2,5-Dimethoxy-benzylidene-rhodanine and its acyclic analogues as selective fluorogenic dyes for lipid droplets of living cells

Capa

Citar

Texto integral

Acesso aberto Acesso aberto
Acesso é fechado Acesso está concedido
Acesso é fechado Acesso é pago ou somente para assinantes

Resumo

We report about a series of arylidene-rhodanines and their acyclic analogues. The fluorescent properties of these substances were studied. We showed that the derivatives containing a 2,5-dimethoxybenzylidene fragment or similar groups are characterized by a noticeable variation in the fluorescence quantum yield depending on the properties of the medium. We discovered that two of the synthesized compounds – dimethoxy-benzylidene-rhodanine and dimethoxy-benzylidene-malononitrile – can be used as selective fluorogenic dyes for lipid droplets (adiposomes) of living cells for labeling under fluorescent microscopy conditions.

Texto integral

Acesso é fechado

Sobre autores

S. Krasnova

Shemyakin–Ovchinnikov Institute of Bioorganic Chemistry RAS; National Research University Higher School of Economics

Autor responsável pela correspondência
Email: svetlanakr2002@mail.ru
Rússia, ul. Miklukho-Maklaya 16/10, Moscow, 117997; ul. Myasnitskaya 20, Moscow, 101000

Yu. Bogdanova

Shemyakin–Ovchinnikov Institute of Bioorganic Chemistry RAS

Email: svetlanakr2002@mail.ru
Rússia, ul. Miklukho-Maklaya 16/10, Moscow, 117997

A. Sokolov

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

Email: svetlanakr2002@mail.ru
Rússia, ul. Miklukho-Maklaya 16/10, Moscow, 117997; ul. Ostrovitianova 1, Moscow, 117997

I. Myasnyanko

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

Email: svetlanakr2002@mail.ru
Rússia, ul. Miklukho-Maklaya 16/10, Moscow, 117997; ul. Ostrovitianova 1, Moscow, 117997

A. Smirnov

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

Email: svetlanakr2002@mail.ru
Rússia, 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
Rússia, ul. Miklukho-Maklaya 16/10, Moscow, 117997; ul. Ostrovitianova 1, Moscow, 117997

Bibliografia

  1. 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. 2016. V. 113. P. 497–502. https://doi.org/10.1073/pnas.1513094113
  2. Bozhanova N.G., Baranov M.S., Klementieva N.V., Sarkisyan K.S., Gavrikov A.S., Yampolsky I.V., Zagaynova E.V., Lukyanov S.A., Lukyanov K.A., Mishin A.S. // Chem. Sci. 2017. V. 8. P. 7138–7142. https://doi.org/10.1039/C7SC01628J
  3. Collot M., Kreder R., Tatarets A.L., Patsenker L.D., Melya Y., Klymchenko A.S. // Chem. Commun. 2015. V. 51. P. 17136–17139. https://doi.org/10.1039/C5CC06094J
  4. Ermakova Y.G., Bogdanova Y.A., Baleeva N.S., Zaitseva S.O., Guglya E.B., Smirnov A.Y., Zagudaylova M.B., Baranov M.S. // Dyes Pigm. 2019. V. 170. P. 107550. https://doi.org/10.1016/j.dyepig.2019.107550
  5. Ermakova Y.G., Sen T., Bogdanova Y.A., Smirnov A.Y., 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. 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
  7. 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 Pigm. 2022. V. 198. P. 110033. https://doi.org/10.1016/j.dyepig.2021.110033
  8. Farese R.V., Walther T.C. // Cell. 2009. V. 139. P. 855–860. https://doi.org/10.1016/j.cell.2009.11.005
  9. Onal G., Kutlu O., Gozuacik D., Dokmeci Emre S. // Lipids Health Dis. 2017. V. 16. P. 128. https://doi.org/10.1186/s12944-017-0521-7
  10. Olzmann J.A., Carvalho P. // Nat. Rev. Mol. Cell Biol. 2019. V. 20. P. 137–155. https://doi.org/10.1038/s41580-018-0085-z
  11. 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
  12. Velázquez A.P., Tatsuta T., Ghillebert R., Drescher I., Graef M. // J. Cell Biol. 2016. V. 212. P. 621–631. https://doi.org/10.1083/jcb.201508102
  13. Fei W., Wang H., Fu X., Bielby C., Yang H. // Biochem. J. 2009. V. 424. P. 61–67. https://doi.org/10.1042/BJ20090785
  14. Nguyen T.B., Louie S.M., Daniele J.R., Tran Q., Dillin A., Zoncu R., Nomura D.K., Olzmann J.A. // Dev. Cell. 2017. V. 42. P. 9–21. https://doi.org/10.1016/j.devcel.2017.06.003
  15. Kong J., Ji Y., Jeon Y.G., Han J.S., Han K.H., Lee J.H., Lee G., Jang H., Choe S.S., Baes M., Kim J.B. // Nat. Commun. 2020. V. 11. P. 578. https://doi.org/10.1038/s41467-019-14176-0
  16. Brookheart R.T., Michel C.I., Schaffer J.E. // Cell Metab. 2009. V. 10. P. 9–12. https://doi.org/10.1016/j.cmet.2009.03.011
  17. Kuramoto K., Okamura T., Yamaguchi T., Nakamura T.Y., Wakabayashi S., Morinaga H., Nomura M., Yanase T., Otsu K., Usuda N., Matsumura S., Inoue K., Fushiki T., Kojima Y., Hashimoto T., Sakai F., Hirose F., Osumi T. // J. Biol. Chem. 2012. V. 287. P. 23852–23863. https://doi.org/10.1074/jbc.M111.328708
  18. Greenberg A.S., Coleman R.A., Kraemer F.B., McManaman J.L., Obin M.S., Puri V., Yan Q.W., Miyoshi H., Mashek D.G. // J. Clin. Investig. 2011. V. 121. P. 2102–2110. https://doi.org/10.1172/JCI46069
  19. Bozza P.T., Viola J.P.B. // Prostaglandins Leukot. Essent. Fatty Acids. 2010. V. 82. P. 243–250. https://doi.org/10.1016/j.plefa.2010.02.005
  20. Chen Z.P., Wang S., Zhao X., Fang W., Wang Z., Ye H., Wang M.J., Ke L., Huang T., Lv P., Jiang X., Zhang Q., Li L., Xie S.T., Zhu J.N., Hang C., Chen D., Liu X., Yan C. // Nat. Neurosci. 2023. V. 26. P. 542–554. https://doi.org/10.1038/s41593-023-01288-6
  21. Tirinato L., Pagliari F., Limongi T., Marini M., Falqui A., Seco J., Candeloro P., Liberale C., Di Fabrizio E. // Stem Cells Int. 2017. V. 2017. P. 1–17. https://doi.org/10.1155/2017/1656053
  22. Scher N., Rechav K., Paul-Gilloteaux P., Avinoam O. // iScience. 2021. V. 24. P. 102714. https://doi.org/10.1016/j.isci.2021.102714
  23. Sánchez-Recillas A., Navarrete-Vázquez G., Hidalgo- Figueroa S., Bonilla-Hernández M., Ortiz-Andrade R., Ibarra-Barajas M., Yáñez-Pérez V., Sánchez-Salgado J.C. // J. Pharm. Pharmacol. 2020. V. 72. P. 1186–1198. https://doi.org/10.1111/jphp.13295
  24. Sokolov A.I., Gorshkova A.A., Baleeva N.S., Baranov M.S. // Russ. J. Bioorg. Chem. 2022. V. 48. P. 1367–1371. https://doi.org/10.1134/S1068162022060243
  25. Durai Ananda Kumar T., Swathi N., Navatha J., Subrahmanyam C.V.S., Satyanarayana K. // J. Sulphur Chem. 2014. V. 36. P. 105–115. https://doi.org/10.1080/17415993.2014.970555
  26. Madasamy K., Kumaraguru S., Sankar V., Mannathan S., Kathiresan M. // New J. Chem. 2019. V. 43. P. 3793–3800. https://doi.org/10.1039/C8NJ05953E
  27. Kharas G.B., Crawford A.L., Payne K.J., Sanidad M.N.T., Sims M.W., Leung D., Watson K. // J. Macromol. Sci. A. 2005. V. 42. P. 683–690. https://doi.org/10.1081/MA-200058623
  28. Swenton J.S., Freskos J.N., Morrow G.W., Sercel A.D. // Tetrahedron. 1984. V. 40. P. 4625–4632. https://doi.org/10.1016/S0040-4020(01)91523-6

Arquivos suplementares

Arquivos suplementares
Ação
1. JATS XML
Baixar
2. Scheme 1. Synthesis of arylidene rhodanines (Ia–Io) and their acyclic analogues (II–V).

Baixar (561KB)
Metadados
3. Fig. 1. Microscopy of living HeLa Kyoto cells with the addition of 7 µM compound (In) (a–c) or 5 µM compound (III) (d–f). (a, d) – Fluorescence of samples of compounds (In) and (III), respectively, upon their penetration into lipid droplets in HeLa Kyoto cells; (b, e) – HeLa Kyoto cells in transmitted light; (c, f) – fluorescent signals of samples of compounds (In) and (III), respectively, superimposed on the image of cells in transmitted light. The scale bar in all cases corresponds to a length of 5 µm.

Baixar (604KB)
Metadados

Declaração de direitos autorais © Russian Academy of Sciences, 2024