Design of Large Stokes Shift Fluorescent Proteins Based on Excited State Proton Transfer of an Engin

Santos, Elizabeth M.; Sheng, Wei; Salmani, Rahele Esmatpour; Nick, Setare Tahmasebi; Ghanbarpour, Alireza; Gholami, Hadi; Vasileiou, Chrysoula; Geiger, James H.; Borhan, Babak

doi:10.1021/jacs.1c05039

Design of Large Stokes Shift Fluorescent Proteins Based on Excited State Proton Transfer of an Engin

Journal Article · 01 September 2021 · J. Am. Chem. Soc.

DOI:https://doi.org/10.1021/jacs.1c05039· OSTI ID:1828929

Santos, Elizabeth M.; Sheng, Wei; Salmani, Rahele Esmatpour; Nick, Setare Tahmasebi; Ghanbarpour, Alireza; Gholami, Hadi; Vasileiou, Chrysoula; Geiger, James H.; Borhan, Babak

Research Organization:: Argonne National Lab. (ANL), Argonne, IL (United States). Advanced Photon Source (APS)

Sponsoring Organization:: DOE - Office Of Science; OTHER U.S. STATES

OSTI ID:: 1828929

Journal Information:: J. Am. Chem. Soc., Vol. 143, Issue (37)

Country of Publication:: United States

Language:: ENGLISH

References (85)

Fluorescent Proteins and Their Applications in Imaging Living Cells and Tissues No authors listed Physiological Reviews https://doi.org/10.1152/physrev.00038.2009		July 2010
Advances in fluorescence labeling strategies for dynamic cellular imaging No authors listed Nature Chemical Biology https://doi.org/10.1038/nchembio.1556		June 2014
Recent progress in the development of near-infrared fluorescent probes for bioimaging applications No authors listed Chem. Soc. Rev. https://doi.org/10.1039/C3CS60271K		January 2014
Near-infrared fluorescence: application to in vivo molecular imaging No authors listed Current Opinion in Chemical Biology https://doi.org/10.1016/j.cbpa.2009.09.029		February 2010
BODIPY-based probes for the fluorescence imaging of biomolecules in living cells No authors listed Chemical Society Reviews https://doi.org/10.1039/C5CS00030K		January 2015
A review of NIR dyes in cancer targeting and imaging No authors listed Biomaterials https://doi.org/10.1016/j.biomaterials.2011.06.024		October 2011
Fluorescent proteins for live-cell imaging with super-resolution No authors listed Chem. Soc. Rev. https://doi.org/10.1039/C3CS60171D		January 2014
The Art of Fluorescence Imaging with Chemical Sensors No authors listed Angewandte Chemie International Edition https://doi.org/10.1002/anie.201105459		March 2012
A Critical and Comparative Review of Fluorescent Tools for Live-Cell Imaging No authors listed Annual Review of Physiology https://doi.org/10.1146/annurev-physiol-022516-034055		February 2017
Far-red to near infrared analyte-responsive fluorescent probes based on organic fluorophore platforms for fluorescence imaging No authors listed Chem. Soc. Rev. https://doi.org/10.1039/C2CS35313J		January 2013
Optical molecular imaging for tumor detection and image-guided surgery No authors listed Biomaterials https://doi.org/10.1016/j.biomaterials.2017.12.002		March 2018
The fluorescent protein palette: tools for cellular imaging No authors listed Chemical Society Reviews https://doi.org/10.1039/b901966a		January 2009
Green fluorescent protein: A perspective No authors listed Protein Science https://doi.org/10.1002/pro.684		July 2011
The structure and function of fluorescent proteins No authors listed Chemical Society Reviews https://doi.org/10.1039/b913033k		January 2009
A guide to choosing fluorescent proteins No authors listed Nature Methods https://doi.org/10.1038/nmeth819		November 2005
Modern fluorescent proteins and imaging technologies to study gene expression, nuclear localization, and dynamics No authors listed Current Opinion in Cell Biology https://doi.org/10.1016/j.ceb.2010.12.004		June 2011
In vivo protein labeling with trimethoprim conjugates: a flexible chemical tag No authors listed Nature Methods https://doi.org/10.1038/nmeth749		March 2005
¹³ C− ¹³ C Correlation Spectroscopy of Membrane-Associated Influenza Virus Fusion Peptide Strongly Supports a Helix-Turn-Helix Motif and Two Turn Conformations No authors listed Journal of the American Chemical Society https://doi.org/10.1021/ja905198q		August 2009
Protein labeling with fluorogenic probes for no-wash live-cell imaging of proteins No authors listed Current Opinion in Chemical Biology https://doi.org/10.1016/j.cbpa.2013.05.015		August 2013
A general method for the covalent labeling of fusion proteins with small molecules in vivo No authors listed Nature Biotechnology https://doi.org/10.1038/nbt765		December 2002
Monitoring protein interactions and dynamics with solvatochromic fluorophores No authors listed Trends in Biotechnology https://doi.org/10.1016/j.tibtech.2009.11.002		February 2010
Creating new fluorescent probes for cell biology No authors listed Nature Reviews Molecular Cell Biology https://doi.org/10.1038/nrm976		December 2002
Identification of PAmKate as a Red Photoactivatable Fluorescent Protein for Cryogenic Super-Resolution Imaging No authors listed Journal of the American Chemical Society https://doi.org/10.1021/jacs.8b05960		September 2018
Photocontrolled Fluorescence “Double-Check” Bioimaging Enabled by a Glycoprobe–Protein Hybrid No authors listed Journal of the American Chemical Society https://doi.org/10.1021/jacs.8b05425		June 2018
Rational Design and Facile Synthesis of a Highly Tunable Quinoline-Based Fluorescent Small-Molecule Scaffold for Live Cell Imaging No authors listed Journal of the American Chemical Society https://doi.org/10.1021/jacs.8b03738		July 2018
Far-Red Photoactivatable BODIPYs for the Super-Resolution Imaging of Live Cells No authors listed Journal of the American Chemical Society https://doi.org/10.1021/jacs.8b09099		September 2018
Systematic Evaluation of Bioorthogonal Reactions in Live Cells with Clickable HaloTag Ligands: Implications for Intracellular Imaging No authors listed Journal of the American Chemical Society https://doi.org/10.1021/jacs.5b06847		August 2015
Discerning the Chemistry in Individual Organelles with Small-Molecule Fluorescent Probes No authors listed Angewandte Chemie International Edition https://doi.org/10.1002/anie.201510721		August 2016
Near-infrared fluorescent proteins for multicolor in vivo imaging No authors listed Nature Methods https://doi.org/10.1038/nmeth.2521		June 2013
Near-infrared fluorescent proteins No authors listed Nature Methods https://doi.org/10.1038/nmeth.1501		September 2010
Versatile single-molecule multi-color excitation and detection fluorescence setup for studying biomolecular dynamics No authors listed Review of Scientific Instruments https://doi.org/10.1063/1.3657153		November 2011
Geometry Relaxation-Induced Large Stokes Shift in Red-Emitting Borondipyrromethenes (BODIPY) and Applications in Fluorescent Thiol Probes No authors listed The Journal of Organic Chemistry https://doi.org/10.1021/jo202215x		February 2012
Two-photon AIE bio-probe with large Stokes shift for specific imaging of lipid droplets No authors listed Chemical Science https://doi.org/10.1039/C7SC01400G		January 2017
Real-Time Monitoring of Endogenous Cysteine Levels In Vivo by near-Infrared Turn-on Fluorescent Probe with Large Stokes Shift No authors listed Analytical Chemistry https://doi.org/10.1021/acs.analchem.7b04407		December 2017
Cell-Permeant Large Stokes Shift Dyes for Transfection-Free Multicolor Nanoscopy No authors listed Journal of the American Chemical Society https://doi.org/10.1021/jacs.7b06412		August 2017
A novel ESIPT-ICT-based near-infrared fluorescent probe with large stokes-shift for the highly sensitive, specific, and non-invasive in vivo detection of cysteine No authors listed Sensors and Actuators B: Chemical https://doi.org/10.1016/j.snb.2019.05.048		October 2019
An ICT-based fluorescent probe with a large Stokes shift for measuring hydrazine in biological and water samples No authors listed Environmental Pollution https://doi.org/10.1016/j.envpol.2019.113427		January 2020
A NIR-emitting cyanine with large Stokes shifts for live cell imaging: large impact of the phenol group on emission No authors listed Chemical Communications https://doi.org/10.1039/C9CC06831G		January 2019
Heptamethine Cyanine Dyes with a Large Stokes Shift and Strong Fluorescence: A Paradigm for Excited-State Intramolecular Charge Transfer No authors listed Journal of the American Chemical Society https://doi.org/10.1021/ja043413z		March 2005
Large Stokes Shift Induced by Intramolcular Charge Transfer in N,O-Chelated Naphthyridine–BF ₂ Complexes No authors listed Organic Letters https://doi.org/10.1021/ol302347m		October 2012
Synthesis, solvatochromism, aggregation-induced emission and cell imaging of tetraphenylethene-containing BODIPY derivatives with large Stokes shifts No authors listed Chemical Communications https://doi.org/10.1039/c2cc35188a		January 2012
Fluorescent aryl naphthalene dicarboximides with large Stokes shifts and strong solvatochromism controlled by dynamics and molecular geometry No authors listed Journal of Materials Chemistry C https://doi.org/10.1039/C6TC04453K		January 2016
Excimer-FRET Cascade in Dual DNA Probes: Open Access to Large Stokes Shift, Enhanced Acceptor Light up, and Robust RNA Sensing No authors listed Analytical Chemistry https://doi.org/10.1021/acs.analchem.0c00270		April 2020
Pyrene Excimer Signaling Molecular Beacons for Probing Nucleic Acids No authors listed Journal of the American Chemical Society https://doi.org/10.1021/ja076411y		January 2008
Excimer Emission-Based Fluorescent Probe Targeting Caspase-3 No authors listed Analytical Chemistry https://doi.org/10.1021/acs.analchem.7b02790		September 2017
Valley-selective optical Stark effect in monolayer WS2 No authors listed Nature Materials https://doi.org/10.1038/nmat4156		December 2014
Impact of quantum confinement and quantum confined Stark effect on biexciton binding energy in GaN∕AlGaN quantum wells No authors listed Applied Physics Letters https://doi.org/10.1063/1.2973897		October 2008
Engineering ESPT Pathways Based on Structural Analysis of LSSmKate Red Fluorescent Proteins with Large Stokes Shift No authors listed Journal of the American Chemical Society https://doi.org/10.1021/ja101974k		July 2010
Monomeric red fluorescent proteins with a large Stokes shift No authors listed Proceedings of the National Academy of Sciences https://doi.org/10.1073/pnas.0914365107		March 2010
mBeRFP, an Improved Large Stokes Shift Red Fluorescent Protein No authors listed PLoS ONE https://doi.org/10.1371/journal.pone.0064849		June 2013
A bright cyan-excitable orange fluorescent protein facilitates dual-emission microscopy and enhances bioluminescence imaging in vivo No authors listed Nature Biotechnology https://doi.org/10.1038/nbt.3550		May 2016
An Orange Fluorescent Protein with a Large Stokes Shift for Single-Excitation Multicolor FCCS and FRET Imaging No authors listed Journal of the American Chemical Society https://doi.org/10.1021/ja3018972		April 2012
Excited-state intramolecular proton-transfer (ESIPT) based fluorescence sensors and imaging agents No authors listed Chemical Society Reviews https://doi.org/10.1039/C8CS00185E		January 2018
Excited state intramolecular proton transfer (ESIPT): from principal photophysics to the development of new chromophores and applications in fluorescent molecular probes and luminescent materials No authors listed Phys. Chem. Chem. Phys. https://doi.org/10.1039/C2CP23144A		January 2012
Effect of amino group on the excited-state intramolecular proton transfer (ESIPT) mechanisms of 2-(2′-hydroxyphenyl)benzoxazole and its amino derivatives No authors listed RSC Advances https://doi.org/10.1039/C5RA23261A		January 2016
Synthesis and Photo-Physical Characteristics of ESIPT Inspired 2-Substituted Benzimidazole, Benzoxazole and Benzothiazole Fluorescent Derivatives No authors listed Journal of Fluorescence https://doi.org/10.1007/s10895-011-0962-8		September 2011
Excited state intramolecular proton transfer (ESIPT) of 6-amino-2-(2′-hydroxyphenyl)benzoxazole in dichloromethane and methanol: A TD-DFT quantum chemical study No authors listed Journal of Luminescence https://doi.org/10.1016/j.jlumin.2015.11.026		April 2016
Excited-State Intramolecular Proton Transfer (ESIPT) Fine Tuned by Quinoline−Pyrazole Isomerism: π-Conjugation Effect on ESIPT No authors listed The Journal of Physical Chemistry A https://doi.org/10.1021/jp1036102		July 2010
Flavone-Based ESIPT Ratiometric Chemodosimeter for Detection of Cysteine in Living Cells No authors listed ACS Applied Materials & Interfaces https://doi.org/10.1021/am500102s		March 2014
Combined TDDFT and AIM Insights into Photoinduced Excited State Intramolecular Proton Transfer (ESIPT) Mechanism in Hydroxyl- and Amino-Anthraquinone Solution No authors listed Scientific Reports https://doi.org/10.1038/s41598-017-14094-5		October 2017
Excited-State Proton Transfer: Indication of Three Steps in the Dissociation and Recombination Process No authors listed The Journal of Physical Chemistry A https://doi.org/10.1021/jp050037b		July 2005
Proton Transfer and Proton Concentrations in Protonated Nafion Fuel Cell Membranes No authors listed The Journal of Physical Chemistry B https://doi.org/10.1021/jp9036777		July 2009
Ultrafast Conformational Dynamics of Pyranine during Excited State Proton Transfer in Aqueous Solution Revealed by Femtosecond Stimulated Raman Spectroscopy No authors listed The Journal of Physical Chemistry B https://doi.org/10.1021/jp3020707		June 2012
Ultrafast Excited-State Proton-Transfer Reaction of 1-Naphthol-3,6-Disulfonate and Several 5-Substituted 1-Naphthol Derivatives No authors listed The Journal of Physical Chemistry B https://doi.org/10.1021/jp308746x		February 2013
Excited-state proton transfer of photoexcited pyranine in water observed by femtosecond stimulated Raman spectroscopy No authors listed Chemical Physics https://doi.org/10.1016/j.chemphys.2013.03.009		August 2013
Ultrafast Dynamics of a “Super” Photobase No authors listed Angewandte Chemie International Edition https://doi.org/10.1002/anie.201806787		October 2018
Proton Abstraction Mediates Interactions between the Super Photobase FR0-SB and Surrounding Alcohol Solvent No authors listed The Journal of Physical Chemistry B https://doi.org/10.1021/acs.jpcb.9b06580		September 2019
Tuning the Electronic Absorption of Protein-Embedded All-trans-Retinal No authors listed Science https://doi.org/10.1126/science.1226135		December 2012
A Near‐Infrared Photoswitchable Protein–Fluorophore Tag for No‐Wash Live Cell Imaging No authors listed Angewandte Chemie International Edition https://doi.org/10.1002/anie.201810065		December 2018
Engineering of a Red Fluorogenic Protein/Merocyanine Complex for Live‐Cell Imaging No authors listed ChemBioChem https://doi.org/10.1002/cbic.201900428		November 2019
“Turn-On” Protein Fluorescence: In Situ Formation of Cyanine Dyes No authors listed Journal of the American Chemical Society https://doi.org/10.1021/ja506376j		January 2015
Mimicking Microbial Rhodopsin Isomerization in a Single Crystal No authors listed Journal of the American Chemical Society https://doi.org/10.1021/jacs.8b12493		December 2018
Engineering the hCRBPII Domain-Swapped Dimer into a New Class of Protein Switches No authors listed Journal of the American Chemical Society https://doi.org/10.1021/jacs.9b04664		September 2019
A Photoisomerizing Rhodopsin Mimic Observed at Atomic Resolution No authors listed Journal of the American Chemical Society https://doi.org/10.1021/jacs.6b03681		July 2016
Fluorescent Molecular Probes II. The Synthesis, Spectral Properties and Use of Fluorescent Solvatochromic Dapoxyl Dyes No authors listed Photochemistry and Photobiology https://doi.org/10.1111/j.1751-1097.1997.tb03168.x		October 1997
Combinatorial Dapoxyl Dye Library and its Application to Site Selective Probe for Human Serum Albumin No authors listed Journal of Combinatorial Chemistry https://doi.org/10.1021/cc0700546		September 2007
Structural characteristics and optical properties of a series of solvatochromic fluorescent dyes displaying long-wavelength emission No authors listed Dyes and Pigments https://doi.org/10.1016/j.dyepig.2009.04.008		November 2009
The Emerging Functions and Mechanisms of Mammalian Fatty Acid–Binding Proteins No authors listed Annual Review of Nutrition https://doi.org/10.1146/annurev.nutr.27.061406.093710		August 2008
Rational Design of a Colorimetric pH Sensor from a Soluble Retinoic Acid Chaperone No authors listed Journal of the American Chemical Society https://doi.org/10.1021/ja404900k		October 2013
Probing Wavelength Regulation with an Engineered Rhodopsin Mimic and a C15-Retinal Analogue No authors listed ChemPlusChem https://doi.org/10.1002/cplu.201100082		February 2012
Engineering a Rhodopsin Protein Mimic No authors listed Journal of the American Chemical Society https://doi.org/10.1021/ja058591m		April 2006
Small Molecule-Photoactive Yellow Protein Labeling Technology in Live Cell Imaging No authors listed Molecules https://doi.org/10.3390/molecules21091163		August 2016
Rapid no-wash labeling of PYP-tag proteins with reactive fluorogenic ligands affords stable fluorescent protein conjugates for long-term cell imaging studies No authors listed Chemical Science https://doi.org/10.1039/D0SC00499E		January 2020
A wash-free SNAP-tag fluorogenic probe based on the additive effects of quencher release and environmental sensitivity No authors listed Chemical Communications https://doi.org/10.1039/C7CC01483J		January 2017
Development of SNAP-Tag Fluorogenic Probes for Wash-Free Fluorescence Imaging No authors listed ChemBioChem https://doi.org/10.1002/cbic.201100173		July 2011

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