Pyrrole-chalcone analogues as DNA binding agents

Munshi, Tasnim and Scowen, Ian and Abdull Manap, Mohd Rashidi and Ismail, Ahmad Zaidi and Ahmad, Haslina and Abdullah, Maryam Aisyah and Mohd Faudzi, Siti Munirah and Azamudin, Nurin Syahmimi (2018) Pyrrole-chalcone analogues as DNA binding agents. In: Industrial Chemistry Seminar XXI, 10 May 2018, Selangor, Malaysia.

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Abstract

Cancer is a gene mutation in the cell that grows uncontrollably. Many drugs have been successfully developed to treat this disease but could not provide effective solutions for cancer treatment, in which the major problem of these drugs is their cytotoxicity. The usual cancer treatment tends to kills the cancerous cell along with healthy cell around it. An alpha,beta- (α,β-) unsaturated ketone at the core of the chalcone feature provides the basis for the wide range of its biological activities including anticancer effect and can be prepared via Claisen-Schmidt condensation reaction between acetophenone and benzaldehydes with base or acid as catalyst1. Pyrrole-chalcones of 3-(2,5-dimethoxy-phenyl)-1-(1H-pyrrole-3-yl)-propenone (compound 1) and 1-(1H-pyrrol-2-yl)-3-m-tolylpropenone (compound 2) were screened for anticancer properties through deoxyribonucleic acid (DNA) binding assay by Ultraviolet Visible (UV/VIS) absorption spectroscopy. The intrinsic binding constant (Kb) of complexes 1 and 2 with calf-thymus DNA (CT-DNA) are 1.08x103 M-1 and 5.225x103 M-1, respectively. It was found that compound 1 has a higher binding affinity than compound 2 due to methoxyl (-OCH3) group is a better electron donating group with an ability to form intramolecular hydrogen bonding with DNA in comparison to methyl (-CH3) moiety. The UV-Visible titration studies suggest that chalcones bind to DNA via intercalation mechanism as it induces hyperchromic effect as shown in the λmax 2. Results obtained from this work would be very useful in understanding the mechanism of interaction of the Pyrrole-chalcone analogues binding to DNA and serve as preliminary information for the development as a new potential anticancer agents.

Keywords:Anticancer, Pyrrole-chalcones, Vibrational spectroscopy, Binding Assay, Molecular structure
Subjects:F Physical Sciences > F150 Medicinal Chemistry
F Physical Sciences > F100 Chemistry
F Physical Sciences > F180 Analytical Chemistry
F Physical Sciences > F130 Structural Chemistry
Divisions:College of Science > School of Chemistry
ID Code:32123
Deposited On:10 Jul 2018 13:33

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