ArticleJournal of the American Chemical Society2008
A versatile amino acid analogue of the solvatochromic fluorophore 4-N,N-dimethylamino-1,8-naphthalimide: a powerful tool for the study of dynamic protein interactions.
Article in Journal of the American Chemical Society, 2008. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 62 papers.
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Who cites it
62 citing papers in PubMed, 244 citations in OpenAlex.
- A general strategy towards multicolour fluorogenic peptides for wash-free bioassays.Nature chemistry · 2026Article
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- A printable, unimolecular, core-shell polymer bottlebrush-based signal transducer using solvatochromatic reporting.Chemical science · 2026Article
- 4-Dimethylamino-1,8-Naphthalimide as a Fluorescence Signal Amplification for Site Selective and in Situ Probing of the Hydroxyl Radical.Chemistry (Weinheim an der Bergstrasse, Germany) · 2025Article
- Expanding the fluorescence toolkit: molecular design, synthesis and biological application of unnatural amino acids.Chemical science · 2025Review
- Structure-function relationships in solvatochromic fluorophores targeting human and bovine carbonic anhydrases.Journal of inorganic biochemistry · 2025Article
- Twisting, Hydrogen Bonding, Exciplex Formation, and Charge Transfer. What Makes a Bright Fluorophore Not So Bright?The Journal of organic chemistry · 2025Article
- Functionalized Nitrobenzothiadiazoles as Embedded Fluorescent Probes.The Journal of organic chemistry · 2025Article
- Trifluoroacetyl-Substituted D-π-A Fluorophores: Design Strategies for Strong Solvatochromism and Giga Stokes Shifts.Chemistry, an Asian journal · 2025Article
- Rational Design of Pyrido[3,2-JACS Au · 2024Article
- Noncanonical Amino Acids in Biocatalysis.Chemical reviews · 2024Review
- PyrAtes: Modular Organic Salts with Large Stokes Shifts for Fluo-rescence Microscopy.Angewandte Chemie (International ed. in English) · 2024Article
- Minimalist TetrazineJournal of the American Chemical Society · 2024Article
- Substrate Sequestration and Chain Flipping in Human Mitochondrial Acyl Carrier Protein.Biochemistry · 2023Article
- Article
- Specific Fluorescent Probes for Imaging DNA in Cell-Free Solution and in Mitochondria in Living Cells.Biosensors · 2023Article
- Xanthone-based solvatochromic fluorophores for quantifying micropolarity of protein aggregates.Chemical science · 2022Article
- The Journey of 1-Keto-1,2,3,4-Tetrahydrocarbazole Based Fluorophores: From Inception to Implementation.Journal of fluorescence · 2022Review
- Structural insights into the design of reversible fluorescent probes for metallo-β-lactamases NDM-1, VIM-2, and IMP-1.Journal of inorganic biochemistry · 2022Article
- Rationales Design von Phe-BODIPY-Aminosäuren als fluorogene Bausteine für den peptidbasierten Nachweis vonAngewandte Chemie (Weinheim an der Bergstrasse, Germany) · 2022Article
2 more citing papers are in PubMed but not listed here.
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Authors and funding
2 authors at 1 institution in 1 country.
Funding
Abstract
We have developed a new unnatural amino acid based on the solvatochromic fluorophore 4-N,N-dimethylamino-1,8-naphthalimide (4-DMN) for application in the study of protein-protein interactions. The fluorescence quantum yield of this chromophore is highly sensitive to changes in the local solvent environment, demonstrating "switch-like" emission properties characteristic of the dimethylaminophthalimide family of fluorophores. In particular, this new species possesses a number of significant advantages over related fluorophores, including greater chemical stability under a wide range of conditions, a longer wavelength of excitation (408 nm), and improved synthetic accessibility. This amino acid has been prepared as an Fmoc-protected building block and may readily be incorporated into peptides via standard solid-phase peptide synthesis. A series of comparative studies are presented to demonstrate the advantageous properties of the 4-DMN amino acid relative to those of the previously reported 4-N,N-dimethylaminophthalimidoalanine and 6-N,N-dimethylamino-2,3-naphthalimidoalanine amino acids. Other commercially available solvatochromic fluorophores are also include in these studies. The potential of this new probe as a tool for the study of protein-protein interactions is demonstrated by introducing it into a peptide that is recognized by calcium-activated calmodulin. The binding interaction between these two components yields an increase in fluorescence emission greater than 900-fold.
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Read under generation 80e0d062 · epoch 390. Bibliography from PubMed, PubMed Central and OpenAlex; grants from NIH RePORTER; trial links from ClinicalTrials.gov; estimates, votes and beliefs from the OpenQuestion graph.