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Quantitative Structure-Cytotoxicity Relationship of 2-Arylazolylchromones and 2-Triazolylchromones.
Nagai, Junko; Shi, Haixia; Sezaki, Natsuko; Yoshida, Nao; Bandow, Kenjiro; Uesawa, Yoshihiro; Sakagami, Hiroshi; Tomomura, Mineko; Tomomura, Akito; Takao, Koichi; Sugita, Yoshiaki.
Afiliación
  • Nagai J; Department of Medical Molecular Informatics, Meiji Pharmaceutical University, Tokyo, Japan.
  • Shi H; Shanghai Ninth People's Hospital, Shanghai Jiatong University School of Medicine, Shanghai, P.R. China.
  • Sezaki N; Meikai University Research Institute of Odontology, Sakado, Japan.
  • Yoshida N; Department of Pharmaceutical Sciences, Faculty of Pharmacy and Pharmaceutical Sciences, Josai University, Sakado, Japan.
  • Bandow K; Department of Pharmaceutical Sciences, Faculty of Pharmacy and Pharmaceutical Sciences, Josai University, Sakado, Japan.
  • Uesawa Y; Division of Biochemistry, Meikai University School of Dentistry, Sakado, Japan.
  • Sakagami H; Department of Medical Molecular Informatics, Meiji Pharmaceutical University, Tokyo, Japan uesawa@my-pharm.ac.jp.
  • Tomomura M; Shanghai Ninth People's Hospital, Shanghai Jiatong University School of Medicine, Shanghai, P.R. China.
  • Tomomura A; Department of Oral Health Sciences, Meikai University, Urayasu, Japan.
  • Takao K; Division of Biochemistry, Meikai University School of Dentistry, Sakado, Japan.
  • Sugita Y; Department of Pharmaceutical Sciences, Faculty of Pharmacy and Pharmaceutical Sciences, Josai University, Sakado, Japan.
Anticancer Res ; 39(12): 6479-6488, 2019 Dec.
Article en En | MEDLINE | ID: mdl-31810912
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.
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Texto completo: 1 Colección: 01-internacional Base de datos: MEDLINE Asunto principal: Neoplasias de la Boca / Carcinoma de Células Escamosas / Cromonas / Antineoplásicos Tipo de estudio: Prognostic_studies Límite: Humans Idioma: En Revista: Anticancer Res Año: 2019 Tipo del documento: Article País de afiliación: Japón Pais de publicación: Grecia
Texto completo
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Texto completo: 1 Colección: 01-internacional Base de datos: MEDLINE Asunto principal: Neoplasias de la Boca / Carcinoma de Células Escamosas / Cromonas / Antineoplásicos Tipo de estudio: Prognostic_studies Límite: Humans Idioma: En Revista: Anticancer Res Año: 2019 Tipo del documento: Article País de afiliación: Japón Pais de publicación: Grecia