European Journal of Chemistry

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

Article Sidebar

PDF
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.


icon graph This Abstract was viewed 1844 times | icon graph Article PDF downloaded 838 times

How to Cite
(1)
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.

Article Details

Share
Links for Article


Crossref - Scopus - Google - European PMC
Crossref
Scopus
Google Scholar
Europe PMC
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

Supporting Agencies

Taif University, Taif, 21985, Saudi Arabia
Most read articles by the same author(s)
TrendMD

Dimensions - Altmetric - scite_ - PlumX

Downloads and views

Downloads

Download data is not yet available.

Metrics

Metrics Loading ...
License Terms

License Terms

by-nc

Copyright © 2025 by Authors. This work is published and licensed by Atlanta Publishing House LLC, Atlanta, GA, USA. The full terms of this license are available at https://www.eurjchem.com/index.php/eurjchem/terms and incorporate the Creative Commons Attribution-Non Commercial (CC BY NC) (International, v4.0) License (http://creativecommons.org/licenses/by-nc/4.0). By accessing the work, you hereby accept the Terms. This is an open access article distributed under the terms and conditions of the CC BY NC License, which permits unrestricted non-commercial use, distribution, and reproduction in any medium, provided the original work is properly cited without any further permission from Atlanta Publishing House LLC (European Journal of Chemistry). No use, distribution, or reproduction is permitted which does not comply with these terms. Permissions for commercial use of this work beyond the scope of the License (https://www.eurjchem.com/index.php/eurjchem/terms) are administered by Atlanta Publishing House LLC (European Journal of Chemistry).