- PII
- S30345111S2686953525030055-1
- DOI
- 10.7868/S3034511125030055
- Publication type
- Article
- Status
- Published
- Authors
- Volume/ Edition
- Volume 522 / Issue number 1
- Pages
- 35-41
- Abstract
- A new approach for the synthesis of the anticancer agent 6-oxofascaplysine has been developed and its photochemical activity has been studied for the first time using the method of chemically induced dynamic nuclear polarization. It was found that 6-oxofascaplysine in triplet excited state enters into electron transfer reaction with biomolecules – aromatic amino acids (tryptophan and tyrosine) and 1,4-dihydropyridine (NADH analogue), as well as into energy transfer reaction with oxygen molecule with formation of singlet oxygen. The structure of the radical intermediate of 6-oxofascaplysine has been established. These data may be useful for evaluating the prospects for the use of 6-oxofascaplysine in photodynamic therapy.
- Keywords
- 6-оксофаскаплизин синтез фотохимическая активность перенос электрона синглетный кислород фотодинамическая терапия химическая поляризация ядер
- Date of publication
- 01.06.2025
- Year of publication
- 2025
- Number of purchasers
- 0
- Views
- 13
References
- 1. Zhidkov M.E., Kantemirov A.V., Koisevnikov A.V., Andin A.N., Kuzmich A.S. // Tetrahedr. Lett. 2018. V. 59. P. 708–711. https://doi.org/10.1016/J.TETLET.2018.01.023
- 2. Luo L., Xu G. // Int. J. Mol. Sci. 2022. V. 23. P. 13774. https://doi.org/10.3390/ijms232213774
- 3. Khokhar S., Feng Y., Campitelli M.R., Ekins M.G., Hooper J.N.A., Beattie K.D., Sadowski M.C., Nelson C.C., Davis R.A. // Bioorg. Med. Chem. Lett. 2014. V. 24. № 15. P. 3329–3332. https://doi.org/10.1016/j.bmcl.2014.05.104
- 4. Wang C., Wang S., Li H., Hou Y., Cao H., Hua H., Li D. // Mar. Drugs. 2023. V. 21. P. 226. https://doi.org/10.3390/md21040226
- 5. Kaptein R. // J. Chem. Soc. D: Chem. Commun. 1971. № 14. P. 732–733. https://doi.org/10.1039/C29710000732
- 6. Salikhov K.M., Molin Yu.N., Sagdeev R.Z.б Buchachenko A.L. Spin polarization and magnetic effects in radical reactions. Molin Yu.N. (ed.). Budapest, Hungary, Academiai Kiadó,1984. 419 p.
- 7. Leshina T.V., Kruppa A.I., Taraban M.B. CIDNP Applications. In: Encyclopedia of spectroscopy and spectrometry. Third Edition. 2017. P. 256–262. http://dx.doi.org/10.1016/B978-0-12-803224-4.00121-7
- 8. Morozova O.B., Ivanov K.L., Kiryutin A.S., Sagdeev R.Z., Köchling T., Vieth H.-M., Yurkovskaya A.V. // Phys. Chem. Chem. Phys. 2011. V. 13. № 14. P. 6619–6627. https://doi.org/10.1039/c0cp02449j
- 9. Morozova O.B., Ivanov K.L. // Chem. Phys. Chem. 2019. V. 20. № 2. P. 197–215. https://doi.org/10.1002/cphc.201800566
- 10. Goez M. Elucidating organic reaction mechanisms using photo-CIDNP spectroscopy. In: Hyperpolarization methods in NMR spectroscopy. Kuhn L.T. (ed.). Berlin, Heidelberg, 2013. P. 1–32. https://doi.org/10.1007/128_2012_348
- 11. Kuhn L.T., Bargon J. Exploiting nuclear spin polarization to investigate free radical reactions via in situ NMR. In: In situ NMR methods in catalysis. Bargon J., Kuhn L.T. (eds.). Berlin, Heidelberg, 2007. P. 125–154. https://doi.org/10.1007/128_2007_119
- 12. Polyakov N.E., Khan V.K., Taraban M.B., Leshina T.V., Luzina O.A., Salakhutdinov N.F., Tolstikov G.A. // Org. Biomol. Chem. 2005. V. 3. P. 881–885. https://doi.org/10.1039/b416133e
- 13. Taraban М.В., Kruppa A.I., Polyakov N.E., Leshina T.V., Lūsis V., Muceniece D., Duburs G. // J. Photochem. Photobiol. A Chem. 1993. V. 73. P. 151–156. https://doi.org/10.1016/1010-6030 (93)80044-A
- 14. Mastova A.V., Selyutina O.Yu., Polyakov N.E. // Membranes. 2022. V. 12. P. 460. https://doi.org/10.3390/membranes12050460
- 15. Baram G.I., Grachev M.A., Komarova N.I., Perelroyzen M.P., Bolvanov Y.A., Kuzmin S.V., Kargaltsev V.V., Kuper E.A. // J. Chromatogr. A. 1983. V. 264. № 1. P. 69–90. https://doi.org/10.1016/S0021-9673 (01)95007-1
- 16. Hermosilla L., Calle P., García de la Vega J.M., Sieiro C. // J. Phys. Chem. A. 2005. V. 109. № 6. P. 1114–1124. https://doi.org/10.1021/jp0466901
- 17. Weigend F. // Phys. Chem. Chem. Phys. 2006. V. 8. № 9. P. 1057–1065. https://doi.org/10.1039/b515623h
- 18. Neese F., Wennmohs F., Hansen A., Becker U. // Chem. Phys. 2009. V. 356. № 1–3. P. 98–109. https://doi.org/10.1016/j.chemphys.2008.10.036
- 19. Barone V., Cossi M. // J. Phys. Chem. A. 1998. V. 102. № 11. P. 1995–2001. https://doi.org/10.1021/jp9716997
- 20. Oberg C., Buthelezi M.T. Binding of Cu2+ ions to indigo derivatives in aqueous media. 2023. Available at SSRN: http://dx.doi.org/10.2139/ssrn.4455433
- 21. Mao Y., Chen H., Zhu W., Ni S., Luo S., Tang S., Chen Z., Wang Q., Xu J., Tu Q., Chen H., Zhu L. // J. Inflam. Res. 2025. V. 18. P. 883–894. https://doi.org/10.2147/JIR.S498340
