title: Preparation of 1,8-di-O-alkylaloe-emodins and 15-amino-, 15-thiocyano-, and 15-selenocyanochrysophanol derivatives from aloe-emodin and studying their cytotoxic effects.
abstract: 1,8-di-O-alkylaloe-emodin derivatives (namely, methyl-, propyl-, hexyl-, dodecyl-, and octadecyl) were synthesized from naturally occurring aloe-emodin. Further, derivatives having various substituents such as diethylamino, pyrrolidinyl, piperidinyl, methylpiperazinyl, imidazolyl, thiocyano and selenocyano groups at the 15 position of chrysophanol and 1,8-di-O-hexylchrysophanol from aloe-emodin were synthesized. The cytotoxic effects of these derivatives on less P-glycoprotein (P-gp)-expressing HCT 116 cells and stably P-gp-expressing Hep G2 cells were evaluated by performing 3-(4,5-dimethylthiazol-2-yl)-2,5-diphenyltetrazolium bromide (MTT) assay. Among these products, several of them exhibited markedly higher potent cytotoxic effects not only on HCT116 cells but also Hep G2 cancer cells as compared to aloe-emodin.
authors: Faculty of Pharmaceutical Sciences, Josai University.
authors: Xing-Ri
authors: XR
authors: Cui
authors: Kazutoshi
authors: K
authors: Takahashi
authors: Takeshi
authors: T
authors: Shimamura
authors: Jyunichi
authors: J
authors: Koyanagi
authors: Fusao
authors: F
authors: Komada
authors: Setsuo
authors: S
authors: Saito
mesh_terms: D020168:ATP Binding Cassette Transporter, Subfamily B, Member 1 / Q000378:metabolism; D000504:Aloe / Q000737:chemistry; D000880:Anthraquinones / Q000737:chemistry*; D000972:Antineoplastic Agents, Phytogenic / Q000737:chemistry* / Q000494:pharmacology*; D045744:Cell Line, Tumor; D002851:Chromatography, High Pressure Liquid; D002855:Chromatography, Thin Layer; D004354:Drug Screening Assays, Antitumor; D006801:Humans; D009682:Magnetic Resonance Spectroscopy; D016566:Organoselenium Compounds / Q000737:chemistry* / Q000494:pharmacology*; D021241:Spectrometry, Mass, Electrospray Ionization; D016339:Spectrometry, Mass, Fast Atom Bombardment; D013778:Tetrazolium Salts; D013844:Thiazoles
chemical_list: D020168:ATP Binding Cassette Transporter, Subfamily B, Member 1; D000880:Anthraquinones; D000972:Antineoplastic Agents, Phytogenic; D016566:Organoselenium Compounds; D013778:Tetrazolium Salts; D013844:Thiazoles; C518327:aloe emodin; C022616:thiazolyl blue