New Potential Fluorogenic Dyes with an Extended π-System Based on Arylidene-Azolones
- 作者: 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
-
隶属关系:
- Shemyakin–Ovchinnikov Institute of Bioorganic Chemistry RAS
- National Research University Higher School of Economics
- Pirogov Russian National Research Medical University
- 期: 卷 51, 编号 2 (2025)
- 页面: 291-299
- 栏目: Articles
- URL: https://journals.rcsi.science/0132-3423/article/view/291762
- DOI: https://doi.org/10.31857/S0132342325020078
- EDN: https://elibrary.ru/LCEJMP
- ID: 291762
如何引用文章
详细
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.
全文:

作者简介
S. Krasnova
Shemyakin–Ovchinnikov Institute of Bioorganic Chemistry RAS; National Research University Higher School of Economics
编辑信件的主要联系方式.
Email: svetlanakr2002@mail.ru
俄罗斯联邦, ul. Miklukho-Maklaya 16/10, Moscow, 117997; ul. Myasnitskaya 20, Moscow, 101000
A. Eshtukov-Shcheglov
Shemyakin–Ovchinnikov Institute of Bioorganic Chemistry RAS
Email: svetlanakr2002@mail.ru
俄罗斯联邦, ul. Miklukho-Maklaya 16/10, Moscow, 117997
A. Smirnov
Shemyakin–Ovchinnikov Institute of Bioorganic Chemistry RAS; Pirogov Russian National Research Medical University
Email: svetlanakr2002@mail.ru
俄罗斯联邦, ul. Miklukho-Maklaya 16/10, Moscow, 117997; ul. Ostrovitianova 1, Moscow, 117997
Y. Bogdanova
Shemyakin–Ovchinnikov Institute of Bioorganic Chemistry RAS; Pirogov Russian National Research Medical University
Email: svetlanakr2002@mail.ru
俄罗斯联邦, ul. Miklukho-Maklaya 16/10, Moscow, 117997; ul. Ostrovitianova 1, Moscow, 117997
M. Baranov
Shemyakin–Ovchinnikov Institute of Bioorganic Chemistry RAS; Pirogov Russian National Research Medical University
Email: svetlanakr2002@mail.ru
俄罗斯联邦, ul. Miklukho-Maklaya 16/10, Moscow, 117997; ul. Ostrovitianova 1, Moscow, 117997
参考
- 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
补充文件
