1 1
Sohag University Faculty of Science " Physicochemical and Biological Studies: Embryos Toxicity, DNA Interaction and In Vitro Antimicrobial activity of Some New Iron(II) Schiff base Amino Acid Complexes." Presented By 2 Ahmed Mohammed Abu-Dief
Under Supervision Prof. Dr . Laila Hamdan Abd El-Rhman Prof. of Inorganic Chemistry, Faculty of Science, Sohag University Dr. Dr. Lobna A. Ebaid Nassr Rafat M. El- Khatib Assistant Prof. of physical chemistry, Assistant Prof. of Inorganic Chemistry, Faculty of Science, Faculty of Science, Sohag University Sohag University 3
• Introduction. • Highlights of the work. • Over view of results 4
5
• Schiff Bases are characterized by the >C=N (imine) group which imports in elucidating the mechanism of transamination reaction in biological system • Schiff bases derived from primary amines and substituted benzaldehydes exhibit antibacterial, anticancer, and antitumor activity. Numerous studies have shown that such an activity of Schiff bases is caused by the presence of the >C=N [1] • Schiff bases have catalytic activity in hydrogenation of olefins and complexing ability towards some toxic metals [2] [1] Sandermann, W., Naturharze Terpentinol-TalloChemie und Technologie, Berlin: Springer, 1960,303-310 [ 2]Gehad G. MOHAMED, Mohamed M. OMAR, Ahmed M. HINDY, Turk J Chem,30 (2006) , 361 6 – 38
• The high affinity for the chelation of the Schiff bases towards the transition metal ions is utilized in preparing their solid complexes • Metal complexes play an essential role in agriculture, pharmaceutical and industrial chemistry. • Schiff base metal complexes have been widely studied because they have industrial, antifungal [3] , antibacterial [4] , anticancer [5] and herbicidal applications [6] [3]- Daniel, V. P.; Murukan, B.; Kumari, B. S.; Mohanan, K. Spectrochim Acta Part A 2008, 70, 403. [4]-Prashanthi, Y.; Kiranmai, K.; Subhashini, N. J. P.; Shivaraj, S. Spectrochim Acta Part A 2008, 70, 30. [5]- Galal, S. A.; Hegab, K. H.; Kassab, A. S.; Rodriguez, M. L.; Kerwin, S. M.; El-Khamry, A.-M. A.; El Diwani, H. I. Eur J Med Chem 2009, 44(4), 1500. [6]-Cozzi, P.G., Chem. Soc. Rev. 2004, 33, 410-42 7
Schiff base complexes have extensive importance as radiotracers in nuclear medicine [7] Monamine oxidase enzyme B [7]Du Preez, J. G. H.; Gerber, T. I. A.; Fourie, P. J.; Van Wyk, A. J., J. Coord. Chem., 1984, 13, 173 8
Aromatic Schiff bases and their metal complexes are used as catalysts for: Oxidation [8]. Epoxidation [9]. Polymerization [10]. Decomposition and hydrolysis reactions [11]. Synthetic Iron (II) Schiff base complexes exhibit catalytic activity to electro-reduction of oxygen [12]. [8]Sheldon, R. A.; Kochi, J. K., Metal Catalyzed Oxidations of Organic Compounds; Academic Press: New York, 1981 [9] Dede, B.; Karipcin, F.; Cengiz, M. J. HazardMater 2009, 163(2 – 3), 1148. [10] K.C. Gupta, A.K. Sutar, J. Mol. Catal. A: Chem. 272 (2007) 64. [ 11]Bagherzadeh, M.; Tahsini, L.; Latifi, R.; Amani, V.; Ellern, A.; Woo, L. K., Inorg. Chem. Commun., 2009, 12, 476 [12] Abbo, H. S.; Titinchi, S. J. J.; Prasad, R.; Chand, S., J. Mol. Catal. A: Chem., 2005, 225, 225 9
• Schiff base transition metal complexes are very important chelates because of their cheap, easy synthesis and because of their chemical and thermal stability. • The central metal ion in these complexes acts as an active site and thus effectively catalyzes chemical reactions. • Moreover, these complexes have extensive applications in the fields of medicine, photo, magnetic chemistry, and electrochemistry [13]. [13]Bagherzadeh, M.; Tahsini, L.; Latifi, R.; Amani, V.; Ellern, A.; Woo, L. K., Inorg. Chem. Commun., 2009, 12, 476 10
Biological activity of Schiff base amino acid complexes. • Schiff base complexes of amino acids have gained importance not only from the inorganic point of view but also because of their physiological and pharmacological activities. • They act as good chelating agents [14] and behave as efficient biologically active [15] and cytotoxic agents. In addition, Schiff base amino acids complexes are considered to constitute new kinds of potential antibacterial and anticancer reagents [16] . [14] El-Said, A. I.; Zidan, A. S. A.; El-Meligy, M. S.; Aly, A. A. M.; Mohammed, O. F. Transition Met Chem 2001, 26, 13. [15] Wang, Z.-M.; Lin, H.-K.; Zhu, S.-R.; Liu, T.-F.; Chen, Y.-T. J Inorg Biochem 2002, 89, 97. [16] Wang, M.-Z.; Meng, Z.-X.; Liu, B.-L.; Cai, G.-L.;Zhang, C.-L.; Wang, X.-Y. Inorg Chem Commun 2005, 8(4), 11 368.
• The complexes of Schiff bases synthesized from amino acids and salicylaldehyde derivatives have gained remarkable attention because they are intermediates in many metabolic reactions[ 17] Transamination Decarboxylation Elimination Racemization, and C- C bond cleavage) • Decarboxylation and transamination reactions are important in the biosynthesis of hormones, neurotransmitters, and pigments. • In addition amino acid Schiff base complexes are considered to constitute new kinds of potential antibacterial and anticancer reagents [18] [17]- Nath, M.; Yadov, R. Bull Chem Soc Jpn 1997, 70, 131.[9 [18]Wang, M.-Z.; Meng, Z.-X.; Liu, B.-L.; Cai, G.-L.; Zhang, C.-L.; Wang, X.-Y., Inorg. Chem. Commun., 2005 12
• The condensation between the NH 2 group of the amino acid and the carbonyl group of the aldehyde or ketone is very difficult because of the Zwitterion effect, and the reaction needs special conditions. • It was found that the formation reaction of amino acid Schiff bases is facilitated by the presence of the metal ion due to the formation of two five membered chelate rings, because in such a case the Schiff base is more planar [19] . [19] Nasser M. Hosny and Farid I. El-Dossoki, J. Chem. Eng. Data 2008, 53, 2567 – 2572 13
• Studying the interaction between transition metal complexes and DNA has attracted many interests[41-46] due to their importance in cancer therapy, design of new types of pharmaceutical molecules and molecular biology. On the other hand, few studies were carried out concerning the interaction of DNA with Schiff base amino acid complexes[47]. • It is known that a compound binding to a DNA in vitro can interact with DNA in vivo to a certain extent, and the anticancer activities of a drug agent obtained both in vivo and in vitro are parallel to each other and have to be related to its interaction with DNA. [41]Morrow, J.R., Inorg. Chem., 2000, 39, 2130. [42]Liu, C.; Wang, M.; Zhang, T.; Sun, H., Coord. Chem. Rev., 2004, 248, 147 [43]Wang, X.Y.; Zhang, J.; Li, K.; Jiang, N.; Chen, S.Y.; Lin, H.H.; Huang, Y.; Ma, L.J.; Yu, X.Q., Bioorg. Med. Chem., 2006, 14, 6745. [44]Raman, N.; Fathima, S. S. A.; Raja, J. D., J. Serb. Chem. Soc., 2008, 73(11) [45]Mahalakshmi, N; Rajavel, R., Inter. J. Pharm. Techn., 2010, 2(4), 1133 [46]Zhang, Y.; Wang, X.; Ding, L., Nucleos. Nucleot. Nucl., 2011, 30, 49 14 [47]Erkkila, K. E.; Odom, D.T.; Barton, J. K., Chem. Rev., 1999, 99, 2777
Design and spectroscopic characterization of some Fe(II) base complexes. The teratogenicity of the studied complexes was tested on chick embryos. Investigation of the interaction between the studied complexes and DNA. The antibacterial and antifungal activities have also been performed against different strain of organism. 15
Over view of results 16
The suggested structures for the synthesized complexes HN + AA → H 2 L 2(H 2 L) + Fe 2+ → Fe (HL) 2 +2H + R O R N OH O O H 2 N + OH OH OH HN AA H 2 L R COO R O H H N O N OH Fe 2+ 2 + 2H + Fe + O N OH H H OOC R H 2 L Fe(HL) 2 17
In case of histidine as amino acid H 3 L + Fe 2+ → FeL + 3H + H H N N N N O HO + 2H + O N + Fe 2+ O N Fe O H 2 H 2 O OH O FeHL H L 3 where HN = 2-hydroxy-1-naphthaldehyde, AA = amino acid, H 2 L = Schiff base amino acid ligand, Fe(H 2 L) 2 = nali, nphali, nasi, nari complexes and FeL = nhi complex. 18
Analytical and physical data of Schiff base amino acid ligands and their Fe(II) complexes. Analysis Found Empirical Decom. Yield Molar conductance (Calculated) Comp. Formula temp. Λ m (Ω -1 cm 2 mol -1 ) (%) ( o C) (Formula Weight) C H N nal C 14 H 13 NO 3 69.25 5.17 5.61 83 162 (243.254) (69.12) (5.39) (5.76) nali C 28 H 28 FeN 2 O 8 58.50 4.67 4.88 75 35.12 260 (576.37) (58.34) (4.90) (4.86) nphal C 20 H 17 NO 3 75.35 5.21 4.45 85 170 (319.346) (75.22) (5.37) (4.39) nphali C 40 H 34 FeN 2 O 7 67.85 4.57 3.76 83 28.24 >350 (710.54) (67.61) (4.82) (3.94) nas C 15 H 13 NO 5 62.81 4.63 4.72 73 97 (287.168) (62.73) (4.56) (4.88) nasi C 30 H 26 FeN 2 O 11 56.01 3.92 4.21 72 39.31 185 (646.38) (55.74) (4.05) (4.33) nh C 17 H 15 N 3 O 3 66.13 4.72 13.44 85 156 (309.32) (66.01) (4.89) (13.59) nhi C 17 H 21 FeN 3 O 7 46.83 4.72 9.58 81 47.61 >350 (435.22) (46.91) (4.86) (9.66) nar C 17 H 20 N 4 O 3 62.29 6.05 17.21 86 133 (328.37) (62.18) (6.14) (17.07) 19 nari C 34 H 44 FeN 8 O 9 53.64 5.72 14.43 84 32.21 235 (764.62) (53.40) (5.80) (14.66)
Recommend
More recommend
