Synthesis, structural characterization, DNA binding and antioxidant potency of new ferrocene incorporated acyl ureas

Faiza Asghar; Amin Badshah; Raja Azadar Hussain; Manzar Sohail; Kamran Akbar; Ian Sydney Butler

doi:10.1016/j.jorganchem.2015.08.010

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Synthesis, structural characterization, DNA binding and antioxidant potency of new ferrocene incorporated acyl ureas

Journal article

Open access

Peer reviewed

Synthesis, structural characterization, DNA binding and antioxidant potency of new ferrocene incorporated acyl ureas

Faiza Asghar, Amin Badshah, Raja Azadar Hussain, Manzar Sohail, Kamran Akbar and Ian Sydney Butler

Journal of Organometallic Chemistry, Vol.797, pp.131-139

2015

DOI: https://doi.org/10.1016/j.jorganchem.2015.08.010

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Abstract

DNA binding constant

diffusion coefficients

desulphurization

binding site size

In this article, we have reported the synthesis of three new ferrocene incorporated ureas namely; 1-(4-Chlorobenzoyl)-3-(4-ferrocenylphenyl)urea (P4Cl), 1-(3-Chlorobenzoyl)-3-(4-ferrocenyl phenyl)urea (P3Cl) and 1-(2-Chlorobenzoyl)-3-(4-ferrocenylphenyl)urea (P2Cl). All new compounds were unambiguously characterized by common analytical techniques (NMR, FT-IR, AAS, CHNS and molecular docking). Furthermore, single crystal XRD analysis was done for 1-(3-Chlorobenzoyl)-3-(4-ferrocenylphenyl)urea. DNA binding is a pre-requisite for a compound to be used as an antitumor agent. The DNA binding study was done by cyclic voltammetry, UV-vis spectroscopy and viscometry. The drug-DNA binding constant was found to vary in the sequence: KP2Cl (6.056 x 104 M-1) > KP4Cl (5.713 x 104 M-1) > KP3Cl (4.631 x 104 M-1). Diffusion coefficient of the drug-DNA adduct for all the compounds is lower than the free drug, indicating that drug-DNA adduct is of higher molecular weight and slow diffusing as compared to the free drug. Small binding site size of 0.440 (P3Cl), 0.585 (P4Cl) and 0.673 (P2Cl) base pairs is consistent with electrostatic interaction. All the compounds exhibited good antioxidant activities with IC50 values of 82, 136 and 54 μM for P4Cl, P3Cl and P2Cl respectively, against DPPH.

Details

Title: Synthesis, structural characterization, DNA binding and antioxidant potency of new ferrocene incorporated acyl ureas
Authors: Faiza Asghar (Author) - McGill University, Canada
Amin Badshah (Author) - Quaid-i-Azam University, Pakistan
Raja Azadar Hussain (Author) - Quaid-i-Azam University, Pakistan
Manzar Sohail (Author) - University of the Sunshine Coast - Faculty of Science, Health, Education and Engineering
Kamran Akbar (Author) - Quaid-i-Azam University, Pakistan
Ian Sydney Butler (Author) - McGill University, Canada
Publication details: Journal of Organometallic Chemistry, Vol.797, pp.131-139
Publisher: Elsevier BV
Date published: 2015
DOI: 10.1016/j.jorganchem.2015.08.010
ISSN: 0022-328X
Organisation Unit: School of Science and Engineering - Legacy; University of the Sunshine Coast, Queensland
Language: English
Record Identifier: 99449597302621
Output Type: Journal article

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Collaboration types: Domestic collaboration; International collaboration
Web Of Science research areas: Chemistry, Inorganic & Nuclear; Chemistry, Organic

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