Methoxy- and acetoxy-8-oxoberbines--synthesis, antitumor activity, and interaction with DNA.

Abstract

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.

• Authors: C Weimar, S von Angerer, W Wiegrebe
• Journal: Archiv der Pharmazie (Arch Pharm (Weinheim)) Vol. 324 Issue 8 Pg. 509-18 (Aug 1991) ISSN: 0365-6233 [Print] Germany
• PMID: 1781733 (Publication Type: Journal Article)

Chemical References

• Antineoplastic Agents
• Berberine Alkaloids
• DNA
• Ethidium

Topics

• Antineoplastic Agents (chemical synthesis, pharmacology)
• Berberine Alkaloids (chemical synthesis, pharmacology)
• DNA (chemistry, drug effects)
• Ethidium
• Humans
• Spectrometry, Fluorescence
• Spectrophotometry, Ultraviolet
• Tumor Cells, Cultured (drug effects)
• Viscosity