N-(3-Pyrene)maleimide: a Long Lifetime Fluorescent Sulfhydryl Reagent

Weltman, Joel K.; Szaro, Robert P.; Frackelton, A. Raymond; Dowben, Robert M.; Bunting, James R.; Cathou, Renata E.

doi:10.1016/s0021-9258(19)44023-4

Cited by 153 publications

(36 citation statements)

References 25 publications

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“…The fluorescent PET sensor/switch principle can also be applied in the form of fluorescent PET reagents when the target reacts irreversibly as in the case of various thiols [58][59][60][61][62][63] Some of these improve selectivity towards cases like glutathione versus simpler thiols by cleverly employing AND logic involving connected chemical inputs. 64 However, we choose to focus on reactive oxygen species (ROS) at this time.…”

Section: Reactive Oxygen Targetsmentioning

confidence: 99%

Current developments in fluorescent PET (photoinduced electron transfer) sensors and switches

2015

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Following a brief introduction to the principle of fluorescent PET (photoinduced electron transfer) sensors and switches, the outputs of laboratories in various countries from the past year or two are categorized and critically discussed. Emphasis is placed on the molecular design and the experimental outcomes in terms of target-induced fluorescence enhancements and input/output wavelengths. The handling of single targets takes up a major fraction of the review, but the extension to multiple targets is also illustrated. Conceptually new channels of investigation are opened up by the latter approach, e.g.'lab-on-a-molecule' systems and molecular keypad locks. The growing trends of theoretically-fortified design and intracellular application are pointed out.

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Section: Reactive Oxygen Targetsmentioning

confidence: 99%

Current developments in fluorescent PET (photoinduced electron transfer) sensors and switches

2015

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“…The shorter- and longer-wavelength bands are similar to those of monomer and excimer emission of other pyrenes except that sharp emission peaks in the monomer band were smeared out by adjacent phenyl rings, as reported previously ( Imai et al., 2012 ; Mizoshita and Inagaki, 2018 ). These assignments were supported by time-resolved fluorescence measurements ( Figure S1 A, Table 1); although the fluorescence lifetime was shorter than that of unmodified pyrenes due to the radiation decay rate enhanced by adjacent phenyl rings, the longer-wavelength emission decayed slowly (tens of nanoseconds), whereas the shorter-wavelength emission decayed rapidly (within several nanoseconds), consistent with the long-lived nature of pyrene excimers ( Weltman et al., 1973 ). The excimer emission was independent of Pyr-A concentration, indicating that the excimer formation is intramolecular ( Figure S1 B).…”

Section: Resultsmentioning

confidence: 53%

A light-switching pyrene probe to detect phase-separated biomolecules

et al. 2021

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Summary Biomolecules may undergo liquid–liquid phase separation (LLPS) to spatiotemporally compartmentalize and regulate diverse biological processes. Because the number of tools to directly probe LLPS is limited (ie. FRAP, FRET, fluorescence microscopy, fluorescence anisotropy, circular dichroism, etc.), the physicochemical traits of phase-separated condensates remain largely elusive. Here, we introduce a light-switching dipyrene probe (Pyr-A) that forms monomers in either hydrophobic or viscous environments, and intramolecular excimers in aqueous solutions. By exploiting their distinct fluorescence emission spectra, we used fluorescent microscopic imaging to study phase-separated condensates formed by in vitro protein droplets and membraneless intracellular organelles (centrosomes). Ratiometric measurement of excimer and monomer fluorescence intensities showed that protein droplets became hydrophobic and viscous as their size increased. Moreover, centrosomes became hydrophobic and viscous during maturation. Our results show that Pyr-A is a valuable tool to characterize LLPS and enhance our understanding of phase separation underlying biological functions.

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“…68,69 In addition to excimer emission, pure PT also showed shorter lifetimes of 7 and 26 ns (3% and 24%, respectively), which was ascribed to emission from monomeric pyrene. 67 Unlike the lifetime at 396 nm, excimer emission was greatly decreased by addition of C 60 . For example, 2PT•C 60 showed a major lifetime component at 18.35 ns (50%), which was consistent with the longest lifetime component (18.17 ns) determined by monitoring at 396 nm.…”

Section: Resultsmentioning

confidence: 93%

“…Figure S10b shows the fluorescence decay profiles observed at 469 nm that were fitted using four exponential functions by considering chisq (χ 2 ). Pure PT showed significantly long lifetimes of 60 and 170 ns (64% and 9%, respectively), which was attributed to excimer emission. , In addition to excimer emission, pure PT also showed shorter lifetimes of 7 and 26 ns (3% and 24%, respectively), which was ascribed to emission from monomeric pyrene . Unlike the lifetime at 396 nm, excimer emission was greatly decreased by addition of C 60 .…”

Section: Resultsmentioning

confidence: 94%

“…The FL lifetime of free PT was described by three discrete exponential components corresponding to 1.2 (τ 1 , 23%), 8.5 (τ 2 , 37%), and 48 ns (τ 3 , 40%). τ 1 and τ 2 were much shorter than the FL lifetimes of nonsubstituted pyrene (40–65 ns), possibly due to the structural complexity of PT. − As mentioned above, free PT can form dimeric structures held together by H bonds, with such molecular interactions probably contributing to the reduced lifetime. The addition of C 60 to PT significantly shortened the fluorescence lifetime of the latter, with the corresponding decay curves described by lifetimes of 0.38 (τ 1 , 47%), 3.47 (τ 2 , 34%), and 18.17 ns (τ 3 , 19%) for Mix-2 and 0.12 (τ 1 , 85%), 2.09 (τ 2 , 9%), and 10.41 ns (τ 3 , 6%) for Mix-1.…”

Section: Resultsmentioning

confidence: 98%

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Hierarchical Hybrid Nanostructures Constructed by Fullerene and Molecular Tweezer

et al. 2019

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For the construction of well-defined hierarchical superstructures of pristine [60]fullerene (C 60 ) arrays, pyrene-based molecular tweezers (PT) were used as host molecules for catching and arranging C 60 guest molecules. The formation of host−guest complexes was systematically studied in solution as well as in the solid state. Two-dimensional proton nuclear magnetic resonance spectroscopic studies revealed that PT−host and C 60 −guest complexes were closely related to the molecular selfassembly of PT. Ultraviolet and fluorescence spectroscopic titrations indicated the formation of stable 1:1 and 2:1 (PT/C 60 ) complexes. From the nonlinear curve-fitting analysis, equilibrium constants for the 1:1 (log K 1 ) and 2:1 (log K 2 ) complexes were estimated to be 4.96 and 5.01, respectively. X-ray diffraction results combined with transmission electron microscopy observations clearly exhibited the construction of well-defined layered superstructures of the PT−host and C 60 −guest complexes. From electron mobility measurements, it was demonstrated that the welldefined hierarchical hybrid nanostructure incorporating a C 60 array exhibited a high electron mobility of 1.7 × 10 −2 cm 2 V −1 s −1 . This study can provide a guideline for the hierarchical hybrid nanostructures of host−guest complex and its applications.

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N-(3-Pyrene)maleimide: a Long Lifetime Fluorescent Sulfhydryl Reagent

Cited by 153 publications

References 25 publications

Current developments in fluorescent PET (photoinduced electron transfer) sensors and switches

Current developments in fluorescent PET (photoinduced electron transfer) sensors and switches

A light-switching pyrene probe to detect phase-separated biomolecules

Hierarchical Hybrid Nanostructures Constructed by Fullerene and Molecular Tweezer

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