Substrates for improved live-cell fluorescence labeling of SNAP-tag

Current Pharmaceutical Design

Volumn 19, Issue 30, 2013, Pages 5414-5420

  Corrêa Jr , Ivan R ^a   Baker, Brenda ^a   Zhang, Aihua ^a   Sun, Luo ^a   Provost, Christopher R ^a   Lukinavičius, Gražvydas ^b   Reymond, Luc ^b   Johnsson, Kai ^b   Xu, Ming Qun ^a  

^a NEW ENGLAND BIOLABS   (United States)

^b EPFL   (Switzerland)

Author keywords

Cell imaging; Covalent labeling; Fluorescent probes; Protein modifications

Indexed keywords

6 CARBOXYRHODAMINE; BENZYLCHLOROPYRIMIDINE; BENZYLGUANINE; FLUORESCENT DYE; GUANINE DERIVATIVE; HYBRID PROTEIN; PLASMID DNA; PYRIMIDINE DERIVATIVE; RHODAMINE; RHODAMINE 110; UNCLASSIFIED DRUG;

ANIMAL CELL; ARTICLE; BIOTECHNOLOGICAL PROCEDURES; CHEMICAL STRUCTURE; CHO CELL; CRYSTAL STRUCTURE; CRYSTALLIZATION; ELECTROSPRAY MASS SPECTROMETRY; FLUORESCENCE; FLUORESCENCE IN SITU HYBRIDIZATION; FLUORESCENCE MICROSCOPY; HUMAN; HUMAN CELL; IN VITRO STUDY; ISOMERISM; NONHUMAN; OSTEOSARCOMA CELL; PRIORITY JOURNAL; PROTEIN ANALYSIS; PROTEIN MODIFICATION; PROTON NUCLEAR MAGNETIC RESONANCE; SIGNAL NOISE RATIO; SNAP TAG TECHNOLOGY; SYNTHESIS; TIME OF FLIGHT MASS SPECTROMETRY;

ANIMALS; CELL LINE; CELL MEMBRANE; CRICETINAE; FLUORESCENT DYES; HUMANS; MOLECULAR IMAGING; MOLECULAR STRUCTURE; PERMEABILITY; RHODAMINES; SUBSTRATE SPECIFICITY;

EID: 84881349263     PISSN: 13816128     EISSN: 18734286     Source Type: Journal    
DOI: 10.2174/1381612811319300011     Document Type: Article

References (36)

1. Giepmans BN, Adams SR, Ellisman MH, Tsien RY. Thefluorescent toolbox for assessing protein location and function. Science 2006; 312: 217-24.
2. Gautier A, Juillerat A, Heinis C, et al. An engineered protein tagfor multiprotein labeling in living cells. Chem Biol 2008; 15: 128-36.
3. Keppler A, Gendreizig S, Gronemeyer T, Pick H, Vogel H,Johnsson K. A general method for the covalent labeling of fusion proteins with small molecules in vivo. Nat Biotechnol 2003; 21: 86-9.
4. Keppler A, Pick H, Arrivoli C, Vogel H, Johnsson K. Labeling offusion proteins with synthetic fluorophores in live cells. Proc Natl Acad Sci USA 2004; 101: 9955-9.
5. O'Hare HM, Johnsson K, Gautier A. Chemical probes shed light onprotein function. Curr Opin Struct Biol 2007; 17: 488-94.
6. Hinner MJ, Johnsson K. How to obtain labeled proteins and whatto do with them. Curr Opin Biotechnol 2010; 21: 766-76.
7. Hoskins AA, Friedman LJ, Gallagher SS, et al. Ordered anddynamic assembly of single spliceosomes. Science 2011; 331: 1289-95.
8. Breitsprecher D, Jaiswal R, Bombardier JP, Gould CJ, Gelles J,Goode BL. Rocket launcher mechanism of collaborative actin assembly defined by single-molecule imaging. Science 2012; 336: 1164-8.
9. Pellett PA, Sun X, Gould TJ, et al. Two-color STED microscopy inliving cells. Biomed Opt Express 2011; 2: 2364-71.
10. Jones SA, Shim SH, He J, Zhuang X. Fast, three-dimensionalsuper-resolution imaging of live cells. Nat Methods 2011; 8: 499-508.
11. Foraker AB, Camus SM, Evans TM, et al. Clathrin promotescentrosome integrity in early mitosis through stabilization of centrosomal ch-TOG. J Cell Biol 2012; 198: 591-605.
12. Ville D, J DEB, Nguyen MA, et al. Ring 14 chromosomepresenting as early-onset isolated partial epilepsy. Dev Med Child Neurol 2009; 51: 917-22.
13. Chidley C, Haruki H, Pedersen MG, Muller E, Johnsson K. Ayeast-based screen reveals that sulfasalazine inhibits tetrahydrobiopterin biosynthesis. Nat Chem Biol 2011; 7: 375-83.
14. Bojkowska K, Santoni de Sio F, Barde I, et al. Measuring in vivoprotein half-life. Chem Biol 2011; 18: 805-15.
15. Lavis LD, Raines RT. Bright ideas for chemical biology. ACSChem Biol 2008; 3: 142-55.
16. Lukinavicius G, Johnsson K. Switchable fluorophores for proteinlabeling in living cells. Curr Opin Chem Biol 2011; 15: 768-74.
17. Komatsu T, Johnsson K, Okuno H, et al. Real-time measurementsof protein dynamics using fluorescence activation-coupled protein labeling method. J Am Chem Soc 2011; 133: 6745-51.
18. Sun X, Zhang A, Baker B, et al. Development of SNAP-tagfluorogenic probes for wash-free fluorescence imaging. Chembiochem 2011; 12: 2217-26.
19. Banala S, Maurel D, Manley S, Johnsson K. A caged, localizablerhodamine derivative for superresolution microscopy. ACS Chem Biol 2011; 7: 289-93.
20. Campos C, Kamiya M, Banala S, Johnsson K, Gonzalez-Gaitan M.Labelling cell structures and tracking cell lineage in zebrafish using SNAP-tag. Dev Dyn 2011; 240: 820-7.
21. Maurel D, Banala S, Laroche T, Johnsson K. Photoactivatable andphotoconvertible fluorescent probes for protein labeling. ACS Chem Biol 2010; 5: 507-16.
22. Bannwarth M, Correa IR, Sztretye M, et al. Indo-1 derivatives forlocal calcium sensing. ACS Chem Biol 2009; 4: 179-90.
23. Kamiya M, Johnsson K. Localizable and highly sensitive calciumindicator based on a BODIPY fluorophore. Anal Chem 2010; 82: 6472-9.
24. Brun MA, Griss R, Reymond L, et al. Semisynthesis of fluorescentmetabolite sensors on cell surfaces. J Am Chem Soc 2011; 133: 16235-42.
25. Brun MA, Tan KT, Griss R, Kielkowska A, Reymond L, Johnsson K. A semisynthetic fluorescent sensor protein for glutamate. J Am Chem Soc 2012; 134: 7676-8.
26. Grimm JB, Lavis LD. Synthesis of rhodamines from fluoresceinsusing Pd-catalyzed C-N cross-coupling. Org Lett 2011; 13: 6354-7.
27. Mitronova GY, Belov VN, Bossi ML, et al. New FluorinatedRhodamines for Optical Microscopy and Nanoscopy. Chemistry 2010; 16: 4477-88.
28. Kvach MV, Stepanova IA, Prokhorenko IA, et al. Practicalsynthesis of isomerically pure 5-and 6-carboxytetramethyl-rhodamines, useful dyes for DNA probes. Bioconjug Chem 2009; 20: 1673-82.
29. Hill ZB, Perera BG, Andrews SS, Maly DJ. Targeting diversesignaling interaction sites allows the rapid generation of bivalent kinase inhibitors. ACS Chem Biol 2012; 7: 487-95.
30. Keppler A, Arrivoli C, Sironi L, Ellenberg J. Fluorophores for livecell imaging of AGT fusion proteins across the visible spectrum. Biotechniques 2006; 41: 167-70, 72, 74-5.
31. Mollwitz B, Brunk E, Schmitt S, et al. Directed evolution of thesuicide protein O(6)-alkylguanine-DNA alkyltransferase for increased reactivity results in an alkylated protein with exceptional stability. Biochemistry 2012; 51: 986-94.
32. Gronemeyer T, Chidley C, Juillerat A, Heinis C, Johnsson K.Directed evolution of O6-alkylguanine-DNA alkyltransferase for applications in protein labeling. Protein Eng Des Sel 2006; 19: 309-16.
33. Demchenko AP, Demchenko A. Comparative Analysis ofFluorescence Reporter Signals Based on Intensity, Anisotropy, Time-Resolution, and Wavelength-Ratiometry. Advanced Fluorescence Reporters in Chemistry and Biology I: Springer Berlin Heidelberg; 2010. p. 3-24.
34. Marme N, Knemeyer JP, Sauer M, Wolfrum J. Inter andintramolecular fluorescence quenching of organic dyes by tryptophan. Bioconjug Chem 2003; 14: 1133-9.
35. Kolmakov K, Belov VN, Bierwagen J, et al. Red-emittingrhodamine dyes for fluorescence microscopy and nanoscopy. Chemistry 2010; 16: 158-66.
36. Koide Y, Urano Y, Hanaoka K, Terai T, Nagano T. Evolution ofgroup 14 rhodamines as platforms for near-infrared fluorescence probes utilizing photoinduced electron transfer. ACS Chem Biol 2011; 6: 600-8.