A water-soluble fluorescence resonance energy transfer probe for hypochlorous acid and its application to cell imaging

Chinese Science Bulletin

Volumn 56, Issue 31, 2011, Pages 3266-3272

  Jia, Jia ^a   Ma, Hui Min ^a  

^a INSTITUTE OF CHEMISTRY   (China)

Author keywords

cell imaging; dansyl rhodamine B piperazinoacetohydrazide; fluorescence resonance energy transfer; hypochlorous acid; water soluble probe

Indexed keywords

EID: 80155142313     PISSN: 10016538     EISSN: 18619541     Source Type: Journal    
DOI: 10.1007/s11434-011-4645-2     Document Type: Article

References (31)

1. Yan Y, Wang S H, Liu Z W, et al. CdSe-ZnS quantum dots for selective and sensitive detection and quantification of hypochlorite. Anal Chem, 2010, 82: 9775-9781.
2. March J G, Simonet B M. A green method for the determination of hypochlorite in bleaching products based on its native absorbance. Talanta, 2007, 73: 232-236.
3. Sun Z N, Liu F Q, Chen Y, et al. A highly specific BODIPY-based fluorescent probe for the detection of hypochlorous acid. Org Lett, 2008, 10: 2171-2174.
4. Gomes A, Fernandes E, Lima J. Fluorescence probes used for detection of reactive oxygen species. J Biochem Biophys Methods, 2005, 65: 45-80.
5. Fink M P. Role of reactive oxygen and nitrogen species in acute respiratory distress syndrome. Curr Opin Crit Care, 2002, 8: 6-11.
6. Li X H, Zhang G X, Ma H M, et al. 4, 5-Dimethylthio-4′-2-(9-anthryloxy) ethylthio tetrathiafulvalene, a highly selective and sensitive chemiluminescence probe for singlet oxygen. J Am Chem Soc, 2004, 126: 11543-11548.
7. Pullar J M, Vissers M C M, Winterbourn C C. Living with a killer: The effects of hypochlorous acid on mammalian cells. IUBMB Life, 2000, 50: 259-266.
8. Yap Y W, Whiteman M, Cheung N S. Chlorinative stress: An under appreciated mediator of neurodegeneration? Cell Signal, 2007, 19: 219-228.
9. Sugiyama S, Okada Y, Sukhova G K, et al. Macrophage myeloperoxidase regulation by granulocyte macrophage colony-stimulating factor in human atherosclerosis and implications in acute coronary syndromes. Am J Pathol, 2001, 158: 879-891.
10. Steinbeck M J, Nesti L J, Sharkey P F, et al. Myeloperoxidase and chlorinated peptides in osteoarthritis: Potential biornarkers of the disease. J Orthop Res, 2007, 25: 1128-1135.
11. Pattison D I, Davies M J. Evidence for rapid inter- and intramolecular chlorine transfer reactions of histamine and carnosine chloramines: Implications for the prevention of hypochlorous-acid-mediated damage. Biochemistry, 2006, 45: 8152-8162.
12. Chen S M, Lu J X, Sun C D, et al. A highly specific ferrocene-based fluorescent probe for hypochlorous acid and its application to cell imaging. Analyst, 2010, 135: 577-582.
13. Chen X Q, Wang X C, Wang S J, et al. A highly selective and sensitive fluorescence probe for the hypochlorite anion. Chem Eur J, 2008, 14: 4719-4724.
14. Yang Y K, Cho H J, Le J, et al. A rhodamine-hydroxamic acid-based fluorescent probe for hypochlorous acid and its applications to biological imagings. Org Lett, 2009, 11: 859-861.
15. Lin W Y, Long L L, Chen B B, et al. Ratiometric fluorescent probe for hypochlorite based on a deoximation reaction. Chem Eur J, 2009, 15: 2305-2309.
16. Shi J, Li Q Q, Zhang X, et al. Simple triphenylamine-based luminophore as a hypochlorite chemosensor. Sens Actuators B, 2010, 145: 583-587.
17. Kenmoku S, Urano Y, Kojima H, et al. Development of a highly spe cific rhodamine-based fluorescence probe for hypochlorous acid and its application to real-time imaging of phagocytosis. J Am Chem Soc, 2007, 129: 7313-7318.
18. Shepherd J, Hilderbrand S A, Waterman P, et al. A fluorescent probe for the detection of myeloperoxidase activity in atherosclerosis-associated macrophages. Chem Biol, 2007, 14: 1221-1231.
19. Panizzi P, Nahrendorf M, Wildgruber M, et al. Oxazine conjugated nanoparticle detects in vivo hypochlorous acid and peroxynitrite generation. J Am Chem Soc, 2009, 131: 15739-15744.
20. Cui K, Zhang D Q, Zhang G X, et al. A highly selective naked-eye probe for hypochlorite with the p-methoxyphenol-substituted aniline compound. Tetrahedron Lett, 2010, 51: 6052-6055.
21. Chen X Q, Sun M, Ma H M. Progress in spectroscopic probes with cleavable active bonds. Curr Org Chem, 2006, 10: 477-489.
22. Jia J, Wang K, Shi W, et al. Rhodamine B piperazinoacetohydrazine: A water-soluble spectroscopic reagent for pyruvic acid labeling. Chem Eur J, 2010, 16: 6638-6643.
23. Jia J, Chen W, Ma H M, et al. Use of a rhodamine-based bifunctional probe in N-terminal specific labeling of Thermomyces lanuginosus xylanase. Mol Biosyst, 2010, 6: 1829-1833.
24. Leffler J E, Bond W B. The influence of polar substituents and polar solvents on radical decomposition reactions. J Am Chem Soc, 1956, 78: 335-341.
25. Kanofsky J R. Singlet oxygen production from the reactions of alkylperoxy radicals-evidence from 1268-nm chemiluminescence. J Org Chem, 1986, 51: 3386-3388.
26. Fery-Forgues S, Lavabre D. Are fluorescence quantum yields so tricky to measure? A demonstration using familiar stationary products. J Chem Educ, 1999, 76: 1260-1264.
27. Zhao H T, Kalivendi S, Zhang H, et al. Superoxide reacts with hydroethidine but forms a fluorescent product that is distinctly different from ethidium: Potential implications in intracellular fluorescence detection of superoxide. Free Radic Biol Med, 2003, 34: 1359-1368.
28. Setsukinai K, Urano Y, Kakinuma K, et al. Development of novel fluorescence probes that can reliably detect reactive oxygen species and distinguish specific species. J Biol Chem, 2003, 278: 3170-3175.
29. Aubry J M, Cazin B, Duprat F. Chemical sources of singlet of oxygen. Peroxidation of water-soluble singlet oxygen carriers with the hydrogen-peroxide molybdate system. J Org Chem, 1989, 54: 726-728.
30. Kikuchi K, Takakusa H, Nagano T. Recent advances in the design of small molecule-based FRET sensors for cell biology. Trend Anal Chem, 2004, 23: 407-415.
31. Lee M H, Kim H J, Yoon S, et al. Metal ion induced FRET OFF-ON in tren/dansyl-appended rhodamine. Org Lett, 2008, 10: 213-216.