ArticleThe journal of physical chemistry. B2016
Utility of 5-Cyanotryptophan Fluorescence as a Sensitive Probe of Protein Hydration.
Article in The journal of physical chemistry. B, 2016. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 19 papers.
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Who cites it
19 citing papers in PubMed.
- Synthesis and Characterization of 4-Indolylcyanamide: A Potential IR Probe for Local Environment.Molecules (Basel, Switzerland) · 2025Article
- Investigation of the Vibrational Characteristics of 6-Isocyano-1-Methyl-1H-Indole: Utilizing the Isonitrile Group as an Infrared Probe.Molecules (Basel, Switzerland) · 2023Article
- Orthogonal translation with 5-cyanotryptophan as an infrared probe for local structural information, electrostatics, and hydrogen bonding.Protein science : a publication of the Protein Society · 2023Article
- Applications of fluorescence spectroscopy in protein conformational changes and intermolecular contacts.BBA advances · 2023Article
- The Magic of Linking Rings: Discovery of a Unique Photoinduced Fluorescent Protein Crosslink.Journal of the American Chemical Society · 2022Article
- Site-Specific Interrogation of Protein Structure and Stability.Methods in molecular biology (Clifton, N.J.) · 2022Article
- Light-Emitting Probes for Labeling Peptides.Cell reports. Physical science · 2020Article
- Exploring long-range proton conduction, the conduction mechanism and inner hydration state of protein biopolymers.Chemical science · 2020Article
- PET and FRET utility of an amino acid pair: tryptophan and 4-cyanotryptophan.Physical chemistry chemical physics : PCCP · 2019Article
- Synthesis and application of the blue fluorescent amino acid l-4-cyanotryptophan to assess peptide-membrane interactions.Chemical communications (Cambridge, England) · 2019Article
- Isonitrile-Derivatized Indole as an Infrared Probe for Hydrogen-Bonding Environments.Molecules (Basel, Switzerland) · 2019Article
- 4-Cyanoindole-2'-deoxyribonucleoside (4CIN): A Universal Fluorescent Nucleoside Analogue.Organic letters · 2018Article
- 7-Cyanoindole fluorescence as a local hydration reporter: application to probe the microheterogeneity of nine water-organic binary mixtures.Physical chemistry chemical physics : PCCP · 2018Article
- Solvent Dependence of Cyanoindole Fluorescence Lifetime.Chemical physics letters · 2017Article
- Blue fluorescent amino acid for biological spectroscopy and microscopy.Proceedings of the National Academy of Sciences of the United States of America · 2017Article
- Do guanidinium and tetrapropylammonium ions specifically interact with aromatic amino acid side chains?Proceedings of the National Academy of Sciences of the United States of America · 2017Article
- Infrared and fluorescence assessment of the hydration status of the tryptophan gate in the influenza A M2 proton channel.Physical chemistry chemical physics : PCCP · 2016Article
- Minimalist IR and fluorescence probes of protein function.Current opinion in chemical biology · 2016Review
- Exciton circular dichroism couplet arising from nitrile-derivatized aromatic residues as a structural probe of proteins.Analytical biochemistry · 2016Article
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4 authors.
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Abstract
Tryptophan (Trp) fluorescence has been widely used to interrogate the structure, dynamics, and function of proteins. In particular, it provides a convenient and site-specific means to probe a protein's hydration status and dynamics. Herein, we show that a tryptophan analogue, 5-cyanotryptophan (TrpCN), can also be used for this purpose, but with the benefit of enhanced sensitivity to hydration. This conclusion is reached based on measurements of the static and time-resolved fluorescence properties of 5-cyanoindole, TrpCN, and TrpCN-containing peptides in different solvents, which indicate that upon dehydration the fluorescence quantum yield (QY) and lifetime (τF) of TrpCN undergo a much greater change in comparison to those of Trp. For example, in H2O the QY of TrpCN is less than 0.01, which increases to 0.11 in 1,4-dioxane. Consistently, the fluorescence decay kinetics of TrpCN in H2O are dominated by a 0.4 ns component, whereas in 1,4-dioxane the kinetics are dominated by a 6.0 ns component. The versatile utility of TrpCN as a sensitive fluorescence reporter is further demonstrated in three applications, where we used it (1) to probe the solvent property of a binary mixture consisting of dimethyl sulfoxide and H2O, (2) to monitor the binding interaction of an antimicrobial peptide with lipid membranes, and (3) to differentiate two differently hydrated environments in a folded protein.
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