Kaede Protein Chromophore Analogue as a Tool for Simultaneous Selective Staining of the Nucleus and Mitochondria

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Abstract

A series of three dyes – analogs of the chromophore of the fluorescent protein Kaede with various substituents – was synthesized. Based on fluorescence microscopy results, a promising fluorogen was identified: 5-((Z)-2-(difluoroboranyl)-4-(dimethylamino)-5-hydroxybenzylidene)-3-methyl-2-((E)-2-(pyridin-4-yl)-vinyl)-3,5-dihydro-4H-imidazol-4-one. The successful application of this dye in wide-field fluorescence microscopy for simultaneous selective staining of nuclei and mitochondria in living cells was demonstrated using the HeLa Kyoto cell line as an example. The synthesized compound may find application in the field of visualization of living system processes.

About the authors

D. I Rudik

Shemyakin–Ovchinnikov Institute of Bioorganic Chemistry RAS

Moscow, Russia

A. R Gilvanov

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

Moscow, Russia; Moscow, Russia

M. S Baranov

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

Moscow, Russia; Moscow, Russia

Yu. A Bogdanova

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

Email: zashiki.vvarashi@gmail.com
Moscow, Russia; Moscow, Russia

References

  1. Klymchenko A.S. // Acc. Chem. Res. 2017. V. 50. P. 366–375. https://doi.org/10.1021/acs.accounts.6b00517
  2. Plamont M.-A., Plamont M., 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., 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. Bogdanova Yu.A., Zaitseva E.R., Smirnov A.Yu., Baleeva N.S., Gavrikov A.S., Myasnyanko I.N., Goncharuk S.A., Kot E.F., Mineev K.S., Mishin A.S., Baranov M.S. // UMS. 2023. V. 24. P. 7958. https://doi.org/10.3390/jims24097958
  5. Filonov G.S., Moon J.D., Svensen N., Jaffrey S.R. // J. Am. Chem. Soc. 2014. V. 136. P. 16299–16308. https://doi.org/10.1021/ja508478x
  6. Paige J.S., Wu K.Y., Jaffrey S.R. // Science. 2011. V. 333. P. 642–646. https://doi.org/10.1126/science
  7. Hu F., Liu B. // Org. Biomol. Chem. 2016. V. 14. P. 9931–9944. https://doi.org/10.1039/C6OB01414C
  8. Hoi N.E., Lee J.Y., Park E.C., Lee J.H., Lee J. // Molecules. 2021. V. 26. P. 217. https://doi.org/10.3390/molecules26010217
  9. Walker C.L., Lukyanov K.A., Yampolsky I.V., Mishin A.S., Bonmartus 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
  10. Baleeva N.S., Baranov M.S. // Chem. Heterocycl. Comp. 2016. V. 52. P. 444–446. https://doi.org/10.1007/3266
  11. Perfilov M.M., Zaitseva E.R., Baleeva N.S., Kublitski V.S., Smirnov A.Yu., Bogdanova Yu.A., Krasnova S.A., Myasnyanko I.N., Mishin A.S., Baranov M.S. // UMS. 2023. V. 24. P. 9923. https://doi.org/10.3390/jims24129923
  12. Rudik D.I., Perfilov M.M., Sokolov A.I., Chen C., Baleeva N.S., Myasnyanko I.N., Mishin A.S., Fang C., Bogdanova Y.A., Baranov M.S. // UMS. 2024. V. 25. P. 10448. https://doi.org/10.3390/jjms251910448
  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. Smirnov A.Yu., Perfilov M.M., Zaitseva E.R., Zagudarylova 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
  15. Ermakova Y.G., Sen T, Bogdanova Y.A., Smirnov A.Yu., Baleeva N.S., Krylov A.I., Baranov M.S. // J. Phys. Chem. Lett. 2018. V. 9. P. 1958–1963. https://doi.org/10.1021/acs.jpclett.8b00512
  16. Rudik D.I., Gil'vanov A.R., Smirnov A.Yu., Bogdanova Yu.A., Krasnova S.A., Baranov M.S. // Russ. J. Bioorg. Chem. 2025. V. 51. P. 145–150. https://doi.org/10.1134/S1068162025010133
  17. Cotter-Rousselle C., Rond X., Leverve X., Mayol J.F. // Cytometry Pt A. 2011. V. 79A. P. 405–425. https://doi.org/10.1002/cyto.a.21061
  18. Prokhorova E.A., Zamaravv A.V., Kopeina G.S., Zhivotovsky B., Lavrik I.N. // Cell. Mol. Life Sci. 2015. V. 72. P. 4593–4612. https://doi.org/10.1007/s00018-015-2031-y
  19. Abate M., Festa A., Falco M., Lombardi A., Luce A., Grimaldi A., Zappavigna S., Sperlongano P., Irace C., Caraglia M., Misso G. // Semin. Cell Dev. Biol. 2020. V. 98. P. 139–153. https://doi.org/10.1016/j.semcdb.2019.05.022
  20. Yang R., He X., Niu G., Meng F., Lu Q., Liu Z., Yu X. // ACS Sens. 2021. V. 6. P. 1552–1559. https://doi.org/10.1021/acssensors.0c02372
  21. Baldridge A., Kowalik J., Tolbert L. // Synthesis. 2010. V. 2010. P. 2424–2436. https://doi.org/10.1055/s-0029-1218796
  22. Chen C., Boulanger S.A., Sokolov A.I., Baranov M.S., Fang C. // Chemosensors. 2021. V. 9. P. 234. https://doi.org/10.3390/chemosensors9080234
  23. Baranov M.S., Lukyanov K.A., Borissova A.O., Shamir J., Kosenkov D., Slipchenko L.V., Tolbert L.M., Yampolsky I.V., Solntsev K.M. // J. Am. Chem. Soc. 2012. V. 134. P. 6025–6032. https://doi.org/10.1021/ja3010144

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