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Nucleophilicity of cysteine and related biothiols and the development of fluorogenic probes and other applications
Organic & Biomolecular Chemistry ( IF 2.9 ) Pub Date : 2020-10-28 , DOI: 10.1039/d0ob01754j Alane P A Dos Santos 1 , Jordan K da Silva 1 , Jannyely M Neri 1 , Ana C O Neves 1 , Djalan F de Lima 1 , Fabrício G Menezes 1
Organic & Biomolecular Chemistry ( IF 2.9 ) Pub Date : 2020-10-28 , DOI: 10.1039/d0ob01754j Alane P A Dos Santos 1 , Jordan K da Silva 1 , Jannyely M Neri 1 , Ana C O Neves 1 , Djalan F de Lima 1 , Fabrício G Menezes 1
Affiliation
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Biothiols such as L-cysteine, L-homocysteine, and glutathione play essential roles in many biological processes, and are directly associated with several health conditions. Therefore, the development of fast, selective, sensitive, and inexpensive methods for quantitatively analyzing biothiols in aqueous solution, but especially in biological samples, is a very attractive research field. In this feature review, we have approached the relevance of biothiols’ nucleophilicity to develop selective fluorogenic probes. Since biothiols have considerable structural similarity, relevant strategies are in full development, including several fluorescent molecular platforms, specific receptor sites, reaction conditions, and optical responses. All of these features are properly presented and discussed. Biothiol sensing protocols are based on traditional organic chemistry reactions such as (hetero)aromatic nucleophilic substitution, addition, and substitution at carbonyl carbon, conjugate addition, and nucleophilic substitution at saturated carbon, amongst others including combined processes; furthermore, mechanistic aspects are detailed herein, including some interesting historical contexts. The feasibility of related fluorogenic probes is illustrated by analysis in complex matrices such as serum, cells, tissues, and animal models. Applications of these reactions in more complex systems such as sulfhydryl-based peptides and proteins are also presented, aiming at functionalizing and detecting these nucleophiles. Most literature cited in this review is recent; however, some other prominent works are also detailed. It is believed that this review may be accessible for many academic levels and may efficiently contribute not only to popularizing science but also to the rational development of fluorogenic probes for biothiol sensing.
中文翻译：
半胱氨酸和相关生物硫醇的亲核性以及荧光探针的开发和其他应用
L-半胱氨酸、 L-高半胱氨酸和谷胱甘肽等生物硫醇在许多生物过程中发挥着重要作用，并且与多种健康状况直接相关。因此，开发快速、选择性、灵敏且廉价的方法来定量分析水溶液中，尤其是生物样品中的生物硫醇，是一个非常有吸引力的研究领域。在这篇专题综述中，我们探讨了生物硫醇亲核性的相关性，以开发选择性荧光探针。由于生物硫醇具有相当大的结构相似性，相关策略正在全面开发中，包括几个荧光分子平台、特定受体位点、反应条件和光学响应。所有这些功能都得到了适当的呈现和讨论。生物硫醇传感方案基于传统的有机化学反应，例如（杂）芳香族亲核取代、加成和羰基碳取代、共轭加成和饱和碳亲核取代等，其中包括组合过程；此外，本文详细介绍了机械方面，包括一些有趣的历史背景。通过对血清、细胞、组织和动物模型等复杂基质的分析，说明了相关荧光探针的可行性。还介绍了这些反应在更复杂的系统（例如基于巯基的肽和蛋白质）中的应用，旨在功能化和检测这些亲核试剂。本评论中引用的大多数文献都是最新的；然而，其他一些著名的作品也有详细介绍。 我们相信这篇综述可能适合许多学术水平，并且不仅可以有效地促进科学普及，而且可以有效地促进生物硫醇传感荧光探针的合理开发。
更新日期：2020-11-17
中文翻译：
半胱氨酸和相关生物硫醇的亲核性以及荧光探针的开发和其他应用
L-半胱氨酸、 L-高半胱氨酸和谷胱甘肽等生物硫醇在许多生物过程中发挥着重要作用，并且与多种健康状况直接相关。因此，开发快速、选择性、灵敏且廉价的方法来定量分析水溶液中，尤其是生物样品中的生物硫醇，是一个非常有吸引力的研究领域。在这篇专题综述中，我们探讨了生物硫醇亲核性的相关性，以开发选择性荧光探针。由于生物硫醇具有相当大的结构相似性，相关策略正在全面开发中，包括几个荧光分子平台、特定受体位点、反应条件和光学响应。所有这些功能都得到了适当的呈现和讨论。生物硫醇传感方案基于传统的有机化学反应，例如（杂）芳香族亲核取代、加成和羰基碳取代、共轭加成和饱和碳亲核取代等，其中包括组合过程；此外，本文详细介绍了机械方面，包括一些有趣的历史背景。通过对血清、细胞、组织和动物模型等复杂基质的分析，说明了相关荧光探针的可行性。还介绍了这些反应在更复杂的系统（例如基于巯基的肽和蛋白质）中的应用，旨在功能化和检测这些亲核试剂。本评论中引用的大多数文献都是最新的；然而，其他一些著名的作品也有详细介绍。 我们相信这篇综述可能适合许多学术水平，并且不仅可以有效地促进科学普及，而且可以有效地促进生物硫醇传感荧光探针的合理开发。
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