The substituted derivative of closo-dodecaborate anion based on para-iodo-L-phenylalanine is a novel compound for BNCT with CT imaging capability

Cover Page

Cite item

Full Text

Open Access Open Access
Restricted Access Access granted
Restricted Access Subscription or Fee Access

Abstract

A substituted derivative of closo-dodecaborate anion [B12H11NH=C(CH3)NHCH2CH-4-I-C6H4(COOCH3)]– containing in its structure elements for vector delivery and diagnostics by beam imaging methods was obtained. The structure of the co-compound was established by multinuclear NMR spectroscopy and ESI-mass spectrometry. For aqueous solutions of the compound Na[B12H11NH=C(CH3)NHCH2CH-4-I-C6H4(COOCH3)], the X-ray density was measured and the distribution of the drug in the organs of laboratory animals was studied by computer tomography.

About the authors

М. N. Ryabchikova

National Research University Higher School of Economics

Email: zhdanov@igic.ras.ru
Russian Federation, Moscow

А. V. Nelyubin

Kurnakov Institute of General and Inorganic Chemistry, Russian Academy of Sciences

Email: zhdanov@igic.ras.ru
Russian Federation, Moscow

Yu. А. Finogenova

Blokhin National Medical Research Center of Oncology, Ministry of Health of the Russian Federation

Email: zhdanov@igic.ras.ru
Russian Federation, Moscow

V. А. Skribitsky

Blokhin National Medical Research Center of Oncology, Ministry of Health of the Russian Federation; National Research Nuclear University MEPhI (Moscow Engineering Physics Institute)

Email: zhdanov@igic.ras.ru
Russian Federation, Moscow; Moscow

А. P. Zhdanov

Kurnakov Institute of General and Inorganic Chemistry, Russian Academy of Sciences

Author for correspondence.
Email: zhdanov@igic.ras.ru
Russian Federation, Moscow

А. А. Lipengolts

Blokhin National Medical Research Center of Oncology, Ministry of Health of the Russian Federation; National Research Nuclear University MEPhI (Moscow Engineering Physics Institute)

Email: zhdanov@igic.ras.ru
Russian Federation, Moscow; Moscow

Е. Yu. Grigorieva

Blokhin National Medical Research Center of Oncology, Ministry of Health of the Russian Federation

Email: zhdanov@igic.ras.ru
Russian Federation, Moscow

К. Yu. Zhizhin

Kurnakov Institute of General and Inorganic Chemistry, Russian Academy of Sciences

Email: zhdanov@igic.ras.ru
Russian Federation, Moscow

N. Т. Kuznetsov

Kurnakov Institute of General and Inorganic Chemistry, Russian Academy of Sciences

Email: zhdanov@igic.ras.ru
Russian Federation, Moscow

References

  1. Kumar R., Shin W.S., Sunwoo K. et al. // Chem. Soc. Rev. 2015. V. 44. № 19. P. 6670. https://doi.org/10.1039/c5cs00224a
  2. Huang H., Lovell J.F. // Adv. Funct. Mater. 2017. V. 27. № 2. P. 1603524. https://doi.org/10.1002/adfm.201603524
  3. Nicolson F., Kircher M.F. // Molecular Imaging: Principles and Practice / Eds. Ross B.D., Gambhir S.S. Academic Press, 2021. P. 655. P. 655. https://doi.org/10.1016/B978-0-12-816386-3.00040-5
  4. Las’kova Yu.N., Serdyukov A.A., Sivaev I.B. // Russ. J. Inorg. Chem. 2023. V. 68. № 6. P. 621. https://doi.org/10.1134/S0036023623600612
  5. Lipengolts A.A., Finogenova Y.A., Skribitsky V.A. et al. // Int. J. Mol. Sci. 2022. V. 24. № 1. P. 70. https://doi.org/10.3390/ijms24010070
  6. Skribitsky V.A., Finogenova Yu.A., Lipengolts A.A. et al. // Phys. Atom. Nuclei. 2022. V. 85. № 9. P. 1598. https://doi.org/10.1134/S1063778822090356
  7. Lux F., Sancey L., Bianchi A. et al. // Nanomedicine. 2015. V. 10. № 11. P. 1801. https://doi.org/10.2217/nnm.15.30
  8. Popova T.V., Pyshnaya I.A., Zakharova O.D. et al. // Biomedicines. 2021. V. 9. № 1. P. 74. https://doi.org/10.3390/biomedicines9010074
  9. Li J., Shi Y., Zhang Z. et al. // Bioconjugate Chem. 2019. V. 30. № 11. P. 2870. https://doi.org/10.1021/acs.bioconjchem.9b00578
  10. Kuthala N., Vankayala R., Li Y.N. et al. // Adv. Mater. 2017. V. 29. № 31. P. 1700850. https://doi.org/10.1002/adma.201700850
  11. Hoffmann S., Justus E., Ratajski M. et al. // J. Organomet. Chem. 2005. V. 690. № 11. P. 2757. https://doi.org/10.1016/j.jorganchem.2005.02.037
  12. Justus E., Vöge A., Gabel D. // Eur. J. Inorg. Chem. 2008. № 33. P. 5245. https://doi.org/10.1002/ejic.200800770
  13. Sivaev I.B., Bruskin A.B., Nesterov V.V. et al. // Inorg. Chem. 1999. V. 38. № 25. P. 5887. https://doi.org/10.1021/ic990013h
  14. Goswami L., Ma L., Chakravarty S. et al. // Inorg. Chem. 2012. V. 52. № 4. P. 1694. https://doi.org/10.1021/ic3017613
  15. Goswami L.N., Chakravarty S., Cai Q.Y. et al. // ACS Appl. Bio Mater. 2021. V. 4. № 9. P. 6658. https://doi.org/10.1021/acsabm.1c00717.
  16. Kanygin V., Zaboronok A., Taskaeva I. et al. // J. Fluor. 2021. V. 31. № 1. P. 73. https://doi.org/10.1007/s10895–020–02637–5
  17. Iguchi Y., Michiue H., Kitamatsu M. et al. // Biomaterials. 2015. V. 56. P. 10. https://doi.org/10.1016/j.biomaterials.2015.03.061
  18. Semioshkin A.A., Sivaev I.B., Bregadze V.I. // Dalton Trans. 2008. V. 11. № 8. P. 977. https://doi.org/10.1039/b715363e
  19. Prikaznov A.V., Bragin V.I., Davydova M.N. et al. // Collect. Czech. Chem. Commun. 2007. V. 72. № 12. P. 1689. https://doi.org/10.1135/cccc20071689
  20. Nelyubin A.V., Selivanov N.A., Bykov A.Yu. et al. // Int. J. Mol. Sci. 2021. V. 22. № 24. P. 13391. https://doi.org/10.3390/ijms222413391
  21. Nelyubin A.V., Selivanov N.A., Bykov A.Yu. et al. // Russ. J. Inorg. Chem. 2022. V. 67. № 11. P. 1776. https://doi.org/10.1134/S0036023622601106
  22. Nelyubin A.V., Sokolov M.S., Selivanov N.A. et al. // Russ. J. Inorg. Chem. 2022. V. 67. № 11. P. 1751. https://doi.org/10.1134/S003602362260109X
  23. Nelyubin A.V., Selivanov N.A., Klyukin I.N. et al. // Russ. J. Inorg. Chem. 2021. V. 66. № 9. P. 1390. https://doi.org/10.1134/S0036023621090096
  24. Nelyubin A.V., Klyukvin I.N., Selivanov N.A. et al. // Russ. J. Inorg. Chem. 2023. V. 68. № 6. P. 684. https://doi.org/10.1134/S003602362360048X
  25. Himmelspach A., Finze M., Vöge A. et al. // Z. Anorg. Allg. Chem. 2012. V. 638. № 3–4. P. 512. https://doi.org/10.1002/zaac.201100458
  26. Peymann T., Knobler C.B., Hawthorne M.F. // Inorg. Chem. 1998. V. 37. № 7. P. 1544. https://doi.org/10.1021/ic9712075
  27. Kultyshev R.G., Liu S., Leung H.T. et al. // Inorg. Chem. 2003. V. 42. № 10. P. 3199. https://doi.org/10.1021/ic020600u
  28. Nelyubin A.V., Selivanov N.A., Bykov A.Y. et al. // Russ. J. Inorg. Chem. 2020. V. 65. № 6. P. 795. https://doi.org/10.1134/S0036023620060133
  29. Kaszyński P., Ringstrand B. // Angew. Chem. Int. Ed. 2015. V. 54. № 22. P. 6576. https://doi.org/10.1002/anie.201411858
  30. Tokarz P., Kaszyński P., Domagała S. et al. // J. Organomet. Chem. 2015. V. 798. P. 70. https://doi.org/10.1016/j.jorganchem.2015.07.035
  31. Ali M.O., Lasseter J.C., Żurawiński R. et al. // Chem. Eur. J. 2019. V. 25. № 10. P. 2616. https://doi.org/10.1002/chem.201805392
  32. Nelyubin A.V., Klyukin I.N., Novikov A.S. et al. // Inorganics (Basel). 2022. V. 10. № 11. P. 196. https://doi.org/10.3390/inorganics10110196
  33. Detta A., Cruickshank G.S. // Cancer Res. 2009. V. 69. № 5. P. 2126. https://doi.org/10.1158/0008–5472.CAN-08–2345
  34. Boyle T.P., Bremner J.B., Coates J.A. et al. // Eur. J. Med. Chem. 2009. V. 44. № 3. P. 1001. https://doi.org/10.1016/j.ejmech.2008.07.001

Supplementary files

Supplementary Files
Action
1. JATS XML
Download

Copyright (c) 2024 Russian Academy of Sciences