E. E.; Couce, M. D.; Ellena, J.; Sanchez, A.; Sordo, J.; Taboada, C. J. Inorg. Biochem. 2006, 100, 124-132.
http://dx.doi.org/10.1016/j.jinorgbio.2005.10.009

[27]. You, Z. L.; Shi, D. H.; Xu, C.; Zhang, Q.; Zhu, H. L. Eur. J. Med. Chem. 2008, 43, 862-871.
http://dx.doi.org/10.1016/j.ejmech.2007.06.015

[28]. Munih, P.; Moulin, A.; Stamper, C. C.; Bennett, B.; Ringe, D.; Petsko, G. A.; Holz, R. C. J. Inorg. Biochem. 2007, 101, 1099-1107.
http://dx.doi.org/10.1016/j.jinorgbio.2007.03.010

[29]. Zhang, H.; Liu, C. S.; Bu, X. H.; Yang, M. J. Inorg. Biochem. 2005, 99, 1119-1125.
http://dx.doi.org/10.1016/j.jinorgbio.2005.02.005

[30]. Sheng, X.; Guo, X.; Lu, X. M.; Lu, G. Y.; Shao, Y.; Liu, F.; Xu, Q. Bioconjug. Chem. 2008, 19, 490-498.
http://dx.doi.org/10.1021/bc700322w

[31]. Reedijk, J. in: Wilkinson, G.; Gillard, R. D.; McCleverty J. A. (Eds.), Heterocyclic Nitrogen-Donor Ligands Comprehensive Coordination Chemistry, vol. 2, Pergamon Press, Oxford, 1987, pp. 73.

[32]. House, D. A.; in: Wilkinson, G.; Gillard, R. D.; McCleverty, J. A. (Eds.), Ammonia and Amines. Comprehensive Coordination Chemistry, vol. 2, Pergamon Press, Oxford, 1987, pp. 23.

[33]. Grob, F.; Müller-Hartmann, A.; Vahrenkamp, H. Eur. J. Inorg. Chem. 2000, 11, 2363-2370.

[34]. Wang, S. X.; Luo, Q. H.; Wang, X. M.; Wang, L. F.; Yu, K. B. J. Chem. Soc. Dalton. Trans. 1995, 12, 2045-2055.
http://dx.doi.org/10.1039/dt9950002045

[35]. Pezzuto, J.; Che, C.; McPherson, D.; Zhu, P.; Topcu, G.; Erdelmeier, C.; Cordell, G. J. Nat. Prod. 1991, 54, 1522-1530.
http://dx.doi.org/10.1021/np50078a006

[36]. Burres, N.; Frigo, A.; Rasmussen, R.; McAlpine, J. J. Nat. Prod. 1992, 55, 1582-1597.
http://dx.doi.org/10.1021/np50089a004

[37]. Muanza, D.; Kim, B.; Euler, K.; Williams, L. Pharm. Biol. 1994, 32, 337-345.
http://dx.doi.org/10.3109/13880209409083012

[38]. Irobi, O.; Moo-Young, M.; Anderson, W. Pharm. Biol. 1996, 34, 87-90.
http://dx.doi.org/10.1076/phbi.34.2.87.13201

[39]. Wunsch, E.; Jaeger, E.; Kisfaludy, L.; Low. M. Angew. Chem. 1977, 16, 317-318.
http://dx.doi.org/10.1002/anie.197703172

[40]. Hanafy, A. I.; El-Bahy, Z. M.; Ali, I. O. J. Coord. Chem. 2012, 65, 1459-1474.
http://dx.doi.org/10.1080/00958972.2012.671936

[41]. Mostafa, H. Y. J. Pigm. Resin. Res. Tech. 2006, 35, 71-75.

[42]. Selvam, P.; Rathore, P.; Karthikumar, S.; Velkumar, K.; Palanisamy, P.; Vijayalakhsmi, S.; Witvrouw, M. Ind. J. Pharm. Sci. 2009, 71, 432-436.
http://dx.doi.org/10.4103/0250-474X.57293

[43]. Majumder, A.; Rosair, G. M.; Mallick, A.; Chattopadhyay, N.; Mitra, S. Polyhedron 2006, 25, 1753-1762.
http://dx.doi.org/10.1016/j.poly.2005.11.029

[44]. Lever, A. B. P. Inorganic Electronic Spectroscopy, Elsevier, Amsterdam, 1984

[45]. Osowole, A. A.; Kolawole, G. A.; Fagade, O. E. Synth. React. Inorg. Met. Org. Chem. Nano-Met. Chem. 2005, 35, 829-836.

[46]. Coats, A. W.; Redfern, J. P. Nature 1964, 201, 68-69.
http://dx.doi.org/10.1038/201068a0

[47]. Hanafya, A. I.; El-Bahy, Z. M.; El-Henawy, A. A.; Faheim, A. A. J. Mol. Catal. A 2012, 355, 192-200.
http://dx.doi.org/10.1016/j.molcata.2011.12.016

[48]. Mohameda, G. G.; Sharaby, C. M. Spectrochim. Acta Part A 2007, 66, 949-958.
http://dx.doi.org/10.1016/j.saa.2006.04.033

[49]. Singh, B. K.; Mishra, P.; Garg, B. S. Spectrochim. Acta Part A 2008, 69, 361-370.
http://dx.doi.org/10.1016/j.saa.2007.04.007

[50]. El-Bendary, E.; El-Sherbeny, M.; Badria, F. Boll. Chim. Farmaceutico 1998, 137, 115-119.

[51]. El-Bendary, E.; Badria, F. Arch. Pharm. Med. Chem. 2000, 333, 99-103
http://dx.doi.org/10.1002/(SICI)1521-4184(20004)333:4<99::AID-ARDP99>3.0.CO;2-O

[52]. Zhao, Y.; Abraham, M. H.; Lee, J.; Hersey, A.; Luscombe, N. C.; Beck, G.; Sherborne, B.; Cooper, I. Pharm. Res. 2002, 19, 1446-1457.
http://dx.doi.org/10.1023/A:1020444330011

[53]. Lipinski, C. A.; Lombardo, F.; Dominy, B. W.; Feeney, P. J. Adv. Drug. Delivery Rev. 1997, 23, 3-25.
http://dx.doi.org/10.1016/S0169-409X(96)00423-1

[54]. Clark, D. E.; Pickett, S. D. Drug Discov. Today 2000, 5, 49-58.
http://dx.doi.org/10.1016/S1359-6446(99)01451-8

[55]. Molecular Operating Environment (MOE), 2009.10; Chemical Computing Group Inc., Montreal, QC, Canada.

[56]. Wildman, S. A.; Crippen, G. M. J. Chem. Inf. Comput. Sci. 1999, 39, 868-873.
http://dx.doi.org/10.1021/ci990307l

[57]. Profeta, S.; Allinger, N. L. J. Am. Chem. Soc. 1985, 107, 1907-1918.
http://dx.doi.org/10.1021/ja00293a019

[58]. Halgren, T. A. J. Comput. Chem. 1996, 17, 490-519.
http://dx.doi.org/10.1002/(SICI)1096-987X(199604)17:5/6<490::AID-JCC1>3.0.CO;2-P

[59]. Dewar, M. J. S.; Zoebisch, E. G.; Healy, E. F.; Stewart, J. J. P. J. Am. Chem. Soc. 1985, 107, 3902-3909.
http://dx.doi.org/10.1021/ja00299a024

[60]. Fukui, K. Science 1982, 218, 747-754.
http://dx.doi.org/10.1126/science.218.4574.747

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