Pyrazole-substituted near-infrared cyanine dyes exhibit pH-dependent fluorescence lifetime properties

Photochemistry and Photobiology

Volumn 89, Issue 2, 2013, Pages 326-331

  Lee, Hyeran ^a   Berezin, Mikhail Y ^a   Tang, Rui ^a   Zhegalova, Natalia ^a   Achilefu, Samuel ^a  

^a WASHINGTON UNIVERSITY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

CARBOCYANINE; DIMETHYL SULFOXIDE; DRUG DERIVATIVE; FLUORESCENT DYE; INDOCYANINE GREEN; IR 820; PYRAZOLE DERIVATIVE;

ARTICLE; CHEMISTRY; ELECTRON; FLUORESCENCE; NEAR INFRARED SPECTROSCOPY; PH; SPECTROFLUOROMETRY;

CARBOCYANINES; DIMETHYL SULFOXIDE; ELECTRONS; FLUORESCENCE; FLUORESCENT DYES; HYDROGEN-ION CONCENTRATION; INDOCYANINE GREEN; PYRAZOLES; SPECTROMETRY, FLUORESCENCE; SPECTROSCOPY, NEAR-INFRARED;

EID: 84874741280     PISSN: 00318655     EISSN: 17511097     Source Type: Journal    
DOI: 10.1111/php.12009     Document Type: Article

References (29)

1. Han, J., and, K. Burgess, (2010) Fluorescent indicators for intracellular pH. Chem. Rev. 110, 2709-2728.
2. Mordon, S., J. M. Devoisselle, and, S. Soulie, (1995) Fluorescence spectroscopy of pH in vivo using a dual-emission fluorophore (C-SNAFL-1). J. Photochem. Photobiol., B 28, 19-23.
3. Sanders, R., A. Draaijer, H. C. Gerritsen, P. M. Houpt, and, Y. K. Levine, (1995) Quantitative pH imaging in cells using confocal fluorescence lifetime imaging microscopy. Anal. Biochem. 227, 302-308.
4. Whitaker, J. E., R. P. Haugland, and, F. G. Prendergast, (1991) Spectral and photophysical studies of benzo[c]xanthene dyes: Dual emission pH sensors. Anal. Biochem. 194, 330-344.
5. Hilderbrand, S. A., K. A. Kelly, M. Niedre, and, R. Weissleder, (2008) Near infrared fluorescence-based bacteriophage particles for ratiometric pH imaging. Bioconjug. Chem. 19, 1635-1639.
6. Boens, N., W. Qin, M. Baruah, W. M. De Borggraeve, A. Filarowski, N. Smisdom, M. Ameloot, L. Crovetto, E. M. Talavera, and, J. M. Alvarez-Pez, (2011) Rational design, synthesis, and spectroscopic and photophysical properties of a visible-light-excitable, ratiometric, fluorescent near-neutral pH indicator based on BODIPY. Chemistry 17, 10924-10934.
7. Kuwana, E., and, E. M. Sevick-Muraca, (2003) Fluorescence lifetime spectroscopy for pH sensing in scattering media. Anal. Chem. 75, 4325-4329.
8. Hassan, M., J. Riley, V. Chernomordik, P. Smith, R. Pursley, S. B. Lee, J. Capala, and, A. H. Gandjbakhche, (2007) Fluorescence lifetime imaging system for in vivo studies. Mol. Imaging 6, 229-236.
9. Hanson, K. M., M. J. Behne, N. P. Barry, T. M. Mauro, E. Gratton, and, R. M. Clegg, (2002) Two-photon fluorescence lifetime imaging of the skin stratum corneum pH gradient. Biophys. J. 83, 1682-1690.
10. Berezin, M. Y., K. Guo, W. Akers, R. E. Northdurft, J. P. Culver, B. Teng, O. Vasalatiy, K. Barbacow, A. Gandjbakhche, G. L. Griffiths, and, S. Achilefu, (2011) Near-infrared fluorescence lifetime pH-sensitive probes. Biophys. J. 100, 2063-2072.
11. Almutairi, A., S. J. Guillaudeu, M. Y. Berezin, S. Achilefu, and, J. M. Frechet, (2008) Biodegradable pH-sensing dendritic nanoprobes for near-infrared fluorescence lifetime and intensity imaging. J. Am. Chem. Soc. 130, 444-445.
12. Baruah, M., W. Qin, N. Basaric, W. M. De Borggraeve, and, N. Boens, (2005) BODIPY-based hydroxyaryl derivatives as fluorescent pH probes. J. Org. Chem. 70, 4152-4157.
13. Baruah, M., W. Qin, C. Flors, J. Hofkens, R. A. Vallee, D. Beljonne, M. Van der Auweraer, W. M. De Borggraeve, and, N. Boens, (2006) Solvent and pH dependent fluorescent properties of a dimethylaminostyryl borondipyrromethene dye in solution. J. Phys. Chem. A 110, 5998-6009.
14. Boens, N., W. Qin, N. Basaric, A. Orte, E. M. Talavera, and, J. M. Alvarez-Pez, (2006) Photophysics of the fluorescent pH indicator BCECF. J. Phys. Chem. A 110, 9334-9343.
15. Qin, W., M. Baruah, M. Van der Auweraer, F. C. De Schryver, and, N. Boens, (2005) Photophysical properties of borondipyrromethene analogues in solution. J. Phys. Chem. A 109, 7371-7384.
16. Szmacinski, H., and, J. R. Lakowicz, (1993) Optical measurements of pH using fluorescence lifetimes and phase-modulation fluorometry. Anal. Chem. 65, 1668-1674.
17. Amali, A. J., N. H. Awwad, R. K. Rana, and, D. Patra, (2011) Nanoparticle assembled microcapsules for application as pH and ammonia sensor. Anal. Chim. Acta 708, 75-83.
18. Murtaza, Z., Q. Chang, G. Rao, H. Lin, and, J. R. Lakowicz, (1997) Long-lifetime metal-ligand pH probe. Anal. Biochem. 247, 216-222.
19. Zhang, Z., and, S. Achilefu, (2005) Design, synthesis and evaluation of near-infrared fluorescent pH indicators in a physiologically relevant range. Chem. Commun. (Camb.), 588, 7-5889.
20. Strekowski, L., J. C. Mason, H. Lee, M. Say, and, G. Patonay, (2004) Water-soluble pH-sensitive 2,6-bis(substituted ethylidene)-cyclohexanone/hydroxy cyanine dyes that absorb in the visible/near-infrared regions. J. Heterocyclic Chem. 41, 227-232.
21. Strekowski, L., J. C. Mason, M. Say, H. Lee, R. Gupta, and, M. Hojjat, (2005) Novel synthetic route to pH-sensitive 2,6-bis(substituted ethylidene)cyclohexanone/hydroxycyanine dyes that absorb in the visible/near-infrared regions. Heterocycl. Commun. 11, 129-134.
22. Lee, H., M. Y. Berezin, K. Guo, J. Kao, and, S. Achilefu, (2009) Near-infrared fluorescent pH-sensitive probes via unexpected barbituric acid mediated synthesis. Org. Lett. 11, 29-32.
23. Berezin, M. Y., J. Kao, and, S. Achilefu, (2009) pH-dependent optical properties of synthetic fluorescent imidazoles. Chemistry 15, 3560-3566.
24. Lee, H., J. C. Mason, and, S. Achilefu, (2006) Heptamethine cyanine dyes with a robust C-C bond at the central position of the chromophore. J. Org. Chem. 71, 7862-7865.
25. Benson, R. C., and, H. A. Kues, (1978) Fluorescence properties of indocyanine green as related to angiography. Phys. Med. Biol. 23, 159-163.
26. Lee, H., M. Y. Berezin, M. Henary, L. Strekowski, and, S. Achilefu, (2008) Fluorescence lifetime properties of near-infrared cyanine dyes in relation to their structures. J. Photochem. Photobiol. A Chem. 200, 438-444.
27. Lakowicz, J. R., (2006) Principles of Fluorescence Spectroscopy. Springer Science, New York.
28. Rosch, U., S. Yao, R. Wortmann, and, F. Wurthner, (2006) Fluoresceut H-aggregates of merocyanine dyes. Angew. Chem. Int. Edit. 45, 7026-7030.
29. Zhang, Z., M. Y. Berezin, J. L. Kao, A. d'Avignon, M. Bai, and, S. Achilefu, (2008) Near-infrared dichromic fluorescent carbocyanine molecules. Angew. Chem. Int. Ed. Engl. 47, 3584-3587.