Cytotoxic properties of the alkaloid rutaecarpine and its oligocyclic derivatives and chemical modifications to enhance water-solubility. Issue 21 (1st November 2017)

• Record Type: Journal Article
• Authors: Huang, Guozheng; Drakopoulos, Antonios; Saedtler, Marco; Zou, Huijuan; Meinel, Lorenz; Heilmann, Jörg; Decker, Michael
• Is Part Of: Bioorganic & medicinal chemistry letters. Volume 27:Issue 21(2017)
• Page Start: 4937
• Page End: 4941
• Publication Date: 2017-11-01
• Subjects: Rutaecarpine -- SiriusT3 -- Cytotoxicity -- Solubility; Bioorganic chemistry -- Periodicals; Pharmaceutical chemistry -- Periodicals; 572
• DOI: 10.1016/j.bmcl.2017.08.045
• Languages: English
• ISSNs: 0960-894X

Abstract

Graphical abstract: Abstract: The alkaloid rutaecarpine and its derivatives have been described as cytotoxic and hold potential as antitumor agents. Nevertheless, their synthesis is demanding and compounds display poor water solubility. Herein, we describe the synthesis of two sets of rutaecarpine derivatives with amine functions to improve solubility. Using a classic shake-flask experiment and a potentiometric titration platform, the water solubility of the compounds was determined. Solubility improved significantly with the amine functions connected over the indole- N atom. Reduction of metabolic activity and cell viability on HeLa cells was in the same range or better for these derivatives compared to the chemically unaltered parent compounds prepared in a new synthetic procedure established in our group.