Synthesis and characterization of copper(II) complexes of 4-alkyl/aryl-1,2-naphthoquinones thiosemicarbazones derivatives as potent DNA cleaving agents

Zahra Afrasiabi, Ekk Sinn, Prasad P. Kulkarni, Vinita Ambike, Subhash Padhye, Deepti Deobagakar, Mark Heron, Chris Gabbutt, Christopher E. Anson, Annie K. Powell

Research output: Contribution to journalArticle

21 Citations (Scopus)

Abstract

Copper (II) complexes of some alkyl/aryl-1,2 naphthoquinones thiosemicarbazone have been prepared and characterized. The crystal structure determined for one of the free ligands viz. 4-Pyrrolidine-1-yl-[1, 2] naphthaquinone thiosemicarbazone (5) indicates it to crystallize in the "E' conformation which is supported by the NMR data. The ligands and copper complexes were evaluated for their DNA cleaving activities in case of circular double stranded plasmid DNA pBR322 under aerobic conditions. Amongst the ligands, compound 8 shows almost quantitative conversion to the linearized DNA in presence of H2O2 oxidant. All copper conjugates show more pronounced interaction with DNA while compounds 3 and 7 are able to yield linearized DNA in presence of the oxidant.

LanguageEnglish
Pages2023-2030
Number of pages8
JournalInorganica Chimica Acta
Volume358
Issue number6
Early online date29 Jan 2005
DOIs
Publication statusPublished - 30 Mar 2005
Externally publishedYes

Fingerprint

Copper
DNA
deoxyribonucleic acid
Derivatives
copper
synthesis
Ligands
Oxidants
ligands
Thiosemicarbazones
plasmids
Conformations
Plasmids
Crystal structure
Nuclear magnetic resonance
1,2-naphthoquinone thiosemicarbazone
nuclear magnetic resonance
crystal structure
interactions

Cite this

Afrasiabi, Zahra ; Sinn, Ekk ; Kulkarni, Prasad P. ; Ambike, Vinita ; Padhye, Subhash ; Deobagakar, Deepti ; Heron, Mark ; Gabbutt, Chris ; Anson, Christopher E. ; Powell, Annie K. / Synthesis and characterization of copper(II) complexes of 4-alkyl/aryl-1,2-naphthoquinones thiosemicarbazones derivatives as potent DNA cleaving agents. In: Inorganica Chimica Acta. 2005 ; Vol. 358, No. 6. pp. 2023-2030.
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Synthesis and characterization of copper(II) complexes of 4-alkyl/aryl-1,2-naphthoquinones thiosemicarbazones derivatives as potent DNA cleaving agents. / Afrasiabi, Zahra; Sinn, Ekk; Kulkarni, Prasad P.; Ambike, Vinita; Padhye, Subhash; Deobagakar, Deepti; Heron, Mark; Gabbutt, Chris; Anson, Christopher E.; Powell, Annie K.

In: Inorganica Chimica Acta, Vol. 358, No. 6, 30.03.2005, p. 2023-2030.

Research output: Contribution to journalArticle

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AU - Afrasiabi, Zahra

AU - Sinn, Ekk

AU - Kulkarni, Prasad P.

AU - Ambike, Vinita

AU - Padhye, Subhash

AU - Deobagakar, Deepti

AU - Heron, Mark

AU - Gabbutt, Chris

AU - Anson, Christopher E.

AU - Powell, Annie K.

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AB - Copper (II) complexes of some alkyl/aryl-1,2 naphthoquinones thiosemicarbazone have been prepared and characterized. The crystal structure determined for one of the free ligands viz. 4-Pyrrolidine-1-yl-[1, 2] naphthaquinone thiosemicarbazone (5) indicates it to crystallize in the "E' conformation which is supported by the NMR data. The ligands and copper complexes were evaluated for their DNA cleaving activities in case of circular double stranded plasmid DNA pBR322 under aerobic conditions. Amongst the ligands, compound 8 shows almost quantitative conversion to the linearized DNA in presence of H2O2 oxidant. All copper conjugates show more pronounced interaction with DNA while compounds 3 and 7 are able to yield linearized DNA in presence of the oxidant.

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