Determination of fluorescence lifetimes of fluorescein from fluorescence quenching data
Keywords:Fluorescein, Benzoquinone, Fluorescence, Quenching, Lifetime.
The fluorescence quenching of fluorescein by 1,4-benzoquinone (BQ) in five solvents â€“ methanol, ethanol, phosphate buffer saline (PBS, pH 7.4), N,N'-dimethylformamide (DMF) and dimethylsulphoxide (DMSO) is hereby investigated. Fluoresceinâ€™s fluorescence was effectively quenched by BQ, and the quenching was dynamic (purely collisional) within the BQâ€™s concentration range (0.001 to 0.004 M) used in this work. Accordingly, the quenching data were in conformity with the Stern-Volmerâ€™s model. Stern-Volmerâ€™s constant (KSV) values range between 17.4 in DMSO and 43.4 in methanol. KSV values, together with the calculated bimolecular rate constants (kD) in the respective solvents, were used to semi-empirically estimate the fluorescence lifetimes (tF) of fluorescein in the individual solvents. Just as for KSV values, tF values are solvent-viscosity dependent, with the lowest values being obtained in methanol and the highest in DMSO, which are the least and most viscous solvents respectively. tF values obtained in this work are 3.55, 3.71, 3.78, 4.13 and 4.51 ns (in methanol, PBS 7.4, ethanol, DMF and DMSO, respectively).
 Al H, Henderson JN, Remington SJ & Campbell RE (2006) Directed evolution of a monomeric, bright and photostable version of Clavularia cyan fluorescent protein: structural characterization and applications in fluorescence imaging. Biochemical Journal 400, 531-540. https://doi.org/10.1371/journal.pone.0017896.
 Al-Aqmar DM, Abdelkader HI & Abou Kana MTH (2015) Spectroscopic properties and amplified spontaneous emission of fluorescein laser dye in ionic liquids as green media. Optical Materials 47, 573-581. https://doi.org/10.1016/j.optmat.2015.06.045.
 Becker W (2012) Fluorescence lifetime imaging-techniques and applications. Journal of Microscopy 247(2), 119-136. https://doi.org/10.1111/j.1365-2818.2012.03618.x.
 Burchak ON, Mugherli L, Chatelain F, Balakirev MY (2006) Fluorescein-Based Amino Acids for Solid Phase Synthesis of Fluorogenic Protease Substrates. Bioorganic and Medicinal Chemistry 14, 2559-2568. https://doi.org/10.1016/j.bmc.2005.11.037.
 Cooper CD, Naff WT & Compton RN (1975) Negative ion properties of p-benzoquinone: Electron affinity and compound states. Journal of Chemical Physics 63(6), 2752-2757. https://doi.org/10.1063/1.431627.
 Fery-Forgues S & Lavabre D (1999) Are Fluorescence Quantum Yields So Tricky to Measure? A demonstration using familiar stationery products. Journal of Chemical Education 76, 1260-1264. https://doi.org/10.1021/ed076p1260.
 Georghiou S & Stacy Gerke L (1999) Excitedâ€state properties of thymidine and their relevance to its heterogeneous emission in doubleâ€stranded DNA. Photochemistry Photobiology 69, 646-652. https://doi.org/10.1111/j.1751-1097.1999.tb03340.x.
 Govindanunny T & Sivaram BM (1980) Solvation effects on the tunability of a fluorescein dye laser. Optics Communications 32, 425-428. https://doi.org/10.1016/0030-4018(80)90276-X.
 Ha SW, Camalier CE, Beck GR Jr & Lee JK (2009) New method to prepare very stable and biocompatible fluorescent silica nanoparticles. Chemical Communications (Camb) 20, 2881â€“2883. https://doi.org/10.1039/b902195g.
 He L, Olson DP, Wu X, Karpova T, McNally JG & Lipsky PE (2003) A flow cytometric method to detect protein-protein interaction in living cells by directly visualizing donor fluorophore quenching during CFP-YFP fluorescence resonance energy transfer (FRET). Cytometry Part A 55A, 71-85. https://doi.org/10.1002/cyto.a.10073.
 Jose M, Nair DK, Reissner C, Hartig R & Zuschratter W (2007) Photophysics of Clomeleon by FLIM: Discriminating Excited State Reactions Along Neuronal Development. Biophysical Journal 92, 2237-2254. https://doi.org/10.1529/biophysj.106.092841.
 Laird T (1979) Comprehensive Organic Chemistry, (Stoddart JF ed.), Pergamon press Ltd., Oxford, Vol. 1, p. 1214.
 Lakowicz JR (1999) Principles of Fluorescence Spectroscopy. Kluwer Academic/Plenum Publishers, New York. https://doi.org/10.1007/978-1-4757-3061-6.
 Losev AP, Volkovich DI & Tikhomirov SA (1999) Intramolecular photoinduced electron transfer in Pd-porphyrin-quinone in the picosecond time. Journal of Applied Spectroscopy 66, 7-14. https://doi.org/10.1007/BF02679212.
 Ma LY, Wang HY & Xie H (2004) A long lifetime chemical sensor: study on fluorescence property of fluorescein isothiocyanate and preparation of pH chemical sensor. Spectrochimica Acta A: Molecular and Biomolecular Spectroscopy. 60(8-9), 1865-72. https://doi.org/10.1016/j.saa.2003.10.004.
 Magde D, Rojas GE & Seybold PG (1999) Solvent Dependence of the Fluorescence Lifetimes of Xanthene Dyes. Photochemistry Photobiology 70(5), 737-744. https://doi.org/10.1111/j.1751-1097.1999.tb08277.x.
 Maree S, Phillips D & Nyokong T (2002) Synthesis, photophysical and photochemical studies of germanium and tin phthalocyanine complexes. Journal of Porphyrins and Phthalocyanines 6, 17-25. https://doi.org/10.1142/S108842460200004X.
 Montalban A, Meunier H, Ostler R, Barrett A, Hoffman B & Rumbles, G (1999) Photoperoxidation of a diamino zinc porphyrazine to the seco-zinc porphyrazine: suicide or murder? Journal of Physical Chemistry A 103(22), 4352-4358. https://doi.org/10.1021/jp9905068.
 Ogunsipe A & Nyokong T (2005a) Photophysical and photochemical studies of sulphonated non-transition metal phthalocyanines in aqueous and non-aqueous media. Journal of Photochemistry and Photobiology A: Chemistry 173, 211-220. https://doi.org/10.1016/j.jphotochem.2005.03.001.
 Ogunsipe A & Nyokong T (2005b) Effects of central metal on the photophysical and photochemical properties of non-transition metal sulfophthalocyanine. Journal of Porphyrins and Phthalocyanines 9, 121-129. https://doi.org/10.1142/S1088424605000186.
 Ogunsipe A & Nyokong T (2011) Solvent effects on the photophysicochemical properties of tetra(tert-butylphenoxy)phthalocyaninato zinc(II). Acta Physico-Chimica Sinica 27(5), 1045-1052.
 Ogunsipe A (2018) Solvent effects on the spectral properties of rhodamine 6G: estimation of ground and excited state dipole moments. Journal of Solution Chemistry 47, 203-219. https://doi.org/10.1007/s10953-017-0706-8.
 Oliveira E, BÃ©rtolo E, NÃºÃ±ez C, Pilla V, Santos HM, FernÃ¡ndez-Lodeiro J, FernÃ¡ndez-Lodeiro A, Djafari J, Capelo JL & Lodeiro C (2018) Green and Red Fluorescent Dyes for Translational Applications in Imaging and Sensing Analytes: A Dual-Color Flag. ChemistryOpen 7, 9-52. https://doi.org/10.1002/open.201700135.
 Rabnowitch E (1945) Photosynthesis and Related Processes, Interscience, New York.
 Rajagopal S, Egorova EA, Bukhov NG & Carpentier R (2003) Quenching of excited states of chlorophyll molecules in submembrane fractions of Photosystem I by exogenous quinones. Biochimica et Biophysica Acta 1606, 147â€“152. https://doi.org/10.1016/S0005-2728(03)00111-7.
 Veres P, KirÃ¡ly G,Nagy G, LÃ¡zÃ¡r I, FÃ¡biÃ¡n I & KalmÃ¡r J (2017) Biocompatible silica-gelatin hybrid aerogels covalently labeled with fluorescein. Journal of Non-Crystalline Solids 473, 17-25. https://doi.org/10.1016/j.jnoncrysol.2017.07.016.
 Xiong X, Song F, Wang J, Zhang Y, Xue Y, Sun L, Jiang N, Gao P, Tian L & Peng X (2014) Thermally Activated Delayed Fluorescence of Fluorescein Derivative for Time-Resolved and Confocal Fluorescence Imaging. J. Am. Chem. Soc 136, 9590-9597. https://doi.org/10.1021/ja502292p.
 Zhang H, Zhang M & Shen T (1997) Photoinduced intramolecular electron transfer of fluorescein and violgen, carbazole. Science in China Series B-Chemistry 40(5), 449-456. https://doi.org/10.1007/BF02875412.
 Zheng H, Zhan XQ, Bian QN & Zhang XJ (2013) Advances in Modifying Fluorescein and Rhodamine Fluorophores as Fluorescent Chemosensors. Chemical Communications 49, 429-447. https://doi.org/10.1039/C2CC35997A.