Synthesis and Characterization of Copper(II) Complexes of 4-alkyl/aryl-1,2-naphthoquinones Thiosemicarbazones Derivatives as Potent DNA Cleaving Agents

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.

Department(s)

Chemistry

Keywords and Phrases

1,2 naphthoquinone derivative; 4 (2,3 dihydroindol 1 yl)[1,2]naphthoquinone 1 thiosemicarbazone; 4 morpholin 4 yl[1,2]naphthoquinone 1 thiosemicarbazone; 4 piperidin 1; 1,2 naphthoquinones; Copper; Nuclease activity; Thiosemicarbazoneyldibenzofuran 1,2 dione 1 thiosemicarbazone; 4 pyrrolidin 1 yl[1,2]naphthoquinone 1 thiosemicarbazone; copper complex; double stranded DNA; hydrogen peroxide; plasmid DNA; thiosemicarbazone derivative; unclassified drug; article; crystal structure; crystallization; DNA cleavage; drug synthesis; nuclear magnetic resonance

International Standard Serial Number (ISSN)

0020-1693

Document Type

Article - Journal

Document Version

Citation

File Type

text

Language(s)

English

Rights

© 2005 American Society for Cell Biology, Elsevier, All rights reserved.

Publication Date

01 Mar 2005

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