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Synthesis, Characterisation Of Stilbene–Arylcinnamide Hybrids And Cytotoxic Studies Against Lung Cancer Cell A549

Numerous anticancer drugs have been designed from natural products. Several compounds derived from nature such as alkaloid, flavonoid, cinnamic acid and stilbene, were reported to possess various biological properties primarily as an anticancer agent. In this study, a total of 24 compounds of a new...

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Main Author: Mohd Zaki, Nurain Syazwani
Format: Thesis
Language:English
Published: 2024
Subjects:
QD1-65 General Including alchemy
Online Access:http://eprints.usm.my/61464/1/NURAIN%20SYAZWANI%20BINTI%20MOHD%20ZAKI%20-%20TESIS%20cut.pdf
http://eprints.usm.my/61464/
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spelling my.usm.eprints.61464 http://eprints.usm.my/61464/ Synthesis, Characterisation Of Stilbene–Arylcinnamide Hybrids And Cytotoxic Studies Against Lung Cancer Cell A549 Mohd Zaki, Nurain Syazwani QD1-65 General Including alchemy Numerous anticancer drugs have been designed from natural products. Several compounds derived from nature such as alkaloid, flavonoid, cinnamic acid and stilbene, were reported to possess various biological properties primarily as an anticancer agent. In this study, a total of 24 compounds of a new hybrid series has been designed and synthesised, resulting from the coupling of stilbene and arylcinnamide scaffolds. All synthesised stilbene-arylcinnamide hybrids were obtained in 42-80% yield. Elucidation and characterisation of these hybrids have been validated using Fourier Transform Infrared (FT-IR), Nuclear Magnetic Resonance (NMR) spectroscopy and High-Resolution Mass Spectrometry (HRMS). The cytotoxicity against human lung cancer A549 cell line was assessed by the 3-(4,5-dimethylthiazol-2-yl)-2,5-diphenyltetrazolium (MTT) assay, using cisplatin as the positive control. Particularly, compounds 66b and 74b have displayed potent activities on A549 cancer cells with IC50 value of 20.0 μM and 19.9 μM, respectively. This result is comparable to cisplatin with IC50 value of 19.9 μM after 72 hrs post-treatment. The structural activity relationship (SAR) analysis revealed that the presence of an isopropyl group attached to para-position of stilbene phenyl ring (ring A) of compounds 66b and 74b was crucial for a good cytotoxic effect on A549 cells. Additionally, 4-methyl group as the substituents on cinnamide phenyl ring (ring C) contributed to an innumerable cancer cell death. 2024-07 Thesis NonPeerReviewed application/pdf en http://eprints.usm.my/61464/1/NURAIN%20SYAZWANI%20BINTI%20MOHD%20ZAKI%20-%20TESIS%20cut.pdf Mohd Zaki, Nurain Syazwani (2024) Synthesis, Characterisation Of Stilbene–Arylcinnamide Hybrids And Cytotoxic Studies Against Lung Cancer Cell A549. Masters thesis, Universiti Sains Malaysia.
institution Universiti Sains Malaysia
building Hamzah Sendut Library
collection Institutional Repository
continent Asia
country Malaysia
content_provider Universiti Sains Malaysia
content_source USM Institutional Repository
url_provider http://eprints.usm.my/
language English
topic QD1-65 General Including alchemy
spellingShingle QD1-65 General Including alchemy
Mohd Zaki, Nurain Syazwani
Synthesis, Characterisation Of Stilbene–Arylcinnamide Hybrids And Cytotoxic Studies Against Lung Cancer Cell A549
description Numerous anticancer drugs have been designed from natural products. Several compounds derived from nature such as alkaloid, flavonoid, cinnamic acid and stilbene, were reported to possess various biological properties primarily as an anticancer agent. In this study, a total of 24 compounds of a new hybrid series has been designed and synthesised, resulting from the coupling of stilbene and arylcinnamide scaffolds. All synthesised stilbene-arylcinnamide hybrids were obtained in 42-80% yield. Elucidation and characterisation of these hybrids have been validated using Fourier Transform Infrared (FT-IR), Nuclear Magnetic Resonance (NMR) spectroscopy and High-Resolution Mass Spectrometry (HRMS). The cytotoxicity against human lung cancer A549 cell line was assessed by the 3-(4,5-dimethylthiazol-2-yl)-2,5-diphenyltetrazolium (MTT) assay, using cisplatin as the positive control. Particularly, compounds 66b and 74b have displayed potent activities on A549 cancer cells with IC50 value of 20.0 μM and 19.9 μM, respectively. This result is comparable to cisplatin with IC50 value of 19.9 μM after 72 hrs post-treatment. The structural activity relationship (SAR) analysis revealed that the presence of an isopropyl group attached to para-position of stilbene phenyl ring (ring A) of compounds 66b and 74b was crucial for a good cytotoxic effect on A549 cells. Additionally, 4-methyl group as the substituents on cinnamide phenyl ring (ring C) contributed to an innumerable cancer cell death.
format Thesis
author Mohd Zaki, Nurain Syazwani
author_facet Mohd Zaki, Nurain Syazwani
author_sort Mohd Zaki, Nurain Syazwani
title Synthesis, Characterisation Of Stilbene–Arylcinnamide Hybrids And Cytotoxic Studies Against Lung Cancer Cell A549
title_short Synthesis, Characterisation Of Stilbene–Arylcinnamide Hybrids And Cytotoxic Studies Against Lung Cancer Cell A549
title_full Synthesis, Characterisation Of Stilbene–Arylcinnamide Hybrids And Cytotoxic Studies Against Lung Cancer Cell A549
title_fullStr Synthesis, Characterisation Of Stilbene–Arylcinnamide Hybrids And Cytotoxic Studies Against Lung Cancer Cell A549
title_full_unstemmed Synthesis, Characterisation Of Stilbene–Arylcinnamide Hybrids And Cytotoxic Studies Against Lung Cancer Cell A549
title_sort synthesis, characterisation of stilbene–arylcinnamide hybrids and cytotoxic studies against lung cancer cell a549
publishDate 2024
url http://eprints.usm.my/61464/1/NURAIN%20SYAZWANI%20BINTI%20MOHD%20ZAKI%20-%20TESIS%20cut.pdf
http://eprints.usm.my/61464/
_version_ 1823273895882391552
score 13.235796

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