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Chemical Compound Review

Pyranine     trisodium8-hydroxypyrene- 1,3,6-trisulfonate

Synonyms: HPTS, Pyrene 1, Pyranine 120, Green 204, H1529_ALDRICH, ...
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Disease relevance of Pyranine

  • The experimental system selected for testing the accuracy of this concept was the reversible dissociation of a proton from a single pyranine molecule (8-hydroxypyrene-1,2,3-trisulfonate) bound by electrostatic forces inside the PhoE ionic channel of the Escherichia coli outer membrane [1].

High impact information on Pyranine

  • The kinetics of proton release into the water phase was observed with the optical pH indicator pyranine [2].
  • The pyranine study is complemented by the use of vibronic side band luminescence from the gadolinium cation that directly exposes the changes in hydrogen bonding between first and second shell waters as a function of added osmolytes [3].
  • Additional evidence that the Ca2+ pump of sarcoplasmic reticulum operated as a Ca2(+)-H+ countertransport was provided by measurements of ATP-dependent intraliposomal alkalinization using entrapped 8-hydroxyl-1,3,6-pyrene trisulfonate (pyranine) and accumulation of the weak acid acetate [4].
  • We have investigated the permeability of protein-free myelin lipid liposomes to inorganic lead by using the fluorescent probes fura-2, oxonol V, pyranine, and carboxyfluorescein [5].
  • We also study the methoxy derivative of pyranine (MPTS), which is similar in electronic structure but does not have the photoacidity property [6].

Biological context of Pyranine


Anatomical context of Pyranine


Associations of Pyranine with other chemical compounds

  • Similar rates of desorption are observed for the transfer of oleic acid from the three donors to pyranine-containing EPC vesicles with rate constants k(1) ranging from 0.4 to 1.3 s(-1) [17].
  • Na+ accumulation was assayed with 22Na+; deltapsi generation was detected by recording absorption changes of oxonol VI; H+ efflux was monitored as an increase in fluorescence intensity of the pH indicator pyranine loaded into the vesicles [18].
  • Initiation of respiration upon the addition of 20 microM ubiquinone-1 to proteoliposomes loaded with the pH-sensitive dye pyranine resulted in an immediate alkalization of the vesicle lumen by an average pH change of 0.11 unit [19].
  • Purified wild-type M2 protein and an amantadine-resistant mutant M2 (M2 delta) with a deletion in the trans-membrane domain (amino acids 28 to 31) were incorporated into lipid vesicles, which were loaded with the fluorescent pH indicator pyranine [20].
  • We now show that the pH probes pyranine and quinacrine behave similarly to NPN [21].

Gene context of Pyranine

  • The reconstituted enzyme catalyzed CaM-stimulated 45Ca(2+) accumulation and H(+) ejection, monitored by the increase of fluorescence of the pH probe pyranine entrapped in the liposomal lumen during reconstitution [22].
  • METHODS: Cervical cells (ECE16-1, Caski, and HT3) were grown on filters, and transepithelial electrical conductance (GT) and the permeability to pyranine (PPyr) were determined [23].
  • Proteoliposomes containing cytochrome c oxidase and an internally trapped fluorescent pH probe (pyranine) were used to monitor respiration-dependent internal alkalinization and membrane potential formation [24].
  • We describe a strategy for intracellular delivery of pyranine based on the reversible activation of purinergic P2x7 receptors, which allow permeation of the dye into otherwise intact cells [25].
  • Liposomes of egg PC/PG (8:2, mol/mol) were multilabelled with PBFI, pyranine and oxonol VI, fluorescent probes for, respectively, K+, H+ and membrane potential [26].

Analytical, diagnostic and therapeutic context of Pyranine


  1. Gauging of the PhoE channel by a single freely diffusing proton. Bransburg-Zabary, S., Nachliel, E., Gutman, M. Biophys. J. (2002) [Pubmed]
  2. Bacteriorhodopsin expressed in Schizosaccharomyces pombe pumps protons through the plasma membrane. Hildebrandt, V., Fendler, K., Heberle, J., Hoffmann, A., Bamberg, E., Büldt, G. Proc. Natl. Acad. Sci. U.S.A. (1993) [Pubmed]
  3. Molecular Level Probing of Preferential Hydration and Its Modulation by Osmolytes through the Use of Pyranine Complexed to Hemoglobin. Roche, C.J., Guo, F., Friedman, J.M. J. Biol. Chem. (2006) [Pubmed]
  4. Evidence for proton countertransport by the sarcoplasmic reticulum Ca2(+)-ATPase during calcium transport in reconstituted proteoliposomes with low ionic permeability. Levy, D., Seigneuret, M., Bluzat, A., Rigaud, J.L. J. Biol. Chem. (1990) [Pubmed]
  5. Protein-independent lead permeation through myelin lipid liposomes. Díaz, R.S., Monreal, J. Mol. Pharmacol. (1995) [Pubmed]
  6. Solvent-dependent photoacidity state of pyranine monitored by transient mid-infrared spectroscopy. Mohammed, O.F., Dreyer, J., Magnes, B.Z., Pines, E., Nibbering, E.T. Chemphyschem : a European journal of chemical physics and physical chemistry. (2005) [Pubmed]
  7. Endocytosis and intracellular fate of liposomes using pyranine as a probe. Straubinger, R.M., Papahadjopoulos, D., Hong, K.L. Biochemistry (1990) [Pubmed]
  8. Gaugement of the inner space of the apomyoglobin's heme binding site by a single free diffusing proton. I. Proton in the cavity. Shimoni, E., Tsfadia, Y., Nachliel, E., Gutman, M. Biophys. J. (1993) [Pubmed]
  9. Somatic vs. dendritic responses to hypercapnia in chemosensitive locus coeruleus neurons from neonatal rats. Ritucci, N.A., Dean, J.B., Putnam, R.W. Am. J. Physiol., Cell Physiol. (2005) [Pubmed]
  10. Oxidative stress decreases pHi and Na(+)/H(+) exchange and increases excitability of solitary complex neurons from rat brain slices. Mulkey, D.K., Henderson, R.A., Ritucci, N.A., Putnam, R.W., Dean, J.B. Am. J. Physiol., Cell Physiol. (2004) [Pubmed]
  11. Effects of estrogen on tight junctional resistance in cultured human umbilical vein endothelial cells. Cho, M.M., Ziats, N.P., Abdul-Karim, F.W., Pal, D., Goldfarb, J., Utian, W.H., Gorodeski, G.I. J. Soc. Gynecol. Investig. (1998) [Pubmed]
  12. Mechanism of proton entry into the cytoplasmic section of the proton-conducting channel of bacteriorhodopsin. Checover, S., Nachliel, E., Dencher, N.A., Gutman, M. Biochemistry (1997) [Pubmed]
  13. The dynamics of proton transfer at the C side of the mitochondrial membrane: picosecond and microsecond measurements. Kotlyar, A.B., Borovok, N., Kiryati, S., Nachliel, E., Gutman, M. Biochemistry (1994) [Pubmed]
  14. Proton pumping and the internal pH of yeast cells, measured with pyranine introduced by electroporation. Peña, A., Ramírez, J., Rosas, G., Calahorra, M. J. Bacteriol. (1995) [Pubmed]
  15. The fluorescent indicator pyranine is suitable for measuring stromal and cameral pH in vivo. Thomas, J.V., Brimijoin, M.R., Neault, T.R., Brubaker, R.F. Exp. Eye Res. (1990) [Pubmed]
  16. Assay of ATP synthesis using single giant mitochondria. Campo, M.L., Bowman, C.L., Tedeschi, H. Eur. J. Biochem. (1984) [Pubmed]
  17. Kinetics and mechanism of long-chain fatty acid transport into phosphatidylcholine vesicles from various donor systems. Thomas, R.M., Baici, A., Werder, M., Schulthess, G., Hauser, H. Biochemistry (2002) [Pubmed]
  18. Electrogenicity of the Na+-ATPase from the marine microalga Tetraselmis (Platymonas) viridis and associated H+ countertransport. Balnokin, Y.V., Popova, L.G., Andreev, I.M. FEBS Lett. (1999) [Pubmed]
  19. Formation of pH and potential gradients by the reconstituted Azotobacter vinelandii cytochrome bd respiratory protection oxidase. Kolonay, J.F., Maier, R.J. J. Bacteriol. (1997) [Pubmed]
  20. Functional reconstitution in lipid vesicles of influenza virus M2 protein expressed by baculovirus: evidence for proton transfer activity. Schroeder, C., Ford, C.M., Wharton, S.A., Hay, A.J. J. Gen. Virol. (1994) [Pubmed]
  21. pH probes respond to redox changes in cytochrome o. Sedgwick, E.G., Bragg, P.D. Arch. Biochem. Biophys. (1990) [Pubmed]
  22. H(+)/Ca(2+) exchange driven by the plasma membrane Ca(2+)-ATPase of Arabidopsis thaliana reconstituted in proteoliposomes after calmodulin-affinity purification. Luoni, L., Bonza, M.C., De Michelis, M.I. FEBS Lett. (2000) [Pubmed]
  23. Characterization of paracellular permeability in cultured human cervical epithelium: regulation by extracellular adenosine triphosphate. Gorodeski, G.I., Merlin, D., De Santis, B.J., Frieden, K.A., Hopfer, U., Eckert, R.L., Utian, W.H., Romero, M.F. J. Soc. Gynecol. Investig. (1994) [Pubmed]
  24. Effects of triorganotin-mediated anion-hydroxide exchange upon reconstituted cytochrome c oxidase proteoliposomes. Singh, A.P., Nicholls, P. Biochem. Cell Biol. (1986) [Pubmed]
  25. Loading pyranine via purinergic receptors or hypotonic stress for measurement of cytosolic pH by imaging. Gan, B.S., Krump, E., Shrode, L.D., Grinstein, S. Am. J. Physiol. (1998) [Pubmed]
  26. Quantitative measurement of cationic fluxes, selectivity and membrane potential using liposomes multilabelled with fluorescent probes. Venema, K., Gibrat, R., Grouzis, J.P., Grignon, C. Biochim. Biophys. Acta (1993) [Pubmed]
  27. Intracellular localization of a group II chaperonin indicates a membrane-related function. Trent, J.D., Kagawa, H.K., Paavola, C.D., McMillan, R.A., Howard, J., Jahnke, L., Lavin, C., Embaye, T., Henze, C.E. Proc. Natl. Acad. Sci. U.S.A. (2003) [Pubmed]
  28. Pyranine (8-hydroxy-1,3,6-pyrenetrisulfonate) as a probe of internal aqueous hydrogen ion concentration in phospholipid vesicles. Clement, N.R., Gould, J.M. Biochemistry (1981) [Pubmed]
  29. Removal of the transducer protein from sensory rhodopsin I exposes sites of proton release and uptake during the receptor photocycle. Olson, K.D., Spudich, J.L. Biophys. J. (1993) [Pubmed]
  30. Protonmotive force and photophosphorylation in single swollen thylakoid vesicles. Campo, M.L., Tedeschi, H. Eur. J. Biochem. (1985) [Pubmed]
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