Synthesis of 10-O-aryl-substituted berberine derivatives by Chan-Evans-Lam coupling and investigation of their DNA-binding properties.

ABSTRACT: Eleven novel 10-O-aryl-substituted berberrubine and berberine derivatives were synthesized by the Cu²⁺-catalyzed Chan-Evans-Lam coupling of berberrubine with arylboronic acids and subsequent 9-O-methylation. The reaction is likely introduced by the Cu²⁺-induced demethylation of berberrubine and subsequent arylation of the resulting 10-oxyanion functionality. Thus, this synthetic route represents the first successful Cu-mediated coupling reaction of berberine substrates. The DNA-binding properties of the 10-O-arylberberine derivatives with duplex and quadruplex DNA were studied by thermal DNA denaturation experiments, spectrometric titrations as well as CD and LD spectroscopy. Fluorimetric DNA melting analysis with different types of quadruplex DNA

SUBMITTER: Wickhorst PJ 

PROVIDER: S-EPMC8111429 | biostudies-literature | 2021

REPOSITORIES: biostudies-literature