ArticleJournal of the American Chemical Society2017
The Color of Cation-π Interactions: Subtleties of Amine-Tryptophan Interaction Energetics Allow for Radical-like Visible Absorbance and Fluorescence.
Article in Journal of the American Chemical Society, 2017. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 13 papers.
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Trials whose registry record cites this paper, or whose number appears in the abstract. A trial that started after this paper was published is citing it as background, not reporting it.
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Who cites it
13 citing papers in PubMed, 60 citations in OpenAlex.
- Cation-π Dynamic Cross-Linking Enabled High-Performance PVA Films With Synchronous Strength-Toughness Enhancement, Self-Healing, and Recyclability.Macromolecular rapid communications · 2026Article
- Breaking the Recycling Bottleneck of Thermosets via Bio-Tailoring Technology.Advanced science (Weinheim, Baden-Wurttemberg, Germany) · 2025Article
- 2D-Graph of intermolecular interactions predicts radical character of anion-π* type charge-transfer complexes.RSC advances · 2024Article
- Primary Processes of Free Radical Formation in Pharmaceutical Formulations of Therapeutic Proteins.Biomolecules · 2023Review
- Advanced Oxidation Processes in Pharmaceutical Formulations: Photo-Fenton Degradation of Peptides and Proteins.International journal of molecular sciences · 2022Review
- Force-reversible chemical reaction at ambient temperature for designing toughened dynamic covalent polymer networks.Nature communications · 2022Article
- Spectroscopic and Theoretical Studies of Hg(II) Complexation with Some Dicysteinyl Tetrapeptides.Bioinorganic chemistry and applications · 2021Article
- Surface Enhanced Raman Scattering Selectivity in Proteins Arises from Electron Capture and Resonant Enhancement of Radical Species.The journal of physical chemistry. C, Nanomaterials and interfaces · 2020Article
- UV oxidation of cyclic AMP receptor protein, a global bacterial gene regulator, decreases DNA binding and cleaves DNA at specific sites.Scientific reports · 2020Article
- Photo-Degradation of Therapeutic Proteins: Mechanistic Aspects.Pharmaceutical research · 2020Review
- Renewable 4-HIF/NaOH aerogel for efficient methylene blue removalRSC advances · 2019Article
- A reversible, colorimetric, pH-responsive indole-based hydrogel and its application in urea detection.RSC advances · 2019Article
- Identification of D-Amino Acids in Light Exposed mAb Formulations.Pharmaceutical research · 2018Article
Corrections and comments
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Authors and funding
2 authors at 2 institutions in 1 country.
Funding
Abstract
Several peptides and a protein with an inter- or intramolecular cation-π interaction between tryptophan (Trp) and an amine cation are shown to absorb and fluoresce in the visible region of the spectrum. Titration of indole with sodium hydroxide or ammonium hydroxide yields an increasing visible fluorescence as well. Visible absorption and multipeaked fluorescence excitation spectra correlate with experimental absorption spectra and the vibrational modes of calculated absorption spectra for the neutral Trp radical. The radical character of the cation-indole interaction is predicted to stem from the electrostatic dislocation of indole highest occupied molecular orbital (HOMO) charge density toward the cation with a subsequent electronic transition from the HOMO-2 to the HOMO. Because this is a vertical transition, fluorescence is possible. Hydrogen bonding at the indole amine most likely stabilizes the radical-like state. These results provide new spectroscopic tools for the investigation of cation-π interactions in numerous biological systems, among them, proteins and their myriad ligands, and show that one, or at most, two, point mutations with natural amino acids are all that is required to impart visible fluorescence to proteins.
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Registered trials
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