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

S. A. Krasnova; Краснова С. А.; A. V. Eshtukov-Shcheglov; Ештуков-Щеглов А. В.; A. Y. Smirnov; Смирнов А. Ю.; Y. A. Bogdanova; Богданова Ю. А.; M. S. Baranov; Баранов М. С.

doi:10.31857/S0132342325020078

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

Autores: Krasnova S.A.¹^,2, Eshtukov-Shcheglov A.V.¹, Smirnov A.Y.¹^,3, Bogdanova Y.A.¹^,3, Baranov M.S.¹^,3
Afiliações:
1. Shemyakin–Ovchinnikov Institute of Bioorganic Chemistry RAS
2. National Research University Higher School of Economics
3. Pirogov Russian National Research Medical University
Edição: Volume 51, Nº 2 (2025)
Páginas: 291-299
Seção: Articles
URL: https://rjmseer.com/0132-3423/article/view/682739
DOI: https://doi.org/10.31857/S0132342325020078
EDN: https://elibrary.ru/LCEJMP
ID: 682739

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Resumo

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.

Palavras-chave

arylidene-azolones, arylallylidene-azolones, fluorogens

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Gao Z., Hao Y., Zheng M., Chen Y. // RSC Adv. 2017. V. 7. P. 7604–7609. https://doi.org/10.1039/c6ra27547h
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
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
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
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
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
Péresse T., Gautier A. // Int. J. Mol. Sci. 2019. V. 20. P. 6142. https://doi.org/10.3390/ijms20246142
Paige J.S., Wu K.Y., Jaffrey S.R. // Science. 2011. V. 333. P. 642–646. https://doi.org/10.1126/science.1207339
Zhou H., Zhang S. // Crit. Rev. Anal. Chem. 2021. V. 52. P. 1644–1661. https://doi.org/10.1080/10408347.2021.1907735
Baleeva N.S., Baranov M.S. // Chem. Heterocycl. Compd. 2016. V. 52. P. 444–446. https://doi.org/10.1007/s10593-016-1909-4
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
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
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
Zaitseva S.O., Baranov M.S. // Russ. J. Bioorg. Chem. 2019. V. 45. P. 214–216. https://doi.org/10.1134/s1068162019030075
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
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
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
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
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
Campaigne E., White R.L. // J. Heterocycl. Chem. 1988. V. 25. P. 367–373. https://doi.org/10.1002/jhet.5570250203
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
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