Three isomeric 4-[(n-bromophenyl)carbamoyl]butanoic acids (n =2,3 and 4) as DNA intercalator: Synthesis, physiochemical characterization, antimicrobial activity, antioxidant potential and in silico study

Hanifa, Bibi and Sirajuddin, Muhammad and Kubicki, Maciej and Tiekink, Edward R. T. * (2022) Three isomeric 4-[(n-bromophenyl)carbamoyl]butanoic acids (n =2,3 and 4) as DNA intercalator: Synthesis, physiochemical characterization, antimicrobial activity, antioxidant potential and in silico study. Journal of Molecular Structure, 1262. p. 133033. ISSN 0022-2860

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Official URL: https://doi.org/10.1016/j.molstruc.2022.133033

Abstract

A series of three isomeric 4-[(n-bromophenyl)carbamoyl]butanoic acids (n=2,3 and 4) were synthesized and their structures confirmed by FTIR, NMR, MS, micro elemental analysis (CHN) and single crystal X-ray crystallography. Kinks are noted in the molecular structures of the n=2 and n=3 compounds, namely about the methylene-C–C(carbonyl) and N–C(phenyl) bonds; no such twist about the former bond is seen in the n=4 molecule. In the molecular packing, supramolecular tapes are carboxylic acid-O-H…O(carbonyl) and amide-N-H…O(amide) hydrogen bonds. The compounds were evaluated for interaction with salmon sperm DNA and found that they bind via an intercalative mode resulting in hypochromism and bathochromic shift as confirmed by the UV-visible spectroscopic and viscometric techniques. The results of antimicrobial activity performed against five bacterial and two fungal strains show that these compounds have < 50% inhibition. The DPPH antioxidant activity results revealed 78% maximum scavenging activity. An in silico study performed using the SwissADME webserver revealed the compounds obey the rules of drug-likeness and exhibit good potential for bioavailability.

Item Type: Article
Uncontrolled Keywords: 4-[(n-bromophenyl) carbamoyl]butanoic acids; X-ray crystallography; DNA intercalator; antimicrobial activity; DPPH scavenging; in silico study
Subjects: Q Science > QD Chemistry
Divisions: Others > Non Sunway Academics
Sunway University > School of Medical and Life Sciences [formerly School of Healthcare and Medical Sciences until 2020] > Sunway Biofunctional Molecules Discovery Centre [formerly Research Centre for Crystalline Materials until 2023]
Depositing User: Ms Yong Yee Chan
Related URLs:
Date Deposited: 21 Apr 2022 03:14
Last Modified: 21 Apr 2022 03:14
URI: http://eprints.sunway.edu.my/id/eprint/2011

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