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Synthesis and Optical Properties of the Conformationally Locked Indole and Indoline Derivatives of the GFP Chromophore

Russian Journal of Bioorganic Chemistry volume 46, pages 862–865 (2020)Cite this article

Abstract

We report novel conformationally locked GFP chromophore amino-derivatives containing indole and indoline moieties. Optical properties of these compounds were studied. The introduction of the indoline group produces a shift in the absorption and emission maxima to the long-wavelength region and stabilizes the quantum yield of fluorescence. The introduce of the indole group leads to a hypsochromic shift and a noticeable decrease of fluorescence intensity.

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REFERENCES

  1. Walker, C.L., Lukyanov, K.A., Yampolsky, I.V., Mishin, A.S., Bommarius, A.S., Duraj-Thatte, A.M., Azizi, B., Tolbert, L.M., and Solntsev, K.M., Curr. Opin. Chem. Biol., 2015, vol. 27, pp. 64–74. https://doi.org/10.1016/j.cbpa.2015.06.002

    CAS  Article  PubMed  Google Scholar 

  2. Baleeva, N.S. and Baranov, M.S., Chem. Heterocycl. Compd., 2016, vol. 52, pp. 444–446. https://doi.org/10.1007/s10593-016-1909-4

    CAS  Article  Google Scholar 

  3. Yampolsky, I.V., Kislukhin, A.A., Amatov, T.T., Shcherbo, D., Potapov, V.K., Lukyanov, S., and Lukyanov, K.A., Bioorg. Chem., 2008, vol. 36, pp. 96–104.

    CAS  Article  Google Scholar 

  4. Feng, G., Luo, C., Yi, H., Yuan, L., Lin, B., Luo, X., Hu, X., Wang, H., Lei, C., Nie, Z., and Yao, S., Nucleic Acids Res., 2017, vol. 45, pp. 10 380–10 392. https://doi.org/10.1093/nar/gkx803

    CAS  Article  Google Scholar 

  5. Filonov, G.S., Moon, J.D., Svensen, N., and Jaffrey, S.R., J. Am. Chem. Soc., 2014, vol. 136, pp. 16 299–16 308. https://doi.org/10.1021/ja508478x

    CAS  Article  Google Scholar 

  6. Ge, S., Deng, H., Su, Y., and Zhu, X., RSC Adv., 2017, vol. 7, pp. 17 980–17 987. https://doi.org/10.1039/C7RA00974G

    Article  Google Scholar 

  7. Chen, C., Baranov, M.S., Zhu, L., Baleeva, N.S., Smirnov, A.Y., Zaitseva, S.O., Yampolsky, I.V., Solntsev, K.M., and Fang, C., Chem. Commun., 2019, vol. 55, pp. 2537–2540. https://doi.org/10.1039/C8CC10007A

    CAS  Article  Google Scholar 

  8. Paige, J.S., Wu, K.Y., and Jaffrey, S.R., Science, 2011, vol. 333, pp. 642–646. https://doi.org/10.1126/science.1207339

    CAS  Article  PubMed  PubMed Central  Google Scholar 

  9. 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., and Baranov, M.S., Chemistry, 2019, vol. 25, pp. 9592–9596. https://doi.org/10.1002/chem.201901151

    CAS  Article  PubMed  Google Scholar 

  10. Zaitseva, S.O., Farkhutdinova, D.A., Baleeva, N.S., Smirnov, A.Yu., Zagudaylova, M.B., Shakhov, A.M., Astafiev, A.A., Baranov, M.S., and Bochenkova, A.V., RSC Adv., 2019, vol. 9, pp. 38 730–38 734. https://doi.org/10.1039/C9RA08808C

    Article  Google Scholar 

  11. Baleeva, N.S., Myannik, K.A., Yampolsky, I.V., and Baranov, M.S., Eur. J. Org. Chem., 2015, vol. 2015, pp. 5716–5721. https://doi.org/10.1002/ejoc.201500721

    CAS  Article  Google Scholar 

  12. Baleeva, N.S., Zaitseva, S.O., Gorbachev, D.A., Zagudaylova, M.B., and Baranov, M.S., Eur. J. Org. Chem., 2017, vol. 35, pp. 5219–5224. https://doi.org/10.1002/ejoc.201700805

    CAS  Article  Google Scholar 

  13. Baranov, M.S., Solntsev, K.M., Baleeva, N.S., Mishin, A.S., Lukyanov, S.A., Lukyanov, K.A., and Yampolsky, I.V., Chemistry, 2014, vol. 20, pp. 13 234–13 241. https://doi.org/10.1002/chem.201403678

    CAS  Article  Google Scholar 

  14. Wu, L. and Burgess, K., J. Am. Chem. Soc., 2008, vol. 130, pp. 4089–4096. https://doi.org/10.1021/ja710388h

    CAS  Article  PubMed  Google Scholar 

  15. Baldridge, A., Solntsev, K.M., Song, C., Tanioka, N., Kowalik, J., Hardcastle, K., and Tolbert, L.M.,Chem. Commun., 2010, vol. 46, pp. 5686–5688. https://doi.org/10.1039/B927313A

    CAS  Article  Google Scholar 

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Funding

The study was carried out with the financial support of the Russian Foundation for Basic Research (project no. 18-03-00094_a).

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Authors and Affiliations

  1. Shemyakin–Ovchinnikov Institute of Bioorganic Chemistry, Russian Academy of Sciences, 117997, Moscow, Russia

    N. S. Baleeva, A. Yu. Smirnov, I. N. Myasnyanko & M. S. Baranov

  2. Pirogov Russian National Research Medical University, 117997, Moscow, Russia

    M. S. Baranov

Authors
  1. N. S. Baleeva
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  2. A. Yu. Smirnov
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  3. I. N. Myasnyanko
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  4. M. S. Baranov
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Corresponding author

Correspondence to N. S. Baleeva.

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This article does not contain any research involving humans and animals as research objects.

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The authors declare no conflict of interest.

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Abbreviations: GFP, green fluorescent protein; MS, molecular sieves.

Corresponding author: phone: +7 (926) 704-13-72; e-mail: nsbaleeva@gmail.com.

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Baleeva, N.S., Smirnov, A.Y., Myasnyanko, I.N. et al. Synthesis and Optical Properties of the Conformationally Locked Indole and Indoline Derivatives of the GFP Chromophore. Russ J Bioorg Chem 46, 862–865 (2020). https://doi.org/10.1134/S1068162020050040

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  • DOI: https://doi.org/10.1134/S1068162020050040

Keywords:

  • imidazolones
  • chromophores
  • fluorescent dyes
  • GFP
  • optical properties