A novel acidotropic pH indicator and its potential application in labeling acidic organelles of live cells

Chemistry and Biology

Volumn 6, Issue 7, 1999, Pages 411-418

  Diwu, Zhenjun ^a   Chen, Chii Shiarng ^a   Zhang, Cailan ^a   Klaubert, Dieter H ^a   Haugland, Richard P ^a  

^a MOLECULAR PROBES INC   (United States)

Author keywords

Acidic organelles; Fluorescence; Lysosome; PH indicator; Ratio imaging

Indexed keywords

EID: 0033169080     PISSN: 10745521     EISSN: None     Source Type: Journal    
DOI: 10.1016/S1074-5521(99)80059-3     Document Type: Article

References (38)

1. 2+] and pH homeostasis in Kaposi sarcoma cells. Cell Physiol. Biochem. 6, 169-184.
2. 2+] during metabolic inhibition. Am. J. Physiol. Heart Circ. Phy. 37, H1239-H1248.
3. Nuccitelli, R. (1994). A Practical Guide to the Study of Calcium in Living Cells. Vol. 40, Academic Press, San Diego, USA.
4. Okamoto, C.T. (1998). Endocytosis and transcytosis. Adv. Drug Deliv Rev. 29, 215-228.
5. Falke, J.J., Bass, R.B., Butler, S.L., Chervitz, S.A. & Danielson, M.A. (1997). The two-component signaling pathway of bacterial chemotaxis: A molecular view of signal transduction by receptors, kinases, and adaptation enzymes. Ann. Rev. Cell Dev. Biol. 13, 457-512.
6. Shimizu, Y. & Hunt III, S.W. (1996). Regulating integrin-mediated adhesion: One more function for PI 3-kinase? Immunol. Today 17, 565-573.
7. Tsien, R.Y. (1989). Fluorescent indicators of ion concentrations. In Fluorescence Microscopy of Living Cells in Culture. (Taylor, D.L. ed.), Vol. 30, Part B, pp. 127-156, Academic Press, San Diego, USA.
8. Haugland, R.P. (1996). Handbook of Fluorescent Probes and Research Chemicals (6th Ed.), Molecular Probes, Inc., Eugene, Oregon, USA.
9. Johnson, I. (1998). Fluorescent probes for living cells. Histochem. J. 30, 123-140.
10. Warner, I.M., Soper, S.A. & McGown, L.B. (1996). Molecular fluorescence, phosphorescence, and chemiluminescence spectrometry. Anal. Chem. 68, R73-R91.
11. Czarnik, A.W. (1995). Desperately seeking sensors. Chem. Biol. 2, 423-428.
12. Overly, C.C., Lee, K.D., Berthiaume, E. & Hollenbeck, P.J. (1995). Quantitative measurement of intraorganelle pH in the endosomal lysosomal pathway in neurons by using ratiometric imaging with pyranine. Proc. Natl Acad. Sci. USA 92, 3156-3160.
13. 2+ probe Fluo-3 and the pH probe BCECF. Mol. Cell Biochem. 178, 77-80.
14. Devoisselle, J.M., Soulie, S., Mordon, S. & Maillols, H. (1996). Fluorescent characteristics and pharmacokinetic profiles of the fluorescent probe BCECF in various tissues: The role of blood content. Photochem. Photobiol. 64, 906-910.
15. Liu, J.X., Diwu, Z.J. & Klaubert, D.H. (1997). Fluorescent molecular probes III. 2′,7′-bis-(3-carboxypropyl)-5-(and-6)-carboxyfluorescein (BCPCF): A new polar dual-excitation and dual-emission pH indicator with a pKa of 7.0. Bioorg. Med. Chem. Letter 7, 3069-3072.
16. Whitaker, J.E., Haugland, R.P. & Prendergast, F.G. (1991). Spectral and photophysical studies of benzo[c]xanthene dyes: Dual emission pH sensors. Anal. Biochem. 194, 330-344.
17. Kneen, M., Farinas, J., Li, Y. & Verkman, A.S. (1998) Green fluorescent protein as a noninvasive intracellular pH indicator. Biophys J. 74, 1591-1599.
18. Bright, G.R., Fisher, G.W., Rogowska, J. & Taylor, D.L. (1989). Fluorescence ratio imaging microscopy. Methods Cell. Biol. 30, 157-192.
19. Martínez-Zaguilán, R., Seftor, E.A., Seftor, R.E.B., Chu, Y.W., Gillies, R.J. & Hendrix, M.J.C. (1996). Acidic pH enhances the invasive behavior of human melanoma cells. Clin. Exp. Metastasis 14, 176-186.
20. Anderson, R.G.W. & Orci, L. (1988). A view of acidic intracelluar compartments. J. Cell Biol. 106, 539-543.
21. Holtzman, E. (1989). Lysosomes. Plenum Press, New York, USA.
22. Diwu, Z., Lu, Y.X., Zhang, C.L., Klaubert, D.H. & Haugland, R.P. (1997). Fluorescent molecular probes .2. The synthesis, spectral properties and use of fluorescent solvatochromic Dapoxyl™ dyes. Photochem. Photobiol. 66, 424-431.
23. King, L.C. & Ostrum, G.K. (1964). Selective bromination with copper(II) bromide. J. Org. Chem. 29, 3459-3461.
24. deSilva, A.P., Gunnlaugsson, T. & Rice, T.E. (1996). Recent evolution of luminescent photoinduced electron transfer sensors - A review. Analyst 121, 1759-1762.
25. Babcock, D.F. (1983). Examination of the intracellular ionic environment and of ionophore action by null point measurements employing the fluorescein chromophore. J. Biol. Chem. 258, 6380-6389.
26. Reeves, J.P. (1984). The mechanism of lysosomal acidification. In Lysosomes in Biology and Pathology. (Dingle, J.T., Dean, R.T. & Sly, W. ed.), Vol. 7, pp. 175-199, Elsevier, Amsterdam, The Netherlands.
27. Wang, Y.X., Shi, L.B. & Verkman, A.S. (1991). Functional water channels and proton pumps are in separate populations of endocytic vesicles in toad bladder granular cells. Biochemistry, 30, 2888-2894.
28. Koval, M. & Pagano, R.E. (1990). Sorting of an internalized plasma membrane lipid between recycling and degradative pathways in normal and Niemann-Pick, Type A fibroblasts. J. Cell Biol. 111, 429-442.
29. Wang, X.F. & Herman, B. (1996). Fluorescence Imaging Spectroscopy and Microscopy. John Wiley & Sons, New York, USA.
30. Galjarrd, H. & Reuser, A.J.J. (1984). Genetic Aspects of Lysosomal Storage Diseases, in Lysosomes in Biology and Pathology. (J.T. Dingle ed.), Vol. 7, pp. 315-379, Elsevier, Amsterdam, The Netherlands.
31. Tassin, M., Lang, T., Antoine, J., Hellio, R. & Ryter, A. (1990). Modified lysosomal compartment as a carrier of slowly and non-degradable tracers in macrophages. Europ. J. Cell Biol. 52, 219-228.
32. Anderson, R.G.W. & Pathak, R.K. (1985). Vesicles and cisternae in the trans Golgi apparatus of human fibroblasts are acidic compartments. Cell 40, 635-643.
33. Barasch, J., Kiss, B., Prince, A., Saiman, L. & Gruenert, D. (1991). Defective acidification of intracellular organelles in cystic fibrosis. Nature 352, 70-73.
34. Kauffman, J.M., Litak, P.T. & Adams, J.K. (1992). Syntheses and photophysical properties of some 5(2)-aryl-2(5)-(4-pyridyl)oxazoles and related oxadiazoles and furans. J. Heterocylic Chem. 29, 1245-1273.
35. Demas, J.N. & Crosby, G.A. (1971). The measurement of photoluminescence quantum yields, a review. J. Phys. Chem. 75, 991-1024.
36. Chen, C.-S., Rosenwald, A.G. & Pagano, R.E. (1995). Ceramide as a modulator of endocytosis. J. Biol. Chem. 270, 13291-13297.
37. Chen, C.-S., Martin, O.C. & Pagano, R.E. (1997). Changes in the spectral properties of a plasma membrane lipid analog during the first seconds of endocytosis in living cells. Biophys. J. 72, 37-50.
38. Bronk, S.F. & Gores, G.J. (1991). Efflux of protons from acidic vesicles contributes to cytosolic acidification of hepatocytes during ATP depletion. Hepatology 14, 626-633.