European Journal of Chemistry

Mixed bivalent transition metal complexes of 1,10-phenanthroline and 2-aminomethylthiophenyl-4-bromosalicylaldehyde Schiff base: Spectroscopic, molecular modeling and biological activities



Main Article Content

Mutlaq Shedeed Aljahdali
Ahmed Abdou El-Sherif
Rifaat Hasan Hilal
Abeer Taha Abdel-Karim

Abstract

Mixed ligand complexes of M(II) {M = Cu(II), Ni(II), Co(II) and Zn(II)} with 1,10-phenanthroline (1,10-Phen) and Schiff base namely 2-aminomethylthiophenyl-4-bromosalicylaldehyde (ATS) have been synthesized. These metal chelates have been characterized by elemental analyses, IR, 1H NMR, solid reflectance, magnetic moment and molar conductance. Spectral data showed that the 1,10-phenanthroline act as neutral bidentate ligand coordinating to the metal ion through two nitrogen donor atoms and Schiff base (ATS) acts as monobasic bidentate coordinating through through azomethine-N and phenolic-oxygen groups. The geometry of the studied M(II) complexes has been fully optimized. The metal chelates have been screened for their antimicrobial activities using the disc diffusion method against different selected types of bacteria and fungi. In vitro antitumor activity assayed against two human cell lines colon (HCT116) and larynx (HEP2) cancer cells. Solution equilibrium studies were also investigated.

4_4_370_378

icon graph This Abstract was viewed 3165 times | icon graph Article PDF downloaded 978 times

How to Cite
(1)
Aljahdali, M. S.; El-Sherif, A. A.; Hilal, R. H.; Abdel-Karim, A. T. Mixed Bivalent Transition Metal Complexes of 1,10-Phenanthroline and 2-Aminomethylthiophenyl-4-Bromosalicylaldehyde Schiff Base: Spectroscopic, Molecular Modeling and Biological Activities. Eur. J. Chem. 2013, 4, 370-378.

Article Details

Share
Crossref - Scopus - Google - European PMC
References

[1]. Sigman, D. S.; Mazumder, A.; Perrin, D. M.; Wang, M. Z.; Meng, Z. X.; Liu, B. L.; Cai, G. L.; Zhang, C. L.; Wang, X. Y. Inorg. Chem. Commun, 2005, 8(4), 368-371.
http://dx.doi.org/10.1016/j.inoche.2005.01.023

[2]. Sharma, V.; Piwnica-Worms, D. Chem. Rev. 1999, 99(9), 2545-2560.
http://dx.doi.org/10.1021/cr980429x
PMid:11749491

[3]. Sattari, D.; Alipour, E.; Shirani, S.; Amighian, J. J. Inorg. Biochem. 1992, 45(2), 115-122.
http://dx.doi.org/10.1016/0162-0134(92)80005-G

[4]. Hitoshi, T.; Tamao, N.; Hideyuki, A.; Manabu, F.; Takayuki, M. Polyhedron 1997, 16, 3787-3794.
http://dx.doi.org/10.1016/S0277-5387(97)00148-4

[5]. Casella, L.; Gullotti, M. Inorg. Chem. 1986, 25(9), 1293-1303.
http://dx.doi.org/10.1021/ic00229a001

[6]. Casella, L.; Gullotti, M. Inorg. Chem. 1983, 22(16), 2259-2266.
http://dx.doi.org/10.1021/ic00158a008

[7]. El-Sherif, A. A.; Shehata, M. R.; Shoukry, M. M.; Barakat, M. H. J. Spectrochim. Acta A 2012, 96, 889-897.
http://dx.doi.org/10.1016/j.saa.2012.07.047
PMid:22935596

[8]. El-Sherif, A. A.; Shoukry, M. M.; Abd-Elgawad, M. M. A. Spectrochim. Acta A 2012, 98, 307-321.
http://dx.doi.org/10.1016/j.saa.2012.08.034
PMid:23021889

[9]. Aminabhavi, T. M.; Biradar, N. S.; Patil, S. B.; Roddabasanagoudar, V. L.; Rudzinski, W. E. Inorg. Chim. Acta 1985, 107(4), 231-234.
http://dx.doi.org/10.1016/S0020-1693(00)82293-8

[10]. Wolfe, A.; Shimer Jr, G. H.; Meehan, T.; Biochem. 1987, 26(20), 6392-6396.
http://dx.doi.org/10.1021/bi00394a013

[11]. Zhang, C.; Janiak, C. J. Chem. Crystllog. 2001, 31(1), 29-35.
http://dx.doi.org/10.1023/A:1013774502147

[12]. Campbell, M. J. M. Coord. Chem. Rev. 1975, 15, 279-312.
http://dx.doi.org/10.1016/S0010-8545(00)80276-3

[13]. Williams, D. R. Chem. Rev. 1972, 72, 203-213.
http://dx.doi.org/10.1021/cr60277a001
PMid:4555559

[14]. Furst, A.; Haro, R. T. Prog. Exp. Tumor Res. 1969, 12, 102-133.
PMid:4905208

[15]. Dwyer, F. B.; Mayhew, E.; Roe, E. M. F.; Shulman, A. Brit. J. Cancer 1965, 19, 195-199.
http://dx.doi.org/10.1038/bjc.1965.24
PMid:14284381 PMCid:PMC2071418

[16]. Sylvain, R.; Bernier, J. L.; Waring, M. J. J. Org. Chem. 1996, 61, 2326-2331.
http://dx.doi.org/10.1021/jo951840c

[17]. Gravert, D. J.; Griffin, J. H.; J. Org. Chem. 1993, 58, 820-822.
http://dx.doi.org/10.1021/jo00056a009

[18]. Balasubramanian, K. P.; Parameswari, K.; Chinnusamy, V.; Prabhakaran, R.; Natarajan, K. Spectrochim. Acta A 2006, 65, 678-683.
http://dx.doi.org/10.1016/j.saa.2005.12.029
PMid:16546440

[19]. Meyer, R.; Brink, S.; Van Rensburg, C. E. J.; Joone, G. K.; Gorls, H.; Lotz, S. J. Org. Met. Chem. 2005, 690, 117-125.
http://dx.doi.org/10.1016/j.jorganchem.2004.08.046

[20]. El-Sherif, A. A.; Eldebss, T. M. A. Spectrochim. Acta A 2011, 79, 1803-1814.
http://dx.doi.org/10.1016/j.saa.2011.05.062
PMid:21705267

[21]. Konstantinivi, S. S.; Radovanovi, B. C.; Caki, Z.; Vasic, V. J. Ser. Chem. Soc. 2003, 68, 641-648.
http://dx.doi.org/10.2298/JSC0309641K

[22]. Sammes, P. G.; Yahioglu, G. Chem. Soc. Rev. 1994, 23, 327-334.
http://dx.doi.org/10.1039/cs9942300327

[23]. Farrell, N. Transition Metal Complexes as Drugs and Chemotherapeutic Agents, Kluwer Academic, Dordrecht, 1989.
http://dx.doi.org/10.1007/978-94-011-7568-5

[24]. El-Sherif, A. A. J. Solution Chem. 2006, 35, 1287-1301.
http://dx.doi.org/10.1007/s10953-006-9062-9

[25]. Mohamed, M. M. A.; El-Sherif, A. A. J. Solution Chem. 2010, 39, 639-653.
http://dx.doi.org/10.1007/s10953-010-9535-8

[26]. El-Sherif, A. A.; Shoukry, M. M. J. Coord. Chem. 2005, 58(16), 1401-1415.
http://dx.doi.org/10.1080/00958970500055435

[27]. El-Sherif, A. A.; Shoukry, M. M. J. Spectrochim. Acta A 2007, 66, 691-700.
http://dx.doi.org/10.1016/j.saa.2006.04.013
PMid:16956788

[28]. El-Sherif, A. A.; Shoukry, M. M. Inorg. Chim. Acta 2007, 360, 473-487.
http://dx.doi.org/10.1016/j.ica.2006.07.108

[29]. El-Sherif, A. A. J. Solution Chem. 2010, 39, 1562-1581.
http://dx.doi.org/10.1007/s10953-010-9593-y

[30]. El-Sherif, A. A. Inorg. Chim. Acta 2009, 362, 4991-5000.
http://dx.doi.org/10.1016/j.ica.2009.08.004

[31]. Frish, M. J.; Trucks, G. W.; Schlegel, H. B.; Scuseria, G. E.; Robb, M. A.; Cheeseman, J. R.; Zakrzewski, V. G.; Gaussian, Inc., Pittsburgh, PA, 2008.

[32]. Zhang, Q.; Li, Z.; Chen, B. J. Mol. Struct. (Theochem.) 2009, 901, 202-210.
http://dx.doi.org/10.1016/j.theochem.2009.01.030

[33]. Zhang, Q.; Chen, B. J. Mol. Struct. (Theochem.) 2010, 941, 41-46.
http://dx.doi.org/10.1016/j.theochem.2009.10.036

[34]. Smith, D. M.; Nicolaides, A.; Golding, B. T.; Radom, L. J. Am. Chem. Soc. 1998, 120, 10223-10233.
http://dx.doi.org/10.1021/ja980635m

[35]. Dunning, T. H.; Hay, P. J. Modern Theoretical Chemistry, Ed. H. F. Schaefer III, 1976, Vol. 3 (Plenum, New York) 1-28.

[36]. Hay, P. J.; Wadt, W. R. J. Chem. Phys. 1985, 82, 270-283.

[37]. Hay, P. J.; Wadt, W. R. J. Chem. Phys. 1985, 82, 299-310.

[38]. Ulic, S. E.; Vedova, C. O. D.; Hermann, A.; Mack, H. G.; Oberhammer, H. J. Phys. Chem. A 2008, 112, 6211-6216.
http://dx.doi.org/10.1021/jp800344m
PMid:18547036

[39]. Bauer, A. W.; Kirby, W. M.; Sherris, C.; Turck, M. J. Am. Clin. Pathol. 1966, 45, 493-496.

[40]. Pfaller, M. A.; Burmeister, L.; Bartlett, M. A.; Rinaldi, M. G. J. Clin. Microbiol. 1988, 26 1437-1441.

[41]. National Committee for Clinical Laboratory Standards (1993), Methods for dilution antimicrobial susceptibility tests for bacteria that grow aerobically. Approved standard M7-A3, Villanova, Pa.

[42]. L. D. Liebowitz, H. R. Ashbee, E. G. V. Evans, Y. Chong, N. Mallatova, M. Zaidi, D. Gibbs, Microbiol. Infet. Dis. 2001, 24, 27-33.
http://dx.doi.org/10.1016/S0732-8893(01)00243-7

[43]. National Committee for Clinical Laboratory Standards, Methods for dilution antimicrobial susceptibility tests for bacteria that grow aerobically. Approved standard M7-A3, Villanova, Pa (1993).

[44]. Matar, M. J., Ostrosky-Zeichner, L., Paetznick, V. L., Rodriguez, J. R., Chen, E., Rex, J. H. Antimicrob. Agents Chemother. 2003, 47, 1647-1651.
http://dx.doi.org/10.1128/AAC.47.5.1647-1651.2003
PMid:12709335 PMCid:PMC153338

[45]. Skehan, P.; Storeng, R.; Scudiero, D.; Monks, A.; McMahon, J.; Vistica, D.; Warren, J. T.; Bokesch, H.; Kenney, S.; Boyd, M. R. J. Nat. Cancer Inst. 1990, 82, 1107-1112.
http://dx.doi.org/10.1093/jnci/82.13.1107

[46]. Gündüz, T.; Kılıc, E.; Koseoglu, F.; Canel, E. Anal. Chim. Acta 1993, 282, 489-495.
http://dx.doi.org/10.1016/0003-2670(93)80112-X

[47]. Van Uitert, G. L.; Hass, C. G. J. Am. Chem. Soc. 1971, 75, 451-455.
http://dx.doi.org/10.1021/ja01098a057

[48]. Serjant, E. P.; Potentiometry and Potentiometric Titrations, Wiley, New York, 1984.

[49]. Gans, P.; Sabatini, A.; Vacca, A. Inorg. Chim. Acta 1976, 18, 237-239.
http://dx.doi.org/10.1016/S0020-1693(00)95610-X

[50]. Zaki, Z. M.; Haggag, S. S.; Soayed, A. A. Spectroscopy Lett. 1983, 31(4), 757-766.
http://dx.doi.org/10.1080/00387019808007397

[51]. Bellamy, L. J.; The Infrared Spectra of Complex Molecules, second ed., J. Wiley, New York, 1964.

[52]. Sarkar, S.; Dey, K. Spectrochim. Acta A 2005, 62, 383-393.
http://dx.doi.org/10.1016/j.saa.2005.01.005
PMid:16257739

[53]. West, X.; Nassar, A. A. Trans. Metal Chem. 1998, 23, 321-326.
http://dx.doi.org/10.1023/A:1006957325074

[54]. Bagihalli, G. B.; Avaji, P. G.; Patil, S. A.; Badami, P. S. Eur. J. Med. Chem. 2008, 43, 2639-2649.
http://dx.doi.org/10.1016/j.ejmech.2008.02.013
PMid:18395942

[55]. Gronowitz, S.; Katritsky, A. R.; Reavill, R. E. J. Am. Chem. Soc. 1964, 86, 3881-3882.
http://dx.doi.org/10.1021/ja01072a062

[56]. Prashanthi, Y.; Kiranmai, K.; Subhashini, N. J. P. Spectrochim. Acta A 2008, 70, 30-35.
http://dx.doi.org/10.1016/j.saa.2007.07.028
PMid:17913572

[57]. Nakamoto, K. Infrared and Raman Spectra of Inorganic and Coordination Compounds, 5th ed., Part II: Applications in Coordination, Organometallic and Bioinorganic Chemistry, Wiley, New York, 1997.

[58]. Percy, C. G.; Thornton, D. A. J. Inorg. Nucl. Chem. 1973, 35, 2719-2725.
http://dx.doi.org/10.1016/0022-1902(73)80502-0

[59]. Hulett, L. G.; Thornton, D. A. Spectrochim. Acta A 1971, 27, 2089-2096.
http://dx.doi.org/10.1016/0584-8539(71)80106-X

[60]. Earnshaw, A. The Introduction to Magnetochemistry, Academic Press, London, 1980, p. 80.

[61]. Abrahim, J.; Narayana, B.; Mahadevi, S.; Ramachandra, B. Turk. J. Chem. 1994, 18, 14-19.

[62]. Lever, A. B. P. Crystal Field Spectra. Inorganic Electronic Spectroscopy first ed., Elsevier, Amsterdam, 1968.

[63]. Sanmartin, J.; Bermejo, M. R.; Deibe, A. M. G.; Maneiro, M.; Lage, C.; Filho, A. J. C. Polyhedron 2000, 19, 185-192.
http://dx.doi.org/10.1016/S0277-5387(99)00341-1

[64]. Krzyminiewska, V. P.; Litkowska, H.; Paryzek, W. R. Monatsh Chem. 1999, 130, 243-249.

[65]. Melnik, M.; Gyoryova, K.; Skorsepa, J.; Holloway, C. E. J. Coord. Chem. 1995, 35, 179-185.
http://dx.doi.org/10.1080/00958979508024038

[66]. Hathaway, B. J.; Tomlinson, A. A. G. Coord. Chem. Rev. 1970, 5, 1-44.
http://dx.doi.org/10.1016/S0010-8545(00)80073-9

[67]. Kivelson, D.; Neiman, R. R. J. Chem. Phys. 1961, 35, 149-151.

[68]. Singh, V. Spectrochim. Acta A 2008, 71, 17-23.
http://dx.doi.org/10.1016/j.saa.2007.11.004
PMid:18155639

[69]. El-Sherif, A. A.; Jeragh, B. J. A. Spectrochim. Acta A 2007, 68, 877-882.
http://dx.doi.org/10.1016/j.saa.2006.12.073
PMid:17320475

[70]. Rao, S. Asian J. Chem. 2005, 17, 2663-2668.

[71]. Nseimi, H.; Safari, J.; Heidarnezhad, A. Dyes Pigments 2007, 73, 251-260.
http://dx.doi.org/10.1016/j.dyepig.2005.12.009

[72]. Martin, D.; Hauthal, H. G.; Dimethyl Sulphoxide, Van Nostrand Reinhold, Workingham, UK, 1975.

[73]. Hermandez-Molina, R.; Mederos, A.; Gili, P.; Dominquez, S.; Numez, P.; Grmain, G.; Debaerdemaeker, T. Inorg. Chim. Acta 1997, 256, 319-325.
http://dx.doi.org/10.1016/S0020-1693(96)05440-0

[74]. Irving, H.; Williams, R. J. P. Nature, 1948, 162, 746-747.
http://dx.doi.org/10.1038/162746a0

[75]. Irving, H.; Williams, R. J. P. J. Chem. Soc. 1953, 8, 3192-3210.

[76]. Cotton, F. A.; Wilkinson. G. Adv. Inorg. Chem. Wiley, London (1962).

[77]. Cakir, S.; Bicer, E.; Odabasoglu, M.; Albayrak, C. J. Braz. Chem. Soc. 2005, 4, 711-717.
http://dx.doi.org/10.1590/S0103-50532005000500005

[78]. Sari, N.; Arslan, S.; Logoglu, E.; Sakiyan, I. J. Sci. 2003, 16, 283-288.

[79]. Jayabalakrishnan, C.; Natarajan, K. Trans. Metal Chem. 2002, 27(1), 75-79.
http://dx.doi.org/10.1023/A:1013437203247

[80]. Carcelli, M.; Mazza, P.; Pelizzi, C.; Pelizzi, G.; Zani, F. J. Inorg. Biochem. 1995, 57, 43-62.
http://dx.doi.org/10.1016/0162-0134(94)00004-T

[81]. Koch, A. L. J. Clin. Microbiol. Rev. 2003, 16, 673-681.
http://dx.doi.org/10.1128/CMR.16.4.673-687.2003
PMid:14557293 PMCid:PMC207114

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 © 2024 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).