[Development of Donor-acceptor-type Molecules and Their Application as Analytical Reagents].

IF 0.3 4区 医学 Q4 PHARMACOLOGY & PHARMACY
Tomohiro Umeno
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引用次数: 0

Abstract

π-Extended donor-acceptor (D-A)-type molecules, which bear both electron-donor and electron-acceptor substituents on the backbone, exhibit unique optical properties, such as bathochromic shifts in absorption and emission, large Stokes shifts, solvatochromic behavior, and fluorescence quenching in polar solvents. These unique properties are attributed to intramolecular charge transfer (ICT) or twisted intramolecular charge transfer (TICT) in the ground and excited states. This review article introduces three types of D-A-type molecules that are used as detection reagents for (1) methanol, (2) amino acids during solid-phase peptide synthesis (SPPS), and (3) amines present in the biological environment. For methanol detection, D-A-type fluorophores with basic guanidine moieties were developed to differentiate between methanol (MeOH) and ethanol (EtOH) based on the small difference in their pKa values (ΔpKa=0.4). Selective protonation of the guanidine moiety in methanol disrupts the D-A structure, allowing emission in the resultant polar environment. Similarly, an acid-base reaction between the hydrogen chloride (HCl) salts of the D-A-type molecules and amines is applied to detect amines during SPPS. In this method, a colorless solution of an HCl salt of the D-A-type molecule is deprotonated by amines, forming a yellow solution. This is the first reported quantitative and non-destructive colorimetric method for detecting amines. Finally, a turn-on-type amine-labeling reagent was developed for the nucleophilic aromatic substitution (SNAr) reaction. This new reagent enables protein staining of living cells with a large Stokes shift and without solvent-polarity-dependent fluorescence quenching.

[供体-受体型分子的开发及其作为分析试剂的应用]。
骨架上同时具有电子供体和电子受体取代基的π-扩展供体-受体(D-A)型分子表现出独特的光学特性,如吸收和发射的浴色偏移、较大的斯托克斯偏移、溶解变色行为以及在极性溶剂中的荧光淬灭。这些独特性质归因于基态和激发态的分子内电荷转移(ICT)或扭曲分子内电荷转移(TICT)。本综述文章介绍了三类 D-A 型分子,它们可用作(1)甲醇、(2)固相肽合成(SPPS)过程中的氨基酸和(3)生物环境中存在的胺的检测试剂。为了检测甲醇,我们开发了具有碱性胍基的 D-A 型荧光团,根据它们 pKa 值的微小差异(ΔpKa=0.4)来区分甲醇(MeOH)和乙醇(EtOH)。甲醇中胍基的选择性质子化会破坏 D-A 结构,使其在极性环境中发射。同样,D-A 型分子的氯化氢(HCl)盐与胺之间的酸碱反应也可用于在 SPPS 过程中检测胺。在这种方法中,D-A 型分子的氯化氢盐的无色溶液被胺类去质子化,形成黄色溶液。这是首次报道的定量和非破坏性比色法检测胺。最后,为亲核芳族取代(SNAr)反应开发了一种开启型胺标记试剂。这种新试剂可以对活细胞的蛋白质进行染色,具有较大的斯托克斯偏移,且不会产生溶剂极性依赖性荧光淬灭。
本文章由计算机程序翻译,如有差异,请以英文原文为准。
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来源期刊
CiteScore
0.60
自引率
0.00%
发文量
169
审稿时长
1 months
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