Research Institute for Medicines (iMed.ULisboa), Faculty of Pharmacy, Universidade de Lisboa, Lisbon, Portugal.
Centro de Química-Física Molecular and Institute of Nanoscience and Nanotechnology, Instituto Superior Técnico, Universidade de Lisboa, Lisboa, Portugal.
Chemistry. 2018 Aug 27;24(48):12495-12499. doi: 10.1002/chem.201802515. Epub 2018 Jul 23.
Herein a new class of iminoboronates obtained from 2-acetylbenzene boronic acids and aminophenols is presented. The N,O-ligand topology enabled the formation of an additional B-O bond that locks the boron center in a tetrahedral geometry. This molecular arrangement decisively contributes to improve the construct's stability in biocompatible conditions and retaining the iminoboronate reversibility in more acidic environments. 2-Acetylbenzene boronic acid was reacted with a fluorescent amino-coumarin to yield a stable and non-fluorescent N,O-iminoboronate. This mechanism was further used to assemble a folate receptor targeting conjugate that selectively delivered the fluorescent amino-coumarin to MDA-MB-231 human breast cancer cells.
本文介绍了一类新型的亚氨基硼酸酯，它是由 2-乙酰苯硼酸和氨基酚得到的。N,O-配体拓扑结构能够形成额外的 B-O 键，使硼中心处于四面体几何构型。这种分子排列显著提高了化合物在生物相容性条件下的稳定性，并在更酸性的环境中保持亚氨基硼酸酯的可逆性。2-乙酰苯硼酸与荧光氨基香豆素反应得到稳定的非荧光 N,O-亚氨基硼酸酯。这种机制进一步用于组装叶酸受体靶向缀合物，该缀合物选择性地将荧光氨基香豆素递送到 MDA-MB-231 人乳腺癌细胞中。
