Synthesis, structure, solution behaviour and biological evaluation of oxidovanadium(IV/V) complexes: Substrate specific DMSO assisted methylation of a thiosemicarbazone
The synthesis and characterization of an oxidovanadium(IV) [VIVO(L)(acac)] (1) and of two dioxidovanadium(V) [VVO2(L')] (2) and [VVO2(L)] (2a) complexes of the Schiff base formed from the reaction of 4-(p-fluorophenyl) thiosemicarbazone with pyridine-2-aldehyde (HL) is described.The oxidovana...
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Royal Society of Chemistry
2018
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my.sunway.eprints.8922020-10-07T09:22:54Z http://eprints.sunway.edu.my/892/ Synthesis, structure, solution behaviour and biological evaluation of oxidovanadium(IV/V) complexes: Substrate specific DMSO assisted methylation of a thiosemicarbazone Saswati, Adao, Pedro Majumder, Sudarshana Dash, Subashree P Roy, Satabdi Kuznetsov, Maxim L Pessoa, Joao Costa Gomes, Claras S B Hardikar, Manasi R Tiekink, Edward R. T. * Dinda, Rupam QD Chemistry The synthesis and characterization of an oxidovanadium(IV) [VIVO(L)(acac)] (1) and of two dioxidovanadium(V) [VVO2(L')] (2) and [VVO2(L)] (2a) complexes of the Schiff base formed from the reaction of 4-(p-fluorophenyl) thiosemicarbazone with pyridine-2-aldehyde (HL) is described.The oxidovanadium(IV) species [VIVO(L)(acac)] (1) was synthesized by the reaction of VIVO(acac)2 with the thiosemicarbazone HL in refluxing ethanol. The recrystallization of [VIVO(L)(acac)] (1) in DMF, CH3CN or EtOH gave the same product i.e. the dioxidovanadium(V) complex [VVO2(L)] (2a); however, upon recrystallization of 1 in DMSO a distinct compound [VVO2(L')] (2) was formed, wherein the original ligand L- is transformed to a rearranged one, L’-. In the presence of DMSO the ligand in complex 1 is found to undergo methylation at the carbon centre attached to imine nitrogen (aldimine) and transformed to the corresponding V VO2- species through in situ reaction. The synthesized HL and the metal 2 complexes were characterized by elemental analysis, IR, UV–Vis, NMR and EPR spectroscopy. The molecular structure of [VVO2(L')] (2) was determined by single crystal X–ray crystallography.The methylation of various other ligands and complexes prepared from different vanadium precursors under similar reaction conditions was also attempted and it was confirmed that the imine methylation observed is both ligand and metal precursor specific. Complexes 1 and 2 show in vitro insulin-like activity against insulin responsive L6 myoblast cells, with complex 1 being more potent. In addition, the in vitro cytotoxicity studies of HL, and of complexes 1 and 2 against the MCF–7 and Vero cell lines were also done. The ligand is not cytotoxic and complex 2 is significantly more cytotoxic than 1. DAPI staining experiments indicate that increase in time of incubation as well as increase of concentration of the complexes lead to increase in cell death. Royal Society of Chemistry 2018 Article PeerReviewed text en cc_by_4 http://eprints.sunway.edu.my/892/1/Tiekink%20Synthesis%20structure%20solultion%20behaviour%20final%20version.pdf Saswati, and Adao, Pedro and Majumder, Sudarshana and Dash, Subashree P and Roy, Satabdi and Kuznetsov, Maxim L and Pessoa, Joao Costa and Gomes, Claras S B and Hardikar, Manasi R and Tiekink, Edward R. T. * and Dinda, Rupam (2018) Synthesis, structure, solution behaviour and biological evaluation of oxidovanadium(IV/V) complexes: Substrate specific DMSO assisted methylation of a thiosemicarbazone. Dalton Transactions, 47. pp. 11358-11374. ISSN 1477-9226 |
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QD Chemistry Saswati, Adao, Pedro Majumder, Sudarshana Dash, Subashree P Roy, Satabdi Kuznetsov, Maxim L Pessoa, Joao Costa Gomes, Claras S B Hardikar, Manasi R Tiekink, Edward R. T. * Dinda, Rupam Synthesis, structure, solution behaviour and biological evaluation of oxidovanadium(IV/V) complexes: Substrate specific DMSO assisted methylation of a thiosemicarbazone |
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The synthesis and characterization of an oxidovanadium(IV) [VIVO(L)(acac)] (1) and of two dioxidovanadium(V)
[VVO2(L')] (2) and [VVO2(L)] (2a) complexes of the Schiff base formed from the reaction of 4-(p-fluorophenyl)
thiosemicarbazone with pyridine-2-aldehyde (HL) is described.The oxidovanadium(IV) species [VIVO(L)(acac)] (1)
was synthesized by the reaction of VIVO(acac)2 with the thiosemicarbazone HL in refluxing ethanol. The
recrystallization of [VIVO(L)(acac)] (1) in DMF, CH3CN or EtOH gave the same product i.e. the dioxidovanadium(V)
complex [VVO2(L)] (2a); however, upon recrystallization of 1 in DMSO a distinct compound [VVO2(L')] (2) was
formed, wherein the original ligand L- is transformed to a rearranged one, L’-. In the presence of DMSO the ligand
in complex 1 is found to undergo methylation at the carbon centre attached to imine nitrogen (aldimine) and
transformed to the corresponding V VO2- species through in situ reaction. The synthesized HL and the metal
2 complexes were characterized by elemental analysis, IR, UV–Vis, NMR and EPR spectroscopy. The molecular
structure of [VVO2(L')] (2) was determined by single crystal X–ray crystallography.The methylation of various other ligands and complexes prepared from different vanadium precursors under similar reaction conditions was also attempted and it was confirmed that the imine methylation observed is both ligand and metal precursor specific. Complexes 1 and 2 show in vitro insulin-like activity against insulin responsive L6 myoblast cells, with complex 1 being more potent. In addition, the in vitro cytotoxicity studies of HL, and of complexes 1 and 2 against the MCF–7 and Vero cell lines were also done. The ligand is not cytotoxic and complex 2 is significantly more cytotoxic than 1. DAPI staining experiments indicate that increase in time of incubation as well as increase of concentration of the complexes lead to increase in cell death. |
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Article |
author |
Saswati, Adao, Pedro Majumder, Sudarshana Dash, Subashree P Roy, Satabdi Kuznetsov, Maxim L Pessoa, Joao Costa Gomes, Claras S B Hardikar, Manasi R Tiekink, Edward R. T. * Dinda, Rupam |
author_facet |
Saswati, Adao, Pedro Majumder, Sudarshana Dash, Subashree P Roy, Satabdi Kuznetsov, Maxim L Pessoa, Joao Costa Gomes, Claras S B Hardikar, Manasi R Tiekink, Edward R. T. * Dinda, Rupam |
author_sort |
Saswati, |
title |
Synthesis, structure, solution behaviour and biological evaluation of oxidovanadium(IV/V) complexes: Substrate specific DMSO assisted methylation of a thiosemicarbazone |
title_short |
Synthesis, structure, solution behaviour and biological evaluation of oxidovanadium(IV/V) complexes: Substrate specific DMSO assisted methylation of a thiosemicarbazone |
title_full |
Synthesis, structure, solution behaviour and biological evaluation of oxidovanadium(IV/V) complexes: Substrate specific DMSO assisted methylation of a thiosemicarbazone |
title_fullStr |
Synthesis, structure, solution behaviour and biological evaluation of oxidovanadium(IV/V) complexes: Substrate specific DMSO assisted methylation of a thiosemicarbazone |
title_full_unstemmed |
Synthesis, structure, solution behaviour and biological evaluation of oxidovanadium(IV/V) complexes: Substrate specific DMSO assisted methylation of a thiosemicarbazone |
title_sort |
synthesis, structure, solution behaviour and biological evaluation of oxidovanadium(iv/v) complexes: substrate specific dmso assisted methylation of a thiosemicarbazone |
publisher |
Royal Society of Chemistry |
publishDate |
2018 |
url |
http://eprints.sunway.edu.my/892/1/Tiekink%20Synthesis%20structure%20solultion%20behaviour%20final%20version.pdf http://eprints.sunway.edu.my/892/ |
_version_ |
1680323400120139776 |
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13.19449 |