著者

恵沢 敏成 井上 裕 村田 勇 高尾 浩一 杉田 義昭 金本 郁男

出版者

Hindawi Publishing Corporation

雑誌

International Journal of Medicinal Chemistry (ISSN:20902069)

巻号頁・発行日

vol.2019, no.7530480, pp.1-14,

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The purpose of this study was to evaluate the physicochemical properties of piperine (PP) in ground mixtures (GMs) of PP with α-, β-, or γ-cyclodextrin (CD) under conditions of humidity, heat, and humidity-heat. In solid-state fluorescence measurements, the fluorescence maxima for GM (PP/αCD = 1/2), GM (PP/βCD = 1/1), and GM (PP/γCD = 1/1) were observed at 463, 472, and 469 nm, respectively. On the other hand, the humidified GMs exhibited maxima at 454, 460, and 465 nm, while the humidified-heated samples displayed fluorescence maxima at 455, 455, and 469 nm, respectively. Therefore, the molecular behavior of PP with α, β, and γCD was concluded to vary upon the coordination of water molecules. NIR and solid-state fluorescence measurements revealed that the molecular behavior of PP inside the α, β, and γCD cavity changed by water and heat factors depends on the mobility of the methylenedioxyphenyl group.This is an open access article distributed under the Creative Commons Attribution License, which permits unrestricted use, distribution, and reproduction in any medium, provided the original work is properly cited.

著者

島田 智哉子 植沢 芳広 Ishii-Nozawa Reiko 石原 真理子 Kagaya Hajime 金本 大成 寺久保 繁美 中島 秀喜 高尾 浩一 杉田 義昭 坂上 宏

出版者

International Institute of Anticancer Research

雑誌

Anticancer Research (ISSN:2507005)

巻号頁・発行日

vol.34, no.10, pp.5405-5412, 2014-10

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Background: Fifteen 3-styrylchromones were subjected to quantitative structure?activity relationship (QSAR) analysis based on their cytotoxicity, tumor selectivity and anti-HIV activity, in order to explore their 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 CC50 (50% cytotoxic concentration) against normal human oral cells to that against OSCC cell lines. Anti-HIV activity was evaluated by the ratio of CC50 to EC50 (50% cytoprotective concentration from HIV infection). Physicochemical, structural and quantum-chemical parameters were calculated based on the conformations optimized by the LowModeMD method followed by the density functional theory (DFT) method. Results: All 3-styrylchromone derivatives showed moderate-to-high tumor selectivity. Especially, compounds that have a methoxy group at 6-position of the chromone ring and hydroxyl group at 4'-position of phenyl group in styryl moiety [11] showed the highest tumor-selectivity. On the other hand, their cytotoxicity against normal cells showed good correlation to the descriptors that reflect hydrophobic interaction and molecular shapes. Conclusion: Multivariate statistics with chemical descriptors for the location of substituted group, molecular shape and electrostatic interaction may be useful for designing the most favorable compound with higher tumor selectivity.