title: Tunable heptamethine-azo dye conjugate as an NIR fluorescent probe for the selective detection of mitochondrial glutathione over cysteine and homocysteine.
abstract: Although a lot of mitochondria-targeting biothiol probes have been developed and applied to cellular imaging through thiol-induced disulfide cleavage or Michael addition reactions, relatively few probes assess mitochondrial GSH with high selectivity over Cys and Hcy and with NIR fluorescence capable of noninvasive imaging in biological samples. In order to monitor mitochondrial GSH with low background autofluorescence, we designed a heptamethine-azo conjugate as an NIR fluorescent probe by introducing a tunable lipophilic cation unit as the biomarker for mitochondria and a nitroazo group as the GSH-selective reaction site as well as the fluorescence quencher. The probe exhibited a dramatic off-on NIR fluorescence response toward GSH with high selectivity over other amino acids including Cys and Hcy. Further application to cellular imaging indicated that the probe was highly responsive to the changes of mitochondrial GSH in cells.
authors.affiliation: Department of Chemistry, Hankuk University of Foreign Studies , Yongin 449-791, Republic of Korea.
authors.forename: Soo-Yeon
authors.initials: SY
authors.lastname: Lim
authors.forename: Keum-Hee
authors.initials: KH
authors.lastname: Hong
authors.forename: Dae Il
authors.initials: DI
authors.lastname: Kim
authors.forename: Hyockman
authors.initials: H
authors.lastname: Kwon
authors.forename: Hae-Jo
authors.initials: HJ
authors.lastname: Kim
mesh_terms: D001391:Azo Compounds / Q000737:chemistry*; D003545:Cysteine / Q000032:analysis*; D005456:Fluorescent Dyes / Q000737:chemistry*; D005978:Glutathione / Q000032:analysis*; D006367:HeLa Cells; D006710:Homocysteine / Q000032:analysis*; D006801:Humans; D007211:Indoles / Q000737:chemistry*; D018613:Microscopy, Confocal; D008928:Mitochondria / Q000737:chemistry; D061848:Optical Imaging; D013050:Spectrometry, Fluorescence
chemical_list: D001391:Azo Compounds; D005456:Fluorescent Dyes; D007211:Indoles; D006710:Homocysteine; D005978:Glutathione; D003545:Cysteine