Functionalized two-photon absorbing diketopyrrolopyrrole-based fluorophores for living cells fluorescent microscopy

Bioconjugate Chemistry

Volumn 24, Issue 6, 2013, Pages 942-950

  Ftouni, Hussein ^a   Bolze, Frédéric ^a   De Rocquigny, Hugues ^a   Nicoud, Jean François ^a  

^a UNIVERSITÉ DE STRASBOURG   (France)

Author keywords

[No Author keywords available]

Indexed keywords

LASER EXCITATION; PHOTONS; TWO PHOTON PROCESSES;

CELLULARS; DIKETOPYRROLOPYRROLES; EXCITATION POWER; FLUORESCENT MICROSCOPY; FUNCTIONALIZED; IN-VIVO IMAGING; LIVING CELL; TWO PHOTON; TWO-PHOTON EXCITATIONS; TWO-PHOTON EXCITED;

FLUOROPHORES;

DIKETOPYRROLOPYRROLE DERIVATIVE; FLUORESCENT DYE; TRANSACTIVATOR PROTEIN; UNCLASSIFIED DRUG;

ARTICLE; CELLULAR DISTRIBUTION; CONTROLLED STUDY; EXCITATION; FLUORESCENCE MICROSCOPY; HELA CELL; HUMAN; HUMAN CELL; LIGHT ABSORPTION; LUMINESCENCE; PEPTIDE SYNTHESIS; PHYSICAL CHEMISTRY; QUANTUM YIELD;

EID: 84879401781     PISSN: 10431802     EISSN: 15204812     Source Type: Journal    
DOI: 10.1021/bc300623q     Document Type: Article

References (26)

1. Helmchen, F. and Denk, W. (2005) Deep tissue two-photon microscopy Nat. Methods 2, 932-940
2. Larson, A. M. (2011) Multiphoton microscopy. Nat. Photonics 5, Advertising feature.
3. Soeller, C. and Cannell, M. B. (1999) Two-photon microscopy: Imaging in scattering samples and three-dimensionally resolved flash photolysis Microsc. Res. Tech. 47, 182-195
4. Warther, D., Gug, S., Specht, A., Bolze, F., Nicoud, J.-F., Mourot, A., and Goeldner, M. (2010) Two-photon uncaging: new prospects in neuroscience and cellular biology Bioorg. Med. Chem. 18, 7753-7758
5. Squirrell, J. M., Wokosin, D. L., White, J. G., and Bavister, B. D. (1999) Long-term two-photon fluorescence imaging of mammalian embryos without compromising viability Nat. Biotechnol. 17, 763-767
6. König, K. (2000) Multiphoton microscopy in life sciences J. Microsc. 200, 83-104
7. Pawlicki, M., Collins, H. A., Denning, R. G., and Anderson, H. L. (2009) Two-photon absorption and the design of two-photon dyes Angew. Chem., Int. Ed. 48, 3244-3266
8. Larson, D. R., Zipfel, W. R., Williams, R. M., Clark, S. W., Bruchez, M. P., Wise, F. W., and Webb, W. W. (2003) Water-soluble quantum dots for multiphoton fluorescence imaging in vivo Science 300, 1434-1436
9. Hayek, A., Ercelen, S., Zhang, X., Bolze, F., Nicoud, J.-F., Schaub, E., Baldeck, P. L., and Mély, Y. (2007) Conjugation of a new two-photon fluorophore to poly(ethylenimine) for gene delivery imaging Bioconjugate Chem. 18, 844-851
10. Bolze, F., Niehl, A., Heinlein, M., Mjdasiri, N., Rehspringer, J.-L., Schaeffer, N., Didier, P., Arntz, Y., Mély, Y., Gug, S., Specht, A., Goeldner, M., and Nicoud, J.-F. (2010) Two-photon excitation in life sciences: From observation to action Nonlinear Opt., Quantum Opt. 40, 253-265
11. Morales, A. R., Yanez, C. O., Schafer-Hales, K. J., Marcus, A. I., and Belfield, K. D. (2009) Biomolecule labeling and imaging with a new fluorenyl two-photon fluorescent probe Bioconjugate Chem. 20, 1992-2000
12. Yao, S. and Belfield, K. D. (2012) Two-photon fluorescent probes for bioimaging Eur. J. Org. Chem. 17, 3199-3217
13. Iqbal, A. and Cassar, L. (Ciba-Geigy) (1982) 1,4-Diketopyrrolo[3,4- c ]pyrrole pigments. Patent EP 98808.
14. Ftouni, H., Bolze, F., and Nicoud, J.-F. (2013) Water-soluble diketopyrrolopyrrole derivatives for two-photon excited fluorescence microscopy Dyes Pigments 97, 77-83
15. Vyňuchal, J., Luňák, S., Jr, Hatlapatková, A., Hrdina, R., Lycka, A., Havel, L. Å., Vyňuchalová, K., and Jirásko, R. (2008) The synthesis, absorption, fluorescence and photoisomerisation of 2-aryl-4-arylmethylidene-pyrroline-5-ones Dyes Pigments 77, 266-276
16. Luňák, S., Jr, Vyňuchal, J., Vala, M., Havel, L., and Hrdina, R. (2009) The synthesis, absorption and fluorescence of polar diketo-pyrrolo-pyrroles Dyes Pigments 82, 102-108
17. Greiner, V. J., Shvadchak, V., Fritz, J., Arntz, Y., Didier, P., Frisch, B., Boudier, C., Mély, I., and de Rocquigny, H. (2011) Characterization of the mechanisms of HIV-1 Vpr(52-96) internalization in cells Biochimie 93, 1647-1658
18. Xu, C., Williams, R. M., Zipfel, W., and Webb, W. W. (1996) Multiphoton excitation cross-sections of molecular fluorophores Bioimaging 4, 198-207
19. Xu, C. and Webb, W. W. (1996) Measurement of two-photon excitation cross-sections of molecular fluorophores with data from 690 to 1050 nm J. Opt. Soc. Am. B 13, 481-491
20. Crosby, G. A. and Demas, J. N. (1971) Measurement of photoluminescence quantum yields J. Phys. Chem. 75, 991-1024
21. Nicoud, J.-F., Bolze, F., Sun, X.-H., Hayek, A., and Baldeck, P. L. (2011) Boron-containing two-photon-absorbing chromophores. 3. (1) One-and two-photon photophysical properties of p-carborane-containing fluorescent bioprobes Inorg. Chem. 50, 4272-4278
22. Henschen, A. and Edman, P. (1972) Large scale preparation of S-carboxymethylated chains of human fibrin and fibrinogen and the occurrence of chain variants Biochim. Biophys. Acta 263, 351-367
23. Guo, E. Q., Ren, P. H., Zhang, Y. L., Zhang, H. C., and Yang, W. J. (2009) Diphenylamine end-capped 1,4-diketo-3,6-diphenylpyrrolo[3,4- c ]pyrrole (DPP) derivatives with large two-photon absorption cross-sections and strong two-photon excitation red fluorescence Chem. Commun. 5859-5861
24. Richard, J. P., Melikov, K., Vives, E., Ramos, C., Verbeure, B., Gait, M. J., Chernomordik, L. V., and Lebleu, B. (2003) Cell-penetrating peptides. A reevaluation of the mechanism of cellular uptake J. Biol. Chem. 278, 585-590
25. Vives, E., Richard, J. P., Rispal, C., and Lebleu, B. (2003) TAT peptide internalization: seeking the mechanism of entry Curr. Protein Pept. Sci. 4, 125-132
26. Brooks, H., Lebleu, B., and Vives, E. (2005) Tat peptide-mediated cellular delivery: back to basics Adv. Drug Delivery Rev. 57, 559-577