Synthesis of polyunsaturated fatty boronic esters and their in vitro inhibition to HCT116 cell lines

• Published in: Tetrahedron 2019-10, Vol.75 (41), p.130578, Article 130578
• Main Authors: Yuan, Yongkai, Chen, Peng, Zhang, Shuaizhong, Lan, Xiang, Liu, Zhuzhu, Wang, Dongfeng, Xu, Ying, Sun, Xun
• Format: Article
• Language: English
• Subjects: Blue LED; Boron; HCT116; Polyunsaturated fatty acids; Synthesis; Vacuum
• ISSN: 0040-4020; 1464-5416
• DOI: 10.1016/j.tet.2019.130578

Five polyunsaturated fatty boronic esters (PUFB) were synthesized using a photoinduced decarboxylative borylation reaction from corresponding polyunsaturated fatty acids (PUFA) and in vitro anti-proliferation activity of these molecules on HCT116 cell lines was tested. The yield of the photoinduced decarboxylative borylation reaction was negatively correlated with the number of double bonds in PUFA. Additionally, application of vacuum to the reaction significantly improved the yield. All PUFBs showed anti-proliferation effect on HCT116 cell lines and the mixture of the 5 PUFBs showed higher toxicity than each individual PUFB. Again, the cytotoxicity was positively correlated with number of double bonds. Furthermore, PUFBs showed weaker anticancer activity than the corresponding PUFAs and this is tentatively attributed to the change of antioxidant potency and we categorize PUFBs to “secondary antioxidants”. We hope our findings deepen the understanding of photoinduced decarboxylative borylation reaction and provide further insights to the design of PUFA based bioactive molecules. [Display omitted] •Five polyunsaturated fatty boronic esters were synthesized.•Application of vacuum to the reaction system significantly improved the yield.•Polyunsaturated fatty boronic esters were categorized to “secondary antioxidants”.