Arylidene-imidazolones with three electron-donating substitutions as fluorogenic dyes for lipid droplets of living cells

封面

如何引用文章

全文:

开放存取 开放存取
受限制的访问 ##reader.subscriptionAccessGranted##
受限制的访问 订阅存取

详细

A pair of new fluorogenic dyes from the arylidene-imidazolones’ family, containing simultaneously three electron-donating groups in the arylidene fragment, has been obtained. The optical properties of the resulting compounds were studied. It was shown that they are characterized by a noticeable bathochromic shift of absorption and emission maxima, as well as a pronounced variation of the position of the emission maximum depending on the properties of the environment. Using the HeLa Kyoto and Huh 7.5 cell lines as an example, we demonstrated that (Z)-5-(3,5-bis(dimethylamino)-4-(ethylamino)benzylidene)-2,3-dimethyl-3,5-dihydro-4H-imidazol-4-one can be used as a selective fluorogenic dye for fluorescent labeling of lipid droplets, which indicates the potential of this fluorogen for staining these organelles in other living systems.

全文:

受限制的访问

作者简介

D. Rudik

Shemyakin–Ovchinnikov Institute of Bioorganic Chemistry RAS

编辑信件的主要联系方式.
Email: svetlanakr2002@mail.ru
俄罗斯联邦, Moscow

A. Gilvanov

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

Email: svetlanakr2002@mail.ru
俄罗斯联邦, Moscow; Moscow

A. Smirnov

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

Email: svetlanakr2002@mail.ru
俄罗斯联邦, Moscow; Moscow

Yu. Bogdanova

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

Email: svetlanakr2002@mail.ru
俄罗斯联邦, Moscow; Moscow

S. Krasnova

Shemyakin–Ovchinnikov Institute of Bioorganic Chemistry RAS

Email: svetlanakr2002@mail.ru
俄罗斯联邦, Moscow

M. Baranov

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

Email: svetlanakr2002@mail.ru
俄罗斯联邦, Moscow; Moscow

参考

  1. 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
  2. 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
  3. 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
  4. Tauchi-Sato K., Ozeki S., Houjou T., Taguchi R., Fujimoto T. // J. Biol. Chem. 2002. V. 277. P. 44507–44512. https://doi.org/10.1074/jbc.M207712200
  5. Wolins N.E., Brasaemle D.L., Bickel P.E. // FEBS Lett. 2006. V. 580. P. 5484–5491. https://doi.org/10.1016/j.febslet.2006.08.040
  6. Farese R.V., Walther T.C. // Cold Spring Harb. Perspect. Biol. 2023. V. 15. Р. a041246. https://doi.org/10.1101/cshperspect.a041246
  7. Valm A.M., Cohen S., Legant W.R., Melunis J., Hershberg U., Wait E., Cohen A.R., Davidson M.W., Betzig E., Lippincott-Schwartz J. // Nature. 2017. V. 546. P. 162–167. https://doi.org/10.1038/nature22369
  8. Kaushik S., Cuervo A.M. // Nat. Cell Biol. 2015. V. 17. P. 759–770. https://doi.org/10.1038/ncb3166
  9. Binns D., Januszewski T., Chen Y., Hill J., Markin V.S., Zhao Y., Gilpin C., Chapman K.D., Anderson R.G.W., Goodman J.M. // J. Cell Biol. 2006. V. 173. P. 719–731. https://doi.org/10.1083/jcb.200511125
  10. Meng Y., Guo D., Lin L., Zhao H., Xu W., Luo S., Jiang X., Li S., He X., Zhu R., Shi R., Xiao L., Wu Q., He H., Tao J., Jiang H., Wang Z., Yao P., Xu D., Lu Z. // Nat. Metab. 2024. V. 6. P. 1092–1107. https://doi.org/10.1038/s42255-024-01047-2
  11. Zechner R., Madeo F., Kratky D. // Nat. Rev. Mol. Cell Biol. 2017. V. 18. P. 671–684. https://doi.org/10.1038/nrm.2017.76
  12. Zadoorian A., Du X., Yang H. // Nat. Rev. Endocrinol. 2023. V. 19. P. 443–459. https://doi.org/10.1038/s41574-023-00845-0
  13. Krahmer N., Farese R.V., Walther T.C. // EMBO Mol. Med. 2013. V. 5. P. 973–983. https://doi.org/10.1002/emmm.201100671
  14. Petan T. // Rev. Physiol. Biochem. Pharmacol. 2023. V. 185. P. 53–86. https://doi.org/10.1007/112_2020_51
  15. Ralhan I., Chang C.-L., Lippincott-Schwartz J., Ioannou M.S. // J. Cell Biol. 2021. V. 220. P. e202102136. https://doi.org/10.1083/jcb.202102136
  16. Papsdorf K., Miklas J.W., Hosseini A., Cabruja M., Morrow C.S., Savini M., Yu Y., Silva-García C.G., Haseley N.R., Murphy L.M., Yao P., Launoit E., Dixon S.J., Snyder M.P., Wang M.C., Mair W.B., Brunet A. // Nat. Cell Biol. 2023. V. 25. P. 672–684. https://doi.org/10.1038/s41556-023-01136-6
  17. Chen C., Tachibana S.R., Baleeva N.S., Myasnyanko I.N., Bogdanov A.M., Gavrikov A.S., Mishin A.S., Malyshevskaya K.K., Baranov M.S., Fang C. // Chemistry. 2021. V. 27. P. 8946–8950. https://doi.org/10.1002/chem.202101250
  18. Li C., Plamont M.-A., Sladitschek H. L., Rodrigues V., Aujard I., Neveu P., Saux T.L., Jullien L., Gautier A. // Chem. Sci. 2017. V. 8. P. 5598–5605. https://doi.org/10.1039/C7SC01364G
  19. 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
  20. 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
  21. Würth C., Grabolle M., Pauli J., Spieles M., Resch-Genger U. // Nat. Protoc. 2013. V. 8. P. 1535–1550. https://doi.org/10.1038/nprot.2013.087

补充文件

附件文件
动作
1. JATS XML
下载
2. Additional materials
下载 (2MB)
索引源数据
3. Fig. 1. Micrographs of living HeLa Kyoto (a–c) and Huh 7.5 (d–e) cells stained with compound (IV). (a, d) – Cells in transmitted light; (b, d) – fluorescence of lipid droplets in the CFP channel (excitation filter: 436/20; emission filter: 480/40); (c, e) – superposition of images obtained in transmitted light and the CFP channel. Scale bar – 10 μm.

下载 (230KB)
索引源数据
4. Scheme 1. Scheme of synthesis of new arylidene-imidazolones (III, IV) with three electron-donating substituents.

下载 (185KB)
索引源数据
5. Table 1.1

下载 (25KB)
索引源数据
6. Table 1.2

下载 (25KB)
索引源数据

版权所有 © Russian Academy of Sciences, 2025