Pyrene trisulfonated

Cascade Blue cadaverine and Cascade Blue ethylenediamine both contain a carboxamide-linked diamine spacer off the 8-methoxy group of the pyrene trisulfonic acid backbone. The cadaverine version contains a 5-carbon spacer, while the ethylenediamine compound has only a 2-carbon arm. Both can be coupled to carboxylic acid-containing molecules using a carbodiimide reaction (Chapter 3, Section 1). Since Cascade Blue derivatives are water-soluble, the carbodiimide EDC can be used to couple these fluorophores to proteins and other carboxylate-containing molecules in aqueous solutions at a pH range of 4.5-7.5. The reaction forms amide bond linkages (Figure 9.39). 

Using pyranine (8-hydroxy-1,3,6-pyrene trisulfonate) as intraliposome pH indicator, the liposomes were prepared as above (as in section Preparation of 100 nm SSL Loaded with DOX via Transmembrane AS Gradient ) with the exception that pyranine (0.5 mM) was included in the hydration solution. Removal of untrapped pyranine was achieved by gel filtration on a Sephadex G-50 column, preequilibrated with either NaCl, KCl, sucrose or AS solution (according to need). All these solutions also contained lOmM Hepes buffer at the desired pH (usually pH 7.5). 

Figure 12 (line A) depicts the emission spectrum of hydroxy pyrene trisulfonate dissolved in diluted buffer (pH 5.0). At this pH, the ground state is fully protonated (pK0 = 7.7), but not so the first excited singlet state (pK = 0.5). The excited molecules dissociate and 95% of the emission is at the wavelength of the excited anion (515 nm). The dissociation can be prevented if the compound is dissolved in acid solution, pH < pK., such as 2MHC1 (line B). Under such conditions, we observe the emission of the neutral form with maximum at 445 nm. Upon ligation to apomyoglobin, the fluorescence of hydroxypyrene trisulfonate consists of two... 

The intensive electrostatic repulsion between the pyrenate trisulfonate anion (Z = -4) and the protonated indicator (BCGH-) lowers the probability of their encounter by a hundredfold (Eigen et al., 1964). Thus, a direct proton exchange between these two reactants is slowed both by slow diffusion (D 2—3 x 10 6 cm2 sec-1) and electric repulsion. 

ATP and GTP as compared to other nucleotides, whereas neghgible selectivity is found for 117 and 119. Compounds 116, 117, and 118 exhibited significant binding interactions with the fluorescent, water-soluble dye 8-hydroxyl-l,3,6-pyrene trisulfonate (HPTS) yielding a quenching of the fluorescence. Titration of the adducts with the nucleotides produces the displacement of the dye and the revival of the fluorescence. 

Scheme 7.7 Hydrolysis of nonanoyl pyrene trisulfonate (35) catalyzed by dendrimer 36...

This procedure is based on the method of Smith, Opie, Waw-zonek, and Prichard3 for the preparation of 2,3,6-trimethyl-phenol. 3-Hydroxypyrene has been prepared by fusion of pyrene-3-sulfonic acid with sodium hydroxide 4 and by desul-fonation of 3-hydroxypyrene-5,8,10-trisulfonic acid with hot, dilute sulfuric acid.5... 

Fig. 1.5. Examples of hydrophobic, hydrophilic and amphiphilic probes. 1 pyrene. 2 8-hydroxypyrene-l,3,6-trisulfonic acid, trisodium salt (pyranine). 3 8-alkoxypyrene-l,3,6-trisulfonic acid, trisodium salt. 4 1-...

Membrane-covered optochemical sensors (optodes) with O2 sensitive or pH sensitive fluorescence indicators (e.g. pyrene butyric acid or hydroxypyrene trisulfonic acid) have been coupled with different enzyme reactions, such as the conversion of glucose, lactate, ethanol, or xanthine, and with antigen-antibody couples (Opitz and Lubbers, 1987). 

Figure 12.2 Molecular structure of 1-hydroxypyrene (IHP), 8-hydroxypyrene-l,3,6-dimethylsulfamide (HPTA) and 8-hydroxy pyrene 1,3,6-trisulfonate (HPTS).

Figure 5. The dependence of the rate of proton dissociation from excited 8-hydroxy-pyrene- 1,3,6-trisulfonate on the mole fraction of ethanol in water, and the respective proton conductivity of the mixtures. The rate of proton dissociation was measured by time resolved ( ) or steady-state ( ) fluorescence. The proton conductivity of the solutions (A) is normalized for pure water conductivity. Data taken from Erdey-Grutz and Lengyel (1977).

Pouxviel J.C., Dunn B., Zink J.I. Fluorescence study of aluminosilicate sols and gels doped with hydroxy trisulfonated pyrene. J. Phys. Chem. 1989 93 2134-2139 Preston D., Ponxviel J., Novinson T., Kaska W.C., Dunn B., Zink J.I. Photochromism of spiropyrans in aluminosilicate gels. J. Phys. Chem. 1990 94 4167-1172 Sakka, Sumio, Sol-Gel Science. Tokyo Aguneshofu-sha, 1988... 

Recently, Hynes and coworkers have proposed a new perspective (a three-step mechanism) on intermolecular photochemical proton transfer in solution [96-99]. They performed femtosecond fluorescence and absorption measurements on pyranine (PyOH 8-hydroxy-l,3,6-trisulfonate pyrene) in aqueous solution, and found that the early events of the photoinduced proton transfer from pyranine to water involve three... 

Other Names 8-Methoxypyrene-l,3,6-trisulfonic acid, trisodium salt MPTS 1,3,6-Pyrenetrisulfonic acid, 8-methoxy-, trisodium salt Trisodium 8-methoxy-1,3,6-pyrene tri sulfonate Merck Index Number Not hsted... 

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