Thiol Reactive Probes and Chemosensors

Peng, Hanjing; Chen, Weixuan; Cheng, Yunfeng; Hakuna, Lovemore; Strongin, Robert M.; Wang, Binghe

doi:10.3390/s121115907

Cited by 258 publications

(147 citation statements)

References 179 publications

(180 reference statements)

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“…Covalent addition of thiols has been previously reported for cyanine dyes (32), although in that case the addition required irradiation with light, whereas here quenching occurs in the absence of light. Other groups have observed a similar spontaneous addition of thiol compounds (33) and phosphine (34) to fluorophores, but to our knowledge this has not been previously shown for fluorescent proteins. We propose that the covalent modification of the chromophore occurs via a Michael addition through the SH group of βME.…”

Section: Resultsmentioning

confidence: 82%

Efficient switching of mCherry fluorescence using chemical caging

Cloin

Zitter

Salas

et al. 2017

Proc. Natl. Acad. Sci. U.S.A.

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Fluorophores with dynamic or controllable fluorescence emission have become essential tools for advanced imaging, such as superresolution imaging. These applications have driven the continuing development of photoactivatable or photoconvertible labels, including genetically encoded fluorescent proteins. These new probes work well but require the introduction of new labels that may interfere with the proper functioning of existing constructs and therefore require extensive functional characterization. In this work we show that the widely used red fluorescent protein mCherry can be brought to a purely chemically induced blue-fluorescent state by incubation with β-mercaptoethanol (βME). The molecules can be recovered to the red fluorescent state by washing out the βME or through irradiation with violet light, with up to 80% total recovery. We show that this can be used to perform single-molecule localization microscopy (SMLM) on cells expressing mCherry, which renders this approach applicable to a very wide range of existing constructs. We performed a detailed investigation of the mechanism underlying these dynamics, using X-ray crystallography, NMR spectroscopy, and ab initio quantummechanical calculations. We find that the βME-induced fluorescence quenching of mCherry occurs both via the direct addition of βME to the chromophore and through βME-mediated reduction of the chromophore. These results not only offer a strategy to expand SMLM imaging to a broad range of available biological models, but also present unique insights into the chemistry and functioning of a highly important class of fluorophores. fluorescent proteins | mCherry | localization microscopy | β-mercaptoethanol | photoactivation

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Section: Resultsmentioning

confidence: 82%

Efficient switching of mCherry fluorescence using chemical caging

Cloin

Zitter

Salas

et al. 2017

Proc. Natl. Acad. Sci. U.S.A.

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show abstract

“…81,[84][85][86][87][88] Recent reports described several small-molecule fluorescent probes for H 2 S detection in living systems. [89][90][91][92][93][94] All these designs are based on H 2 S-specific reactions. A reaction-based FP sensor for H 2 S was also constructed by Chen and co-workers.…”

Section: Hydrogen Sulfide (H 2 S) Sensorsmentioning

confidence: 99%

Expanding the chemistry of fluorescent protein biosensors through genetic incorporation of unnatural amino acids

Niu

Guo

2013

Mol. BioSyst.

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“…15 The other components of the Citrus aurantifolia swingle essential oil, geranial (α-citral) and neral (β-citral) can inhibit the growth of bacteria, both negative Gram and positive Gram. 19 Based on the results of LSD test, there was a significant difference in term of the average between the negative control and all other treatment groups. This was supported by the significant value which was less than 0.05 (p <0.05) which was 0.001.…”

mentioning

confidence: 98%