Design, Synthesis And Biological Evaluation Of Emodin Derivatives And Aloe-emodin Derivatives

Emodin and Aloe-emodin are all belong to the anthraquinones of emodin type which have several hydroxys on the aromatic ring. They all have the biological activity of antibiosis, anti-inflammatory and anti-tumor. They can embed in the DNA and combine with it, then to interdict the replication and transcription of DNA so that to make the cancer cells apotosis because the coplanar of the three rings. The excess ROS which could be produced largely by anthraquinone would make the limit capability of cancer cells adapting itself to it. In this article, some anti-tumor drugs which target point to DNA or mitochondria and the mechanism of anti-tumor were summarized.The previous study shows that the quatermary ammonium salt group is contribute to improve the cytotoxicity largely. We have synthesized two kinds of new tertiary amines whose shortest alkyl chain is ethyl rather than methyl. The two compounds were used to combine with emodin and then we got four new compounds of the derivatives of emodin-quaternary ammonium slat. These new compounds could be used to make comparison with the former molecules. Even though the cytotoxicity of the new molecules is better, the route of synthesis is too long and the productivity is lower. For getting over the short coming, the author used aloe-emodin to instead of emodin and synthesized 23 kinds of derivatives of quaternary ammonium salt of aloe-emodin, so that we can make the route shorter and the productivity higher. The structure of all of the new compounds were characterized by 1H NMR, ESI-MS and melting point, apart of them also characterized by 13C NMR and Elemental analysis.The great majority of the new compounds have been tested in cell growth inhibitory of effects in vitro by MTT assay. The results showed that the appropriate length and amount of alkyl chain in the quatermary ammonium salt group are so important to the cytotoxicity of the molecules. This maybe relate to the fat-solution.In addition, it is important that the hydroxys are exposed or not, because the hydroxys are contribute to produce the ROS.