New generation of bioorthogonally applicable fluorogenic dyes with visible excitations and large stokes shifts

Bioconjugate Chemistry

Volumn 25, Issue 7, 2014, Pages 1370-1374

  Herner, András ^a   Estrada Girona, Gemma ^b   Nikić, Ivana ^b   Kállay, Mihály ^c   Lemke, Edward A ^b   Kele, Péter ^a  

^a INSTITUTE OF EXPERIMENTAL MEDICINE   (Hungary)

^b EUROPEAN MOLECULAR BIOLOGY LABORATORY   (Germany)

^c BUDAPEST UNIVERSITY OF TECHNOLOGY AND ECONOMICS   (Hungary)

Author keywords

[No Author keywords available]

Indexed keywords

FLUOROGENICS; LYSATES; PERFORMANCE; STOKES SHIFT;

AZIDE; DYE; TRIAZOLE DERIVATIVE; CYCLOOCTANE DERIVATIVE; FLUORESCENT DYE; MALTOSE BINDING PROTEIN;

ARTICLE; CELL LYSATE; DENSITY FUNCTIONAL THEORY; ENERGY TRANSFER; EXCITATION; FLUORESCENCE; LARGE STOKES SHIFT; SPECTRAL SENSITIVITY; SYNTHESIS; CHEMISTRY; FLUORESCENCE IMAGING; HUMAN; PROCEDURES;

AZIDES; CYCLOOCTANES; FLUORESCENCE; FLUORESCENT DYES; HUMANS; MALTOSE-BINDING PROTEINS; OPTICAL IMAGING; TRIAZOLES;

EID: 84904430272     PISSN: 10431802     EISSN: 15204812     Source Type: Journal    
DOI: 10.1021/bc500235p     Document Type: Article

References (38)

1. Sahoo, H. (2012) Fluorescent labeling techniques in biomolecules: a flashback RSC Adv. 2, 7017-7029
2. Gonçalves, M. S. T. (2009) Fluorescent labeling of biomolecules with organic probes Chem. Rev. 109, 190-212
3. Kele, P., Li, X., Link, M., Nagy, K., Herner, A., Lorincz, K., Béni, Sz., and Wolfbeis, O. S. (2009) Clickable fluorophores for biological labeling-with or without copper Org. Biomol. Chem. 7, 3486-3490
4. Fernández-Suárez, M. and Ting, A. Y. (2008) Fluorescent probes for super-resolution imaging in living cells Nat. Rev. Mol. Cell. Biol. 9, 929-943
5. Lee, J. H., So, J.-H., Jeon, J. H., Choi, E. B., Lee, Y.-R., Chang, Y.-T., Kim, C.-H., Bae, M. A., and Ahn, J. H. (2011) Synthesis of a new fluorescent small molecule probe and its use for in vivo lipid imaging Chem. Commun. 47, 7500-7502
6. Ehrenschwender, T., Varga, B. R., Kele, P., and Wagenknecht, H.-A. (2010) New far-red and near-infrared fluorescent probes with large stokes shifts for dual covalent labeling of DNA Chem.-Asian J. 5, 1761-1764
7. Sato, M., Ito, Y., Arima, N., Baba, M., Sobel, M., Wakao, M., and Suda, Y. (2009) High-sensitivity analysis of naturally occurring sugar chains, using a novel fluorescent linker molecule J. Biochem. 146, 33-41
8. Nadler, A. and Schultz, C. (2013) The power of fluorogenic probes Angew. Chem., Int. Ed. 52, 2408-2410
9. Nikolova, K., Kaloyanova, S., Mihaylova, N., Stoitsova, S., Chausheva, S., Vasilev, A., Lesev, N., Dimitrova, P., Deligeorgiev, T., and Tchorbanov, A. (2013) New fluorogenic dyes for analysis of cellular processes by flow cytometry and confocal microscopy J. Photochem. Photobiol., B: Biol. 129, 125-134
10. Le Droumaguet, C., Wang, C., and Wang, Q. (2010) Fluorogenic click reaction Chem. Soc. Rev. 39, 1233-1239
11. Jewett, J. C. and Bertozzi, C. R. (2011) Synthesis of a fluorogenic cyclooctyne activated by Cu-free click chemistry Org. Lett. 13, 5937-5939
12. Lukinavičius, G. and Johnsson, K. (2011) Switchable fluorophores for protein labeling in living cells Curr. Opin. Biol. 15, 768-774
13. Rong, L., Liu, L.-H., Chen, S., Cheng, H., Chen, C.-S., Li, Z.-Y., Qin, S.-Y., and Zhang, X.-Z. (2014) A coumarin derivative as a fluorogenic glycoproteomic probe for biological imaging Chem. Commun. 50, 667-669
14. Maglione, M. and Sigrist, S. J. (2013) Seeing the forest tree by tree: super-resolution light microscopy meets the neurosciences Nat. Neurosci. 16, 790-797
15. Debets, M. F., van Hest, J. C. M., and Rutjes, F. P. J. T. (2013) Bioorthogonal labelling of biomolecules: new functional handles and ligation methods Org. Biomol. Chem. 11, 6439-6455
16. Karver, M. R., Weissleder, R., and Hilderbrand, S. A. (2012) Bioorthogonal reaction pairs enable simultaneous, selective, multi-target imaging Angew. Chem., Int. Ed. 51, 920-922
17. Carroll, L., Evans, H. L., Aboagye, E. O., and Spivey, A. C. (2013) Bioorthogonal chemistry for pre-targeted molecular imaging-progress and prospects Org. Biomol. Chem. 11, 5772-5781
18. Patterson, D. M., Nazarova, L. A., and Prescher, J. A. (2014) Finding the right (bioorthogonal) chemistry ACS Chem. Biol. 9, 592-605
19. Ramil, C. P. and Lin, Q. (2013) Bioorthogonal chemistry: strategies and recent developments Chem. Commun. 49, 11007-11022
20. Debets, M. F., van der Doelen, C. W. J., Rutjes, F. P. J. T., and van Delft, F. L. (2010) Azide: a unique dipole for metal-free bioorthogonal ligations ChemBioChem 11, 1168-1184
21. Baskin, J. M. and Bertozzi, C. R. (2010) Copper-free click chemistry: bioorthogonal reagents for tagging azides Aldrichimica Acta 43, 15-23
22. Varga, B. R., Kállay, M., Hegyi, K., Béni, Sz., and Kele, P. (2012) A non-fluorinated monobenzocyclooctyne for rapid copper-free click reactions Chem.-Eur. J. 18, 822-828
23. Dommerholt, J., Schmidt, S., Temming, R., Hendriks, L. J. A., Rutjes, F. P. J. T., van Hest, J. C. M., Lefber, D. J., Friedl, P., and van Delft, F. L. (2010) Readily accessible bicyclononynes for bioorthogonal labeling and three-dimensional imaging of living cells Angew. Chem., Int. Ed. 49, 9422-9425
24. van Berkel, S. S., van Eldijk, M. B., and van Hest, J. C. M. (2011) Staudinger ligation as a method for bioconjugation Angew. Chem., Int. Ed. 50, 8806-8827
25. Schilling, C. I., Jung, N., Biskup, M., Schepers, U., and Bräse, S. (2011) Bioconjugation via azide-Staudinger ligation: an overview Chem. Soc. Rev. 40, 4840-4871
26. Sivakumar, K., Xie, F., Cash, B. M., Long, S., Barnhill, H. N., and Wang, Q. (2004) A fluorogenic 1,3-dipolar cycloaddition reaction of 3-azidocoumarins and acetylenes Org. Lett. 6, 4603-4606
27. Shieh, P., Hangauer, M. J., and Bertozzi, C. R. (2012) Fluorogenic azidofluoresceins for biological imaging J. Am. Chem. Soc. 134, 17428-17431
28. Herner, A., Nikić, I., Kállay, M., Lemke, E. A., and Kele, P. (2013) A new family of bioorthogonally applicable fluorogenic labels Org. Biomol. Chem. 11, 3297-3306
29. Gonda, Zs. and Novák, Z. (2010) Highly active copper-catalysts for azide-alkyne cycloaddition Dalton Trans. 39, 726-729
30. Plass, T., Milles, S., Koehler, C., Schultz, C., and Lemke, E. A. (2011) Genetically encoded copper-free click chemistry Angew. Chem., Int. Ed. 50, 3878-3881
31. Plass, T., Milles, S., Koehler, C., Szymański, J., Mueller, R., Wießler, M., Schultz, C., and Lemke, E. A. (2012) Amino acids for Diels-Alder reactions in living cells Angew. Chem., Int. Ed. 51, 4166-4170
32. Borrmann, A., Milles, S., Plass, T., Dommerholt, J., Verkade, J. M. M., Wießler, M., Schultz, C., van Hest, J. C. M., van Delft, F. L., and Lemke, E. A. (2012) Genetic encoding of a bicyclo[6.1.0]nonyne-charged amino acid enables fast cellular protein imaging by metal-free ligation ChemBioChem 13, 2094-2099
33. Perdew, J. P., Burke, K., and Ernzerhof, M. (1996) Generalized gradient approximation made simple Phys. Rev. Lett. 77, 3865-3868
34. (1997), Phys. Rev. Lett. 78, 1396-1396.
35. Adamo, C. and Barone, V. (1999) Toward reliable density functional methods without adjustable parameters: the PBE0 model J. Chem. Phys. 110, 6158-6170
36. Miertuš, S. (1981) Electrostatic interaction of a solute with a continuum. A direct utilization of ab initio molecular potentials for the prevision of solvent effects Chem. Phys. 55, 117-129
37. Stratmann, R. E., Scuseria, G. E., and Frisch, M. J. (1998) An efficient implementation of time-dependent density-functional theory for the calculation of excitation energies of large molecules J. Chem. Phys. 109, 8218-8224
38. Frisch, M. J., Trucks, G. W., and Schlegel, H. B., (2009) Gaussian 09, revision B.01, Gaussian, Inc., Wallingford, CT.