論文 - 詳細
| RRC ID | 58638 |
|---|---|
| 著者 | Nagai J, Shi H, Sezaki N, Yoshida N, Bandow K, Uesawa Y, Sakagami H, Tomomura M, Tomomura A, Takao K, Sugita Y. |
| タイトル | Quantitative Structure-Cytotoxicity Relationship of 2-Arylazolylchromones and 2-Triazolylchromones. |
| ジャーナル | Anticancer Res |
| Abstract |
BACKGROUND/AIM:4H-1-Benzopyran-4-one (chromone), present in various flavonoids as a backbone structure, has been used for the synthesis of anticancer drugs. The study aimed at investigating the cytotoxicity of eight 2-arylazolylchromones and twelve 2-triazolylchromones against four human oral squamous cell carcinoma (OSCC) cell lines and three human normal mesenchymal oral cells, and then performed a quantitative structure-activity relationship (QSAR) analysis. MATERIALS AND METHODS:Cell viability was determined by the 3-(4,5-dimethylthiazol-2-yl)-2,5-diphenyltetrazolium bromide method. The distribution of cells to various phases of cell cycle was determined by cell cycle analysis. A total of 3,218 physicochemical, structural and quantum chemical features were calculated for QSAR analysis from the most stabilized structure optimized using CORINA. RESULTS:2-[4-(4-fluorophenyl)-1H-imidazol-1-yl]-4H-1-benzopyran-4-one [6] had the highest tumor-specificity (TS), comparable with that of 5-flurouracil (5-FU) and doxorubicin, inducing cytostatic growth inhibition, accumulation of G2+M phase cells with no cells in the G1 phase. All eight 2-triazolylchromones showed much lower tumor-specificity, confirming our previous finding. Tumor-specificity was also correlated with 3D shape, topological shape, size, ionization potential, and the presence of more than two aromatic rings in the molecule and imidazole ring in the nitrogen-containing heterocyclic ring. CONCLUSION:[6] can be a lead compound for designing anticancer drugs. |
| 巻・号 | 39(12) |
| ページ | 6479-6488 |
| 公開日 | 2019-12-1 |
| DOI | 10.21873/anticanres.13862 |
| PII | 39/12/6479 |
| PMID | 31810912 |
| MeSH | Antineoplastic Agents / chemical synthesis* Antineoplastic Agents / chemistry Antineoplastic Agents / pharmacology Carcinoma, Squamous Cell / drug therapy* Cell Cycle / drug effects Cell Line, Tumor Cell Proliferation / drug effects Cell Survival / drug effects Chromones / chemical synthesis* Chromones / chemistry Chromones / pharmacology Drug Screening Assays, Antitumor Humans Mouth Neoplasms / drug therapy* Quantitative Structure-Activity Relationship Quantum Theory |
| IF | 1.994 |
| 引用数 | 1 |
| リソース情報 | |
| ヒト・動物細胞 | Ca9-22(RCB1976) HSC-2(RCB1945) HSC-3(RCB1975) HSC-4(RCB1902) |