RAS BiologyБиоорганическая химия Russian Journal of Bioorganic Chemistry

  • ISSN (Print) 0132-3423
  • ISSN (Online) 1998-2860

New Potential Fluorogenic Dyes with an Extended π-System Based on Arylidene-Azolones

PII
S0132342325020078-1
DOI
10.31857/S0132342325020078
Publication type
Review
Status
Published
Authors
Volume/ Edition
Volume 51 / Issue number 2
Pages
291-299
Abstract
We propose a new series of 19 potential fluorogenic dyes with an increased system of conjugated bonds based on arylidene-imidazolones and arylidene-rhodanines. The optical properties of the synthesized compounds were studied. We demonstrated that new substances are characterized by a noticeable bathochromic shift of absorption and emission maxima, as well as a remarkable Stokes shift and a significant FQY variation depending on the properties of the environment. The obtained arylallylideneimidazolones and arylallylidene-rhodanines can be potentially used in fluorescence microscopy for selective staining of living cell organelles.
Keywords
арилиден-азолоны арилаллилиден-азолоны флуорогены
Date of publication
09.11.2025
Year of publication
2025
Number of purchasers
0
Views
45

References

  1. 1. Gao Z., Hao Y., Zheng M., Chen Y. // RSC Adv. 2017. V. 7. P. 7604–7609. https://doi.org/10.1039/c6ra27547h
  2. 2. Chen H., Liu L., Qian K., Liu H., Wang Z., Gao F., Qu C., Dai W., Lin D., Chen K., Liu H., Cheng Z. // Sci. Adv. 2022. V. 8. Р. eabo3289. https://doi.org/10.1126/sciadv.abo3289
  3. 3. Ermakova Y.G., Bogdanova Y.A., Baleeva N.S., Zaitseva S.O., Guglya E.B., Smirnov A.Yu., Zagudaylova M.B., Baranov M.S. // Dyes Pigm. 2019. V. 170. P. 107550. https://doi.org/10.1016/j.dyepig.2019.107550
  4. 4. Povarova N.V., Zaitseva S.O., Baleeva N.S., Smirnov A.Yu., Myasnyanko I.N., Zagudaylova M.B., Bozhanova N.G., Gorbachev D.A., Malyshevskaya K.K., Gavrikov A.S., Mishin A.S., Baranov M.S. // Chem. Eur. J. 2019. V. 25. P. 9592–9596. https://doi.org/10.1002/chem.201901151
  5. 5. 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
  6. 6. Smirnov A.Yu., Perfilov M.M., Zaitseva E.R., Zagudaylova M.B., Zaitseva S.O., Mishin A.S., Baranov M.S. // Dyes Pigm. 2020. V. 177. P. 108258. https://doi.org/10.1016/j.dyepig.2020.108258
  7. 7. Péresse T., Gautier A. // Int. J. Mol. Sci. 2019. V. 20. P. 6142. https://doi.org/10.3390/ijms20246142
  8. 8. Paige J.S., Wu K.Y., Jaffrey S.R. // Science. 2011. V. 333. P. 642–646. https://doi.org/10.1126/science.1207339
  9. 9. Zhou H., Zhang S. // Crit. Rev. Anal. Chem. 2021. V. 52. P. 1644–1661. https://doi.org/10.1080/10408347.2021.1907735
  10. 10. Baleeva N.S., Baranov M.S. // Chem. Heterocycl. Compd. 2016. V. 52. P. 444–446. https://doi.org/10.1007/s10593-016-1909-4
  11. 11. Krasnova S.A., Bogdanova Y.A., Sokolov A.I., Myasnyanko I.N., Smirnov A.Yu., Baranov M.S. // Russ. J. Bioorg. Chem. 2024. V. 50. P. 251–259. https://doi.org/10.1134/s1068162024010059
  12. 12. 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. 2015. V. 113. P. 497–502. https://doi.org/10.1073/pnas.1513094113
  13. 13. Li C., Tebo A.G., Thauvin M., Plamont M.-A., Volovitch M., Morin X., Vriz S., Gautier A. // Angew. Chem. Int. Ed. 2020. V. 59. P. 17917–17923. https://doi.org/10.1002/anie.202006576
  14. 14. Zaitseva S.O., Baranov M.S. // Russ. J. Bioorg. Chem. 2019. V. 45. P. 214–216. https://doi.org/10.1134/s1068162019030075
  15. 15. Ye S., Zhang H., Fei J., Wolstenholme C.H., Zhang X. // Angew. Chem. Int. Ed. 2020. V. 60. P. 1339–1346. https://doi.org/10.1002/anie.202011108
  16. 16. Li C., Plamont M.-A., Aujard I., Saux T.L., Jullien L., Gautier A. // Org. Biomol. Chem. 2016. V. 14. P. 9253– 9261. https://doi.org/10.1039/c6ob01612j
  17. 17. Perfilov M.M., Zaitseva E.R., Smirnov A.Yu., Mikhaylov A.A., Baleeva N.S., Myasnyanko I.N., Mishin A.S., Baranov M.S. // Dyes Pigm. 2022. V. 198. P. 110033. https://doi.org/10.1016/j.dyepig.2021.110033
  18. 18. Zhuang B.-Y., Jin J.-K., Zhang F.-L., Wang Y.-F. // Synlett. 2020. V. 32. P. 383–386. https://doi.org/10.1055/s-0040-1707142
  19. 19. Shrestha K., Hilyard M.A., Alahakoon I., Young M.C. // Org. Biomol. Chem. 2022. V. 20. P. 6646–6653. https://doi.org/10.1039/d2ob01171a
  20. 20. Campaigne E., White R.L. // J. Heterocycl. Chem. 1988. V. 25. P. 367–373. https://doi.org/10.1002/jhet.5570250203
  21. 21. Voliani V., Bizzarri R., Nifosì R., Abbruzzetti S., Grandi E., Viappiani C., Beltram F. // J. Phys. Chem. B. 2008. V. 112. P. 10714–10722. https://doi.org/10.1021/jp802419h
  22. 22. Würth C., Grabolle M., Pauli J., Spieles M., ReschGenger U. // Nat. Protoc. 2013. V. 8. P. 1535–1550. https://doi.org/10.1038/nprot.2013.087
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