title: In vitro cytotoxicity of the protoberberine-type alkaloids.
abstract: In vitro cytotoxic activities of 24 quaternary protoberberine alkaloids related to berberine have been evaluated using a human cancer cell line panel coupled with a drug sensitivity database. Extending the alkyl chain at position 8 or 13 strongly influenced the cytotoxic activity, that is, relative lipophilicity as well as the size of the substituent affects cytotoxicity. The highest level of activity was observed in 8- or 13-hexyl-substituted derivatives of berberine. Structure-activity relationships are described.
authors.affiliation: Kobe Pharmaceutical University, 4-19-1 Motoyamakita, Higashinada-ku, Kobe 658-8558, Japan. K-iwasa@kobepharma-u.ac.jp
authors.forename: K
authors.initials: K
authors.lastname: Iwasa
authors.forename: M
authors.initials: M
authors.lastname: Moriyasu
authors.forename: T
authors.initials: T
authors.lastname: Yamori
authors.forename: T
authors.initials: T
authors.lastname: Turuo
authors.forename: D U
authors.initials: DU
authors.lastname: Lee
authors.forename: W
authors.initials: W
authors.lastname: Wiegrebe
mesh_terms: D000818:Animals; D000972:Antineoplastic Agents, Phytogenic / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology; D001599:Berberine / Q000031:analogs & derivatives* / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology; D001600:Berberine Alkaloids / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology; D001932:Brain Neoplasms / Q000378:metabolism; D001943:Breast Neoplasms / Q000378:metabolism; D003110:Colonic Neoplasms / Q000378:metabolism; D018360:Crystallography, X-Ray; D016208:Databases, Factual; D004317:Doxorubicin / Q000494:pharmacology; D005260:Female; D006801:Humans; D008175:Lung Neoplasms / Q000378:metabolism; D009682:Magnetic Resonance Spectroscopy; D051379:Mice; D016685:Mitomycin / Q000494:pharmacology; D015394:Molecular Structure; D010051:Ovarian Neoplasms / Q000378:metabolism; D010207:Papaver / Q000737:chemistry; D010946:Plants, Medicinal; D013274:Stomach Neoplasms / Q000378:metabolism; D013329:Structure-Activity Relationship; D014407:Tumor Cells, Cultured / Q000187:drug effects
chemical_list: D000972:Antineoplastic Agents, Phytogenic; D001600:Berberine Alkaloids; C034384:coptisine; D001599:Berberine; D016685:Mitomycin; D004317:Doxorubicin; C005413:palmatine