Arylidene-imidazolones and their acyclic analogue as fluorescent sensors of metal ions

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Resumo

We report about a series of methylene-imidazolones with complexing groups. The fluorescent properties of these compounds were studied in various solvents as well as in the presence of different salts. We discovered that two of the synthesized substances – hydroxyquinolinidene-imidazolone and difluorobenzimidazolidene-imidazolone – can be used as selective fluorescent sensors for cadmium and zinc ions and potentially as markers for monitoring intracellular processes.

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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, 117997, Moscow, ul. Miklukho-Maklaya, 16/10; 101000, Moscow, ul. Myasnitskaya, 20

E. Zaitseva

Shemyakin–Ovchinnikov Institute of Bioorganic Chemistry RAS

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

D. Rudik

Shemyakin–Ovchinnikov Institute of Bioorganic Chemistry RAS; Peoples’ Friendship University of Russia named after Patrice Lumumba

Email: svetlanakr2002@mail.ru
Rússia, 117997, Moscow, ul. Miklukho-Maklaya, 16/10; 117198, Moscow, ul. Miklukho-Maklaya, 6

D. Ivanov

Shemyakin–Ovchinnikov Institute of Bioorganic Chemistry RAS; M. Lomonosov Moscow State University

Email: svetlanakr2002@mail.ru
Rússia, 117997, Moscow, ul. Miklukho-Maklaya, 16/10; 119991, Moscow, ul. Leninskiye Gory, 1

A. Mikhaylov

Shemyakin–Ovchinnikov Institute of Bioorganic Chemistry RAS

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

M. Baranov

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

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

Bibliografia

  1. Klementieva N.V., Snopova L.B., Prodanets N.N., Furman O.E., Dudenkova V.V., Zagaynova E.V., Lukyanov K.A., Mishin A.S. // Anticancer Res. 2016. V. 36. P. 5287–5294. https://doi.org/10.21873/anticanres.11100
  2. Povarova N.V., Petri N.D., Blokhina A.E., Bogdanov A.M., Gurskaya N.G., Lukyanov K.A. // Int. J. Mol. Sci. 2017. V. 18. P. 1503. https://doi.org/10.3390/ijms18071503
  3. 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
  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. Baleeva N.S., Myannik K.A., Yampolsky I.V., Baranov M.S. // Eur. J. Org. Chem. 2015. V. 26. P. 5716– 5721. https://doi.org/10.1002/ejoc.201500721
  7. 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
  8. 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
  9. Olsen S., Baranov M.S., Baleeva N.S., Antonova M.M., Johnson K.A., Solntsev K.M. // Phys. Chem. Chem. Phys. 2016. V. 18. P. 26703–26711. https://doi.org/10.1039/C6CP02423H
  10. Davie E.W., Fujikawa K., Kisiel W. // Biochemistry. 1991. V. 30. P.10363–10370. https://doi.org/10.1021/bi00107a001
  11. Dascal N. // Trends Endocrinol. Metab. 2001. V. 12. P. 391–398. https://doi.org/10.1016/S1043-2760(01)00475-1
  12. Bren V.A. // Russ. Chem. Rev. 2001. V. 70. P. 1017– 1036. https://doi.org/10.1070/RC2001v070n12ABEH000667
  13. Kubo K., Sakurai T. // Heterocycles. 2000. V. 52. P. 945. https://doi.org/10.3987/REV-99-SR3
  14. Valeur B. // Coord. Chem. Rev. 2000. V. 205. P. 3–40. https://doi.org/10.1016/S0010-8545(00)00246-0
  15. Ghosh P., Bharadwaj P.K., Roy J., Ghosh S. // J. Am. Chem. Soc. 1997. V. 119. P. 11903–11909. https://doi.org/10.1021/ja9713441
  16. Hirano T., Kikuchi K., Urano Y., Higuchi T., Nagano T. // J. Am. Chem. Soc. 2000. V. 122. P. 12399– 12400. https://doi.org/10.1021/ja002467f
  17. Iwamoto K., Araki K., Fujishima H., Shinkai S. // J. Chem. Soc., Perkin Trans. 1. 1992. V. 1992. P. 1885. https://doi.org/10.1039/P19920001885
  18. Kubo Y., Obara S., Tokita S. // Chem. Commun. 1999. V. 1999. P. 2399–2400. https://doi.org/10.1039/A908001E
  19. Shabunina O.V., Starnovskaya E.S., Shaitz Ya.K., Kopchuk D.S., Sadieva L.K., Kim G.A., Taniya O.S., Nikonov I.L., Santra S., Zyryanov G.V., Charu- shin V.N. // J. Photochem. Photobiol. A. 2021. V. 408. P. 113101. https://doi.org/10.1016/j.jphotochem.2020.113101
  20. Kopchuk D.S., Slepukhin P.A., Kovalev I.S., Khasa- nov A.F., Taniya O.S., Shabunina O.V., Zyryanov G.V., Rusinov V.L., Chupakhin O.N. // Polyhedron. 2016. V. 110. P. 235–240. https://doi.org/10.1016/j.poly.2016.02.047
  21. He H., Jenkins K., Lin C. // Anal. Chim. Acta. 2008. V. 611. P. 197–204. https://doi.org/10.1016/j.aca.2008.01.059
  22. 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
  23. Baleeva N.S., Baranov M.S. // Chem. Heterocycl. Compd. 2016. V. 52. P. 444–446. https://doi.org/10.1007/s10593-016-1909-4
  24. Zaitseva S.O., Golodukhina S.V., Baleeva N.S., Le- vina E.A., Smirnov A.Y., Zagudaylova M.B., Bara- nov M.S. // ChemistrySelect. 2018. V. 3. P. 8593–8596. https://doi.org/10.1002/slct.201801349
  25. 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
  26. Bozhanova N.G., Baranov M.S., Sarkisyan K.S., Gritcenko R., Mineev K.S., Golodukhina S.V., Baleeva N.S., Lukyanov K.A., Mishin A.S. // ACS Chem. Biol. 2017. V. 12. P. 1867–1873. https://doi.org/10.1021/acschembio.7b00337

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2. Scheme 1. Scheme of synthesis of arylidene-imidazolones (I–VI) and their acyclic analog (VII) with complexing functional groups.

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3. Fig. 1. Absorption and emission spectra of compounds (III) and (IV) in a mixture of MeCN–H2O in free form and with the addition of Cd2+ and Zn2+ ions.

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4. Additional materials
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