Quantitative Structure-Cytotoxicity Relationship of Aurones

Seventeen aurones were subjected to quantitative structure-activity relationship (QSAR) analysis based on their cytotoxicity and tumor-specificity, in order to find their new biological activities. Cytotoxicity against three human oral squamous cell carcinoma cell lines and three oral mesenchymal ce...

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Bibliographic Details
Published in:Anticancer research 2017-11, Vol.37 (11), p.6169-6176
Main Authors: Uesawa, Yoshihiro, Sakagami, Hiroshi, Ikezoe, Naruhiko, Takao, Koichi, Kagaya, Hajime, Sugita, Yoshiaki
Format: Article
Language:English
Subjects:
Antineoplastic Agents - pharmacology
Apoptosis - drug effects
Benzofurans - pharmacology
Carcinoma, Squamous Cell - drug therapy
Carcinoma, Squamous Cell - pathology
Cell Proliferation - drug effects
Child
Female
Humans
Molecular Structure
Mouth Neoplasms - drug therapy
Mouth Neoplasms - pathology
Quantitative Structure-Activity Relationship
Tumor Cells, Cultured
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Summary:Seventeen aurones were subjected to quantitative structure-activity relationship (QSAR) analysis based on their cytotoxicity and tumor-specificity, in order to find their new biological activities. Cytotoxicity against three human oral squamous cell carcinoma cell lines and three oral mesenchymal cells was determined by the 3-(4,5-dimethylthiazol-2-yl)-2,5-diphenyltetrazolium bromide (MTT) method. Tumor specificity (TS) was evaluated by the ratio of the mean 50% cytotoxic concentration (CC ) against normal cells to that against tumor cell lines. Potency-selectivity expression (PSE) value was calculated by dividing TS by CC against tumor cells. Physicochemical, structural and quantum-chemical parameters were calculated based on the conformations optimized by force-field minimization. Sixteen out of seventeen aurones showed relatively higher cytotoxicity and tumor specificity. Among them, (2Z)-2-[(4-hydroxyphenyl)methylene]-3(2H)-benzofuranone [ ] showed the highest TS value and PSE values, comparable with those of doxorubicin and higher than 5-FU, respectively. TS values were correlated with molecular shape, size and polarizability rather than the types of substituted groups. Chemical modification of the lead compound may be a potential choice for designing a new type of anticancer drugs.
ISSN:0250-7005
1791-7530
DOI:10.21873/anticanres.12066