論文 - 詳細
| RRC ID | 45274 |
|---|---|
| 著者 | Shimada C, Uesawa Y, Ishihara M, Kagaya H, Kanamoto T, Terakubo S, Nakashima H, Takao K, Miyashiro T, Sugita Y, Sakagami H. |
| タイトル | Quantitative structure-cytotoxicity relationship of piperic acid amides. |
| ジャーナル | Anticancer Res |
| Abstract |
BACKGROUND:A total of 12 piperic acid amides, including piperine, were subjected to quantitative structure-activity relationship (QSAR) analysis, based on their cytotoxicity, tumor selectivity and anti-HIV activity, in order to find new biological activities. MATERIALS AND METHODS:Cytotoxicity against four human oral squamous cell carcinoma (OSCC) cell lines and three human oral normal cells was determined by the 3-(4,5-dimethylthiazol-2-yl)-2,5-diphenyltetrazolium bromide (MTT) method. Tumor selectivity was evaluated by the ratio of the mean 50% cytotoxic concentration (CC50) against normal oral cells to that against OSCC cell lines. Anti-HIV activity was evaluated by the ratio of the CC50 to 50% HIV infection-cytoprotective concentration (EC50). Physicochemical, structural, and quantum-chemical parameters were calculated based on the conformations optimized by LowModeMD method followed by density functional theory method. RESULTS:All compounds showed low-to-moderate tumor selectivity, but no anti-HIV activity. N-Piperoyldopamine ( 8: ) which has a catechol moiety, showed the highest tumor selectivity, possibly due to its unique molecular shape and electrostatic interaction, especially its largest partial equalization of orbital electronegativities and vsurf descriptors. CONCLUSION:The present study suggests that molecular shape and ability for electrostatic interaction are useful parameters for estimating the tumor selectivity of piperic acid amides. |
| 巻・号 | 34(9) |
| ページ | 4877-84 |
| 公開日 | 2014-9-1 |
| PII | 34/9/4877 |
| PMID | 25202069 |
| MeSH | Amides / chemistry* Amides / toxicity* Anti-HIV Agents / chemistry Anti-HIV Agents / pharmacology Cell Line Cell Line, Tumor Fatty Acids, Unsaturated / chemistry* Humans Inhibitory Concentration 50 Microbial Sensitivity Tests Molecular Structure Quantitative Structure-Activity Relationship* |
| IF | 1.994 |
| 引用数 | 11 |
| WOS 分野 | ONCOLOGY |
| リソース情報 | |
| ヒト・動物細胞 | Ca9-22(RCB1976) HSC-3(RCB1975) HSC-2(RCB1945) HSC-4(RCB1902) |