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Synthesis of novel chlorophyll a derivatives bearing glucose moieties and estimation of their photocytotoxic activity

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Abstract

A series of chlorophyll a derivatives bearing glucose moieties linked to the porphyrin macrocycle via ester bonds were synthesized. The dark cytotoxicity and photocytotoxicity of new chlorin-glucose conjugates were competitively evaluated in comparison with those of structurally similar chlorin-galactose derivatives synthesized previously. It was revealed that the introduction of the glucose moiety into the molecule of chlorophyll a derivative facilitates a decrease in the dark cytotoxicity relative to chlorin-galactose conjugates.

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References

  1. M. Imran, M. Ramzan, A. K. Qureshi, M. A. Khan, M. Tariq, Biosensors, 2018, 8, 1.

    Article  CAS  Google Scholar 

  2. H. Abrahamse, M. R. Hamblin, Biochem. J., 2016, 473, 347.

    Article  CAS  Google Scholar 

  3. D. Straten, V. Mashayekhin, H. S. Bruijn, S. Oliveira, D. J. Robinson, Cancers, 2017, 9, 1.

    Google Scholar 

  4. A. Glowacka-Sobotta, M. Wrotynski, M. Kryjewski, L. Sobotta, J. Mielcarek, J. Porphyrins Phthalocyanines, 2019, 23, 1.

    Article  CAS  Google Scholar 

  5. A. Aggarwal, D. Samaroo, I. R. Jovanovic, S. Singh, M. P. Tuz, M. R. Mackiewicz, J. Porphyrins Phthalocyanines, 2019, 23, 729.

    Article  CAS  Google Scholar 

  6. S. Singh, A. Aggarwal, N. V. S. D. K. Bhupathiraju, G. Arianna, K. Tiwari, C. Michael, Chem. Rev., 2015, 115, 10261.

    Article  CAS  Google Scholar 

  7. P. M. R. Pereira, S. Silva, J. S. Ramalho, C. M. Gomes, H. Girão, J. A. S. Cavaleiro, C. A. F. Ribeiro, J. P. C. Tomé, R. Fernandes, Eur. J. Cancer, 2016, 68, 60.

    Article  CAS  Google Scholar 

  8. J. P. C. Tomé, E. M. P. Silva, A. M. V. M. Pereira, C. M. A. Alonso, M. A. F. Faustino, M. G. P. M. S. Neves, A. C. Tomé, J. A. S. Cavaleiro, S. A. P. Tavares, R. R. Duarte, M. F. Caeiro, M. L. Valdeira, Bioorg. Med. Chem., 2007, 15, 4705–4713.

    Article  Google Scholar 

  9. P. M. R. Pereira, W. Rizvi, N. V. S. D. K. Bhupathiraju, N. Berisha, R. Fernandes, J. P. C. Tomé, C. M. Drain, Bioconjugate Chem., 2018, 29, 306.

    Article  CAS  Google Scholar 

  10. M. A. Grin, I. S. Lonin, A. A. Lakhina, E. S. Ol’shanskaya, A. I. Makarov, Yu. L. Sebyakin, L. Y. Guryeva, P. V. Toukach, A. S. Kononikhin, V. A. Kuzmin, A. F. Mironov, J. Porphyrins Phthalocyanines, 2009, 13, 336.

    Article  CAS  Google Scholar 

  11. S. Silva, P. M. R. Pereira, P. Silva, P. F. A. Almeida, M. A. F. Faustino, J. A. S. Cavaleiro, J. P. C. Tomé, Chem. Commun., 2012, 48, 3608.

    Article  CAS  Google Scholar 

  12. G. Zheng, A. Graham, M. Shibata, J. R. Missert, A. R. Oseroff, T. J. Dougherty, R. K. Pandey, J. Org. Chem., 2001, 66, 8709.

    Article  CAS  Google Scholar 

  13. S. K. Pandey, X. Zheng, J. Morgan, J. R. Missert, T.-H. Liu, M. Shibata, D. A. Bellnier, A. R. Oseroff, B. W. Henderson, T. J. Dougherty, R. K. Pandey, Mol. Pharmaceutics, 2007, 4, 448.

    Article  CAS  Google Scholar 

  14. Z. Iqbal, N. Masilela, T. Nyokong, A. Lyubimtsev, M. Hanack, T. Zieglerb, Photochem. Photobiol. Sci., 2012, 11, 679.

    Article  CAS  Google Scholar 

  15. M. A. Grin, N. S. Suvorov, A. F. Mironov, Mendeleev Commun., 2020, 30, 406.

    Article  CAS  Google Scholar 

  16. N. S. Kuzmina, V. F. Otvagin, L. V. Krylova, A. V. Nyuchev, Y. V. Romanenko, O. I. Koifman, I. V. Balalaeva, A. Yu. Fedorov, Mendeleev Commun., 2020, 30, 159.

    Article  CAS  Google Scholar 

  17. D. V. Titov, M. L. Gening, Yu. E. Tsvetkov, N. E. Nifantiev, Russ. Chem. Rev., 2014, 83, 523.

    Article  CAS  Google Scholar 

  18. H. Kataoka, H. Nishie, N. Hayashi, M. Tanaka, A. Nomoto, S. Yano, T. Joh, Ann. Transl. Med., 2017, 5, No. 8, 183.

    Article  Google Scholar 

  19. O. Warburg, Science, 1956, 123, 309; DOI: https://doi.org/10.1126/science.123.3191.309.

    Article  CAS  Google Scholar 

  20. E. M. Wright, Mol. Aspects Medicine, 2013, 34, 183.

    Article  CAS  Google Scholar 

  21. P.-B. Ancey, C. Contat, E. Meylan, FEBS J., 2018, 285, 2926.

    Article  CAS  Google Scholar 

  22. A. V. Kustov, M. A. Krestyaninov, S. O. Kruchin, O. V. Shukhto, T. V. Kustova, D. V. Belykh, I. S. Khudyaeva, M. O. Koifman, P. B. Razgovorovd, D. B. Berezin, Mendeleev Commun., 2021, 31, 65; DOI: https://doi.org/10.1016/j.mencom.2021.01.019.

    Article  CAS  Google Scholar 

  23. A. V. Kustov, T. V. Kustova, D. V. Belykh, I. S. Khudyaeva, D. B. Berezin, Dyes Pigm., 2020, 173, 107948; DOI: https://doi.org/10.1016/j.dyepig.2019.107948.

    Article  CAS  Google Scholar 

  24. M. A. Gradova, T. G. Movchan, I. S. Khudyaeva, A. Yu. Chernyad’ev, E. V. Plotnikova, A. V. Lobanov, D. V. Belykh, Macroheterocycles, 2020, 13, 23; DOI: https://doi.org/10.6060/mhc191072g.

    Article  CAS  Google Scholar 

  25. Y. I. Pylina, O. M. Startseva, E. E. Rasova, D. V. Belykh, Macroheterocycles, 2019, 12, 165; DOI: https://doi.org/10.6060/mhc181219b.

    Article  CAS  Google Scholar 

  26. D. V. Belykh, A. S. Kozlov, Y. I. Pylina, I. S. Khudyaeva, A. S. Benditkis, A. A. Krasnovsky, Macroheterocycles, 2019, 12, 68; DOI: https://doi.org/10.6060/mhc190128b.

    Article  CAS  Google Scholar 

  27. I. S. Khudyaeva, O. G. Shevchenko, D. V. Belykh, Russ. Chem. Bull., 2020, 69, 742; DOI: https://doi.org/10.1007/s11172-020-2827-2.

    Article  CAS  Google Scholar 

  28. L. A. Tulaeva, E. I. Pushkareva, O. V. Tolstikova, D. V. Belykh, Russ. Chem. Bull., 2021, 70, 359; DOI: https://doi.org/10.1007/s11172-021-3093-7.

    Article  CAS  Google Scholar 

  29. Yu. A. Zhdanov, G. H. Dorofeyenko, G. A. Korol’chenko, G. V. Bogdanova, Praktikum po khimii uglevodov (monosakharidy) [Workshop on the Chemistry of Carbohydrates (Monosaccharides)], Vyssh. Shkola, Moscow, 1973, 96 p.

    Google Scholar 

  30. M. V. Mal’shakova, Y. I. Pylina, D. V. Belykh, Bioorg. Med. Chem. Lett., 2019, 29, 2064.

    Article  Google Scholar 

  31. E. Lindhagen, P. Nygren, R. Larsson, Nat. Protoc., 2008, 3, 1364.

    Article  CAS  Google Scholar 

  32. M. V. Mal’shakova, I. O. Velegzhaninov, E. E. Rasova, D. V. Belykh, J. Porphyrins Phthalocyanines, 2021, 25, 135.

    Article  Google Scholar 

  33. S. Pedatella, A. Guaragna, D. D’Alonzo, M. De Nisco, G. Palumbo, Synthesis, 2006, 305.

  34. G. W. Kenner, S. W. McCombie, K. M. Smith, J. Chem. Soc., Perkin Trans. 1, 1973, 2517; DOI: https://doi.org/10.1039/P19730002517.

  35. L. A. Tulayeva, D. V. Belykh, H. M. Yakovleva, I. A. Cel’kova, A. V. Rocheva, A. V. Kuchin, Izv. vuzov. Khimiya i khim. tekhnologiya [Russian Journal of Chemistry and Chemical Technology], 2006, 49, No. 4, 82 (in Russian).

    Google Scholar 

  36. V. F. Otvagin, A. V. Nyuchev, N. S. Kuzmina, I. D. Grishin, A. E. Gavryushin, Y. V. Romanenko, O. I. Koifman, D. V. Belykh, N. N. Peskova, N. Y. Shilyagina, I. V. Balalaeva, A. Y. Fedorov, Eur. J. Med. Chem., 2018, 144, 740.

    Article  CAS  Google Scholar 

  37. Y. I. Pylina, D. M. Shadrin, O. G. Shevchenko, I. S. Khudyaeva, D. V. Belykh, I. O. Velegzhaninov, Macroheterocycles, 2017, 10, 279.

    Article  CAS  Google Scholar 

  38. Ya. I. Pylina, I. C. Khudyayeva, Ye. A. Osipova, D. M. Shadrin, I. O. Velegzhaninov, Ye. C. Belykh, D. V. Belykh, Butlerov Commun., 2018, 55, No. 8, 10.

    Google Scholar 

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Authors and Affiliations

  1. Institute of Chemistry, Federal Research Centre “Komi Scientific Centre”, Ural Branch of the Russian Academy of Sciences, 48 ul. Pervomayskaya, 167000, Syktyvkar, Russian Federation

    M. V. Mal’shakova & D. V. Belykh

  2. Institute of Biology, Federal Research Centre “Komi Scientific Centre”, Ural Branch of the Russian Academy of Sciences, 28 ul. Kommunisticheskaya, 167982, Syktyvkar, Russian Federation

    E. E. Rasova & I. O. Velegzhaninov

Authors
  1. M. V. Mal’shakova
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  2. E. E. Rasova
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  3. I. O. Velegzhaninov
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  4. D. V. Belykh
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Correspondence to M. V. Mal’shakova.

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Additional information

The work was financially supported by the Ministry of Science and Higher Education of the Russian Federation (State Assignment No. 1021062211116-4-1.4.1). The evaluation of dark and photoinduced cytotoxicities of the compounds was carried out within the framework of the research work topic “The effect of ionizing radiation and non-radiation factors onto biological objects and biogenic migration of heavy natural radionuclides” (No. 021051101422-0-1.6.23) in the Institute of Biology of the Federal Research Center “Komi Scientific Centre”, Ural Branch of the Russian Academy of Sciences.

No human or animal subjects were used in this research.

Published in Russian in Izvestiya Akademii Nauk. Seriya Khimicheskaya, No. 3, pp. 531–537, March, 2022.

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Mal’shakova, M.V., Rasova, E.E., Velegzhaninov, I.O. et al. Synthesis of novel chlorophyll a derivatives bearing glucose moieties and estimation of their photocytotoxic activity. Russ Chem Bull 71, 531–537 (2022). https://doi.org/10.1007/s11172-022-3444-z

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  • DOI: https://doi.org/10.1007/s11172-022-3444-z

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