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.
Similar content being viewed by others
References
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.
S. Saito, Y. Yamamoto, T. Maki, et al., Acta Neuropathol. Commun., 26(5), 1 – 16 (2017).
I. R. Ilyasov, V. L. Beloborodov, and I. A. Selivanova, Chem. Pap., 72, 1917 – 1925 (2018).
M. B. Plotnikov, N. A. Tyukavkina, and T. M. Plotnikova, Medicines Based on Diquertin [in Russian], Tomskii Universitet, Tomsk (2005), pp. 125 – 191.
G. V. Ramenskaya, I. E. Shokhin, and Yu. I. Kulinich, Vestn. VGU, Ser.: Khim., Bio. Farm., 1, 212 – 215 (2012).
R. Terehov, M. Buchholz, D. Ramsbeck, et al., in: Abstracts Book, 11thWorld Congress on Polyphenols Applications, University of Vienna-Austria (2017), p. 154.
Y. Zu, W. Wu, X. Zhao, et al., Int. J. Pharm., 477, 148 – 158 (2014).
Ch.-J. Yang, Z.-B. Wang, Y.-Y. Mi, et al., Molecules, 21(4), 494 (2016).
I. A. Selivanova, N. A. Tyukavkina, Yu. A. Kolesnik, et al., Khim.-farm. Zh., 33(4), 51 – 53 (1999).
G. R. Desiraju, J. Am. Chem. Soc., 135, 9952 – 9967 (2013).
U. Kotak, V. Parajapati, H. Solanki, et al., World J. Pharm. Pharm. Sci., 4(4), 1484 – 1508 (2015).
R. Chadha, Y. Bhalla, M. Karan, and K. Chadha, in: Recrystallization in Materials Processing, V. Glebovsky (ed.), IntechOpen Ltd., London (2015), pp. 171 – 190.
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).
I. Sathisaran and S. V. Dalvi, Pharmaceutics, 10(3), E108 (2018).
State Pharmacopoeia of the Russian Federation, 13th Ed., Vol. 1, Ministerstvo Zdravookhraneniya Rossiiskoi Federatsii, Moscow (2015), pp. 531 – 534.
P. Kavuru, Thesis for Master of Science Degree, Tampa (2008), pp. 18 – 25.
J. Xu, C.-L. Toh, X. Liu, et al., Macromolecules, 38, 1684 – 1690 (2005).
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
Corresponding author
Additional information
Translated from Khimiko-Farmatsevticheskii Zhurnal, Vol. 53, No. 11, pp. 53 – 57, November, 2019.
Rights and permissions
About this article
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
Received:
Published:
Issue Date:
DOI: https://doi.org/10.1007/s11094-020-02126-w