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建構液相平行合成芬布芬與利尿酸之醯胺分子庫以篩選有效抗癌活性分子之研究
Dissertation

建構液相平行合成芬布芬與利尿酸之醯胺分子庫以篩選有效抗癌活性分子之研究

林坤沂
Doctor of Philosophy (PHD), 國立清華大學, 生醫工程與環境科學系
2010

Abstract

芬布芬 利尿酸 醯胺鍵之形成 細胞生存能力 抗發炎 fenbufen ethacrynic acid amide formation Cell viability anti-inflammatory
Aim of this research is to construct a library screening at a cellular level via amide bond formation under the solution-phase combinatorial chemistry condition without isolation and purification. Amine group and carboxylic acid (fenbufen and ethacrynic acid) were used as raw materials in this research to synthesize N-(4-(4-(biphenyl-4-yl)-4-oxobutanamido) butyl)- 5-(2,5- dimethylphenoxy)-2,2-dimethylpentanamide、N-(4-(4- (biphenyl -4-yl)- 4-oxobutanamide) butyl)-2- ethylhexanamide and 4-(biphenyl-4-yl)- N-(4-(2-(2,3- dichloro-4 -(2-methylenebutanoyl) phenoxy)acetamido) butyl)- 4-oxobutanamide which could be serve as anti-cancers potential compounds. Amide derivatives to establish a molecular library, the success of screening out a number of potential compounds for future laboratory of cellular mechanisms (such as Flow cytometry) or as a blueprint to continue modifying compounds for SAR (structure and reactivity) aspects of drug mechanisms. The previous discoveries of butyl fenbufen amide analogs with antitumor effects were further examined. The amide analogs with 1, 3, 4 and 8 carbons chains were prepared. We probed into the length of the alkyl amide side chain increased, the cytotoxic effects increased, and the octyl fenbufen amide had the greatest cytotoxic effect on RAW 264.7 cells by using the MTT assay. Butyl fenbufen and ethacrynic acid amide analogs exhibited significant cytotoxic effects at a concentration of 100 μM. As the length of the alkyl amide side chain increased, the cytotoxic effects increased, and the octyl fenbufen amide had the greatest cytotoxic effect. In addition, NO in LPS-activated RAW 264.7 cells were measured. At the concentration of 10 μM used in the study, the fenbufen amide analogs did not show cytotoxicity according to the MTT assay results. The NO scavenging activities of the fenbufen amide analogs were not significant different from that of fenbufen.

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