Aqueous Red‐Emissive Probe for the Selective Fluorescent Detection of Cysteine by Deprotection/Cyclization Cascade Resulting in Large Stokes' Shift. Issue 21 (5th March 2018)

• Record Type: Journal Article
• Authors: Kim, Youngsam; Choi, Minsuk; Mulay, Sandip V.; Jang, Minkyung; Kim, Jin Yong; Lee, Woo‐Hyun; Jon, Sangyong; Churchill, David G.
• Is Part Of: Chemistry. Volume 24:Issue 21(2018)
• Page Start: 5623
• Page End: 5629
• Publication Date: 2018-03-05
• Subjects: biological chemistry -- cysteine -- IVIS imaging -- fluorescent probes -- sensors; Chemistry -- Periodicals; 540
• DOI: 10.1002/chem.201706073
• Languages: English
• ISSNs: 0947-6539

Abstract

Abstract: Cysteine plays a crucial role in cellular functions and in human pathologies. However, the development of cysteine probes with extremely accurate detection is still a key challenge for the field. Herein, we have fully characterized and developed a novel selective fluorescent probe: red emission, aqueous detection and large Stokes' shift for cysteine (Reals‐C ). Key in the probe synthesis is a Michael addition onto an acroylate group and subsequent intramolecular cyclization. The probe exhibits analyte detection via an intricate role set up by the leaving groups so to discriminate and form the red‐emissive analyte sensing platform ( λ ex =471 nm, λ em =637 nm) through a chemical cascade pathway. Furthermore, the sensing ability of the probe was demonstrated by both in vitro and in vivo assays. This probe enables for successfully endogenous cysteine sensing in HaCaT human keratinocytes through comparison with a commercial thiol‐sensitive probe;Reals‐C shows excellent in vivo cysteine detection in a drug‐induced animal liver injury model. Abstract : An animal model and ex vivo follow‐up helped to validate the design of a cysteine reactive probe. The probe bears two adjacent amino groups; the triggering action of the probe with Cys resulted in ring closure at the probe and formation of a red‐shifted skeleton the fluorescence response of which can easily be visualized in cells.