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Synthesis and biological evaluation of peptidyl organotrifluoroborates and their corresponding boron analogs

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Abstract

Six peptidyl organotrifluoroborates and their corresponding boronate esters and/or boronic acid analogs were designed and synthesized. Their anti-proliferative activity against hepatocellular carcinoma cells (HepG2) and human metastatic breast cancer cells (MDA-MB231) were evaluated by use of an MTT assay. Potassium {4-[(3S,6S,9S)-3,6-dibenzyl-9-isopropyl-4,7,10-trioxo-11-oxa-2,5,8-triazadodecyl]phenyl}trifluoroborate (B6) was potent (IC50 = 29.9 μM) against MDA-MB231, and {4-[(3S,6S,9S)-6-benzyl-3-((benzyloxy)methyl)-9-isopropyl-4,7,10-trioxo-11-oxa-2,5,8-triazadodecyl]phenyl}boronic acid (B9) and Potassium {4-[(3S,6S,9S)-6-benzyl-3-((benzyloxy)methyl)-9-isopropyl-4,7,10-trioxo-11-oxa-2,5,8-triazadodecyl]phenyl}trifluoroborate (B10) had broad anti-proliferative activity against HepG2 (IC50 = 24.7 and 21.8 μM, respectively) and MDA-MB231 (IC50 = 24.5 and 18.9 μM, respectively).

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Authors and Affiliations

  1. Department of Chemistry, Tamkang University, No. 151 Yingzhuan Rd., Tamsui Dist., New Taipei City, 25137, Taiwan, ROC

    Chia-Hua Tsai, Chia-Hung Lin, Ching-Tien Hsieh, Chih-Cheng Cai, Ting-Ju Lin, Pin-Yi Liu, Meng-Hsuan Lin, Meng-Ju Wu, Chia-Chieh Fu & Po-Shen Pan

  2. Graduate Institute of Natural Products, Kaohsiung Medical University, 100 Shi-Chuan 1st Rd., Kaohsiung, 80708, Taiwan, ROC

    Yang-Chang Wu & Fang-Rong Chang

  3. Graduate Institute of Integrated Medicine, College of Chinese Medicine, China Medical University, Taichung, 404, Taiwan, ROC

    Yang-Chang Wu

  4. Cancer Center, Kaohsiung Medical University Hospital, Kaohsiung, 807, Taiwan, ROC

    Fang-Rong Chang

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  1. Chia-Hua Tsai
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  2. Chia-Hung Lin
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  12. Po-Shen Pan
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Correspondence to Po-Shen Pan.

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Tsai, CH., Lin, CH., Hsieh, CT. et al. Synthesis and biological evaluation of peptidyl organotrifluoroborates and their corresponding boron analogs. Res Chem Intermed 40, 2187–2198 (2014). https://doi.org/10.1007/s11164-014-1596-7

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  • DOI: https://doi.org/10.1007/s11164-014-1596-7

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