Synthesis, spectral properties, and use of 6-acryloyl-2-dimethylaminonaphthalene (Acrylodan). A thiol-selective, polarity-sensitive fluorescent probe.

Prendergast, F. G.; Meyer, Markus; Carlson, Gerald L.; Iida, Shoichi; Potter, James D.

doi:10.1016/s0021-9258(18)32211-7

Cited by 261 publications

(137 citation statements)

References 21 publications

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“…a blue-shift, as expected (Hibbs et al, 2004;Stuart et al, 2011;Sun et al, 2007). This is due to a reduction in polarity of acrylodan's surrounding environment upon binding (Figure S2C) (Prendergast et al, 1983). All labeling positions tested exhibited emission blueshifting upon binding tubulin, although there was significant site-dependent and tubulin concentration-dependent variability in the magnitudes of the shifts (Figure 1D).…”

Section: Structural Features Of Tubulin-and Mt-bound Tau Are Similarsupporting

confidence: 58%

Structural Characterization of Tau in Fuzzy Tau:Tubulin Complexes

et al. 2020

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Tau is a neuronal microtubule (MT) associated protein of significant interest due to its association with several neurodegenerative disorders. Tau's intrinsic disorder and the dynamic nature of its interactions with tubulin and MTs make its structural characterization challenging. Here we use an environmentally sensitive fluorophore as a site-specific probe of tau bound to soluble tubulin. Comparison of our results with recently published tau:MT cryo-EM model reveals structural similarities between tubulin-and MTbound tau. Analysis of residues across the repeat regions reveal a hierarchy in tubulin occupancy, which may be relevant to tau's ability to differentiate between tubulin and MTs. As binding to soluble tubulin is a critical first step in MT polymerization, our characterization of the structural features of tau in dynamic, fuzzy tau:tubulin assemblies advances our understanding of how tau functions in the cell and how function may be disrupted in disease.

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Section: Structural Features Of Tubulin-and Mt-bound Tau Are Similarsupporting

confidence: 58%

Structural Characterization of Tau in Fuzzy Tau:Tubulin Complexes

et al. 2020

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“…29,32 The corresponding uorescence regulation mechanism was fully illustrated by the Wang group in 2016. 33 Over the past 40 years, other structures such as Ndansylaziridine (4), 34 Acrylodan ( 8) 35 and 4-oxobut-2-enoate derivatives ( 9), 36 and a variety of Michael acceptors (squaraine (12), 7oxanorbornadiene, quinone, chromene and nitroolen) were then reported to detect thiols via the one step NAR process. [37][38][39][40] Fig.…”

Section: Evolution Of Fluorescent Probes For Thiolsmentioning

confidence: 99%

The chronological evolution of small organic molecular fluorescent probes for thiols

2021

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“…The protein was then eluted using 500 mM imidazole containing buffer, pooled, and dialyzed into PBS buffer overnight. The degree of labeling was determined by measuring the protein concentration using a BCA protein assay, as well as acrylodan concentration measured by absorption at 370 nm (extinction coefficient 16,400 M −1 cm −1 ) (Prendergast et al, 1983). Degree of labeling for C69S/F50C hLFABP was 1.0.…”

Section: Acrylodan Labelingmentioning

confidence: 99%

Engineering human liver fatty acid binding protein for detection of poly‐ and perfluoroalkyl substances

Mann

Tang

Berger

2021

Biotech & Bioengineering

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Per-and polyfluoroalkyl substances (PFAS) are a large group of synthetic fluorinated chemicals with surface active and water-repellent properties. The combination of wide-spread use in numerous consumer and industrial products and extended biological half-lives arising from strong carbon-fluorine bonds has led to significant accumulation of PFAS in humans. As most human interaction with PFAS comes from ingestion, it is important to be able to detect PFAS in drinking water as well as in agricultural water. Here we present an approach to designing a fluorescence-based biosensor for the rapid detection of PFAS based on human liver fatty acid binding protein (hLFABP). Introduction of solvatochromic fluorophores within the ligand binding pocket (L50) allowed for intrinsic detection of perfluorooctanoic acid (PFOA), perfluorooctanesulfonic acid (PFOS), and perfluorohexanesulfonic acid (PFHxS) via blue-shifts in fluorescence emission spectra. Initially, a single tryptophan mutation (L50W) was found to be able to detect PFOA with a limit of detection (LOD) of 2.8 ppm. We improved the sensitivity of the biosensor by exchanging tryptophan for the thiol reactive fluorophore, acrylodan. The acrylodan conjugated C69S/F50C hLFABP variant is capable of detecting PFOA, PFOS, and PFHxS in PBS with LODs of 112 ppb, 345 ppb, and 1.09 ppm, respectively. The protein-based sensor is also capable of detecting these contaminants at similar ranges in spiked environmental water samples, including samples containing an interfering anionic surfactant sodium dodecyl sulfate. Overall, this study demonstrates engineered hLFABP is a useful platform for detection of PFAS in environmental water samples and highlights its ease of use and versatility in field applications.

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Synthesis, spectral properties, and use of 6-acryloyl-2-dimethylaminonaphthalene (Acrylodan). A thiol-selective, polarity-sensitive fluorescent probe.

Cited by 261 publications

References 21 publications

Structural Characterization of Tau in Fuzzy Tau:Tubulin Complexes

Structural Characterization of Tau in Fuzzy Tau:Tubulin Complexes

The chronological evolution of small organic molecular fluorescent probes for thiols

Engineering human liver fatty acid binding protein for detection of poly‐ and perfluoroalkyl substances

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