Skip to main content
Log in

Engineering of Dihydroquercetin Crystals

  • Published:
Pharmaceutical Chemistry Journal Aims and scope

Dihydroquercetin (DHQ) is a commercially available bioflavonoid with a wide range of pharmacological activity. The low water solubility at room temperature of the commercial drug substance limits development of DHQ-related medicines. Basic concepts of crystal engineering were used to obtain DHQ cocrystals with benzaldehyde, vanillin, cinnamaldehyde, urea, and nicotinic acid. The formation of supramolecular complexes of DHQ with the coformers was confirmed using IR spectroscopy. An estimate of the physicochemical parameters of the cocrystals established that crystal engineering was promising for obtaining new DHQ forms with improved water solubility.

This is a preview of subscription content, log in via an institution to check access.

Access this article

Price excludes VAT (USA)
Tax calculation will be finalised during checkout.

Instant access to the full article PDF.

Fig. 1.
Fig. 2.
Fig. 3.

Similar content being viewed by others

References

  1. M. B. Plotnikov, O. I. Aliev, N. A. Tyukavkina, et al., in: Frontiers of Antioxidant Research, H. V. Panglossi (ed.), Nova Science Publishers Inc., New York (2006), pp. 103 – 132.

  2. S. Saito, Y. Yamamoto, T. Maki, et al., Acta Neuropathol. Commun., 26(5), 1 – 16 (2017).

    Google Scholar 

  3. I. R. Ilyasov, V. L. Beloborodov, and I. A. Selivanova, Chem. Pap., 72, 1917 – 1925 (2018).

    Article  CAS  Google Scholar 

  4. M. B. Plotnikov, N. A. Tyukavkina, and T. M. Plotnikova, Medicines Based on Diquertin [in Russian], Tomskii Universitet, Tomsk (2005), pp. 125 – 191.

  5. G. V. Ramenskaya, I. E. Shokhin, and Yu. I. Kulinich, Vestn. VGU, Ser.: Khim., Bio. Farm., 1, 212 – 215 (2012).

  6. R. Terehov, M. Buchholz, D. Ramsbeck, et al., in: Abstracts Book, 11thWorld Congress on Polyphenols Applications, University of Vienna-Austria (2017), p. 154.

  7. Y. Zu, W. Wu, X. Zhao, et al., Int. J. Pharm., 477, 148 – 158 (2014).

    Article  CAS  Google Scholar 

  8. Ch.-J. Yang, Z.-B. Wang, Y.-Y. Mi, et al., Molecules, 21(4), 494 (2016).

    Article  Google Scholar 

  9. I. A. Selivanova, N. A. Tyukavkina, Yu. A. Kolesnik, et al., Khim.-farm. Zh., 33(4), 51 – 53 (1999).

  10. G. R. Desiraju, J. Am. Chem. Soc., 135, 9952 – 9967 (2013).

    Article  CAS  Google Scholar 

  11. U. Kotak, V. Parajapati, H. Solanki, et al., World J. Pharm. Pharm. Sci., 4(4), 1484 – 1508 (2015).

    CAS  Google Scholar 

  12. R. Chadha, Y. Bhalla, M. Karan, and K. Chadha, in: Recrystallization in Materials Processing, V. Glebovsky (ed.), IntechOpen Ltd., London (2015), pp. 171 – 190.

  13. R. P. Terekhov, I. A. Selivanova, N. A. Tyukavkina, et al., Acta Crystallogr., Sect. B: Struct. Sci., Cryst. Eng. Mater., 75(2), 175 – 182 (2019).

  14. I. Sathisaran and S. V. Dalvi, Pharmaceutics, 10(3), E108 (2018).

    Article  Google Scholar 

  15. State Pharmacopoeia of the Russian Federation, 13th Ed., Vol. 1, Ministerstvo Zdravookhraneniya Rossiiskoi Federatsii, Moscow (2015), pp. 531 – 534.

  16. P. Kavuru, Thesis for Master of Science Degree, Tampa (2008), pp. 18 – 25.

  17. J. Xu, C.-L. Toh, X. Liu, et al., Macromolecules, 38, 1684 – 1690 (2005).

    Article  CAS  Google Scholar 

Download references

Acknowledgments

We thank Prof. N. A. Tyukavkina, Sechenov University; E. O. Bakhrushina, Head of the Pharmaceutical Technology Department, Institute of Pharmacy, Sechenov University; and Drs. M. Buchholz and D. Ramsbeck, Fraunhofer-Institute for Cell Therapy and Immunology (Germany), for assistance with performing the work and constructive advice.

Author information

Authors and Affiliations

Authors

Corresponding author

Correspondence to R. P. Terekhov.

Additional information

Translated from Khimiko-Farmatsevticheskii Zhurnal, Vol. 53, No. 11, pp. 53 – 57, November, 2019.

Rights and permissions

Reprints and permissions

About this article

Check for updates. Verify currency and authenticity via CrossMark

Cite this article

Selivanova, I.A., Terekhov, R.P. Engineering of Dihydroquercetin Crystals. Pharm Chem J 53, 1081–1085 (2020). https://doi.org/10.1007/s11094-020-02126-w

Download citation

  • Received:

  • Published:

  • Issue Date:

  • DOI: https://doi.org/10.1007/s11094-020-02126-w

Keywords

Navigation