Abstract
Original language | English |
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Journal | Metal-Based Drugs |
Volume | 2008 |
DOIs | |
Publication status | Published - 2008 |
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In: Metal-Based Drugs, Vol. 2008, 2008.
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TY - JOUR
T1 - Synthesis, structure, electrochemistry, and spectral characterization of bis-isatin thiocarbohydrazone metal complexes and their antitumor activity against ehrlich ascites carcinoma in Swiss Albino mice
AU - Sathisha, M.P.
AU - Revankar, V.K.
AU - Pai, K.S.R.
N1 - Cited By :21 Export Date: 10 November 2017 CODEN: MBADE Correspondence Address: Revankar, V.K.; P. G. Department of Studies in Chemistry, Karnatak University, Dharwad, 580 003, India; email: vkrevankar@redi.mail.com Chemicals/CAS: cisplatin, 15663-27-1, 26035-31-4, 96081-74-2; cobalt, 7440-48-4; copper, 15158-11-9, 7440-50-8; nickel, 7440-02-0; zinc, 7440-66-6 References: Ali, M.A., Livingstone, S.E., Metal complexes of sulphur-nitrogen chelating agents (1974) Coordination Chemistry Reviews, 13 (2-3), pp. 101-132; Stunzi, H., Can chelationbe important in the antiviral activity of isatin β-thiosemicarbazones? 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Synthesis, solid-state characterization and in vivo cytotoxicity of diorganotin(IV)chloro and triorganotin(IV)chloro derivatives of penicillin G (1994) Applied Organometallic Chemistry, 8 (1), pp. 71-85; Narayanan, V.A., Nasr, M., Paull, K.D., (1990) Tin Based Antitumour Drugs, 37. , NATO ASI Series Springer Berlin, Germany; Chohan, Z.H., Arif, M., Akhtar, M.A., Supuran, C.T., Metal-based antibacterial and antifungal agents: Synthesis, characterization, and in vitro biological evaluation of Co(II), Cu(II), Ni(II), and Zn(II) complexes with amino acid-derived compounds (2006) Bioinorganic Chemistry and Applications, 2006, p. 13. , 83131; Audrieth, L.F., Scott, E.S., Kippur, P.S., Hydrazine derivatives of the carbonic and thiocarbonic acids. 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Bombay, India; Geary, W.J., The use of conductivity measurements in organic solvents for the characterisation of coordination compounds (1971) Coordination Chemistry Reviews, 7 (1), pp. 81-122; Nakomoto, K., (1970) Infrared Spectra of Inorganic and Coordination Compounds, , 2ndWiley-Interscience New York, NY, USA; Bindu, P., Kurup, M.R., Satyakeerty, T.R., Epr, cyclic voltammetric and biological activities of copper(II) complexes of salicylaldehyde N(4)-substituted thiosemicarbazone and heterocyclic bases (1998) Polyhedron, 18 (3-4), pp. 321-331; Alcock, N.W., Tracy, V.M., Waddington, T.C., Acetates and acetato-complexes - Part 2: Spectroscopic studies (1979) Journal of Chemical Society, Dalton Transactions, (21), pp. 2243-2246; Estes, W.E., Wasson, J.R., Hall, J.W., Hatfield, W.E., Characterization of some mixed-halide copper(II) dimers of the general formula [ (1978) Inorganic Chemistry, 17 (12), pp. 3657-3664. , Cu2XnX6-n′]2- (X = Cl- and X′ = Br-): evidence for the preference of chloride bridges in the mixed-halide species; Balakrishnan, K., Aravindakshan, K.K., Metal complexes of 3,4-dimethoxybenzaldehyde thiosemicarbazone (1991) Journal of the Indian Chemical Society, 68 (4), pp. 187-190; Lever, A.B.P., (1984) Inorganic Electronic Spectroscopy, , Elsevier Amsterdam, The Netherlands; Shirin, Z., Mukherj, R.N., Synthesis, spectra and electrochemistry of ruthenium(III) complexes with cage-like Schiff-base ligands (1992) Polyhedron, 11 (20), pp. 2625-2630; Geran, R.I., Greenberg, N.H., MacDonald, M.M., Schumacher, A.M., Abbott, B.J., Protocols for screening chemical agents and natural products against animal tumors and other biological systems (1972) Cancer Chemotherapy Reports, 3, p. 1; Orberlling, C., Guerin, M., The role of virus in the production of cancer (1954) Advances in Cancer Research, 2, pp. 353-423; Vincent, J.M., Distortion of fungal hyphae in the presence of certain inhibitors (1947) Nature, 159, p. 850
PY - 2008
Y1 - 2008
N2 - The synthesis, structure, electrochemistry, and biological studies of Co(II), Ni(II), Cu(II), and Zn(II) complexes of thiocarbohydrazone ligand are described. The ligand is synthesized starting from thiocarbohydrazide and isatin. It is evident from the IR data that in all the complexes, only one part of the ligand is coordinated to the metal ion resulting mononuclear complexes. The ligand coordinates essentially through the carbonyl oxygen of the isatin fragment, the nitrogen atom of the azomethine group, and sulfur atom after deprotonation to give five membered rings. 1H NMR spectrum of the ligand shows only one set of signals for the aromatic protons, while the NH of isatin and NH of hydrazone give rise to two different singlets in the 11-14 ppm range. The formulations, [Cu(L)Cl]·2H2O, [Cu(L)(C H 3COO)]·2H2O, [Ni(L)Cl], [Ni(L)(C H 3COO)], [Co(L2)], and [Zn(L2)]·2H 2O are in accordance with elemental analyses, physical, and spectroscopic measurements. The complexes are soluble in organic solvents. Molar conductance values in DMF indicate the nonelectrolytic nature of the complexes. Copper complex displays quasireversible cyclic voltametric responses with Ep near -0.659 v and 0.504 v Vs Ag/AgCl at the scan rate of 0.1 V/s. Copper(II) complexes show a single line EPR signals. For the observed magnetic moment and electronic spectral data possible explanation has been discussed. From all the available data, the probable structures for the complexes have been proposed. The compounds synthesized in present study have shown promising cytotoxic activity when screened using the in vitro method and at the same time were shown to have good activity when tested using the Ehrlich ascites carcinoma (EAC) model. The antimicrobial screening showed that the cobalt complex possesses enhanced antimicrobial activity towards fungi. Copyright © 2008 M. P. Sathisha et al.
AB - The synthesis, structure, electrochemistry, and biological studies of Co(II), Ni(II), Cu(II), and Zn(II) complexes of thiocarbohydrazone ligand are described. The ligand is synthesized starting from thiocarbohydrazide and isatin. It is evident from the IR data that in all the complexes, only one part of the ligand is coordinated to the metal ion resulting mononuclear complexes. The ligand coordinates essentially through the carbonyl oxygen of the isatin fragment, the nitrogen atom of the azomethine group, and sulfur atom after deprotonation to give five membered rings. 1H NMR spectrum of the ligand shows only one set of signals for the aromatic protons, while the NH of isatin and NH of hydrazone give rise to two different singlets in the 11-14 ppm range. The formulations, [Cu(L)Cl]·2H2O, [Cu(L)(C H 3COO)]·2H2O, [Ni(L)Cl], [Ni(L)(C H 3COO)], [Co(L2)], and [Zn(L2)]·2H 2O are in accordance with elemental analyses, physical, and spectroscopic measurements. The complexes are soluble in organic solvents. Molar conductance values in DMF indicate the nonelectrolytic nature of the complexes. Copper complex displays quasireversible cyclic voltametric responses with Ep near -0.659 v and 0.504 v Vs Ag/AgCl at the scan rate of 0.1 V/s. Copper(II) complexes show a single line EPR signals. For the observed magnetic moment and electronic spectral data possible explanation has been discussed. From all the available data, the probable structures for the complexes have been proposed. The compounds synthesized in present study have shown promising cytotoxic activity when screened using the in vitro method and at the same time were shown to have good activity when tested using the Ehrlich ascites carcinoma (EAC) model. The antimicrobial screening showed that the cobalt complex possesses enhanced antimicrobial activity towards fungi. Copyright © 2008 M. P. Sathisha et al.
U2 - 10.1155/2008/362105
DO - 10.1155/2008/362105
M3 - Article
SN - 0793-0291
VL - 2008
JO - Metal-Based Drugs
JF - Metal-Based Drugs
ER -