The use of fluorescence time-resolved microscopy to increase the endoplasmic reticulum selectivity of arylidene-imidazolones fluorogenic dyes

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Using fluorescence time-resolved microscopy (FLIM), a number of previously synthesized fluorogenic aryliden-imidazolone analogues, predominantly staining the endoplasmic reticulum (ER) of living cells, were studied. It has been shown that the use of this type of fluorescence microscopy can increase the selectivity of ER staining.

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Sobre autores

A. Gilvanov

Shemyakin–Ovchinnikov Institute of Bioorganic Chemistry RAS

Autor responsável pela correspondência
Email: aidar_gilvanov@mail.ru
Rússia, ul. Miklukho-Maklaya 16/10, Moscow, 117997

A. Smirnov

Shemyakin–Ovchinnikov Institute of Bioorganic Chemistry RAS

Email: aidar_gilvanov@mail.ru
Rússia, ul. Miklukho-Maklaya 16/10, Moscow, 117997

S. Krasnova

Shemyakin–Ovchinnikov Institute of Bioorganic Chemistry RAS

Email: aidar_gilvanov@mail.ru
Rússia, ul. Miklukho-Maklaya 16/10, Moscow, 117997

I. Solovyev

A.N. Bach Institute of Biochemistry, Research Center of Biotechnology of the Russian Academy of Sciences

Email: aidar_gilvanov@mail.ru
Rússia, Leninskiy prosp. 33/2, 119071 Moscow

A. Savitsky

A.N. Bach Institute of Biochemistry, Research Center of Biotechnology of the Russian Academy of Sciences

Email: aidar_gilvanov@mail.ru
Rússia, Leninskiy prosp. 33/2, 119071 Moscow

Yu. Bogdanova

Shemyakin–Ovchinnikov Institute of Bioorganic Chemistry RAS

Email: aidar_gilvanov@mail.ru
Rússia, ul. Miklukho-Maklaya 16/10, Moscow, 117997

M. Baranov

Shemyakin–Ovchinnikov Institute of Bioorganic Chemistry RAS; Pirogov Russian National Research Medical University

Email: aidar_gilvanov@mail.ru
Rússia, ul. Miklukho-Maklaya 16/10, Moscow, 117997; ul. Ostrovitianova 1, Moscow, 117997

Bibliografia

  1. Jana P., Patel N., Mukherjee T., Soppina V., Kanvah S. // New J. Chem. 2019. V. 43. P. 10859–10867. https://doi.org/10.1039/C9NJ01972C
  2. Plamont M.-A., Billon-Denis E., Maurin S., Gauron C., Pimenta F.M., Specht C.G., Shi J., Quérard J., Pan B., Rossignol J., Moncoq K., Morellet N., Volovitch M., Lescop E., Chen Y., Triller A., Vriz S., Le Saux T., Jullien L., Gautier A. // Proc. Natl. Acad. Sci. USA. 2016. V. 113. P. 497–502. https://doi.org/10.1073/pnas.1513094113
  3. Szent-Gyorgyi C., Schmidt B.F., Creeger Y., Fisher G.W., Zakel K.L., Adler S., Fitzpatrick J.A.J., Woolford C.A., Yan Q., Vasilev K.V., Berget P.B., Bruchez M.P., Jarvik J.W., Waggoner A. // Nat. Biotechnol. 2008. V. 26. P. 235–240. https://doi.org/10.1038/nbt1368
  4. Hori Y., Norinobu T., Sato M., Arita K., Shirakawa M., Kikuchi K. // J. Am. Chem. Soc. 2013. V. 135. P. 12360– 12365. https://doi.org/10.1021/ja405745v
  5. Schoen I., Ries J., Klotzsch E., Ewers H., Vogel V. // Nano Lett. 2011. V. 11. P. 4008–4011. https://doi.org/10.1021/nl2025954
  6. Pal K., Samanta I., Gupta R.K., Goswami D., Koner A.L. // Chem. Commun. (Camb). 2018. V. 54. P. 10590–10593. https://doi.org/10.1039/C8CC03962C
  7. Hu R., Chen B., Wang Z., Qin A., Zhao Z., Lou X., Tang B.Z. // Biomaterials. 2019. V. 203. P. 43–51. https://doi.org/10.1016/j.biomaterials.2019.03.002
  8. Hu P.F., Liu B. // Org. Biomol. Chem. 2016. V. 14. P. 9931–9944. https://doi.org/10.1039/C6OB01414C
  9. Collot M., Kreder R., Tatarets A.L., Patsenker L.D., Mely Y., Klymchenko A.S. // Chem. Commun. (Camb). 2015. V. 51. P. 17136–17139. https://doi.org/10.1039/C5CC06094J
  10. Baleeva N.S., Baranov M.S. // Chem. Heterocycl. Comp. 2016. V. 52. P. 444–446. https://doi.org/10.1007/s10593-016-1909-4
  11. Walker C.L., Lukyanov K.A., Yampolsky I.V., Mishin A.S., Bommarius A.S., Duraj-Thatte A.M., Azizi B., Tolbert L.M., Solntsev K.M. // Curr. Opin. Chem. Biol. 2015. V. 27. P. 64–74. https://doi.org/10.1016/j.cbpa.2015.06.002
  12. Smirnov A.Y., Perfilov M.M., Zaitseva E.R., Zagudaylova M.B., Zaitseva S.O., Mishin A.S., Baranov M.S. // Dyes and Pigments. 2020. V. 177. P. 108258. https://doi.org/10.1016/j.dyepig.2020.108258
  13. Perfilov M.M., Zaitseva E.R., Smirnov A.Y., Mikhaylov A.A., Baleeva N.S., Myasnyanko I.N., Mishin A.S., Baranov M.S. // Dyes and Pigments. 2022. V. 198. P. 110033. https://doi.org/10.1016/j.dyepig.2021.110033
  14. Perfilov M.M., Zaitseva E.R., Baleeva N.S., Kublitski V.S., Smirnov A.Y., Bogdanova Y.A., Krasnova S.A., Myasnyanko I.N., Mishin A.S., Baranov M.S. // Int. J. Mol. Sci. 2023. V. 24. P. 9923. https://doi.org/10.3390/ijms24129923
  15. Braakman I., Hebert D.N. // Cold Spring Harb. Perspect. Biol. 2013. V. 5. P. a013201. https://doi.org/10.1101/cshperspect.a013201
  16. Viotti C. // Methods Mol. Biol. 2016. V. 1459. P. 3–29. https://doi.org/10.1007/978-1-4939-3804-9_1
  17. Fagone P., Jackowski S. // J. Lipid Res. 2009. V. 50 Suppl. P. S311–S316. https://doi.org/10.1194/jlr.R800049-JLR200
  18. Clapham D.E. // Cell. 2007. V. 131. P. 1047–1058. https://doi.org/10.1016/j.cell.2007.11.028
  19. Celik C., Lee S.Y.T., Yap W.S., Thibault G. // Prog. Lipid Res. 2023. V. 89. P. 101198. https://doi.org/10.1016/j.plipres.2022.101198
  20. Yousuf M.S., Maguire A.D., Simmen T., Kerr B.J. // Mol. Pain. 2020. V. 16. P. 1744806920946889. https://doi.org/10.1177/1744806920946889
  21. Park S.-J., Li C., Chen Y.M. // Am. J. Pathol. 2021. V. 191. P. 256–265. https://doi.org/10.1016/j.ajpath.2020.11.006
  22. Jin C., Kumar P., Gracia-Sancho J., Dufour J.-F. // FEBS Lett. 2021. V. 595. P. 1411–1421. https://doi.org/10.1002/1873-3468.14078
  23. Zeeshan H.M.A., Lee G.H., Kim H.-R., Chae H.-J. // Int. J. Mol. Sci. 2016. V. 17. P. 327. https://doi.org/10.3390/ijms17030327
  24. Farese R.V., Walther T.C. // Cell. 2009. V. 139. P. 855–860. https://doi.org/10.1016/j.cell.2009.11.005
  25. Onal G., Kutlu O., Gozuacik D., Dokmeci Emre S. // Lipids Health Dis. 2017. V. 16. P. 128. https://doi.org/10.1186/s12944-017-0521-7
  26. Datta R., Heaster T.M., Sharick J.T., Gillette A.A., Skala M.C. // J. Biomed. Opt. 2020. V. 25. P. 1–43. https://doi.org/10.1117/1.JBO.25.7.071203
  27. Hille C., Berg M., Bressel L., Munzke D., Primus P., Löhmannsröben H.-G., Dosche C. // Anal. Bioanal. Chem. 2008. V. 391. P. 1871–1879. https://doi.org/10.1007/s00216-008-2147-0.
  28. Koda K., Keller S., Kojima R., Kamiya M., Urano Y. // Anal. Chem. 2022. V. 94. P. 11264–11271. https://doi.org/10.1021/acs.analchem.2c01840
  29. Hille C., Lahn M., Löhmannsröben H.-G., Dosche C. // Photochem. Photobiol. Sci. 2009. V. 8. P. 319–327. https://doi.org/10.1039/b813797h
  30. Despa S., Vecer J., Steels P., Ameloot M. // Anal. Biochem. 2000. V. 281. P. 159–175. https://doi.org/10.1006/abio.2000.4560
  31. Jahn K., Hille C. // PLoS One. 2014. V. 9. P. e105334. https://doi.org/10.1371/journal.pone.0105334
  32. Wilms C.D., Eilers J. // J. Microsc. 2007. V. 225. P. 209–213. https://doi.org/10.1111/j.1365-2818.2007.01746.x
  33. Okabe K., Inada N., Gota C., Harada Y., Funatsu T., Uchiyama S. // Nat. Commun. 2012. V. 3. P. 705. https://doi.org/10.1038/ncomms1714
  34. Kuimova M.K. // Phys. Chem. Chem. Phys. 2012. V. 14. P. 12671–12686. https://doi.org/10.1039/c2cp41674c
  35. Sha J., Liu W., Zheng X., Guo Y., Li X., Ren H., Qin Y., Wu J., Zhang W., Lee C.-S., Wang P. // Anal. Chem. 2023. V. 95. P. 15350–15356. https://doi.org/10.1021/acs.analchem.3c03047
  36. Levitt J.A., Chung P.-H., Suhling K. // J. Biomed. Opt. 2015. V. 20. P. 96002. https://doi.org/10.1117/1.JBO.20.9.096002
  37. Stöckl M.T., Herrmann A. // Biochim. Biophys. Acta. 2010. V. 1798. P. 1444–1456. https://doi.org/10.1016/j.bbamem.2009.12.015

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3. Fig. 1. Micrographs of living HeLa Kyoto cells stained with dyes (I) (a), (II) (b), (III) (c), and (IV) (d), obtained using time-resolved fluorescence microscopy. Color coding reflects the fluorescence lifetimes of the dyes depending on their environment. The corresponding range of lifetimes in nanoseconds is indicated under each micrograph. For dyes with two spectral components ((I), (III), and (IV)) the amplitude-weighted average lifetime was used as the fluorescence lifetime value. Scale bar is 5 μm.

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4. Fig. 2. Micrographs of living HeLa Kyoto cells stained with dyes (I) and (III) before (a, c, respectively) and after (b, d) removal of image areas containing lipid droplets. Removal of areas containing lipid droplets was performed based on differences in the fluorescence lifetimes of substances when stained with EPR and lipid droplets. Scale bar is 5 μm.

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5. Scheme 1. Structures of dyes of the arylidene-imidazolone series studied in the work.

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