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Enhanced cellular uptake efficiency of DCM probes or SN38 conjugating with phenylboronic acids.
Bioorganic & Medicinal Chemistry ( IF 3.3 ) Pub Date : 2020-02-17 , DOI: 10.1016/j.bmc.2020.115377 Qiumeng Zhang 1 , Rui Che 1 , Wei Lu 1
Bioorganic & Medicinal Chemistry ( IF 3.3 ) Pub Date : 2020-02-17 , DOI: 10.1016/j.bmc.2020.115377 Qiumeng Zhang 1 , Rui Che 1 , Wei Lu 1
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High-level of sialic acid (SA) expression on the surface of cancer cells is observed extremely common. Phenylboronic acids (PBAs) have a high affinity with SA. The cellular uptake efficiency could be enhanced by the strategy of introducing PBA fragments to the compounds. In this work, we synthesized five new probes with the Dicyanomethylene-4H-pyran (DCM) fluorophore, three of them conjugated with different phenylboronic acid fragments. By cellular uptake experiments, DLCB and DLAB showed enhanced cellular uptake abilities compared with DLN and DLO. These two effective phenylboronic acid fragments were then conjugated with SN-38 and the conjugates showed enhanced cellular uptake abilities by 3-fold or 7-fold compared with irinotecan. In summary, the strategy of introducing 4-carboxyphenylboronic acid and 3-amino-benzoxaborole groups shows great potential in drug delivery system. Moreover, the released linkers between boric acid and drugs deserve further studies.
中文翻译：
与苯基硼酸结合的DCM探针或SN38的增强的细胞摄取效率。
观察到癌细胞表面高水平的唾液酸（SA）表达非常普遍。苯硼酸（PBA）与SA具有高亲和力。通过将PBA片段引入化合物中的策略可以提高细胞摄取效率。在这项工作中，我们用双氰基亚甲基-4H-吡喃（DCM）荧光团合成了五个新探针，其中三个与不同的苯基硼酸片段缀合。通过细胞摄取实验，与DLN和DLO相比，DLCB和DLAB显示出增强的细胞摄取能力。然后将这两个有效的苯基硼酸片段与SN-38偶联，与伊立替康相比，偶联物的细胞摄取能力提高了3倍或7倍。综上所述，引入4-羧基苯基硼酸和3-氨基-苯并a硼烷基的策略在药物递送系统中显示出巨大的潜力。此外，硼酸和药物之间释放的连接子值得进一步研究。
更新日期：2020-02-12
中文翻译：
与苯基硼酸结合的DCM探针或SN38的增强的细胞摄取效率。
观察到癌细胞表面高水平的唾液酸（SA）表达非常普遍。苯硼酸（PBA）与SA具有高亲和力。通过将PBA片段引入化合物中的策略可以提高细胞摄取效率。在这项工作中，我们用双氰基亚甲基-4H-吡喃（DCM）荧光团合成了五个新探针，其中三个与不同的苯基硼酸片段缀合。通过细胞摄取实验，与DLN和DLO相比，DLCB和DLAB显示出增强的细胞摄取能力。然后将这两个有效的苯基硼酸片段与SN-38偶联，与伊立替康相比，偶联物的细胞摄取能力提高了3倍或7倍。综上所述，引入4-羧基苯基硼酸和3-氨基-苯并a硼烷基的策略在药物递送系统中显示出巨大的潜力。此外，硼酸和药物之间释放的连接子值得进一步研究。
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