Premium
N,O ‐Iminoboronates: Reversible Iminoboronates with Improved Stability for Cancer Cells Targeted Delivery
Author(s) -
Lopes Ricardo M. R. M.,
Ventura Ana E.,
Silva Liana C.,
Faustino Hélio,
Gois Pedro M. P.
Publication year - 2018
Publication title -
chemistry – a european journal
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.687
H-Index - 242
eISSN - 1521-3765
pISSN - 0947-6539
DOI - 10.1002/chem.201802515
Subject(s) - conjugate , fluorescence , coumarin , boronic acid , chemistry , ligand (biochemistry) , amino acid , yield (engineering) , combinatorial chemistry , boron , biophysics , stereochemistry , receptor , materials science , biochemistry , organic chemistry , biology , mathematics , mathematical analysis , physics , quantum mechanics , metallurgy
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.