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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

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, nam...

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Main Authors: Hanifa, Bibi, Sirajuddin, Muhammad, Kubicki, Maciej, Tiekink, Edward R. T. *
Format: Article
Language:English
Published: Elsevier 2022
Subjects:
QD Chemistry
Online Access:http://eprints.sunway.edu.my/2011/1/18_4_Three%20isomeric.pdf
http://eprints.sunway.edu.my/2011/
https://doi.org/10.1016/j.molstruc.2022.133033
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spelling my.sunway.eprints.20112022-04-21T03:14:04Z http://eprints.sunway.edu.my/2011/ 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 Sirajuddin, Muhammad Kubicki, Maciej Tiekink, Edward R. T. * QD Chemistry 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. Elsevier 2022-08-15 Article PeerReviewed text en cc_by_nc_4 http://eprints.sunway.edu.my/2011/1/18_4_Three%20isomeric.pdf 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 https://doi.org/10.1016/j.molstruc.2022.133033 doi:10.1016/j.molstruc.2022.133033
institution Sunway University
building Sunway Campus Library
collection Institutional Repository
continent Asia
country Malaysia
content_provider Sunway University
content_source Sunway Institutional Repository
url_provider http://eprints.sunway.edu.my/
language English
topic QD Chemistry
spellingShingle QD Chemistry
Hanifa, Bibi
Sirajuddin, Muhammad
Kubicki, Maciej
Tiekink, Edward R. T. *
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
description 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.
format Article
author Hanifa, Bibi
Sirajuddin, Muhammad
Kubicki, Maciej
Tiekink, Edward R. T. *
author_facet Hanifa, Bibi
Sirajuddin, Muhammad
Kubicki, Maciej
Tiekink, Edward R. T. *
author_sort Hanifa, Bibi
title 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
title_short 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
title_full 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
title_fullStr 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
title_full_unstemmed 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
title_sort 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
publisher Elsevier
publishDate 2022
url http://eprints.sunway.edu.my/2011/1/18_4_Three%20isomeric.pdf
http://eprints.sunway.edu.my/2011/
https://doi.org/10.1016/j.molstruc.2022.133033
_version_ 1731228855972134912
score 13.211869

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