Synthesis, chemical characterization, DNA interaction and antioxidant studies of ortho, meta and para fluoro substituted ferrocene incorporated selenoureas

R A Hussain; A Badshash; Manzar Sohail; B Lal; A A Altaf

doi:10.1016/j.ica.2013.04.003

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Synthesis, chemical characterization, DNA interaction and antioxidant studies of ortho, meta and para fluoro substituted ferrocene incorporated selenoureas

Journal article

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Synthesis, chemical characterization, DNA interaction and antioxidant studies of ortho, meta and para fluoro substituted ferrocene incorporated selenoureas

R A Hussain, A Badshash, Manzar Sohail, B Lal and A A Altaf

Inorganica Chimica Acta, Vol.402, pp.133-139

2013

DOI: https://doi.org/10.1016/j.ica.2013.04.003

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Abstract

ferrocene

DNA binding constant

antioxidant

We have reported a one pot synthesis of three new ferrocene incorporated selenoureas namely; 1-(2-fluorobenzoyl)-3-(4-ferrocenyl-3-methylphenyl)selenourea (MeP2F), 1-(3-fluorobenzoyl)-3-(4-ferrocenyl-3-methylphenyl)selenourea (MeP3F) and 1-(4-fluorobenzoyl)-3-(4-ferrocenyl-3-methylphenyl)selenourea (MeP2F) by the reaction of corresponding carboxylic acid chlorides with potassium selenocyanate (KSeCN) and 3-methyl-4-ferrocenyl aniline in acetone under constant stirring. Synthesized compounds were characterized by FTIR, NMR (1H and 13C), CHNS and AAS. We have also presented X-rays single crystal structure for MeP2F. DNA binding studies were evaluated with the help of cyclic voltammetry in the presence of TBAP (tertiary butyl ammonium perchlorate) as supporting electrolyte in DMSO/water mixture of 70:30. Binding constant for MeP2F is 1.499 × 103 M-1, MeP3F is 1.706 × 103 M-1 and MeP4F is 1.035 × 103 M-1. Binding site size for MeP2F (0.334 bp) < MeP4F (0.410 bp) < MeP3F (0.463 bp). In all the compounds diffusion coefficients of drug-DNA adduct is lower than the free drug indicating slow diffusion of comparatively high molecular weight drug towards the electrode in cyclic voltammetry. Mode of interaction has further been reconfirmed with the help of viscometry. All the three compounds have good antioxidant activities against DPPH with IC50 values of 132 μg/ml, 108 μg/ml and 84 μg/ml for MeP2F, MeP4F and MeP3F respectively.

Details

Title: Synthesis, chemical characterization, DNA interaction and antioxidant studies of ortho, meta and para fluoro substituted ferrocene incorporated selenoureas
Authors: R A Hussain (Author) - Quaid-i-Azam University, Pakistan
A Badshash (Author) - Quaid-i-Azam University, Pakistan
Manzar Sohail (Author) - University of the Sunshine Coast
B Lal (Author) - Quaid-i-Azam University, Pakistan
A A Altaf (Author) - University of Malakand, Pakistan
Publication details: Inorganica Chimica Acta, Vol.402, pp.133-139
Publisher: Elsevier BV
Date published: 2013
DOI: 10.1016/j.ica.2013.04.003
ISSN: 0020-1693
Copyright note: Copyright © 2013. This manuscript version is made available under the CC-BY-NC-ND 4.0 license http://creativecommons.org/licenses/by-nc-nd/4.0/
Organisation Unit: School of Science and Engineering - Legacy; University of the Sunshine Coast, Queensland
Language: English
Record Identifier: 99448981102621
Output Type: Journal article

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