Monoalkoxy BODIPYs-A fluorophore class for bioimaging

Bioconjugate Chemistry

Volumn 25, Issue 6, 2014, Pages 1043-1051

  Courtis, Alexandra M ^a   Santos, Sofia A ^a,b   Guan, Yinghua ^c   Hendricks, J Adam ^a   Ghosh, Balaram ^a   Szantai Kis, D Miklos ^a   Reis, Surya A ^a   Shah, Jagesh V ^c   Mazitschek, Ralph ^a,d  

^a MASSACHUSETTS GENERAL HOSPITAL   (United States)

^b RESEARCH INSTITUTE FOR MEDICINES IMED ULISBOA   (Portugal)

^c BRIGHAM AND WOMEN S HOSPITAL   (United States)

^d BROAD INSTITUTE OF MIT AND HARVARD   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

DIES; MEDICAL IMAGING;

AQUEOUS SOLUBILITY; BIO-IMAGING; BIOMEDICAL IMAGING; BORON DIPYRROMETHENE; FLUORESCENT DYES; IN-VITRO; INDISPENSABLE TOOLS; ONE POT; PHYSICOCHEMICAL PROPERTY; SMALL MOLECULES;

FLUOROPHORES;

4 FLUORO 4 AMINOETHOXY 1,3,5,7,8 PENTAMETHYL 4 BORA 3A.4A DIAZA INDACENE; 4 FLUORO 4 HYDROXYETHOXY 1,3,5,7 TERAMETHYL 8 [3 [[2 [2 [(6 CHLOROHEXYL)OXY]ETHOXY]ETHYL]AMINO] 3 OXOPROPYL] 4 BORA 3A,4A DIAZA INDACENE; 4 FLUORO 4 HYDROXYETHOXY 1,3,5,7 TETRAMETHYL 8 (N SUCCINIMIDYL CARBOXYPROPYL) 4 BORA 3A.4A DIAZA INDACENE; 4 FLUORO 4 HYDROXYETHOXY 1,3,5,7,8 PENTAMETHYL 4 BORA 3A.4A DIAZA INDACENE; 4 FLUORO 4 HYDROXYPROPOXY 1,3,5,7,8 PENTAMETHYL 4 BORA 3A.4A DIAZA INDACENE; 4 FLUORO 4 METHOXY 1,3,5,7,8 PENTAMETHYL 4 BORA 3A,4A DIAZA INDACENE; 4 FLUORO 4 TRIFLUOROETHOXY 1,3,5,7,8 PENTAMETHYL 4 BORA 3A.4A DIAZA INDACENE; 4 FLUORO 4 [4 (4 METHYL 1,2,4,5 TETRAZIN 2 YL)PHENYL] METHOXY 1,3,5,7,8 PENTAMETHYL 4 BORA 3A.4A DIAZA INDACENE; 4,4 DIFLUORO 1,3,5,7 TETRAMETHYL 8 [3 [[2 [2 [(6 CHLOROHEXYL)OXY]ETHOXY]ETHYL]AMIO 3 OXOPROPYL] 4 BORA 3A,4A DIAZA INDACENE; CYANINE DYE; DIFLUORO BORON DIPYRROMETHENE DYE; FLUORESCENT DYE; UNCLASSIFIED DRUG; 4,4-DIFLUORO-4-BORA-3A,4A-DIAZA-S-INDACENE; BORON DERIVATIVE;

ARTICLE; CYTOTOXICITY; DRUG PENETRATION; DRUG SOLUBILITY; ENDOPLASMIC RETICULUM; GOLGI COMPLEX; HYDROLYSIS; IN VITRO STUDY; LIPOPHILICITY; MEMBRANE PERMEABILITY; ONE POT SYNTHESIS; PH; PHYSICAL CHEMISTRY; QUANTUM YIELD; CELL MEMBRANE PERMEABILITY; CELL SURVIVAL; CHEMICAL STRUCTURE; CHEMISTRY; FEMALE; HUMAN; MCF 7 CELL LINE; MOLECULAR IMAGING; PROCEDURES; SOLUBILITY; SYNTHESIS; TUMOR CELL CULTURE;

BORON COMPOUNDS; CELL MEMBRANE PERMEABILITY; CELL SURVIVAL; FEMALE; FLUORESCENT DYES; HUMANS; MCF-7 CELLS; MOLECULAR IMAGING; MOLECULAR STRUCTURE; SOLUBILITY; TUMOR CELLS, CULTURED;

EID: 84902679785     PISSN: 10431802     EISSN: 15204812     Source Type: Journal    
DOI: 10.1021/bc400575w     Document Type: Article

References (35)

1. Lavis, L. D. and Raines, R. T. (2008) Bright ideas for chemical biology ACS Chem. Biol. 3, 142-155
2. Pepperkok, R. and Ellenberg, J. (2006) High-throughput fluorescence microscopy for systems biology Nat. Rev. Mol. Cell. Biol. 7, 690-696
3. Tsien, R. Y. (2010) Fluorescence readouts of biochemistry in live cells and organisms, In Molecular imaging: principles and practice (Weissleder, R., Ross, B. D., Rehemtulla, A., and Gambhir, S., Eds.) pp 808-828, People's Medical Publishing House, Shelton, CT.
4. Weissleder, R. and Pittet, M. J. (2008) Imaging in the era of molecular oncology Nature 452, 580-589
5. Wennmalm, S. and Simon, S. M. (2007) Studying individual events in biology Annu. Rev. Biochem. 76, 419-446
6. Johnson, T. W., Dress, K. R., and Edwards, M. (2009) Using the golden triangle to optimize clearance and oral absorption Bioorg. Med. Chem. Lett. 19, 5560-5564
7. Shank, N. I., Pham, H. H., Waggoner, A. S., and Armitage, B. A. (2013) Twisted cyanines: a non-planar fluorogenic dye with superior photostability and its use in a protein-based fluoromodule J. Am. Chem. Soc. 135, 242-251
8. Lukinavicius, G., Umezawa, K., Olivier, N., Honigmann, A., Yang, G., Plass, T., Mueller, V., Reymond, L., Correa, I. R. J., Luo, Z. G., Schultz, C., Lemke, E. A., Heppenstall, P., Eggeling, C., Manley, S., and Johnsson, K. (2013) A near-infrared fluorophore for live-cell super-resolution microscopy of cellular proteins Nat. Chem. 5, 132-139
9. Ulrich, G., Ziessel, R., and Harriman, A. (2008) The chemistry of fluorescent bodipy dyes: versatility unsurpassed Angew. Chem., Int. Ed. Engl. 47, 1184-1201
10. Beatty, K. E., Szychowski, J., Fisk, J. D., and Tirrell, D. A. (2011) A BODIPY-cyclooctyne for protein imaging in live cells ChemBioChem 12, 2137-2139
11. Didier, P., Ulrich, G., Mely, Y., and Ziessel, R. (2009) Improved push-pull-push E-Bodipy fluorophores for two-photon cell-imaging Org. Biomol. Chem. 7, 3639-3642
12. Hapuarachchige, S., Montaño, G., Ramesh, C., Rodriguez, D., Henson, L. H., Williams, C. C., Kadavakkollu, S., Johnson, D. L., Shuster, C. B., and Arterburn, J. B. (2011) Design and synthesis of a new class of membrane-permeable triazaborolopyridinium fluorescent probes J. Am. Chem. Soc. 133, 6780-6790
13. Wang, S., Guo, J., Ono, T., and Kool, E. T. (2012) DNA polyfluorophores for real-time multicolor tracking of dynamic biological systems Angew. Chem., Int. Ed. Engl. 51, 7176-7180
14. Zheng, Q., Xu, G., and Prasad, P. N. (2008) Conformationally restricted dipyrromethene boron difluoride (BODIPY) dyes: highly fluorescent, multicolored probes for cellular imaging Chemistry 14, 5812-5819
15. Bura, T. and Ziessel, R. (2011) Water-soluble phosphonate-substituted BODIPY derivatives with tunable emission channels Org. Lett. 13, 3072-3075
16. Niu, S. L., Ulrich, G., Ziessel, R., Kiss, A., Renard, P.-Y., and Romieu, A. (2009) Water-soluble BODIPY derivatives Org. Lett. 11, 2049-2052
17. Zhu, S., Zhang, J., Vegesna, G., Luo, F.-T., Green, S. A., and Liu, H. (2011) Highly water-soluble neutral BODIPY dyes with controllable fluorescence quantum yields Org. Lett. 13, 438-441
18. Gabe, Y., Ueno, T., Urano, Y., Kojima, H., and Nagano, T. (2006) Tunable design strategy for fluorescence probes based on 4-substituted BODIPY chromophore: improvement of highly sensitive fluorescence probe for nitric oxide Anal. Bioanal. Chem. 386, 621-626
19. Jiang, X.-D., Zhang, J., Furuyama, T., and Zhao, W. (2012) Development of mono- and di-AcO substituted BODIPYs on the boron center Org. Lett. 14, 248-251
20. Tahtaoui, C., Thomas, C., Rohmer, F., Klotz, P., Duportail, G., Mély, Y., Bonnet, D., and Hibert, M. (2007) Convenient method to access new 4,4-dialkoxy- and 4,4-diaryloxy-diaza- s-indacene dyes: synthesis and spectroscopic evaluation J. Org. Chem. 72, 269-272
21. Hendricks, J. A., Keliher, E. J., Wan, D., Hilderbrand, S. A., Weissleder, R., and Mazitschek, R. (2012) Synthesis of [18F]BODIPY: bifunctional reporter for hybrid optical/positron emission tomography imaging Angew. Chem., Int. Ed. Engl. 51, 4603-4606
22. Guo, B., Peng, X., Cui, A., Wu, Y., Tian, M., Zhang, L., Chen, X., and Gao, Y. (2007) Synthesis and spectral properties of new boron dipyrromethene dyes Dyes Pigm. 73, 206-210
23. Wang, D., Fan, J., Gao, X., Wang, B., Sun, S., and Peng, X. (2009) Carboxyl BODIPY dyes from bicarboxylic anhydrides: one-pot preparation, spectral properties, photostability, and biolabeling J. Org. Chem. 74, 7675-7683
24. Yang, J., Seckute, J., Cole, C. M., and Devaraj, N. K. (2012) Live-cell imaging of cyclopropene tags with fluorogenic tetrazine cycloadditions Angew. Chem., Int. Ed. Engl. 51, 7476-7479
25. Bonnier, C., Piers, W. E., Parvez, M., and Sorensen, T. S. (2008) Borenium cations derived from BODIPY dyes Chem. Commun. 4593-4595
26. Hudnall, T. W. and Gabbai, F. P. (2008) A BODIPY boronium cation for the sensing of fluoride ions Chem. Commun. 4596-4597
27. Blackman, M. L., Royzen, M., and Fox, J. M. (2008) Tetrazine ligation: fast bioconjugation based on inverse-electron-demand Diels-Alder reactivity J. Am. Chem. Soc. 130, 13518-13519
28. Devaraj, N. K., Weissleder, R., and Hilderbrand, S. A. (2008) Tetrazine-based cycloadditions: application to pretargeted live cell imaging Bioconjugate Chem. 19, 2297-2299
29. Devaraj, N. K., Hilderbrand, S., Upadhyay, R., Mazitschek, R., and Weissleder, R. (2010) Bioorthogonal turn-on probes for imaging small molecules inside living cells Angew. Chem., Int. Ed. Engl. 49, 2869-2872
30. Demchenko, A. P., Mély, Y., Duportail, G., and Klymchenko, A. S. (2009) Monitoring biophysical properties of lipid membranes by environment-sensitive fluorescent probes Biophys. J. 96, 3461-3470
31. Loudet, A. and Burgess, K. (2007) BODIPY dyes and their derivatives: syntheses and spectroscopic properties Chem. Rev. 107, 4891-4932
32. Los, G. V., Encell, L. P., McDougall, M. G., Hartzell, D. D., Karassina, N., Zimprich, C., Wood, M. G., Learish, R., Ohana, R. F., Urh, M., Simpson, D., Mendez, J., Zimmerman, K., Otto, P., Vidugiris, G., Zhu, J., Darzins, A., Klaubert, D. H., Bulleit, R. F., and Wood, K. V. (2008) HaloTag: a novel protein labeling technology for cell imaging and protein analysis ACS Chem. Biol. 3, 373-382
33. Bergström, F., Mikhalyov, I., Hägglöf, P., Wortmann, R., Ny, T., and Johansson, L. B. Å. (2002) Dimers of dipyrrometheneboron difluoride (BODIPY) with Light spectroscopic applications in chemistry and biology J. Am. Chem. Soc. 124, 196-204
34. Campagnola, P. J., Wei, M. D., Lewis, A., and Loew, L. M. (1999) High-resolution nonlinear optical imaging of live cells by second harmonic generation Biophys. J. 77, 3341-3349
35. Li, Z., Lin, T.-P., Liu, S., Huang, C.-W., Hudnall, T. W., Gabbai, F. P., and Conti, P. S. (2011) Rapid aqueous [18F]-labeling of a bodipy dye for positron emission tomography/fluorescence dual modality imaging Chem. Commun. 47, 9324-9326