The first comparative study of the ability of different hydrophilic groups to water-solubilise fluorescent BODIPY dyes
作者:Anthony Romieu、Cédrik Massif、Sandra Rihn、Gilles Ulrich、Raymond Ziessel、Pierre-Yves Renard
DOI:10.1039/c3nj41093e
日期:——
A green-emitting BODIPY dye carrying a carboxylic acid at the meso-phenyl ring was derivatised with a set of eight different hydrophilic groups neutral, negatively- or positively-charged at physiological pH. The determination of both partition coefficient (log P) and fluorescence quantum yield (ΦF) for each polar BODIPY dye allows building the first water-solubility scale for such fluorescent organic materials. This valuable tool can be used to select the most suitable molecular candidate for converting a hydrophobic BODIPY scaffold into a water-soluble and brightly fluorescent dye, and for tuning its net electric charge/polarity according to the biolabelling application targeted for this specific fluorescent marker.
在内消旋苯环上带有羧酸的发绿光的 BODIPY 染料由一组八种不同的亲水基团衍生而成,这些亲水基团在生理 pH 下呈中性、带负电或带正电。通过测定每种极性 BODIPY 染料的分配系数 (log P) 和荧光量子产率 (ΦF),可以为此类荧光有机材料建立第一个水溶性标度。这一有价值的工具可用于选择最合适的候选分子,将疏水性 BODIPY 支架转化为水溶性且明亮的荧光染料,并根据针对该特定荧光标记的生物标记应用来调整其净电荷/极性。