Kinetics of alkaline hydrolysis of dilaurylfluorescein in aqueous ethanol and micellar solution of cetyltrimethylammonium bromide

Keywords: dilauryl fluorescein, hydrolysis, rate constant, CTAB micelles, diester

Abstract

The rate constants of two consecutive reactions of dilaurylfluorescein hydrolysis in the aqueous ethanol (50% wt.) and cetyltrimethylammonium bromide (CTAB) micellar solutions were determined by spectrophotometrical method. In both systems, the rate of hydrolysis of the second ester group exceeds the rate of hydrolysis of the first one ca. in 4-fold, due to the significant stabilization of the neutral lactone form of indicator in low-polar media.

Downloads

Download data is not yet available.

References

Li X., Higashikubo R., Taylor J.-S. Use of мultiple сarboxylates to increase intracellular reten-tion of fluorescent probes following release from cell penetrating fluorogenic conjugates // Bioconjug. Chem. – 2008. – Vol. 19. – № 1. – P. 50–56.

Swisher R., Carroll G.C. Fluorescein diacetate as an estimator of microbial biomass on conif-erous needle surfaces // Microb. Ecol. – 1980. – Vol. 6. – № 3. – P. 217–226.

Sontag W. Changes of fluoresceindiacetat hydrolysis and transport in mammalian cells after ultra-violet and gamma irradiation // Radiat. Environ. Biophys. – 1977. – Vol. 14. – № 1. – P. 13–20.

Maljovany S.V., Vodolazkaya N.A., Mchedlov-Petrossyan N.O., Orlov V.D. Stabilizaciya ho-linesterazy' v micellyarnoy srede cvitterionnogo poverhnostno-aktivnogo vesch'estva // Dop. NAN Ukrainy. – 2003. – № 1. – P. 145–148 [in Russian].

Maljovany S.V., Vodolazkaya N.A., Mchedlov-Petrossyan N.O., Orlov V.D. Diacetilfluo-rescein kak fluorogenny'y substrat holinesterazy' // Visn. Hark. nac. univ., № 495, Ser. Him., issue 6(29), P. 34–39 [in Russian].

Taylor J.P., Wilson B., Mills M.S., Burns R.G. Comparison of microbial numbers and enzy-matic activities in surface soils and subsoils using various techniques // Soil Biol. Biochem. – 2002. – Vol. 34. – № 3. – P. 387–401.

Green V.S., Stott D.E., Diack M. Assay for fluorescein diacetate hydrolytic activity: Optimi-zation for soil samples // Soil Biol. Biochem. – 2006. – Vol. 38. – № 4. – P. 693–701.

Battin T.J. Assessment of fluorescein diacetate hydrolysis as a measure of total esterase activ-ity in natural stream sediment biofilms // Sci. Total Environ. – 1997. – Vol. 198. –№ 1. – P. 51–60.

Adam G., Duncan H. Development of a sensitive and rapid method for the measurement of total microbial activity using fuorescein diacetate (FDA) in a range of soils // Soil Biol. Bio-chem. – 2001. – Vol. 33. – № 7-8. – P. 943–951.

Blaskó A., Taylor J.P., Wilson B., Mills M.S. Burns R.G. Micellar rate effects on reactions of hydroxide ion with phosphate and thiophosphinate esters // J. Phys. Org. Chem. – 1991. –Vol. 4. – № 10. –P. 618–628.

Bunton C.A. Micellar rate effects: assumptions and approximations // Arkivoc. – 2011 (vii). – P. 490–504.

Mchedlov-Petrossyan N.O. Protolytic equilibrium in lyophilic nanosized dispersions: Differ-entiating influence of the pseudophase and salt effects // Pure Appl. Chem. – 2008. – Vol. 80. – № 7. – P. 1459–1510.

Bunton C.A., Nome F., Quina F.H. Romsted L.S. Ion binding and reactivity at charged aque-ous interfaces // Acc. Chem. Res. – 1991. – Vol. 24. – № 12. – P. 357–364.

Schnürer J., Rosswall T. Fluorescein Diacetate Hydrolysis as a measure of total microbial ac-tivity in soil and litter // Appl. Environ. Microbiol. – 1982. – Vol. 43. – № 6. – P. 1256–1261.

Breeuwer P., Drocourt J.-L., Bunschoten N., Zwietering M.H., Rombouts F.M., Abee T. Characterization of uptake and hydrolysis of fluorescein diacetate and carboxyfluorescein di-acetate by intracellular esterases in Saccharomyces cerevisiae, which result in accumulation of fluorescent product. // Appl. Environ. Microbiol. – 1995. – Vol. 61. – № 4. – P. 1614–1619.

Vitecek J., Petrlova J., Adam V. Havel L., Kramer K.J., Babula P., Kizek R.A. A fluorimetric sensor for detection of one living cell // Sensors. – 2007. – Vol. 7. – № 3. – P. 222–238.

Ge F.-Y., Chen L.-G., Zhou X.-L., Pan H.-Y., Yan F.-Y. Bai G.-Y. Yan X.-L. Synthesis and study on hydrolytic properties of fluorescein esters // Dyes and Pigments – 2007. – Vol. 72. – № 3. – P. 322–326.

Eshghi H., Mirzaie N., Asoodeh A. Synthesis of fluorescein aromatic esters in the presence of P2O5/SiO2 as catalyst and their hydrolysis studies in the presence of lipase // Dyes and Pig-ments – 2011. – Vol. 89, – № 2. – P. 120–126.

Rotman B., Papermaster B.W. Membrane properties of living mammalian cells as studied by enzymatic hydrolysis of fluorogenic esters // Proc. Natl. Acad. Sci. – 1966. – Vol. 55, – № 1. – P. 134–141.

Sontag W. A Comparative kinetic study on the conversion of fluoresceindiacetate to fluo-rescein in living cells and in vitro // Radiat. Environ. Biophys. – 1977. – Vol. 14. – № 1. – P. 1–12.

Anzo K., Harada M., Okada T. Enhanced kinetics of pseudo first-order hydrolysis in liquid phase coexistent with ice // J. Phys. Chem. A. – 2013. – Vol. 117. – № 41. – P. 10619–10625.

Hofmann J., Sernetz M. A Kinetic study on the enzymatic hydrolysis of fluoresceindiacetate and fluorescein-di-β-D-galactopyranoside // Anal. Biochem. – 1983. – Vol. 131. – № 1. – P. 180–186.

Emanuel N. M., Knorre D. G. Kurs himicheskoy kinetiki. – Moskow: Vy'sshaya shkola, 1984. – P. 251 – 254 [in Russian].

Niwayama S. Highly efficient selective monohydrolysis of symmetric diesters // J. Org. Chem. – 2000. – Vol. 65. – № 18. – P. 5834–5836.

Niwayama S., Wang H., Hiraga Y., Clayton J.C. Influence of co-solvents in the highly effi-cient selective monohydrolysis of a symmetric diester // Tetrahedron Lett. – 2007. – Vol. 48. – № 48. – P. 8508–8510.

Bahram M. Mean centering of ratio spectra as a new method for determination of rate con-stants of consecutive reactions. // Anal. Chim. Acta. – 2007. – Vol. 603. – № 1. – P. 13–19.

Tjahjono M., Huiheng Ch., Widjaja E., Sa-ei K., Garland M. Combined on-line transmission FTIR measurements and BTEM analysis for the kinetic study of a consecutive reaction in aqueous-organic phase medium // Talanta. – 2009. – Vol. 79. – № 3. – P. 856–862.

Mchedlov-Petrossyan N.O., Mayorga R.S. Extraordinary character of the solvent influence on protolytic equilibria: inversion of the fluorescein ionization constants in H2O-DMSO mixtures // J. Chem. Soc., Faraday Trans. – 1992. – Vol. 88. – № 20. – P. 3025–3032.

Published
2014-09-03
Cited
How to Cite
Cheipesh, T. A., Taranets, Y. V., & Mchedlov-Petrossyan, N. O. (2014). Kinetics of alkaline hydrolysis of dilaurylfluorescein in aqueous ethanol and micellar solution of cetyltrimethylammonium bromide. Kharkiv University Bulletin. Chemical Series, (23), 5-13. https://doi.org/10.26565/2220-637X-2014-23-01

Most read articles by the same author(s)