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Fluorescein isothiocyanate stability in different solvents

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Abstract

Well-established label in biomolecules analysis, fluorescein isothiocyanate is commercially available in its two different isomers with equal fluorescence sensitivity, differing in meta- vs. para-isothiocyanate position. It was found in this study that the stability of the isomers depends on the polarity of different solvents and the pyridine (stabiliser) presence. The lowest stability has fluorescein isothiocyanate in water solvent. In acidic solution, their quinoid (acid) form switches to the lactone form. The p-quinoid form has higher tendency to create dimers and trimers and is less soluble in acetone than the lactone form.

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References

  1. Staines WA, Meister B, Melander T, Nagy JI, Hokfelt T (1988) J Histochem Cytochem 36:145

    Article  CAS  Google Scholar 

  2. Haraguchi T, Shimi T, Koujin T, Hashiguchi N, Hiraoka Y (2002) Genes Cells 7:881

    Article  CAS  Google Scholar 

  3. Karlish SJD (1988) Methods Enzymol 156:271

    Article  CAS  Google Scholar 

  4. Jullian M, Hernandez A, Maurras A, Puget K, Amblard M, Martinez J, Subra G (2009) Tetrahedron Lett 50:260

    Article  CAS  Google Scholar 

  5. Burtnick LD (1984) Biochim Biophys Acta 791:57

    Article  CAS  Google Scholar 

  6. Dufour V, Stahl M, Baysse C (2015) Microbiology 161:229

    Article  CAS  Google Scholar 

  7. Fang XX, Li HY, Fang P, Pan JZ, Fang Q (2016) Talanta 150:135

    Article  CAS  Google Scholar 

  8. Sierra T, Crevillen AG, Escarpa A (2017) Electrophoresis 38:2695

    Article  CAS  Google Scholar 

  9. Fujiwara K, Pollard TD (1980) Curr Top Dev Biol 14:271

    Article  CAS  Google Scholar 

  10. Coons AH, Kaplan MH (1950) J Exp Med 91:1

    Article  CAS  Google Scholar 

  11. Sjöback R, Nygren J, Kubista M (1995) Spectrochim Acta A 51:L7

    Article  Google Scholar 

  12. Klonis N, Sawyer WH (2000) Photochem Photobiol 72:179

    Article  CAS  Google Scholar 

  13. Naderi F, Farajtabar A, Gharib F (2014) J Mol Liq 190:126

    Article  CAS  Google Scholar 

  14. Hermanson GT (2013) Bioconjugate techniques, 3rd edn. Academic Press, London

    Google Scholar 

  15. Krull IS, Strong R, Sosic Z, Cho BY, Beale SC, Wang CC, Cohen S (1997) J Chromatogr B 699:173

    Article  CAS  Google Scholar 

  16. Banks PR (1998) TRAC Trends Anal Chem 17:612

    Article  CAS  Google Scholar 

  17. Schnaible V, Przybylski M (1999) Bioconjugate Chem 10:861

    Article  CAS  Google Scholar 

  18. Turkia H, Siren H, Penttila M, Pitkanen JP (2015) Talanta 131:366

    Article  CAS  Google Scholar 

  19. Brando T, Pardin C, Prandi J, Puzo G (2002) J Chromatogr A 973:203

    Article  CAS  Google Scholar 

  20. Axelrod HD, Engel NA (1975) Anal Chem 47:922

    Article  CAS  Google Scholar 

  21. Coelho F, Eberlin MN (2011) Angew Chem Int Ed 50:5261

    Article  CAS  Google Scholar 

  22. Tsybizova A, Ryland BL, Tsierkezos N, Stahl SS, Roithová J, Schröder D (2014) Eur J Inorg Chem 2014:1407

    Article  CAS  Google Scholar 

  23. Cheng YF, Dovichi NJ (1988) Science 242:562

    Article  CAS  Google Scholar 

  24. Lalljie SPD, Sandra P (1995) Chromatographia 40:519

    Article  CAS  Google Scholar 

  25. Hu J, Wen CY, Zhang ZL, Xie M, Xie HY, Pang DW (2014) Biophys J 107:165

    Article  CAS  Google Scholar 

  26. Kaneta T, Maeda H, Miyazaki M, Miyake R, Izaki H, Sakoda Y, Kinoshita S, Imasaka T (2008) J Chromatogr Sci 46:712

    Article  CAS  Google Scholar 

Download references

Acknowledgements

This work was supported by the Ministry of Education, Youth and Sport of the Czech Republic and the EU (Grant Number CZ.02.2.69/0.0/0.0/16_027/0008477).

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Authors and Affiliations

  1. Institute of Organic Chemistry and Biochemistry of the Czech Academy of Sciences, Prague, Czech Republic

    Jana Jaklová Dytrtová

  2. Department of Physiology and Biochemistry, Faculty of Physical Education and Sport, Charles University, Prague, Czech Republic

    Jana Jaklová Dytrtová

  3. Department of Chemistry, Faculty of Science, University of Helsinki, Helsinki, Finland

    Karina Moslova, Heli Sirén & Marja-Liisa Riekkola

  4. Department of Agro-Environmental Chemistry and Plant Nutrition, Faculty of Agrobiology, Food and Natural Resources, Czech University of Life Sciences Prague, Prague, Czech Republic

    Michal Jakl

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  1. Jana Jaklová Dytrtová
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  2. Karina Moslova
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  5. Marja-Liisa Riekkola
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Correspondence to Jana Jaklová Dytrtová.

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Jaklová Dytrtová, J., Moslova, K., Jakl, M. et al. Fluorescein isothiocyanate stability in different solvents. Monatsh Chem 152, 1299–1306 (2021). https://doi.org/10.1007/s00706-021-02852-1

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  • DOI: https://doi.org/10.1007/s00706-021-02852-1

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