Synthesis, structure, electrochemistry, and spectral characterization of bis-isatin thiocarbohydrazone metal complexes and their antitumor activity against ehrlich ascites carcinoma in Swiss Albino mice

M.P. Sathisha, V.K. Revankar, K.S.R. Pai

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Abstract

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.
Original languageEnglish
JournalMetal-Based Drugs
Volume2008
DOIs
Publication statusPublished - 2008

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Isatin
Electrochemistry
Coordination Complexes
Ascites
Ligands
Carcinoma
Copper
Hydrazones
Atoms
Deprotonation
Cobalt
Magnetic moments
Fungi
Sulfur
Organic solvents
Metal ions
Paramagnetic resonance
Protons
Screening
Nitrogen

Cite this

@article{e5409ddd051c4a1dac4b4f73592b2791,
title = "Synthesis, structure, electrochemistry, and spectral characterization of bis-isatin thiocarbohydrazone metal complexes and their antitumor activity against ehrlich ascites carcinoma in Swiss Albino mice",
abstract = "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 {\circledC} 2008 M. P. Sathisha et al.",
author = "M.P. Sathisha and V.K. Revankar and K.S.R. Pai",
note = "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? (1982) Australian Journal of Chemistry, 35 (6), pp. 1145-1155; Campbell, M.J.M., Transition metal complexes of thiosemicarbazide and thiosemicarbazones (1975) Coordination Chemistry Reviews, 15 (2-3), pp. 279-319; Padhy{\'e}, S.B., Kauffman, G.B., Transition metal complexes of semicarbazones and thiosemicarbazones (1985) Coordination Chemistry Reviews, 63, pp. 127-160; Emara, A.A.A., Khalil, S.M.E., Salib, K.A.R., Di-, tri- and poly-nuclear transition metal complexes of 3,4-diacetyl-2,5-hexanedione (1995) Journal of Coordination Chemistry, 36 (4), pp. 289-301; Cheng, H., Chun-Ying, D., Chen-Jie, F., Yong-Jiang, L., Qing-Jin, M., Self-assembled macrocyclic tetranuclear molecular square (2000) Journal of the Chemical Society, Dalton Transactions, (7), pp. 1207-1212. , diiancy@njit.edii.cn [Ni(HL)]44+ and molecular rectangle [Cu2Cl2L]2 {H2L = bis[phenyl(2-pyridyl)methanone] thiocarbazone}; Rosenberg, B., Some biological effects of platinum compounds: New agents for the control of tumours (1971) Platinum Metals Review, 15 (2), pp. 42-51; Williams, D.R., Metals, ligands, and cancer (1972) Chemical Reviews, 72 (3), pp. 203-213; Patil, B.G., Havinale, B.R., Shallom, J.M., Chitnis, M.P., Syntheses and spectroscopic studies of potential antitumor copper(II) complexes with 5-phenylazo-3-methoxy salicylidene thiosemicarbazone and (1989) Journal of Inorganic Biochemistry, 36 (2), pp. 107-113. , N4 substituted thiosemicarbazones; Klayman, D.L., Scovill, J.P., Bartosevich, J.F., Bruce, J., 2-Acetylpyridine thiosemicarbazones. 5. 1-[1-(2-Pyridyl)ethyl]-3- thiosemicarbazides as potential antimalarial agents (1983) Journal of Medicinal Chemistry, 26 (1), pp. 35-39; Elsome, A.M., Hamilton-Miller, J.M.T., Brumfitt, W., Noble, W.C., Antimicrobial activities in vitro and in vivo of transition element complexes containing gold(I) and osmium(VI) (1996) Journal of Antimicrobial Chemotherapy, 37 (5), pp. 911-918; Scozzafava, A., Menabuoni, L., Mincione, F., Mincione, G., Supuran, C.T., Carbonic anhydrase inhibitors: Synthesis of sulfonamides incorporating dtpa tails and of their zinc complexes with powerful topical antiglaucoma properties (2001) Bioorganic and Medicinal Chemistry Letters, 11 (4), pp. 575-582. , cts@bio.chim.unifi.it; Walsh, C., Enabling the chemistry of life (2001) Nature, 409 (6817), pp. 226-231; Kirschner, S., Wei, Y.-K., Francis, D., Bergman, J., Anticancer and potential antiviral activity of complex inorganic compounds (1966) Journal of Medicinal Chemistry, 9 (3), pp. 369-372; Beerheide, W., Sim, M.M., Tan, Y.-J., Bernard, H.-U., Ting, A.E., Inactivation of the human papillomavirus-16 e6 oncoprotein by organic disulfides (2000) Bioorganic and Medicinal Chemistry, 8 (11), pp. 2549-2560. , w.beerheide@DKFZ-Heidelberg.de mcbaet@imcb.nus.edu.sg; Chohan, Z.H., Scozzafava, A., Supuran, C.T., Unsymmetrical 1,1′-disubstituted ferrocenes: Synthesis of Co(ii), Cu(ii), Ni(ii) and Zn(ii) chelates of ferrocenyl -1-thiadiazolo-1′- tetrazole, -1-thiadiazolo-1′-triazole and -1-tetrazolo-1′-triazole with antimicrobial properties (2002) Journal of Enzyme Inhibition and Medicinal Chemistry, 17 (4), pp. 261-266; Ul-Hassan, M., Chohan, Z.H., Scozzafava, A., Supuran, C.T., Carbonic anhydrase inhibitors: Schiff's bases of aromatic and heterocyclic sulfonamides and their metal complexes (2004) Journal of Enzyme Inhibition and Medicinal Chemistry, 19 (3), pp. 263-267. , claudiu.supuran@unifi.it; Ul-Hassan, M., Chohan, Z.H., Supuran, C.T., Antibacterial Zn(II) compounds of Schiff bases derived from some benzothiazoles (2002) Main Group Metal Chemistry, 25 (5), pp. 291-296; Chohan, Z.H., Scozzafava, A., Supuran, C.T., Zinc complexes of benzothiazole-derived Schiff bases with antibacterial activity (2003) Journal of Enzyme Inhibition and Medicinal Chemistry, 18 (3), pp. 259-263. , claudiu.supuran@unifi.it; Maggio, F., Pellerito, A., Pellerito, L., Grimaudo, S., Mansueto, C., Vitturi, R., Organometallic complexes with biological molecules II. 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. I. the preparation and properties of thiocarbohydrazide (1954) Journal of Organic Chemistry, 19 (5), pp. 733-741; Mayer, B.N., Ferrigni, N.R., Putnam, J.E., Jacobsen, L.B., Nichols, D.E., McLaughlin, J.L., Brine shrimp: A convenient general bioassay for active plants constituents (1982) Planta Medica, 45, pp. 31-34; Ghosh, M.N., (1984) Fundamentals of Experimental Pharmacology, , 2ndScientific Book Agency Calcutta, India; Devi, P.U., Solomon, F.E., Sharada, A.C., In vivo tumor inhibitory and radiosensitizing effects of an Indian medicinal plant, Plumbago rosea on experimental mouse tumors (1994) Indian Journal of Experimental Biology, 32 (8), pp. 523-528; Devi, P.U., Rao, B.S.S., Solomon, F.E., Effect of plumbagin on the radiation induced cytogenetic and cell cycle changes in mouse Ehrlich ascites carcinoma in vivo (1998) Indian Journal of Experimental Biology, 36 (9), pp. 891-895; Eckhardt, A.E., Malone, B.N., Goldstein, I.J., Inhibition of Ehrlich ascites tumor cell growth by Griffonia simplicifolia I lectin in vivo (1982) Cancer Research, 42 (8), pp. 2977-2979; D'Amour, F.E., Blood, F.R., Belden Jr., D.A., (1965) Manual for Laboratory Work in Mammalian Physiology, , 3rdThe University of Chicago Press Chicago, Tex, USA; Seeley, H.W., Van Demark, P.J., (1975) Microbs in Action: A Laboratory Manual of Microbiology, , 2ndD. B. Taraporevala Sons & Co. Pvt. 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",
year = "2008",
doi = "10.1155/2008/362105",
language = "English",
volume = "2008",
journal = "Metal-Based Drugs",
issn = "0793-0291",
publisher = "Hindawi Publishing Corporation",

}

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? (1982) Australian Journal of Chemistry, 35 (6), pp. 1145-1155; Campbell, M.J.M., Transition metal complexes of thiosemicarbazide and thiosemicarbazones (1975) Coordination Chemistry Reviews, 15 (2-3), pp. 279-319; Padhyé, S.B., Kauffman, G.B., Transition metal complexes of semicarbazones and thiosemicarbazones (1985) Coordination Chemistry Reviews, 63, pp. 127-160; Emara, A.A.A., Khalil, S.M.E., Salib, K.A.R., Di-, tri- and poly-nuclear transition metal complexes of 3,4-diacetyl-2,5-hexanedione (1995) Journal of Coordination Chemistry, 36 (4), pp. 289-301; Cheng, H., Chun-Ying, D., Chen-Jie, F., Yong-Jiang, L., Qing-Jin, M., Self-assembled macrocyclic tetranuclear molecular square (2000) Journal of the Chemical Society, Dalton Transactions, (7), pp. 1207-1212. , diiancy@njit.edii.cn [Ni(HL)]44+ and molecular rectangle [Cu2Cl2L]2 {H2L = bis[phenyl(2-pyridyl)methanone] thiocarbazone}; Rosenberg, B., Some biological effects of platinum compounds: New agents for the control of tumours (1971) Platinum Metals Review, 15 (2), pp. 42-51; Williams, D.R., Metals, ligands, and cancer (1972) Chemical Reviews, 72 (3), pp. 203-213; Patil, B.G., Havinale, B.R., Shallom, J.M., Chitnis, M.P., Syntheses and spectroscopic studies of potential antitumor copper(II) complexes with 5-phenylazo-3-methoxy salicylidene thiosemicarbazone and (1989) Journal of Inorganic Biochemistry, 36 (2), pp. 107-113. , N4 substituted thiosemicarbazones; Klayman, D.L., Scovill, J.P., Bartosevich, J.F., Bruce, J., 2-Acetylpyridine thiosemicarbazones. 5. 1-[1-(2-Pyridyl)ethyl]-3- thiosemicarbazides as potential antimalarial agents (1983) Journal of Medicinal Chemistry, 26 (1), pp. 35-39; Elsome, A.M., Hamilton-Miller, J.M.T., Brumfitt, W., Noble, W.C., Antimicrobial activities in vitro and in vivo of transition element complexes containing gold(I) and osmium(VI) (1996) Journal of Antimicrobial Chemotherapy, 37 (5), pp. 911-918; Scozzafava, A., Menabuoni, L., Mincione, F., Mincione, G., Supuran, C.T., Carbonic anhydrase inhibitors: Synthesis of sulfonamides incorporating dtpa tails and of their zinc complexes with powerful topical antiglaucoma properties (2001) Bioorganic and Medicinal Chemistry Letters, 11 (4), pp. 575-582. , cts@bio.chim.unifi.it; Walsh, C., Enabling the chemistry of life (2001) Nature, 409 (6817), pp. 226-231; Kirschner, S., Wei, Y.-K., Francis, D., Bergman, J., Anticancer and potential antiviral activity of complex inorganic compounds (1966) Journal of Medicinal Chemistry, 9 (3), pp. 369-372; Beerheide, W., Sim, M.M., Tan, Y.-J., Bernard, H.-U., Ting, A.E., Inactivation of the human papillomavirus-16 e6 oncoprotein by organic disulfides (2000) Bioorganic and Medicinal Chemistry, 8 (11), pp. 2549-2560. , w.beerheide@DKFZ-Heidelberg.de mcbaet@imcb.nus.edu.sg; Chohan, Z.H., Scozzafava, A., Supuran, C.T., Unsymmetrical 1,1′-disubstituted ferrocenes: Synthesis of Co(ii), Cu(ii), Ni(ii) and Zn(ii) chelates of ferrocenyl -1-thiadiazolo-1′- tetrazole, -1-thiadiazolo-1′-triazole and -1-tetrazolo-1′-triazole with antimicrobial properties (2002) Journal of Enzyme Inhibition and Medicinal Chemistry, 17 (4), pp. 261-266; Ul-Hassan, M., Chohan, Z.H., Scozzafava, A., Supuran, C.T., Carbonic anhydrase inhibitors: Schiff's bases of aromatic and heterocyclic sulfonamides and their metal complexes (2004) Journal of Enzyme Inhibition and Medicinal Chemistry, 19 (3), pp. 263-267. , claudiu.supuran@unifi.it; Ul-Hassan, M., Chohan, Z.H., Supuran, C.T., Antibacterial Zn(II) compounds of Schiff bases derived from some benzothiazoles (2002) Main Group Metal Chemistry, 25 (5), pp. 291-296; Chohan, Z.H., Scozzafava, A., Supuran, C.T., Zinc complexes of benzothiazole-derived Schiff bases with antibacterial activity (2003) Journal of Enzyme Inhibition and Medicinal Chemistry, 18 (3), pp. 259-263. , claudiu.supuran@unifi.it; Maggio, F., Pellerito, A., Pellerito, L., Grimaudo, S., Mansueto, C., Vitturi, R., Organometallic complexes with biological molecules II. 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. I. the preparation and properties of thiocarbohydrazide (1954) Journal of Organic Chemistry, 19 (5), pp. 733-741; Mayer, B.N., Ferrigni, N.R., Putnam, J.E., Jacobsen, L.B., Nichols, D.E., McLaughlin, J.L., Brine shrimp: A convenient general bioassay for active plants constituents (1982) Planta Medica, 45, pp. 31-34; Ghosh, M.N., (1984) Fundamentals of Experimental Pharmacology, , 2ndScientific Book Agency Calcutta, India; Devi, P.U., Solomon, F.E., Sharada, A.C., In vivo tumor inhibitory and radiosensitizing effects of an Indian medicinal plant, Plumbago rosea on experimental mouse tumors (1994) Indian Journal of Experimental Biology, 32 (8), pp. 523-528; Devi, P.U., Rao, B.S.S., Solomon, F.E., Effect of plumbagin on the radiation induced cytogenetic and cell cycle changes in mouse Ehrlich ascites carcinoma in vivo (1998) Indian Journal of Experimental Biology, 36 (9), pp. 891-895; Eckhardt, A.E., Malone, B.N., Goldstein, I.J., Inhibition of Ehrlich ascites tumor cell growth by Griffonia simplicifolia I lectin in vivo (1982) Cancer Research, 42 (8), pp. 2977-2979; D'Amour, F.E., Blood, F.R., Belden Jr., D.A., (1965) Manual for Laboratory Work in Mammalian Physiology, , 3rdThe University of Chicago Press Chicago, Tex, USA; Seeley, H.W., Van Demark, P.J., (1975) Microbs in Action: A Laboratory Manual of Microbiology, , 2ndD. B. Taraporevala Sons & Co. Pvt. 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

VL - 2008

JO - Metal-Based Drugs

JF - Metal-Based Drugs

SN - 0793-0291

ER -