title: Mitochondria-Targeting Chromogenic and Fluorescence Turn-On Probe for the Selective Detection of Cysteine by Caged Oxazolidinoindocyanine.
abstract: We report a chromogenic and fluorescence turn-on probe based on crotonoyl ester-functionalized oxazolidinoindole for the selective detection of cysteine in neutral buffer. The probe rapidly formed indocyanophenolate through the Michael addition and a subsequent cyclization reaction of cysteine, inducing both a dramatic bathochromic shift (>130 nm) and a large fluorescence turn-on response (F/F0 12) in the UV-vis and fluorescence spectra and affording a micromolar limit of detection (LOD = 5.0 μM) of cysteine in HEPES buffer. When cysteine was added, the probe exhibited a dual optical change with strong green fluorescence and dramatic red color by the oxazolidinoindole-to-hydroxyethylindolium transformation. Further cellular application of the probe was successfully performed for the mitochondrial imaging of HeLa cells.
authors.affiliation: Department of Chemistry, Dongguk University , Seoul 04620, Republic of Korea.
authors.forename: Chae Yeong
authors.initials: CY
authors.lastname: Kim
authors.affiliation: Department of Chemistry, Dongguk University , Seoul 04620, Republic of Korea.
authors.forename: Hyo Jin
authors.initials: HJ
authors.lastname: Kang
authors.affiliation: Department of Chemistry, Dongguk University , Seoul 04620, Republic of Korea.
authors.forename: Sang J
authors.initials: SJ
authors.lastname: Chung
authors.affiliation: Division of Curriculum and Textbook, Korea Institute for Curriculum and Evaluation , Seoul 04518, Republic of Korea.
authors.forename: Hyun-Kyung
authors.initials: HK
authors.lastname: Kim
authors.affiliation: Department of Chemistry, Hankuk University of Foreign Studies , Yongin 17035, Republic of Korea.
authors.forename: Sang-Yun
authors.initials: SY
authors.lastname: Na
authors.affiliation: Department of Chemistry, Hankuk University of Foreign Studies , Yongin 17035, Republic of Korea.
authors.forename: Hae-Jo
authors.initials: HJ
authors.lastname: Kim
mesh_terms: D003437:Crotonates / Q000737:chemistry; D003545:Cysteine / Q000032:analysis*; D005453:Fluorescence; D005456:Fluorescent Dyes / Q000138:chemical synthesis / Q000737:chemistry*; D006367:HeLa Cells; D006801:Humans; D007211:Indoles / Q000138:chemical synthesis / Q000737:chemistry*; D057230:Limit of Detection; D018613:Microscopy, Confocal / Q000379:methods; D008856:Microscopy, Fluorescence / Q000379:methods; D008928:Mitochondria / Q000378:metabolism*; D008956:Models, Chemical; D010080:Oxazoles / Q000138:chemical synthesis / Q000737:chemistry*
chemical_list: D003437:Crotonates; D005456:Fluorescent Dyes; D007211:Indoles; D010080:Oxazoles; D003545:Cysteine