“Turn-On” Protein Fluorescence: In Situ Formation of Cyanine Dyes

Yapici, Ipek; Lee, Kin Sing Stephen; Berbasova, Tetyana; Nosrati, Meisam; Jia, Xiaofei; Vasileiou, Chrysoula; Wang, Wenjing; Santos, Elizabeth M.; Geiger, James H.; Borhan, Babak

doi:10.1021/ja506376j

Title: “Turn-On” Protein Fluorescence: In Situ Formation of Cyanine Dyes

Journal Article · Mon Dec 22 00:00:00 EST 2014 · Journal of the American Chemical Society

DOI:https://doi.org/10.1021/ja506376j· OSTI ID:1237768

Yapici, Ipek ^[1]; Lee, Kin Sing Stephen ^[1]; Berbasova, Tetyana ^[1]; Nosrati, Meisam ^[1]; Jia, Xiaofei ^[1]; Vasileiou, Chrysoula ^[1]; Wang, Wenjing ^[1]; Santos, Elizabeth M. ^[1]; Geiger, James H. ^[1]; Borhan, Babak ^[1]

Michigan State Univ., East Lansing, MI (United States). Dept. of Chemistry

Protein reengineering of cellular retinoic acid binding protein II (CRABPII) has yielded a genetically addressable system, capable of binding a profluorophoric chromophore that results in fluorescent protein/chromophore complexes. These complexes exhibit far-red emission, with high quantum efficiencies and brightness and also exhibit excellent pH stability spanning the range of 2$$-$$11. In the course of this study, it became evident that single mutations of L121E and R59W were most effective in improving the fluorescent characteristics of CRABPII mutants as well as the kinetics of complex formation. The readily crystallizable nature of these proteins was invaluable to provide clues for the observed spectroscopic behavior that results from single mutation of key residues.

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

Sponsoring Organization:: USDOE Office of Science (SC), Basic Energy Sciences (BES)

Grant/Contract Number:: W-31-109-ENG-38

OSTI ID:: 1237768

Journal Information:: Journal of the American Chemical Society, Vol. 137, Issue 3; ISSN 0002-7863

Publisher:: American Chemical Society (ACS)Copyright Statement

Country of Publication:: United States

Language:: ENGLISH

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Cited by: 53 works

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References (81)

Analysis of a data set of paired uncomplexed protein structures: New metrics for side-chain flexibility and model evaluation Zhao, Shanrong; Goodsell, David S.; Olson, Arthur J. Proteins: Structure, Function, and Genetics, Vol. 43, Issue 3 https://doi.org/10.1002/prot.1038	journal	January 2001
The nature of the different environmental sensitivity of symmetrical and unsymmetrical cyanine dyes: an experimental and theoretical study Cao, Jianfang; Wu, Tong; Hu, Chong Physical Chemistry Chemical Physics, Vol. 14, Issue 39 https://doi.org/10.1039/c2cp42122d	journal	January 2012
The photochemical determinants of color vision: Revealing how opsins tune their chromophore's absorption wavelength Wang, Wenjing; Geiger, James H.; Borhan, Babak BioEssays, Vol. 36, Issue 1 https://doi.org/10.1002/bies.201300094	journal	October 2013
Cyanine dyes in biophysical research: the photophysics of polymethine fluorescent dyes in biomolecular environments Levitus, Marcia; Ranjit, Suman Quarterly Reviews of Biophysics, Vol. 44, Issue 1 https://doi.org/10.1017/S0033583510000247	journal	November 2010
Diels–Alder Cycloaddition for Fluorophore Targeting to Specific Proteins inside Living Cells Liu, Daniel S.; Tangpeerachaikul, Anupong; Selvaraj, Ramajeyam Journal of the American Chemical Society, Vol. 134, Issue 2 https://doi.org/10.1021/ja209325n	journal	December 2011
A Bilirubin-Inducible Fluorescent Protein from Eel Muscle Kumagai, Akiko; Ando, Ryoko; Miyatake, Hideyuki Cell, Vol. 153, Issue 7 https://doi.org/10.1016/j.cell.2013.05.038	journal	June 2013
Development of Fluorogenic Probes for Quick No-Wash Live-Cell Imaging of Intracellular Proteins Hori, Yuichiro; Norinobu, Tomoya; Sato, Motoki Journal of the American Chemical Society, Vol. 135, Issue 33 https://doi.org/10.1021/ja405745v	journal	August 2013
Fluorogen-activating proteins as biosensors of cell-surface proteins in living cells Holleran, John; Brown, Dara; Fuhrman, Margaret H. Cytometry Part A, Vol. 77A, Issue 8 https://doi.org/10.1002/cyto.a.20925	journal	June 2010
Bioorthogonal Reactions for Labeling Proteins Lang, Kathrin; Chin, Jason W. ACS Chemical Biology, Vol. 9, Issue 1 https://doi.org/10.1021/cb4009292	journal	October 2013
An Engineered Protein Tag for Multiprotein Labeling in Living Cells Gautier, Arnaud; Juillerat, Alexandre; Heinis, Christian Chemistry & Biology, Vol. 15, Issue 2 https://doi.org/10.1016/j.chembiol.2008.01.007	journal	February 2008
Development of SNAP-Tag Fluorogenic Probes for Wash-Free Fluorescence Imaging Sun, Xiaoli; Zhang, Aihua; Baker, Brenda ChemBioChem, Vol. 12, Issue 14 https://doi.org/10.1002/cbic.201100173	journal	July 2011
A FRET-Based Fluorogenic Phosphine for Live-Cell Imaging with the Staudinger Ligation Hangauer, Matthew J.; Bertozzi, Carolyn R. Angewandte Chemie International Edition, Vol. 47, Issue 13 https://doi.org/10.1002/anie.200704847	journal	March 2008
Far-red fluorescent tags for protein imaging in living tissues Shcherbo, Dmitry; Murphy, Christopher S.; Ermakova, Galina V. Biochemical Journal, Vol. 418, Issue 3 https://doi.org/10.1042/BJ20081949	journal	February 2009
Labeling of fusion proteins with synthetic fluorophores in live cells Keppler, A.; Pick, H.; Arrivoli, C. Proceedings of the National Academy of Sciences, Vol. 101, Issue 27, p. 9955-9959 https://doi.org/10.1073/pnas.0401923101	journal	June 2004
Genetically Encoded Cyclopropene Directs Rapid, Photoclick-Chemistry-Mediated Protein Labeling in Mammalian Cells Yu, Zhipeng; Pan, Yanchao; Wang, Zhiyong Angewandte Chemie International Edition, Vol. 51, Issue 42 https://doi.org/10.1002/anie.201205352	journal	September 2012
Engineering a Rhodopsin Protein Mimic Crist, Rachael M.; Vasileiou, Chrysoula; Rabago-Smith, Montserrat Journal of the American Chemical Society, Vol. 128, Issue 14 https://doi.org/10.1021/ja058591m	journal	April 2006
NIR dyes for bioimaging applications Escobedo, Jorge O.; Rusin, Oleksandr; Lim, Soojin Current Opinion in Chemical Biology, Vol. 14, Issue 1 https://doi.org/10.1016/j.cbpa.2009.10.022	journal	February 2010
Experimental and Computational Investigation of Unsymmetrical Cyanine Dyes: Understanding Torsionally Responsive Fluorogenic Dyes Silva, Gloria L.; Ediz, Volkan; Yaron, David Journal of the American Chemical Society, Vol. 129, Issue 17 https://doi.org/10.1021/ja070025z	journal	May 2007
Second-Generation Covalent TMP-Tag for Live Cell Imaging Chen, Zhixing; Jing, Chaoran; Gallagher, Sarah S. Journal of the American Chemical Society, Vol. 134, Issue 33 https://doi.org/10.1021/ja303374p	journal	August 2012
Elucidating the exact role of engineered CRABPII residues for the formation of a retinal protonated Schiff base Vasileiou, Chrysoula; Wang, Wenjing; Jia, Xiaofei Proteins: Structure, Function, and Bioinformatics, Vol. 77, Issue 4 https://doi.org/10.1002/prot.22495	journal	December 2009
Selective Dye-Labeling of Newly Synthesized Proteins in Bacterial Cells Beatty, Kimberly E.; Xie, Fang; Wang, Qian Journal of the American Chemical Society, Vol. 127, Issue 41 https://doi.org/10.1021/ja054643w	journal	October 2005
Near-infrared fluorescent proteins for multicolor in vivo imaging Shcherbakova, Daria M.; Verkhusha, Vladislav V. Nature Methods, Vol. 10, Issue 8 https://doi.org/10.1038/nmeth.2521	journal	June 2013
Site specific protein labeling by enzymatic posttranslational modification Sunbul, Murat; Yin, Jun Organic & Biomolecular Chemistry, Vol. 7, Issue 17 https://doi.org/10.1039/b908687k	journal	January 2009
Bioconjugation by Copper(I)-Catalyzed Azide-Alkyne [3 + 2] Cycloaddition Wang, Qian; Chan, Timothy R.; Hilgraf, Robert Journal of the American Chemical Society, Vol. 125, Issue 11, p. 3192-3193 https://doi.org/10.1021/ja021381e	journal	March 2003
Mammalian Expression of Infrared Fluorescent Proteins Engineered from a Bacterial Phytochrome Shu, X.; Royant, A.; Lin, M. Z. Science, Vol. 324, Issue 5928 https://doi.org/10.1126/science.1168683	journal	May 2009
Ultrafast Radiationless Deactivation of Organic Dyes: Evidence for a Two-State Two-Mode Pathway in Polymethine Cyanines Sanchez-Galvez, Adelaida; Hunt, Patricia; Robb, Michael A. Journal of the American Chemical Society, Vol. 122, Issue 12 https://doi.org/10.1021/ja993985x	journal	March 2000
Fluorescent proteins at a glance Kremers, G. -J.; Gilbert, S. G.; Cranfill, P. J. Journal of Cell Science, Vol. 124, Issue 2 https://doi.org/10.1242/jcs.072744	journal	December 2010
Chemical Tags for Labeling Proteins Inside Living Cells Jing, Chaoran; Cornish, Virginia W. Accounts of Chemical Research, Vol. 44, Issue 9 https://doi.org/10.1021/ar200099f	journal	September 2011
Extraction, Purification and Properties of Aequorin, a Bioluminescent Protein from the Luminous Hydromedusan,Aequorea Shimomura, Osamu; Johnson, Frank H.; Saiga, Yo Journal of Cellular and Comparative Physiology, Vol. 59, Issue 3 https://doi.org/10.1002/jcp.1030590302	journal	June 1962
Specific Covalent Labeling of Recombinant Protein Molecules Inside Live Cells Griffin, B. Albert; Adams, Stephen R.; Tsien, Roger Y. Science, Vol. 281, Issue 5374, p. 269-272 https://doi.org/10.1126/science.281.5374.269	journal	July 1998
An In Vivo Covalent TMP-Tag Based on Proximity-Induced Reactivity Gallagher, Sarah S.; Sable, Julia E.; Sheetz, Michael P. ACS Chemical Biology, Vol. 4, Issue 7 https://doi.org/10.1021/cb900062k	journal	July 2009
Non-invasive intravital imaging of cellular differentiation with a bright red-excitable fluorescent protein Chu, Jun; Haynes, Russell D.; Corbel, Stéphane Y. Nature Methods, Vol. 11, Issue 5 https://doi.org/10.1038/nmeth.2888	journal	March 2014
Bright and stable near-infrared fluorescent protein for in vivo imaging Filonov, Grigory S.; Piatkevich, Kiryl D.; Ting, Li-Min Nature Biotechnology, Vol. 29, Issue 8 https://doi.org/10.1038/nbt.1918	journal	July 2011
Polymethine dyes as spectral-fluorescent probes for biomacromolecules Tatikolov, Alexander S. Journal of Photochemistry and Photobiology C: Photochemistry Reviews, Vol. 13, Issue 1 https://doi.org/10.1016/j.jphotochemrev.2011.11.001	journal	March 2012
Tuning the Electronic Absorption of Protein-Embedded All-trans-Retinal Wang, W.; Nossoni, Z.; Berbasova, T. Science, Vol. 338, Issue 6112 https://doi.org/10.1126/science.1226135	journal	December 2012
Protein Design: Reengineering Cellular Retinoic Acid Binding Protein II into a Rhodopsin Protein Mimic Vasileiou, Chrysoula; Vaezeslami, Soheila; Crist, Rachael M. Journal of the American Chemical Society, Vol. 129, Issue 19 https://doi.org/10.1021/ja067546r	journal	May 2007
Structures of cellular retinoic acid binding proteins I and II in complex with synthetic retinoids Chaudhuri, Barnali Neel; Kleywegt, Gerard J.; Broutin-L'Hermite, Isabelle Acta Crystallographica Section D Biological Crystallography, Vol. 55, Issue 11 https://doi.org/10.1107/S0907444999011026	journal	November 1999
Tetrazine-Based Cycloadditions: Application to Pretargeted Live Cell Imaging Devaraj, Neal K.; Weissleder, Ralph; Hilderbrand, Scott A. Bioconjugate Chemistry, Vol. 19, Issue 12 https://doi.org/10.1021/bc8004446	journal	December 2008
A fluorophore ligase for site-specific protein labeling inside living cells Uttamapinant, C.; White, K. A.; Baruah, H. Proceedings of the National Academy of Sciences, Vol. 107, Issue 24 https://doi.org/10.1073/pnas.0914067107	journal	June 2010
A guide to choosing fluorescent proteins Shaner, Nathan C.; Steinbach, Paul A.; Tsien, Roger Y. Nature Methods, Vol. 2, Issue 12 https://doi.org/10.1038/nmeth819	journal	November 2005
Amino Acids for Diels-Alder Reactions in Living Cells Plass, Tilman; Milles, Sigrid; Koehler, Christine Angewandte Chemie International Edition, Vol. 51, Issue 17 https://doi.org/10.1002/anie.201108231	journal	March 2012
A Rapid SNAP-Tag Fluorogenic Probe Based on an Environment-Sensitive Fluorophore for No-Wash Live Cell Imaging Liu, Tao-Kai; Hsieh, Pei-Ying; Zhuang, Yu-De ACS Chemical Biology, Vol. 9, Issue 10 https://doi.org/10.1021/cb500502n	journal	August 2014
Improved green fluorescence Heim, Roger; Cubitt, Andrew B.; Tsien, Roger Y. Nature, Vol. 373, Issue 6516 https://doi.org/10.1038/373663b0	journal	February 1995
Enzymatic Labeling of Proteins: Techniques and Approaches Rashidian, Mohammad; Dozier, Jonathan K.; Distefano, Mark D. Bioconjugate Chemistry, Vol. 24, Issue 8 https://doi.org/10.1021/bc400102w	journal	August 2013
Fluorescence Visualization of Newly Synthesized Proteins in Mammalian Cells Beatty, Kimberly E.; Liu, Julie C.; Xie, Fang Angewandte Chemie International Edition, Vol. 45, Issue 44 https://doi.org/10.1002/anie.200602114	journal	November 2006
Advances in fluorescence labeling strategies for dynamic cellular imaging Dean, Kevin M.; Palmer, Amy E. Nature Chemical Biology, Vol. 10, Issue 7 https://doi.org/10.1038/nchembio.1556	journal	June 2014
How to obtain labeled proteins and what to do with them Hinner, Marlon J.; Johnsson, Kai Current Opinion in Biotechnology, Vol. 21, Issue 6 https://doi.org/10.1016/j.copbio.2010.09.011	journal	December 2010
Areas, Volumes, Packing, and Protein Structure Richards, F. M. Annual Review of Biophysics and Bioengineering, Vol. 6, Issue 1 https://doi.org/10.1146/annurev.bb.06.060177.001055	journal	June 1977
A Fluorogenic TMP-Tag for High Signal-to-Background Intracellular Live Cell Imaging Jing, Chaoran; Cornish, Virginia W. ACS Chemical Biology, Vol. 8, Issue 8 https://doi.org/10.1021/cb300657r	journal	June 2013
An improved monomeric infrared fluorescent protein for neuronal and tumour brain imaging Yu, Dan; Gustafson, William Clay; Han, Chun Nature Communications, Vol. 5, Issue 1 https://doi.org/10.1038/ncomms4626	journal	May 2014
Choosing the Sequence of dsRNA for RNAi in Mouse Svoboda, P. Cold Spring Harbor Protocols, Vol. 2009, Issue 1 https://doi.org/10.1101/pdb.ip63	journal	January 2009
Computational design of a red fluorophore ligase for site-specific protein labeling in living cells Liu, D. S.; Nivon, L. G.; Richter, F. Proceedings of the National Academy of Sciences, Vol. 111, Issue 43 https://doi.org/10.1073/pnas.1404736111	journal	October 2014
Green fluorescent protein as a marker for gene expression Chalfie, M.; Tu, Y.; Euskirchen, G. Science, Vol. 263, Issue 5148 https://doi.org/10.1126/science.8303295	journal	February 1994
Probing Wavelength Regulation with an Engineered Rhodopsin Mimic and a C15-Retinal Analogue Lee, Kin Sing S.; Berbasova, Tetyana; Vasileiou, Chrysoula ChemPlusChem, Vol. 77, Issue 4 https://doi.org/10.1002/cplu.201100082	journal	February 2012
New Biarsenical Ligands and Tetracysteine Motifs for Protein Labeling in Vitro and in Vivo: Synthesis and Biological Applications Adams, Stephen R.; Campbell, Robert E.; Gross, Larry A. Journal of the American Chemical Society, Vol. 124, Issue 21 https://doi.org/10.1021/ja017687n	journal	May 2002
Reversible Synthesis and Characterization of Dynamic Imino Analogues of Trimethine and Pentamethine Cyanine Dyes Meguellati, Kamel; Spichty, Martin; Ladame, Sylvain Organic Letters, Vol. 11, Issue 5 https://doi.org/10.1021/ol802913b	journal	February 2009
A Red Cy3-Based Biarsenical Fluorescent Probe Targeted to a Complementary Binding Peptide Cao, Haishi; Xiong, Yijia; Wang, Ting Journal of the American Chemical Society, Vol. 129, Issue 28 https://doi.org/10.1021/ja070003c	journal	July 2007
A Strain-Promoted [3 + 2] Azide−Alkyne Cycloaddition for Covalent Modification of Biomolecules in Living Systems Agard, Nicholas J.; Prescher, Jennifer A.; Bertozzi, Carolyn R. Journal of the American Chemical Society, Vol. 126, Issue 46 https://doi.org/10.1021/ja044996f	journal	November 2004
Mutational Analysis of Deinococcus radiodurans Bacteriophytochrome Reveals Key Amino Acids Necessary for the Photochromicity and Proton Exchange Cycle of Phytochromes Wagner, Jeremiah R.; Zhang, Junrui; von Stetten, David Journal of Biological Chemistry, Vol. 283, Issue 18 https://doi.org/10.1074/jbc.M709355200	journal	January 2008
Photophysics of Indocarbocyanine Dyes in Organic Solvents Zhifei, Dai; Bixian, Peng Journal of the Chinese Chemical Society, Vol. 45, Issue 2 https://doi.org/10.1002/jccs.199800038	journal	April 1998
Development of Protein-Labeling Probes with a Redesigned Fluorogenic Switch Based on Intramolecular Association for No-Wash Live-Cell Imaging Hori, Yuichiro; Nakaki, Kyohei; Sato, Motoki Angewandte Chemie International Edition, Vol. 51, Issue 23 https://doi.org/10.1002/anie.201200867	journal	April 2012
Merocyanines as Extremely Bathochromically Absorbing Chromophores in the Halobacterial Membrane Protein Bacteriorhodopsin Gärtner, Wolfgang; Buss, Volker; Steinmüller, Siegfried Angewandte Chemie International Edition in English, Vol. 36, Issue 15 https://doi.org/10.1002/anie.199716301	journal	August 1997
Chemical labeling strategies for cell biology Marks, Kevin M.; Nolan, Garry P. Nature Methods, Vol. 3, Issue 8 https://doi.org/10.1038/nmeth906	journal	July 2006
Copper-free click chemistry for dynamic in vivo imaging Baskin, J. M.; Prescher, J. A.; Laughlin, S. T. Proceedings of the National Academy of Sciences, Vol. 104, Issue 43, p. 16793-16797 https://doi.org/10.1073/pnas.0707090104	journal	October 2007
Side-chain flexibility in proteins upon ligand binding Najmanovich, Rafael; Kuttner, Josef; Sobolev, Vladimir Proteins: Structure, Function, and Genetics, Vol. 39, Issue 3 https://doi.org/10.1002/(SICI)1097-0134(20000515)39:3<261::AID-PROT90>3.0.CO;2-4	journal	May 2000
Fluorogen-activating single-chain antibodies for imaging cell surface proteins Szent-Gyorgyi, Christopher; Schmidt, Brigitte F.; Creeger, Yehuda Nature Biotechnology, Vol. 26, Issue 2 https://doi.org/10.1038/nbt1368	journal	December 2007
HaloTag: A Novel Protein Labeling Technology for Cell Imaging and Protein Analysis Los, Georgyi V.; Encell, Lance P.; McDougall, Mark G. ACS Chemical Biology, Vol. 3, Issue 6 https://doi.org/10.1021/cb800025k	journal	June 2008
Rational Design of a Colorimetric pH Sensor from a Soluble Retinoic Acid Chaperone Berbasova, Tetyana; Nosrati, Meisam; Vasileiou, Chrysoula Journal of the American Chemical Society, Vol. 135, Issue 43 https://doi.org/10.1021/ja404900k	journal	October 2013
Structure/Function of Cytoplasmic Vitamin A-Binding Proteins Li, Ellen; Norris, Andrew W. Annual Review of Nutrition, Vol. 16, Issue 1 https://doi.org/10.1146/annurev.nu.16.070196.001225	journal	July 1996
Primary structure of the Aequorea victoria green-fluorescent protein Prasher, Douglas C.; Eckenrode, Virginia K.; Ward, William W. Gene, Vol. 111, Issue 2 https://doi.org/10.1016/0378-1119(92)90691-H	journal	February 1992
High-throughput flow cytometry compatible biosensor based on fluorogen activating protein technology Wu, Yang; Tapia, Phillip H.; Fisher, Gregory W. Cytometry Part A, Vol. 83A, Issue 2 https://doi.org/10.1002/cyto.a.22242	journal	January 2013
Bioorthogonal Chemistry: Fishing for Selectivity in a Sea of Functionality Sletten, Ellen M.; Bertozzi, Carolyn R. Angewandte Chemie International Edition, Vol. 48, Issue 38, p. 6974-6998 https://doi.org/10.1002/anie.200900942	journal	September 2009
Cyanine dye labeling reagents: Sulfoindocyanine succinimidyl esters Mujumdar, Ratnakar B.; Ernst, Lauren A.; Mujumdar, Swati R. Bioconjugate Chemistry, Vol. 4, Issue 2 https://doi.org/10.1021/bc00020a001	journal	March 1993
A Rainbow of Fluoromodules: A Promiscuous scFv Protein Binds to and Activates a Diverse Set of Fluorogenic Cyanine Dyes Pow, Crystal Lee; Marks, Sarah A.; Jesper, Lawrence D. Journal of the American Chemical Society, Vol. 130, Issue 38 https://doi.org/10.1021/ja805042p	journal	September 2008
A general method for the covalent labeling of fusion proteins with small molecules in vivo Keppler, Antje; Gendreizig, Susanne; Gronemeyer, Thomas Nature Biotechnology, Vol. 21, Issue 1 https://doi.org/10.1038/nbt765	journal	December 2002
Polarity as a criterion in protein design Baumann, G.; Froömmel, C.; Sander, C. "Protein Engineering, Design and Selection", Vol. 2, Issue 5 https://doi.org/10.1093/protein/2.5.329	journal	January 1989
Photophysics of Cy3-Encapsulated Calcium Phosphate Nanoparticles Muddana, Hari S.; Morgan, Thomas T.; Adair, James H. Nano Letters, Vol. 9, Issue 4 https://doi.org/10.1021/nl803658w	journal	April 2009
Fluorescence efficiency of four infrared polymethine dyes Casalboni, M.; De Matteis, F.; Prosposito, P. Chemical Physics Letters, Vol. 373, Issue 3-4 https://doi.org/10.1016/S0009-2614(03)00608-0	journal	May 2003
Chemical biology-based approaches on fluorescent labeling of proteins in live cells Jung, Deokho; Min, Kyoungmi; Jung, Juyeon Molecular BioSystems, Vol. 9, Issue 5 https://doi.org/10.1039/c2mb25422k	journal	January 2013
Bioorthogonal Turn-On Probes for Imaging Small Molecules inside Living Cells Devaraj, Neal K.; Hilderbrand, Scott; Upadhyay, Rabi Angewandte Chemie International Edition, Vol. 49, Issue 16 https://doi.org/10.1002/anie.200906120	journal	March 2010
Fluorescent Protein Tracking and Detection: Fluorescent Protein Structure and Color Variants Rizzo, Mark A.; Davidson, Michael W.; Piston, David W. Cold Spring Harbor Protocols, Vol. 2009, Issue 12 https://doi.org/10.1101/pdb.top63	journal	December 2009

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Cyanine polyene reactivity: scope and biomedical applications Gorka, Alexander P.; Nani, Roger R.; Schnermann, Martin J. Organic & Biomolecular Chemistry, Vol. 13, Issue 28 https://doi.org/10.1039/c5ob00788g	journal	January 2015
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