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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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.

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