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Development of Approaches for Obtaining Fluorine-Containing Derivatives of Boronated Amidines Based on the closo-Dodecaborate Anion

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Abstract

The reactivity of model amidines with general structure (NBu4)[B12H11NHC(CH3)HNCH(CH2OTos)2] under nucleophilic fluorination conditions has been investigated in the study. The obtained products have been characterized using multinuclear NMR and IR spectroscopies, RP-HPLC, and high-resolution mass spectrometry. The results obtained can be applied in the synthesis of similar derivatives containing 18F atoms for studying the pharmacokinetic parameters of BNCT agents using the PET method.

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REFERENCES

  1. A. Monti Hughes and N. Hu, Cancers 15, 4091 (2023). https://doi.org/10.3390/cancers15164091

    Article  CAS  PubMed  PubMed Central  Google Scholar 

  2. C. N. Yeh, C. W. Chang, Y. H. Chung, et al., Eur. J. Pharm. Sci. 107, 217 (2017). https://doi.org/10.1016/j.ejps.2017.07.019

    Article  CAS  PubMed  Google Scholar 

  3. P. Coghi, J. Li, N.S. Hosmane, and Y. Zhu, Med. Res. Rev. 43, 1809 (2023). https://doi.org/10.1002/med.21964

    Article  CAS  PubMed  Google Scholar 

  4. X. Zhao, Z. Yang, H. Chen, et al., Coord. Chem. Rev. 444, 214042 (2021). https://doi.org/10.1016/j.ccr.2021.214042

    Article  CAS  Google Scholar 

  5. V. V. Avdeeva, T. M. Garaev, N. V. Breslav, et al., J. Biol. Inorg. Chem. 27, 421 (2022). https://doi.org/10.1007/s00775-022-01937-4

    Article  CAS  PubMed  PubMed Central  Google Scholar 

  6. E. Yu. Matveev, T. M. Garaev, S. S. Novikov, et al., Russ. J. Inorg. Chem. 68, 670 (2023)https://doi.org/10.1134/S0036023623600533

  7. S. Okada, K. Nishimura, Q. Ainaya, et al., Mol. Pharm. 20, 6311 (2023)https://doi.org/10.1021/acs.molpharmaceut.3c00726

  8. A. V. Nelyubin, N. A. Selivanov, A. Yu. Bykov, et al., Int. J. Mol. Sci. 22, 13391 (2021). https://doi.org/10.3390/ijms222413391

    Article  CAS  PubMed  PubMed Central  Google Scholar 

  9. S. Kusaka, Y. Hattori, K. Uehara, et al., Appl. Rad. Isot. 69, 1768 (2011). https://doi.org/10.1016/j.apradiso.2011.03.042

    Article  CAS  Google Scholar 

  10. A. V. Nelyubin, I. N. Klyukin, A. P. Zhdanov, et al., Russ. J. Inorg. Chem. 64, 1499 (2019). https://doi.org/10.1134/S003602361912012X

    Article  CAS  Google Scholar 

  11. A. V. Nelyubin, N. A. Selivanov, I. N. Klyukin, et al., Russ. J. Inorg. Chem. 66, 1390 (2021). https://doi.org/10.1134/S0036023621090096

    Article  CAS  Google Scholar 

  12. D. S. Novopashina, M. A. Dymova, A. S. Davydova, et al., Int. J. Mol. Sci. 24, 306 (2022). https://doi.org/10.3390/ijms24010306

    Article  CAS  PubMed  PubMed Central  Google Scholar 

  13. G. Yan, Y. Zhang, J. Wang, Adv. Synth. Catal. 359, 4068 (2017). https://doi.org/10.1002/adsc.201700875

    Article  CAS  Google Scholar 

  14. M. Wang, Y. Tong, Q. Luo, S. Hu, Rad. Res. 193, 249 (2020). https://doi.org/10.1667/RR15473.1

    Article  CAS  Google Scholar 

  15. E. Hao, M.G.H. Vicente, Chem. Commun. 1306 (2005). https://doi.org/10.1039/B415649H

  16. A.R. Genady, M.E. El-Zaria, and D. Gabel, J. Organomet. Chem. 689, 3242 (2004). https://doi.org/10.1016/j.jorganchem.2004.07.029

    Article  CAS  Google Scholar 

  17. E. Hao, T. J. Jensen, B. H. Courtney, and M. G. H. Vicente, Bioconjug. Chem. 16, 1495 (2005). https://doi.org/10.1021/bc0502098

    Article  CAS  PubMed  Google Scholar 

  18. R. Satapathy, B. P. Dash, B. P. Bode, et al., Dalton Trans. 41, 8982 (2012). https://doi.org/10.1039/c2dt30874f

    Article  CAS  PubMed  Google Scholar 

  19. J. Laskova, I. Ananiev, I. Kosenko, et al., Dalton Trans. 51, 3051 (2022). https://doi.org/10.1039/D1DT04174F

    Article  CAS  PubMed  Google Scholar 

  20. E. Rzeszotarska, I. Novozhilova, and P. Kaszyński, Inorg. Chem. 56, 14351 (2017). https://doi.org/10.1021/acs.inorgchem.7b02477

    Article  CAS  PubMed  Google Scholar 

  21. P. Tokarz, P. Kaszyński, S. Domagała, and K. Woźniak, J. Organometallic Chem. 798, 70 (2015). https://doi.org/10.1016/j.jorganchem.2015.07.035

    Article  CAS  Google Scholar 

  22. P. Xie, M. Jia, X.-H. Xu, et al., Asian J. Org. Chem. 7, 586 (2018). https://doi.org/10.1002/ajoc.201700625

    Article  CAS  Google Scholar 

  23. Y. Sun, J. Zhang, Y. Zhang, et al., Chem. - A Eur. J. 24, 10364 (2018). https://doi.org/10.1002/chem.201801602

    Article  CAS  Google Scholar 

  24. M. N. Ryabchikova, A. V. Nelyubin, I. N. Klyukin, et al., Russ. J. Inorg. Chem. 68, 1357 (2023)https://doi.org/10.1134/S0036023623700341

  25. S. Harfst, D. Moller, H. Ketz, J. Rösler, and D. Gabel, J. Chromatogr. A 678, 41 (1994)https://doi.org/10.1016/0021-9673(94)87072-1

  26. S. V. Ivanov, A. J. Lupinetti, K. A. Solntsev, S. H. Strauss, J. Fluorine Chem. 89, 65 (1998). https://doi.org/10.1016/S0022-1139(98)00088-8

    Article  CAS  Google Scholar 

  27. A. V. Nelyubin, I. N. Klyukin, A. S. Novikov, et al., Mendeleev Commun. 31, 201 (2021). https://doi.org/10.1016/j.mencom.2021.03.018

    Article  CAS  Google Scholar 

  28. S. Mushtaq, P. J. Ae, J. Y. Kim, K. C. Lee, K. Il Kim, Theranostics 13, 5247 (2023). https://doi.org/10.7150/thno.88998

    Article  CAS  PubMed  PubMed Central  Google Scholar 

  29. T.-Y. Chang, W.-Y. Chang, Y.-W. Chen, et al., Nucl. Med. Biol. 116–117, 108313 (2023). https://doi.org/10.1016/j.nucmedbio.2022.108313

    Article  CAS  PubMed  Google Scholar 

  30. L. Chappel, L. C. Wong, C.-O. Leong, C.-W. Mai, I. T. Meikle, S. P. Stanforth, and T. V. Truong, Bioorg. Med. Chem. Lett. 30, 126910 (2020). https://doi.org/10.1016/j.bmcl.2019.126910

    Article  CAS  PubMed  Google Scholar 

  31. S. S. Makhathini, R. S. Kalhapure, M. Jadhav, A. Y. Waddad, R. Gannimani, C. A. Omolo, S. Rambharose, C. Mocktar, and T. Govender, J. Drug Target. 27, 1094 (2019). https://doi.org/10.1080/1061186X.2019.1599380

    Article  CAS  PubMed  Google Scholar 

  32. R. F. W. Jackson and M. Perez-Gonzalez, Org. Synth. 81, 77 (2005). https://doi.org/10.15227/orgsyn.081.0077

    Article  CAS  Google Scholar 

  33. D. Pedersen and C. Rosenbohm, Synthesis 2001, 2431 (2004). https://doi.org/10.1055/s-2001-18722

    Article  Google Scholar 

  34. M. Sadeghzadeh, B. Wenzel, J. Nikodemus, et al., J. Label. Compd. Radiopharm. 66, 116 (2023). https://doi.org/10.1002/jlcr.4018

    Article  CAS  Google Scholar 

  35. G. R. Fulmer, A. N. Herndon, W. Kaminsky, et al., J. Am. Chem. Soc. 133, 17713 (2011). https://doi.org/10.1021/ja205824q

    Article  CAS  PubMed  Google Scholar 

  36. N. K. Neumolotov, N. A. Selivanov, A. Yu. Bykov, et al., Russ. J. Inorg. Chem. 67, 1583 (2022). https://doi.org/10.1134/S0036023622600861

    Article  CAS  Google Scholar 

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ACKNOWLEDGMENTS

This research was performed using the equipment of the Center for the Collective Use of the Physical Methods of Investigation of the Institute of General and Inorganic Chemistry of the Russian Academy of Sciences.

Funding

This work was carried out with the support of the Russian Science Foundation (21-13-00450), https://rscf.ru/project/21-13-00450/.

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Authors and Affiliations

  1. Faculty of Chemistry, Higher School of Economics, 101000, Moscow, Russia

    M. N. Ryabchikova

  2. Kurnakov Institute of General and Inorganic Chemistry, Russian Academy of Sciences, 119991, Moscow, Russia

    N. K. Neumolotov, A. V. Nelyubin, N. A. Selivanov, I. N. Klyukin, A. Yu. Bykov, A. P. Zhdanov, K. Yu. Zhizhin & N. T. Kuznetsov

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  1. M. N. Ryabchikova
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  2. N. K. Neumolotov
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  3. A. V. Nelyubin
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  4. N. A. Selivanov
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  5. I. N. Klyukin
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  6. A. Yu. Bykov
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  7. A. P. Zhdanov
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  8. K. Yu. Zhizhin
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Correspondence to A. P. Zhdanov.

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Ryabchikova, M.N., Neumolotov, N.K., Nelyubin, A.V. et al. Development of Approaches for Obtaining Fluorine-Containing Derivatives of Boronated Amidines Based on the closo-Dodecaborate Anion. Russ. J. Inorg. Chem. 68, 1923–1928 (2023). https://doi.org/10.1134/S0036023623603252

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