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A fully synthetic 6-aza-artemisinin bearing an amphiphilic chain generates aggregates and exhibits anti-cancer activities

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Abstract

Installation of a nitrogen at the C6 position of artemisinin facilitates the addition of a functional unit on the cyclohexane moiety (C-ring). In this study, conjugation of an amphiphilic chain, composed of sequentially connected hydrophilic oligoethylene glycol, hydrophobic alkyl chain, urea, and 4,4′-disubstituted biphenyl linker, imparted self-assembling properties. The fully synthetic mid-molecular weight 6-aza-artemisinin 6 bearing the amphiphilic moiety formed aggregates (approx. 200 nm) at ambient temperature and exhibited increased in vitro anti-cancer activities compared to the N-benzylated aza-artemisinin 5.

Graphical abstract: A fully synthetic 6-aza-artemisinin bearing an amphiphilic chain generates aggregates and exhibits anti-cancer activities

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Article information


Submitted
03 May 2020
Accepted
26 Jun 2020
First published
26 Jun 2020

Org. Biomol. Chem., 2020, Advance Article
Article type
Communication

A fully synthetic 6-aza-artemisinin bearing an amphiphilic chain generates aggregates and exhibits anti-cancer activities

H. Koi, N. Takahashi, Y. Fuchi, T. Umeno, Y. Muramatsu, H. Seimiya, S. Karasawa and H. Oguri, Org. Biomol. Chem., 2020, Advance Article , DOI: 10.1039/D0OB00919A

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