| ID | JOS-0258851X-21-715 |
| 著者：名前 | |
| 著者：別形式 | Kurihara, Teruo / Satoh, Rie / Miyagawa, Takashi / Wakabayashi, Hidetsugu / Motohashi, Noboru / Sakagami, Hiroshi |
| 著者：カナ | |
| 著者：所属 | 城西大学理学部化学科 / 城西大学理学部化学科 / 城西大学理学部化学科 / 城西大学理学部化学科 / 明治薬科大学 / 明海大学歯学部 |
| 著者：所属(別形式） | Josai University, Faculty of Science, Department of Chemistry / Josai University, Faculty of Science, Department of Chemistry / Josai University, Faculty of Science, Department of Chemistry / Josai University, Faculty of Science, Department of Chemistry / Meiji Pharmaceutical University / Meikai University School of Dentistry |
| 著者版フラグ | publisher |
| 出版地 | Athens |
| 出版者 | International Institute of Anticancer Research |
| NCID | AA10714348 |
| 冊子ISSN | 0258851X |
| 掲載誌名 | |
| 巻 | 21 |
| 号 | 5 |
| 刊行年月 | 2007-09 |
| 開始ページ | 715 |
| 終了ページ | 720 |
| コンテンツ作成日 | 2007-06-11 |
| コンテンツ登録日 | 2011-10-31 |
| 抄録 | The relationship between the structure and cytotoxicactivity of azulenequinones and trihaloacetylazulenes wasinvestigated based on theoretical calculations. Four differentdipole moments (?G, ?ESP-G, ?W and ?ESP-W) and heats offormation (?Hf) of the azulenequinones [1-27] andtrihaloacetylazulenes [28a,b-40a,b] were separately calculatedin gas phase and aqueous solution using the conductor-likescreening model/parametric method 3 (COSMO/PM3)method. The cytotoxic activity of azulenequinones was wellcorrelated to ??Hf, HOMO energy and ?ESP-w. The cytotoxicactivity of trihaloacetylazulenes was correlated to ??Hf,LUMO energy and ?ESP-W. QSAR may be applicable topredict the cytotoxicity of azulenequinones andtrihaloacetylazulenes.Azulene chemistry, including synthesis and their physicaland chemical properties, has been extensively studied formore than four decades (1-4).Azulene derivatives have shown diverse biologicalactivities, such as antibacterial (5), anti-ulcer (6) and relaxantactivities (7), inhibition of thromboxane A2-inducedvasoconstriction and thrombosis (8), acute toxicity and localanesthetic activity (9). Naphthoquinones have shownantifungal, antibiotic, antimalarial and antitumor activities(10-11). Azulenequinone is a nonbenzenoid aromaticquinone (10-13) and also a naphthoquinone isomer. Werecently reported the cytotoxic activity of azulenequinonesagainst human oral tumor cell lines (14) and the inhibitionof LPS-stimulated NO production in mouse macrophage-like Raw 264.7 cells by azulenequinones (15). We found that 7-isopropyl-3-(4-methylanilino)-2-methyl-1,5-azulenequinone[13] and 3-(3-guaiazulenyl)-1,5-azulenequinone [20] showedhigher tumor-specific cytotoxicity and induced apoptosis inhuman promyelocytic leukemia HL-60 and oral squamouscell carcinoma HSC-2 cells, possibly via the activation ofboth mitochondria-independent (extrinsic) and -dependent(intrinsic) pathways (14). We also reported the apoptosisinducingactivity of trihaloacetylazulenes against human oraltumor cell lines (16) and the inhibition of NO productionin LPS-stimulated mouse macrophage-like Raw 264.7cells by trihaloacetylazulenes (17). We also found thattrichloroacetylazulenes [28a-40a] generally showed highercytotoxicity and higher tumor-specific cytotoxicity ascompared with the corresponding trifluoroacetylazulenes[28b-40b] (16). Based on a molecular orbital calculationconcerning their physicochemical parameters and cytotoxicactivities, we investigated the QSAR of azulenequinones andtrihaloacetylazulenes. |
| キーワード | |
| 注記 | 6p. |
| 言語 | eng |
| 資源タイプ | text |
| ジャンル | |
| フォーマット | application/pdf |
| このアイテムを表示する：本文(pdf) |  ( 184.3KB) ダウンロード回数： 回 |
| このアイテムを表示する：URI | |
