Determination of the Stability Constants of Supramolecular Complexes of Ester Derivatives of Betulin with Randomly Methylated β-Cyclodextrin by Affinity Capillary Electrophoresis

Cover Page

Cite item

Full Text

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

Abstract

Using affinity capillary electrophoresis, the stability constants of inclusion complexes of a number of betulin ester derivatives with randomly methylated β-cyclodextrin in 0.0100 M sodium tetraborate (pH 9.18, ionic strength 0.0200 M) at 25°С were determined for the first time. The decimal logarithms of the stability constants of 1 : 1 complexes of betulin 3,28-diphthalate, betulin 3,28-disulfate, and betulin 3,28-disuccinate in a 95% confidence interval were 4.64 ± 0.05, 4.78 ± 0.02, and 4.94 ± 0.02, respectively. The logarithms of the stability constants of 1 : 2 complexes of betulin 3,28-diphthalate and betulin 3,28-disulfate were 7.91 (6.66–8.19) and 8.02 (7.63–8.23), respectively. It was determined that betulin 3,28-disuccinate forms only 1 : 1 complex. The obtained stability constants of 1 : 1 complexes are generally higher than those of the complexes of the same compounds with β-cyclodextrin (β-CD) and lower than those for dimethyl-β-CD, γ-CD, and (2-hydroxypropyl)-γ-CD complexes.

About the authors

V. V. Sursyakova

Institute of Chemistry and Chemical Technology, Federal Research Center “Krasnoyarsk Scientific Center,” Siberian Branch, Russian Academy of Sciences

Email: viktoria_vs@list.ru
660036, Krasnoyarsk, Russia

V. A. Levdansky

Institute of Chemistry and Chemical Technology, Federal Research Center “Krasnoyarsk Scientific Center,” Siberian Branch, Russian Academy of Sciences

Email: viktoria_vs@list.ru
660036, Krasnoyarsk, Russia

A. I. Rubaylo

Institute of Chemistry and Chemical Technology, Federal Research Center “Krasnoyarsk Scientific Center,” Siberian Branch, Russian Academy of Sciences; Siberian Federal University

Author for correspondence.
Email: viktoria_vs@list.ru
660036, Krasnoyarsk, Russia; 660041, Krasnoyarsk, Russia

References

  1. Crini G. // Chem. Rev. 2014. V. 114. P. 10940. https://doi.org/10.1021/cr500081p
  2. Толстиков Г.А., Флехтер О.Б., Шульц Э.Э. и др. // Химия в интересах устойчивого развития. 2005. Т. 13. С. 1. Tolstikov G.A., Flekhter O.B., Shultz E.E. et al. // Chem. Sustainable Develop. 2005. V. 13. P. 1.
  3. Sbârcea L., Ledeţi A., Udrescu L. et al. // J. Therm. Anal. Calorimetry. 2019. V. 138. P. 2787. https://doi.org/10.1007/s10973-019-08359-6
  4. Claude B., Morin Ph., Lafosse M., Andre P. // J. Chromatogr. A. 2004. V. 1049. P. 37. https://doi.org/10.1016/j.chroma.2004.06.133
  5. Fontanay S., Kedzierewicz F., Duval R.E., Clarot I. // J. Incl. Phenom. Macrocycl. Chem. 2012. V. 73. P. 341. https://doi.org/10.1007/s10847-011-0063-y
  6. Попова О.В., Сурсякова В.В., Бурмакина Г.В. и др. // Докл. АН. 2015. Т. 461. № 1. С. 41. Popova O.V., Sursyakova V.V., Burmakina G.V. et al. // Dokl. Chem. 2015. V. 461. № 1. P. 67. https://doi.org/10.1134/S001250081503003910.1134/S0012500815030039https://doi.org/10.7868/S0869565215070154
  7. Ren T., Xu Z. // Electrophoresis. 2018. V. 39. P. 1006. https://doi.org/10.1002/elps.201700408
  8. Sursyakova V.V., Levdansky V.A., Rubaylo A.I. // J. Mol. Liq. 2019. V. 283. P. 325. https://doi.org/10.1016/j.molliq.2019.03.092
  9. Sursyakova V.V., Levdansky V.A., Rubaylo A.I. // Electrophoresis. 2020. V. 41. P. 112. https://doi.org/10.1002/elps.201900347
  10. Sursyakova V.V., Levdansky V.A., Rubaylo A.I. // Anal. Bioanal. Chem. 2020. V. 412. P. 5615. https://doi.org/10.1007/s00216-020-02777-4
  11. Sursyakova V.V., Levdansky V.A., Rubaylo A.I. // J. Sib. Fed. Univ. Chem. 2020. V. 13. № 4. P. 534. https://doi.org/10.17516/1998-2836-0203
  12. Sursyakova V.V., Levdansky V.A., Rubaylo A.I. // Electrophoresis. 2021. V. 42. P. 700. https://doi.org/10.1002/elps.202000189
  13. Sursyakova V.V., Rubaylo A.I. // J. Sep. Sci. 2021. V. 44. № 22. P. 4200. https://doi.org/10.1002/jssc.202100507
  14. Sursyakova V.V., Levdansky V.A., Rubaylo A.I. // Electrophoresis. 2022. V. 43. P. 535. https://doi.org/10.1002/elps.202100173
  15. Sursyakova V.V., Levdansky V.A., Rubaylo A.I. // J. Sep. Sci. 2022. V. 45. № 19. P. 3745. https://doi.org/10.1002/jssc.202200453
  16. Sursyakova V.V., Maksimov N.G., Levdansky V.A., Rubaylo A.I. // J. Incl. Phenom. Macrocycl. Chem. 2023. V. 103. № 3–4. P. 109. https://doi.org/10.1007/s10847-023-01182-5
  17. Buko V., Zavodnik I., Palecz B. et al. // J. Mol. Liq. 2020. V. 309. art. № 113118. https://doi.org/10.1016/j.molliq.2020.113118
  18. Dehelean C.A., Soica C., Peev C. et al. // Farmacia. 2011. V. 59. № 1. P. 51.
  19. Popova O.V., Sursyakova V.V., Burmakina G.V. et al. // J. Sib. Fed. Univ. Chem. 2016. V. 9. № 2. P. 171. https://doi.org/10.17516/1998-2836-2016-9-2-171-176
  20. Sursyakova V.V., Maksimov N.G., Levdansky V.A., Rubaylo A.I. // J. Pharm. Biomed. Anal. 2018. V. 160. P. 12. https://doi.org/10.1016/j.jpba.2018.07.038
  21. Sursyakova V.V., Levdansky V.A., Rubaylo A.I. // Electrophoresis. 2019. V. 40. P. 1656. https://doi.org/10.1002/elps.201800516
  22. Olabi M., Stein M., Wätzig H. // Methods. 2018. V. 146. P. 76. https://doi.org/10.1016/j.ymeth.2018.05.006
  23. Dubský P., Dvořák M., Ansorge M. // Anal. Bioanal. Chem. 2016. V. 408. P. 8623. https://doi.org/10.1007/s00216-016-9799-y
  24. Bowser M.T., Chen D.D.Y. // J. Phys. Chem. A. 1999. V. 103. P. 197. https://doi.org/10.1021/jp982917e
  25. Bowser M.T., Chen D.D.Y. // Anal. Chem. 1998. V. 70. P. 3261. https://doi.org/10.1021/ac9713114
  26. Levdanskii V.A., Levdanskii A.V., Kuznetsov B.N. // Chem. Nat. Compounds. 2017. V. 53 P. 310. https://doi.org/10.1007/s10600-017-1976-5
  27. Левданский В.А., Левданский А.В., Кузнецов Б.Н. Способ получения дифталата бетулинола: патент 2614149 РФ // Опубл. 23.03.2017.
  28. Левданский В.А., Левданский А.В., Кузнецов Б.Н. Способ получения дисукцината бетулинола: патент 2638160 РФ // Опубл. 12.12.2017.
  29. Le Saux T., Varenne A., Gareil P. // Electrophoresis. 2005. V. 26. P. 3094. https://doi.org/10.1002/elps.200500029
  30. Dubský P., Ördögová M., Malý M., Riesová M. // J. Chromatogr. A. 2016. V. 1445. P. 158. https://doi.org/10.1016/j.chroma.2016.04.004

Supplementary files

Supplementary Files
Action
1. JATS XML
Download
2.

Download (182KB)
Indexing metadata
3.

Download (122KB)
Indexing metadata
4.

Download (114KB)
Indexing metadata
5.

Download (105KB)
Indexing metadata

Copyright (c) 2023 В.В. Сурсякова, В.А. Левданский, А.И. Рубайло