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Synthesis and Optical Properties of the New Acetylene Kaede Chromophore Analog

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Abstract

A novel derivative of acetylene Kaede protein chromophore (Z)-2-((4-(diethylamino) phenyl) ethynyl)-5-(4-hydroxybenzylidene)-3-methyl-3,5-dihydro-4H-imidazol-4-one was synthesized by a modified Sonogashira reaction. In comparison with the classical GFP chromophore analog, the compound exhibits a prominent shift of absorption and emission maxima to the long-wavelength region. The value of Stock’s shift of the newly synthesized compound reached almost 150 nm.

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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.

    Article  CAS  Google Scholar 

  2. Ge, S., Deng, H., Su, Y., and Zhu, X., RSC Adv., 2017, vol. 7, pp. 17 980–17 987.

    Article  Google Scholar 

  3. Povarova, N.V., Bozhanova, N.G., Sarkisyan, K.S., Gritcenko, R., Baranov, M.S., Yampolsky, I.V., Lukyanov, K.A., and Mishin, A.S., J. Mater. Chem., vol. 4, pp. 3036–3040.

  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.

    Article  Google Scholar 

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

    Article  CAS  Google Scholar 

  6. Baleeva, N.S., Myannik, K.A., Yampolsky, I.V., and Baranov, M.S., Eur. J. Org. Chem., 2015, vol. 2015, pp. 5716–5721.

  7. Ermakova, Y.G., Sen, T., Bogdanova, Y.A., Smirnov, A.Y., Baleeva, N.S., Krylov, A.I., and Baranov, M.S., J. Phys. Chem. Lett., 2018, vol. 9, pp. 1958–1963.

    Article  CAS  Google Scholar 

  8. Povarova, N.V., Zaitseva, S.O., Baleeva, N.S., Smirnov, A.Y., 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.

    Article  CAS  Google Scholar 

  9. Jung, K.H., Fares, M., Grainger, L.S., Wolstenholme, C.H., Hou, A., Liu, Y., and Zhang, X.A., Org. Biomol. Chem., 2019, vol. 17, pp. 1906–1915.

    Article  CAS  Google Scholar 

  10. Mehta, V.P., Sharma, A., and Van der Eycken, E., Org. Lett., 2008, vol. 10, pp. 1147–1150.

    Article  CAS  Google Scholar 

  11. Iwasaki M., Topolovčan N., Hu H., Nishimura Y., Gagnot G., Nanakorn, R., Yuvacharaskul, R., Nakajima, K., and Nishihara, Y., Org. Lett., 2016, vol. 18, pp. 1642–1645.

    Article  CAS  Google Scholar 

  12. Gosling, S., Rollin, P., and Tatibouet, A., Synthesis, 2011, pp. 3649–3660.

  13. Oumouch, S., Bourotte, M., Schmitt, M., and Bourguignon, J.-J., Synthesis, 2005, pp. 25–27.

  14. Shook, B.C., Chakravarty, D., and Jackson, P.F., Tetrahedron Lett., 2009, vol. 50, pp. 1013–1015.

    Article  CAS  Google Scholar 

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Funding

The study was supported by the Russian Science Foundation as part of research project No. 16-14-10364.

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Authors and Affiliations

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

    E. R. Zaitseva, A. Yu. Smirnov, A. S. Mishin & M. S. Baranov

  2. Mendeleev University of Chemical Technology of Russia, 125047, Moscow, Russia

    E. R. Zaitseva

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

    M. S. Baranov

Authors
  1. E. R. Zaitseva
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  2. A. Yu. Smirnov
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  3. A. S. Mishin
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  4. M. S. Baranov
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Corresponding author

Correspondence to A. S. Mishin.

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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 they have no conflict of interest.

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Corresponding author: phone: +7 (495) 995-55-57 (2074); e-mail: mishin@ibch.ru.

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Zaitseva, E.R., Smirnov, A.Y., Mishin, A.S. et al. Synthesis and Optical Properties of the New Acetylene Kaede Chromophore Analog. Russ J Bioorg Chem 46, 458–461 (2020). https://doi.org/10.1134/S1068162020030231

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  • DOI: https://doi.org/10.1134/S1068162020030231

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