Literature DB >> 29225366

Solvent Dependence of Cyanoindole Fluorescence Lifetime.

Mary Rose Hilaire1, Debopreeti Mukherjee1, Thomas Troxler1,2, Feng Gai1,2.   

Abstract

Several cyanotryptophans have been shown to be useful biological fluorophores. However, how their fluorescence lifetimes vary with solvent has not been examined. In this regard, herein we measure the fluorescence decay kinetics as well as the absorption and emission spectra of six cyanoindoles in different solvents. In particular, we find, among other results, that only 4-cyanoindole affords a long fluorescence lifetime and hence high quantum yield in H2O. Therefore, our measurements provide not only a guide for choosing which cyanotryptophan to use in practice but also data for computational modeling of the substitution effect on the electronic transitions of indole.

Entities:  

Year:  2017        PMID: 29225366      PMCID: PMC5720157          DOI: 10.1016/j.cplett.2017.07.038

Source DB:  PubMed          Journal:  Chem Phys Lett        ISSN: 0009-2614            Impact factor:   2.328


  21 in total

1.  The structure of 5-cyanoindole in the ground and the lowest electronically excited singlet states, deduced from rotationally resolved electronic spectroscopy and ab initio theory.

Authors:  Olivia Oeltermann; Christian Brand; Bernd Engels; Jörg Tatchen; Michael Schmitt
Journal:  Phys Chem Chem Phys       Date:  2012-06-22       Impact factor: 3.676

Review 2.  Enhancement of protein spectra with tryptophan analogs: fluorescence spectroscopy of protein-protein and protein-nucleic acid interactions.

Authors:  J B Ross; A G Szabo; C W Hogue
Journal:  Methods Enzymol       Date:  1997       Impact factor: 1.600

3.  Controlling bacterial behavior with indole-containing natural products and derivatives.

Authors:  Roberta J Melander; Marine J Minvielle; Christian Melander
Journal:  Tetrahedron       Date:  2014-09-16       Impact factor: 2.457

4.  Blue fluorescent amino acid for biological spectroscopy and microscopy.

Authors:  Mary Rose Hilaire; Ismail A Ahmed; Chun-Wei Lin; Hyunil Jo; William F DeGrado; Feng Gai
Journal:  Proc Natl Acad Sci U S A       Date:  2017-05-22       Impact factor: 11.205

5.  On the Additivity of Molecular Fragment Dipole Moments of 5-Substituted Indole Derivatives.

Authors:  Josefin Wilke; Martin Wilke; Christian Brand; W Leo Meerts; Michael Schmitt
Journal:  Chemphyschem       Date:  2016-07-08       Impact factor: 3.102

6.  Time-dependent density functional theory (TD-DFT) coupled with reference interaction site model self-consistent field explicitly including spatial electron density distribution (RISM-SCF-SEDD).

Authors:  D Yokogawa
Journal:  J Chem Phys       Date:  2016-09-07       Impact factor: 3.488

7.  Substituent Effects on the Absorption and Fluorescence Properties of Anthracene.

Authors:  Salsabil Abou-Hatab; Vincent A Spata; Spiridoula Matsika
Journal:  J Phys Chem A       Date:  2017-02-01       Impact factor: 2.781

8.  5-Cyanotryptophan as an Infrared Probe of Local Hydration Status of Proteins.

Authors:  Matthias M Waegele; Matthew J Tucker; Feng Gai
Journal:  Chem Phys Lett       Date:  2009-09-01       Impact factor: 2.328

9.  Cyanotryptophans as Novel Fluorescent Probes for Studying Protein Conformational Changes and DNA-Protein Interaction.

Authors:  Poulami Talukder; Shengxi Chen; Basab Roy; Petro Yakovchuk; Michelle M Spiering; Mohammad P Alam; Manikandadas M Madathil; Chandrabali Bhattacharya; Stephen J Benkovic; Sidney M Hecht
Journal:  Biochemistry       Date:  2015-12-16       Impact factor: 3.162

Review 10.  Indole as an intercellular signal in microbial communities.

Authors:  Jin-Hyung Lee; Jintae Lee
Journal:  FEMS Microbiol Rev       Date:  2009-12-15       Impact factor: 16.408

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  6 in total

1.  7-Cyanoindole fluorescence as a local hydration reporter: application to probe the microheterogeneity of nine water-organic binary mixtures.

Authors:  Debopreeti Mukherjee; Lilliana I Ortiz Rodriguez; Mary Rose Hilaire; Thomas Troxler; Feng Gai
Journal:  Phys Chem Chem Phys       Date:  2018-01-09       Impact factor: 3.676

2.  PET and FRET utility of an amino acid pair: tryptophan and 4-cyanotryptophan.

Authors:  Ismail A Ahmed; Jeffrey M Rodgers; Christina Eng; Thomas Troxler; Feng Gai
Journal:  Phys Chem Chem Phys       Date:  2019-06-10       Impact factor: 3.676

3.  4-Cyanoindole-2'-deoxyribonucleoside (4CIN): A Universal Fluorescent Nucleoside Analogue.

Authors:  Kellan T Passow; Daniel A Harki
Journal:  Org Lett       Date:  2018-07-10       Impact factor: 6.005

4.  Site-Specific Interrogation of Protein Structure and Stability.

Authors:  Debopreeti Mukherjee; Ismail A Ahmed; Feng Gai
Journal:  Methods Mol Biol       Date:  2022

5.  Tuning the electronic transition energy of indole via substitution: application to identify tryptophan-based chromophores that absorb and emit visible light.

Authors:  Robert J Micikas; Ismail A Ahmed; Arusha Acharyya; Amos B Smith; Feng Gai
Journal:  Phys Chem Chem Phys       Date:  2021-03-12       Impact factor: 3.676

6.  Modeling solvation effects on absorption and fluorescence spectra of indole in aqueous solution.

Authors:  Salsabil Abou-Hatab; Vincenzo Carnevale; Spiridoula Matsika
Journal:  J Chem Phys       Date:  2021-02-14       Impact factor: 3.488

  6 in total

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