The Study Of Anticancer Properties Of Benzyl-O-Vanillin And Its Derivatives
| dc.contributor.author | Al-Mudaris, Zena A. Abdul Hameed | |
| dc.date.accessioned | 2018-08-08T02:32:33Z | |
| dc.date.available | 2018-08-08T02:32:33Z | |
| dc.date.issued | 2011 | |
| dc.description.abstract | Benzyl-o-vanillin and benzimidazole nucleus serve as important pharmacophore in drug discovery as it has a significant medicinal importance. Thus we explored the anticancer activity of three compounds namely 2-(2-benzyloxy-3-methoxyphenyl)-1H-benzimidazole, 2MP, N-1-(2-benzyloxy-3-methoxybenzyl)-2-(2-benzyloxy-3-methoxyphenyl)-1H-benzimidazole, 2XP, and (R) and (S)-1-(2-benzyloxy-3-methoxyphenyl)-2, 2, 2-trichloroethyl benzenesulfonate, 3BS and compared their activity to 2-benzyloxy-3-methoxybenzaldehyde, (Bn1) the parent compound. 2XP and 3BS were found to be selectively cytotoxic towards U937 leukemic cell causing cell death via apoptosis by activating caspase 9 activity. DNA binding studies primarily by the equilibrium binding titration assay indicate DNA binding activity with binding constant of 7.39μM/bp and 6.86μM/bp for 3BS and 2XP respectively. Viscometry studies show that 3BS and 2XP bind mainly in the groove region. The higher mutagenicity of 3BS suggests that this compound targets the N7 of guanine in the major groove and the GC in the wider minor groove while the lack of significant mutagenic outcome by 2XP suggests that this compound may target mainly the AT rich sequences, found largely in the narrow minor groove region of the nucleic acid. Our results show that the benzylvanillin alone have no strong anticancer activity even after it was combined with the benzimidazole, but after being disubstituted with another benzylvanillin, stronger activity was observed. Also, the combination of benzylvanillin with benzenesulfonate significantly improved the activity of 3BS as the presence of benzenesulfonate enabled it to have good alkylating activity. The findings of this study support our computer modeling results which also shows that 3BS and 2XP have good DNA binding. Both compounds (2XP and 3BS) failed to form any direct linkage with the DNA unlike Bn1 and 2MP. However these two compounds (Bn1 and 2MP) failed to show any cytotoxic activity. Hence, the present study provides a new insight of the novel benzylvanillin derivatives serving as potential therapeutic agents against leukemia. | en_US |
| dc.identifier.uri | http://hdl.handle.net/123456789/6245 | |
| dc.language.iso | en | en_US |
| dc.publisher | Universiti Sains Malaysia | en_US |
| dc.subject | Benzyl-o-vanillin and benzimidazole nucleus | en_US |
| dc.subject | important pharmacophore in drug discovery | en_US |
| dc.title | The Study Of Anticancer Properties Of Benzyl-O-Vanillin And Its Derivatives | en_US |
| dc.type | Thesis | en_US |
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