Methoxy- and acetoxy-8-oxoberbines--synthesis, antitumor activity, and interaction with DNA.
Most of the methoxy-8H-dibenzo[a,g]isoquinolin-8-ones 3a-h and their acetoxy derivatives 6a-e were synthesized by condensation of 1-oxo-1,2,3,4-tetrahydroisoquinolines 4a-c and homophthalic acid anhydrides 5a and b, ether cleavage and acetylation. These protoberberinones were tested for cytostatic activity in vitro using MDA-MB-231 mammary tumor cells and for interaction with native calf thymus DNA. Tetramethoxy-8-oxoberbine 3f shows an inhibition of cell proliferation of 87% at a concentration of 10(-5) mole; its cytostatic effect does not depend on intercalation into DNA.
Weimar
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C
Institute of Pharmacy and Sonderforschungsbereich 234, University of Regensburg, Germany.
von Angerer
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Wiegrebe
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D000970:Antineoplastic Agents / Q000138:chemical synthesis* / Q000494:pharmacology; D001600:Berberine Alkaloids / Q000138:chemical synthesis* / Q000494:pharmacology; D004247:DNA / Q000737:chemistry / Q000187:drug effects*; D004996:Ethidium; D006801:Humans; D013050:Spectrometry, Fluorescence; D013056:Spectrophotometry, Ultraviolet; D014407:Tumor Cells, Cultured / Q000187:drug effects; D014783:Viscosity
D000970:Antineoplastic Agents; D001600:Berberine Alkaloids; D004247:DNA; D004996:Ethidium