Towards a selective cytotoxic agent for prostate cancer: interaction of zinc complexes of polyhydroxybenzaldehyde thiosemicarbazones with topoisomerase I
Four thiosemicarbazones ligands,H3T(1),H3M(2),H3E(3) andH3P(4) have been prepared with good yield by refluxing 2,4-dihydroxybenzaldehyde with N(4)-substituted thiosemicarbazide in ethanol (H3T(1) = 2,4-dihydroxybenzaldehyde thiosemicarbazone;H3M(2) = 2,4-dihydroxybenzaldehyde 4-methylthiosemicarbazo...
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| Language: | en |
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2012
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| Online Access: | http://eprints.um.edu.my/3295/1/Towards_a_selective_cytotoxic_agent_for_prostate_cancer_Interaction_of_zinc.pdf http://eprints.um.edu.my/3295/ http://www.sciencedirect.com/science/article/pii/S0277538712001404 |
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| author | Tan, K.W. Seng, H.L. Lim, F.S. Cheah, S.C. Ng, C.H. Koo, K.S. Mustafa, Mohd Rais Ng, S.W. Maah, M.J. |
| author_facet | Tan, K.W. Seng, H.L. Lim, F.S. Cheah, S.C. Ng, C.H. Koo, K.S. Mustafa, Mohd Rais Ng, S.W. Maah, M.J. |
| author_sort | Tan, K.W. |
| building | UM Library |
| collection | Institutional Repository |
| content_provider | Universiti Malaya |
| content_source | UM Research Repository |
| continent | Asia |
| country | Malaysia |
| description | Four thiosemicarbazones ligands,H3T(1),H3M(2),H3E(3) andH3P(4) have been prepared with good yield by refluxing 2,4-dihydroxybenzaldehyde with N(4)-substituted thiosemicarbazide in ethanol (H3T(1) = 2,4-dihydroxybenzaldehyde thiosemicarbazone;H3M(2) = 2,4-dihydroxybenzaldehyde 4-methylthiosemicarbazone; H3E(3) = 2,4-dihydroxybenzaldehyde 4-ethylthiosemicarbazone and H3P(4) = 2,4-dihydroxybenzaldehyde 4-phenylthiosemicarbazone). Reactions of these ligands with zinc acetates in the presence of 2,20-bipyridine lead to the formation of zinc(II) complexes of formulation Zn(bpy)L(5�8) (bpy = 2,20-bipyridine; L = doubly deprotonated thiosemicarbazones = HT(5); HM(6); HE(7) and HP(8)). These compounds were characterized and their cytotoxicity and topoisomerase I inhibition activities studied. X-ray diffraction study indicates that complex 8 is five coordinated and the coordination geometry around zinc(II) is trigonal bipyramidal distorted square based pyramid (TBDSBP). The doubly deprotonated thiosemicarbazone acts as a tridentate ONS-donor ligand while 2,2-bipyridne as the NN-donor ligand. Complexes 6, 7 and 8 are more cytotoxic towards PC3 (prostate cancer cell line) than RWPE-1 (prostate normal cell line). The cytotoxicity and topoisomerase I inhibition activities seem to be dependent on the N(4) substituent of the thiosemicarbazone moiety. |
| format | Article |
| id | my.um.eprints-3295 |
| institution | Universiti Malaya |
| language | en |
| publishDate | 2012 |
| record_format | eprints |
| spelling | my.um.eprints-32952019-08-21T09:18:22Z http://eprints.um.edu.my/3295/ Towards a selective cytotoxic agent for prostate cancer: interaction of zinc complexes of polyhydroxybenzaldehyde thiosemicarbazones with topoisomerase I Tan, K.W. Seng, H.L. Lim, F.S. Cheah, S.C. Ng, C.H. Koo, K.S. Mustafa, Mohd Rais Ng, S.W. Maah, M.J. R Medicine Four thiosemicarbazones ligands,H3T(1),H3M(2),H3E(3) andH3P(4) have been prepared with good yield by refluxing 2,4-dihydroxybenzaldehyde with N(4)-substituted thiosemicarbazide in ethanol (H3T(1) = 2,4-dihydroxybenzaldehyde thiosemicarbazone;H3M(2) = 2,4-dihydroxybenzaldehyde 4-methylthiosemicarbazone; H3E(3) = 2,4-dihydroxybenzaldehyde 4-ethylthiosemicarbazone and H3P(4) = 2,4-dihydroxybenzaldehyde 4-phenylthiosemicarbazone). Reactions of these ligands with zinc acetates in the presence of 2,20-bipyridine lead to the formation of zinc(II) complexes of formulation Zn(bpy)L(5�8) (bpy = 2,20-bipyridine; L = doubly deprotonated thiosemicarbazones = HT(5); HM(6); HE(7) and HP(8)). These compounds were characterized and their cytotoxicity and topoisomerase I inhibition activities studied. X-ray diffraction study indicates that complex 8 is five coordinated and the coordination geometry around zinc(II) is trigonal bipyramidal distorted square based pyramid (TBDSBP). The doubly deprotonated thiosemicarbazone acts as a tridentate ONS-donor ligand while 2,2-bipyridne as the NN-donor ligand. Complexes 6, 7 and 8 are more cytotoxic towards PC3 (prostate cancer cell line) than RWPE-1 (prostate normal cell line). The cytotoxicity and topoisomerase I inhibition activities seem to be dependent on the N(4) substituent of the thiosemicarbazone moiety. 2012 Article PeerReviewed application/pdf en http://eprints.um.edu.my/3295/1/Towards_a_selective_cytotoxic_agent_for_prostate_cancer_Interaction_of_zinc.pdf Tan, K.W. and Seng, H.L. and Lim, F.S. and Cheah, S.C. and Ng, C.H. and Koo, K.S. and Mustafa, Mohd Rais and Ng, S.W. and Maah, M.J. (2012) Towards a selective cytotoxic agent for prostate cancer: interaction of zinc complexes of polyhydroxybenzaldehyde thiosemicarbazones with topoisomerase I. Polyhedron, 38 (2012). pp. 275-284. ISSN 0277-5387, DOI https://doi.org/10.1016/j.poly.2012.03.014 <https://doi.org/10.1016/j.poly.2012.03.014>. http://www.sciencedirect.com/science/article/pii/S0277538712001404 10.1016/j.poly.2012.03.014 |
| spellingShingle | R Medicine Tan, K.W. Seng, H.L. Lim, F.S. Cheah, S.C. Ng, C.H. Koo, K.S. Mustafa, Mohd Rais Ng, S.W. Maah, M.J. Towards a selective cytotoxic agent for prostate cancer: interaction of zinc complexes of polyhydroxybenzaldehyde thiosemicarbazones with topoisomerase I |
| title | Towards a selective cytotoxic agent for prostate cancer: interaction of zinc complexes of polyhydroxybenzaldehyde thiosemicarbazones with topoisomerase I |
| title_full | Towards a selective cytotoxic agent for prostate cancer: interaction of zinc complexes of polyhydroxybenzaldehyde thiosemicarbazones with topoisomerase I |
| title_fullStr | Towards a selective cytotoxic agent for prostate cancer: interaction of zinc complexes of polyhydroxybenzaldehyde thiosemicarbazones with topoisomerase I |
| title_full_unstemmed | Towards a selective cytotoxic agent for prostate cancer: interaction of zinc complexes of polyhydroxybenzaldehyde thiosemicarbazones with topoisomerase I |
| title_short | Towards a selective cytotoxic agent for prostate cancer: interaction of zinc complexes of polyhydroxybenzaldehyde thiosemicarbazones with topoisomerase I |
| title_sort | towards a selective cytotoxic agent for prostate cancer: interaction of zinc complexes of polyhydroxybenzaldehyde thiosemicarbazones with topoisomerase i |
| topic | R Medicine |
| url | http://eprints.um.edu.my/3295/1/Towards_a_selective_cytotoxic_agent_for_prostate_cancer_Interaction_of_zinc.pdf http://eprints.um.edu.my/3295/ http://www.sciencedirect.com/science/article/pii/S0277538712001404 |
| url_provider | http://eprints.um.edu.my/ |