2015
DOI: 10.1016/j.bios.2015.06.039
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A near-infrared ratiometric fluorescent probe for cysteine detection over glutathione indicating mitochondrial oxidative stress in vivo

Abstract: a b s t r a c tWe establish a near-infrared (NIR) ratiometric fluorescent probe Cy-NB for the selective detection of cysteine (Cys) over glutathione (GSH) and homocysteine (Hcy) in mitochondria to indicate oxidative stress. Heptamethine cyanine dye is chosen as the fluorophore of Cy-NB whose emission locates in NIR region. And p-nitrobenzoyl is employed as the fluorescent modulator due to its capability of selective-Cys response. Once triggered by Cys, the uncaged p-nitrobenzoyl rearranges the polymethine π-el… Show more

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Cited by 117 publications
(37 citation statements)
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“…Very recently, another Cys-specific sensor (69) was reported. 119 In this design, a p-nitrobenzoyl unit was used as a recognition moiety. In the presence of Cys, the intermolecular addition−elimination reaction between Cys and the ester moiety of a Cy7 dye created a cyanine-ketone analogue.…”
Section: Sensors Based On Modulating the π-Conjugated System Of Cyanimentioning
confidence: 99%
“…Very recently, another Cys-specific sensor (69) was reported. 119 In this design, a p-nitrobenzoyl unit was used as a recognition moiety. In the presence of Cys, the intermolecular addition−elimination reaction between Cys and the ester moiety of a Cy7 dye created a cyanine-ketone analogue.…”
Section: Sensors Based On Modulating the π-Conjugated System Of Cyanimentioning
confidence: 99%
“…Briefly, rhodamine B derivative 1 was condensed with Fmoc-Gly-OH followed by Fmoc deprotection to give 2, which then was refluxed with 3 in ethanol and followed by reaction with DNBS-Cl in the presence of Et 3 N to give MT-1. The intermediate and final product was characterized by mass spectrometry, 1 H NMR and 13 according to the reported procedure [51,52]. Briefly, rhodamine B derivative 1 was condensed with Fmoc-Gly-OH followed by Fmoc deprotection to give 2, which then was refluxed with 3 in ethanol and followed by reaction with DNBS-Cl in the presence of Et3N to give MT-1.…”
Section: Design and Synthesis Of Mt-1mentioning
confidence: 99%
“…Therefore, the fluctuation in the levels of mitochondrial thiols is very important and has been linked to mitochondria's functions and dysfunctions [8,9]. Although GSH is the major biological thiol in mitochondria, cysteine (Cys), homocysteine (Hcy) and likely other short peptide thiols are also present in mitochondria [10][11][12][13]. Many pieces of evidence have suggested that GSH and Cys/Hcy levels are interrelated in biological systems [14][15][16][17].…”
Section: Introductionmentioning
confidence: 99%
“…It has been demonstrated that this fluorophore can be used in living mice as a sensor of Cys [79] and glutathione levels in living cells [80]. …”
Section: Properties Of Synthetic Fluorophoresmentioning
confidence: 99%