Aqueous Red-Emissive Probe for the Selective Fluorescent Detection of Cysteine by Deprotection/Cyclization Cascade Resulting in Large Stokes' Shift

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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 (lambda(ex) = 471 nm, lambda(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.
Publisher
WILEY-V C H VERLAG GMBH
Issue Date
2018-04
Language
English
Article Type
Article
Keywords

TURN-ON PROBE; LIVING CELLS; HOMOCYSTEINE; CYS; GLUTATHIONE; CHEMOSENSORS; MITOCHONDRIA; BIOTHIOLS; PROGRESS; THIOLS

Citation

CHEMISTRY-A EUROPEAN JOURNAL, v.24, no.21, pp.5623 - 5629

ISSN
0947-6539
DOI
10.1002/chem.201706073
URI
http://hdl.handle.net/10203/242358
Appears in Collection
BS-Journal Papers(저널논문)CH-Journal Papers(저널논문)
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