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Fluorescent probes guided by a new practical performance regulation strategy to monitor glutathione in living systems.

ABSTRACT: Glutathione (GSH) plays an important role in the body's biochemical defense system, and the detection of GSH in a physiological system is an important tool for understanding redox homeostasis. Protection-deprotection strategies have proven to be the most reliable, among existing detection methods. However, the understanding of how various electronic and steric effects influence a probe's ability to recognize a substrate is still lacking. In this study, we have analyzed various substituent effects on a GSH probe template via theoretical calculations and constructed the performance regulation and control strategy for this kind of probe. We then developed a series of guided probes using eighteen different acrylic ester derivatives to mask the fluorescence of fluorescein. The optical performance differences between the guided probes strongly supported the applicability of our proposed guiding strategy. Moreover, the positively guided probes are excellent for imaging GSH distribution in living cells and mice.

SUBMITTER: She M

PROVIDER: S-EPMC6249757 | biostudies-literature | 2018 Nov

REPOSITORIES: biostudies-literature

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Fluorescent probes guided by a new practical performance regulation strategy to monitor glutathione in living systems.

She Mengyao M Wang Zhaohui Z Luo Tianyou T Yin Bing B Liu Ping P Liu Jing J Chen Fulin F Zhang Shengyong S Li Jianli J

Chemical science 20180925 42

Glutathione (GSH) plays an important role in the body's biochemical defense system, and the detection of GSH in a physiological system is an important tool for understanding redox homeostasis. Protection-deprotection strategies have proven to be the most reliable, among existing detection methods. However, the understanding of how various electronic and steric effects influence a probe's ability to recognize a substrate is still lacking. In this study, we have analyzed various substituent effect ...[more]

PMID: 30542554

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Project description:Metals are essential for life, playing critical roles in all aspects of the central dogma of biology (e.g., the transcription and translation of nucleic acids and synthesis of proteins). Redox-inactive alkali, alkaline earth, and transition metals such as sodium, potassium, calcium, and zinc are widely recognized as dynamic signals, whereas redox-active transition metals such as copper and iron are traditionally thought of as sequestered by protein ligands, including as static enzyme cofactors, in part because of their potential to trigger oxidative stress and damage via Fenton chemistry. Metals in biology can be broadly categorized into two pools: static and labile. In the former, proteins and other macromolecules tightly bind metals; in the latter, metals are bound relatively weakly to cellular ligands, including proteins and low molecular weight ligands. Fluorescent probes can be useful tools for studying the roles of transition metals in their labile forms. Probes for imaging transition metal dynamics in living systems must meet several stringent criteria. In addition to exhibiting desirable photophysical properties and biocompatibility, they must be selective and show a fluorescence turn-on response to the metal of interest. To meet this challenge, we have pursued two general strategies for metal detection, termed "recognition" and "reactivity". Our design of transition metal probes makes use of a recognition-based approach for copper and nickel and a reactivity-based approach for cobalt and iron. This Account summarizes progress in our laboratory on both the development and application of fluorescent probes to identify and study the signaling roles of transition metals in biology. In conjunction with complementary methods for direct metal detection and genetic and/or pharmacological manipulations, fluorescent probes for transition metals have helped reveal a number of principles underlying transition metal dynamics. In this Account, we give three recent examples from our laboratory and collaborations in which applications of chemical probes reveal that labile copper contributes to various physiologies. The first example shows that copper is an endogenous regulator of neuronal activity, the second illustrates cellular prioritization of mitochondrial copper homeostasis, and the third identifies the "cuprosome" as a new copper storage compartment in Chlamydomonas reinhardtii green algae. Indeed, recognition- and reactivity-based fluorescent probes have helped to uncover new biological roles for labile transition metals, and the further development of fluorescent probes, including ones with varied Kd values and new reaction triggers and recognition receptors, will continue to reveal exciting and new biological roles for labile transition metals.

Dataset Information

Fluorescent probes guided by a new practical performance regulation strategy to monitor glutathione in living systems.

Publications

Fluorescent probes guided by a new practical performance regulation strategy to monitor glutathione in living systems.

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