Synthesis of polyunsaturated fatty boronic esters and their in vitro inhibition to HCT116 cell lines |
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| Institution: | 1. Department of Food Science and Engineering, Ocean University of China, 5 Yushan Rd., Qingdao, 266003, China;2. Beijing Advanced Innovation Center for Food Nutrition and Human Health, Beijing Technology and Business University, Beijing 100048, China;1. Department of Chemistry, Xihua University, Chengdu 610039, China;2. Chengdu Institute of Organic Chemistry, Chinese Academy of Sciences, Chengdu 610041, China;3. University of Chinese Academy of Sciences, Beijing 100049, China;4. College of Chemistry, Sichuan University, China;1. College of Food Science and Engineering, Ocean University of China, No. 5, Yushan Road, Qingdao 266003, Shandong Province, China;2. Technology Center of Qingdao Customs District, No. 70, Qutangxia Road, Qingdao 266002, Shandong Province, China;3. Laboratory of Marine Drugs and Biological Products, Pilot National Laboratory for Marine Science and Technology, (Qingdao), No. 1, Wenhai Road, Qingdao 266237, Shandong Province, China |
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| Abstract: | 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. |
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| Keywords: | Polyunsaturated fatty acids Synthesis Boron Blue LED Vacuum HCT116 |
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