Synthesis, characterization and biological studies of S-4-methylbenzyl-β-N-(2-furylmethylene)dithiocarbazate (S4MFuH) its Zn2+, Cu2+, Cd2+ and Ni2+ complexes
S-4-methylbenzyl-β-N-(2-furylmethylene)dithiocarbazate (S4MFuH, 1) derived from the condensation reaction of furaldehyde (Fu) with S-4-methylbenzyldithiocarbazate (S4MBDTC) has been complexed with transition metal acetates to give Zn(S4MFu)2 (2), Cd(S4MFu)2 (3), Cu(S4MFu)2 (4) and Ni(S4MFu)2 (5). It...
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Elsevier
2015
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| author | Yusof, E.N.M. Ravoof, T.B.S.A. Jamsari, J. Tiekink, E.R.T. Veerakumarasivam, A. Crouse, K.A. Tahir, M.I.M. Ahmad, Haslina |
| author_facet | Yusof, E.N.M. Ravoof, T.B.S.A. Jamsari, J. Tiekink, E.R.T. Veerakumarasivam, A. Crouse, K.A. Tahir, M.I.M. Ahmad, Haslina |
| author_sort | Yusof, E.N.M. |
| collection | UM |
| description | S-4-methylbenzyl-β-N-(2-furylmethylene)dithiocarbazate (S4MFuH, 1) derived from the condensation reaction of furaldehyde (Fu) with S-4-methylbenzyldithiocarbazate (S4MBDTC) has been complexed with transition metal acetates to give Zn(S4MFu)2 (2), Cd(S4MFu)2 (3), Cu(S4MFu)2 (4) and Ni(S4MFu)2 (5). It is evident from the shift in ν(C=N) and ν(N-N) in the IR spectra of the complexes that deprotonated 1 acts as a bidentate ligand coordinating through the azomethine nitrogen and thiolato sulfur atoms. This was confirmed by single crystal X-ray diffractometry. The U-shaped dithiocarbazate 1 exists in the E configuration with the thione bond anti to the azo bond. A change in conformation is noted in the transition metal complexes resulting from deprotonation and N-S-chelation. 2 and 3 display a distorted tetrahedral geometry with the major cause of the distortion being two close intramolecular M...O interactions. Binding interaction studies with calf thymus DNA demonstrated that 4 also had the strongest DNA binding affinity (Kb = 2.85 × 104 M-1) among all compounds prepared in this work. The Cu(II) complex, 4, was also moderately active against estrogen receptor-positive breast cancer cells, MCF-7 (IC50 = 3.02 μM) while the remainder were inactive against MCF-7 and all showed no activity towards receptor negative breast cancer cells, MDA-MB-231. |
| first_indexed | 2024-03-06T05:47:58Z |
| format | Article |
| id | um.eprints-19331 |
| institution | Universiti Malaya |
| last_indexed | 2024-03-06T05:47:58Z |
| publishDate | 2015 |
| publisher | Elsevier |
| record_format | dspace |
| spelling | um.eprints-193312018-10-11T02:55:18Z http://eprints.um.edu.my/19331/ Synthesis, characterization and biological studies of S-4-methylbenzyl-β-N-(2-furylmethylene)dithiocarbazate (S4MFuH) its Zn2+, Cu2+, Cd2+ and Ni2+ complexes Yusof, E.N.M. Ravoof, T.B.S.A. Jamsari, J. Tiekink, E.R.T. Veerakumarasivam, A. Crouse, K.A. Tahir, M.I.M. Ahmad, Haslina Q Science (General) QD Chemistry S-4-methylbenzyl-β-N-(2-furylmethylene)dithiocarbazate (S4MFuH, 1) derived from the condensation reaction of furaldehyde (Fu) with S-4-methylbenzyldithiocarbazate (S4MBDTC) has been complexed with transition metal acetates to give Zn(S4MFu)2 (2), Cd(S4MFu)2 (3), Cu(S4MFu)2 (4) and Ni(S4MFu)2 (5). It is evident from the shift in ν(C=N) and ν(N-N) in the IR spectra of the complexes that deprotonated 1 acts as a bidentate ligand coordinating through the azomethine nitrogen and thiolato sulfur atoms. This was confirmed by single crystal X-ray diffractometry. The U-shaped dithiocarbazate 1 exists in the E configuration with the thione bond anti to the azo bond. A change in conformation is noted in the transition metal complexes resulting from deprotonation and N-S-chelation. 2 and 3 display a distorted tetrahedral geometry with the major cause of the distortion being two close intramolecular M...O interactions. Binding interaction studies with calf thymus DNA demonstrated that 4 also had the strongest DNA binding affinity (Kb = 2.85 × 104 M-1) among all compounds prepared in this work. The Cu(II) complex, 4, was also moderately active against estrogen receptor-positive breast cancer cells, MCF-7 (IC50 = 3.02 μM) while the remainder were inactive against MCF-7 and all showed no activity towards receptor negative breast cancer cells, MDA-MB-231. Elsevier 2015 Article PeerReviewed Yusof, E.N.M. and Ravoof, T.B.S.A. and Jamsari, J. and Tiekink, E.R.T. and Veerakumarasivam, A. and Crouse, K.A. and Tahir, M.I.M. and Ahmad, Haslina (2015) Synthesis, characterization and biological studies of S-4-methylbenzyl-β-N-(2-furylmethylene)dithiocarbazate (S4MFuH) its Zn2+, Cu2+, Cd2+ and Ni2+ complexes. Inorganica Chimica Acta, 438. pp. 85-93. ISSN 0020-1693, DOI https://doi.org/10.1016/j.ica.2015.08.029 <https://doi.org/10.1016/j.ica.2015.08.029>. http://dx.doi.org/10.1016/j.ica.2015.08.029 doi:10.1016/j.ica.2015.08.029 |
| spellingShingle | Q Science (General) QD Chemistry Yusof, E.N.M. Ravoof, T.B.S.A. Jamsari, J. Tiekink, E.R.T. Veerakumarasivam, A. Crouse, K.A. Tahir, M.I.M. Ahmad, Haslina Synthesis, characterization and biological studies of S-4-methylbenzyl-β-N-(2-furylmethylene)dithiocarbazate (S4MFuH) its Zn2+, Cu2+, Cd2+ and Ni2+ complexes |
| title | Synthesis, characterization and biological studies of S-4-methylbenzyl-β-N-(2-furylmethylene)dithiocarbazate (S4MFuH) its Zn2+, Cu2+, Cd2+ and Ni2+ complexes |
| title_full | Synthesis, characterization and biological studies of S-4-methylbenzyl-β-N-(2-furylmethylene)dithiocarbazate (S4MFuH) its Zn2+, Cu2+, Cd2+ and Ni2+ complexes |
| title_fullStr | Synthesis, characterization and biological studies of S-4-methylbenzyl-β-N-(2-furylmethylene)dithiocarbazate (S4MFuH) its Zn2+, Cu2+, Cd2+ and Ni2+ complexes |
| title_full_unstemmed | Synthesis, characterization and biological studies of S-4-methylbenzyl-β-N-(2-furylmethylene)dithiocarbazate (S4MFuH) its Zn2+, Cu2+, Cd2+ and Ni2+ complexes |
| title_short | Synthesis, characterization and biological studies of S-4-methylbenzyl-β-N-(2-furylmethylene)dithiocarbazate (S4MFuH) its Zn2+, Cu2+, Cd2+ and Ni2+ complexes |
| title_sort | synthesis characterization and biological studies of s 4 methylbenzyl β n 2 furylmethylene dithiocarbazate s4mfuh its zn2 cu2 cd2 and ni2 complexes |
| topic | Q Science (General) QD Chemistry |
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