Physico-chemical characterization of coamorphous modifications based on dihydroquercetin and L-lysine
- Authors: Svotin A.A.1, Khodyachikh A.A.1, Korochkina M.D.1, Taldaev A.K.2,3, Utenyshev A.N.4, Dzuban A.V.5, Krivosheeva E.A.1, Shilov G.V.4, Bocharov E.V.3, Terekhov R.P.1, Selivanova I.A.1
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Affiliations:
- Sechenov First Moscow State Medical University (Sechenov University)
- Research Institute of Biomedical Chemistry named after V.N. Orekhovich
- State Scientific Center of the Russian Federation Institute of Bioorganic Chemistry named after academicians M.M. Shemyakin and Yu.A. Ovchinnikov of the Russian Academy of Sciences
- Federal Research Center of Problems of Chemical Physics and Medicinal Chemistry, Russian Academy of Sciences
- Lomonosov Moscow State University
- Issue: Vol 74, No 6 (2025)
- Pages: 5-13
- Section: Pharmaceutical chemistry and pharmacognosy
- URL: https://journals.eco-vector.com/0367-3014/article/view/690540
- DOI: https://doi.org/10.29296/25419218-2025-06-01
- ID: 690540
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Abstract
Introduction. Dihydroquercetin (DHQ) is a flavonoid that is characterized by limited bioavailability, that particularly associates with low solubility in water under normal conditions. Previously, DHQ was combined with the proteinogenic amino acid L-lysine to create a composition that exhibited strong anti-inflammatory and wound healing effects in models of grade III burn injuries in rats.
Objective: To obtain and characterize solid monophasic systems based on DHQ and L-lysine using a complex of physico-chemical methods.
Material and methods. To obtain DHQ compositions containing L-lysine, grinding techniques were used with the following lyophilization or drying of the aqueous solution at 65 °C. Scanning electron microscopy was employed to examine the microstructure of the resulting objects. The structure and properties of the solid phase were characterized using X-ray powder diffraction and thermal analysis methods. The chemical composition was analyzed using infrared spectroscopy and nuclear magnetic resonance methods. Quantitative analysis was performed using high performance liquid chromatography (HPLC).
Results. Coamorphous modifications based on DHQ and L-lysine, in the form of films and mesoporous lyophilizates, have been obtained and characterized using physico-chemical methods. No formation of new covalent bonds between the components during the preparation of these modifications was observed. A glass transition effect at a temperature of 64 °C was detected for the films. To monitor the quantitative composition of the components, a method based on HPLC with pre-column derivatization using o-phthalaldehyde and UV-detection was developed.
Conclusion. Thus, the obtained objects are coamorphous systems in the form of glass-like film and porous materials formed through intermolecular interactions between DHQ and L-lysine. In the future, it will be interesting to develop dosage forms based on these objects.
Key words: dihydroquercetin, amino acids, HPLC, NMR 1H, coamorphous modifications.
Keywords
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About the authors
Artem Aleksandrovich Svotin
Sechenov First Moscow State Medical University (Sechenov University)
Author for correspondence.
Email: svotin_a_a@staff.sechenov.ru
ORCID iD: 0009-0001-5360-8816
SPIN-code: 3228-2500
Assistant Professor, Department of Chemistry of Nelyubin Institute of Pharmacy
Russian Federation, Trubetskaya str., 8/2, Mosсow, 119048Anastasia Alekseevna Khodyachikh
Sechenov First Moscow State Medical University (Sechenov University)
Email: khodyachikh_a_a@student.sechenov.ru
ORCID iD: 0000-0003-2905-7732
Student, Nelyubin Institute of Pharmacy
Russian Federation, Trubetskaya str., 8/2, Mosсow, 119048Maria Dmitrievna Korochkina
Sechenov First Moscow State Medical University (Sechenov University)
Email: korochkina_m_d@student.sechenov.ru
ORCID iD: 0000-0002-2790-9041
SPIN-code: 4273-2724
Student, Nelyubin Institute of Pharmacy
Russian Federation, Trubetskaya str., 8/2, Mosсow, 119048Amir Khalilevich Taldaev
Research Institute of Biomedical Chemistry named after V.N. Orekhovich; State Scientific Center of the Russian Federation Institute of Bioorganic Chemistry named after academicians M.M. Shemyakin and Yu.A. Ovchinnikov of the Russian Academy of Sciences
Email: t-amir@bk.ru
ORCID iD: 0000-0003-2593-1963
SPIN-code: 7790-9947
Junior Researcher, Laboratory for the Study of Single Biomacromolecules, Research Institute of Biomedical Chemistry named after V.N. Orekhovich; Еngineer, State Scientific Center of the Russian Federation Institute of Bioorganic Chemistry named after academicians M.M. Shemyakin and Yu.A. Ovchinnikov of the Russian Academy of Sciences
Russian Federation, Pogodinskaya street, 10, Moscow, 119121; Miklukho-Maklaya str., 16/10, GSP-7, Moscow, 117997Andrey Nikolaevich Utenyshev
Federal Research Center of Problems of Chemical Physics and Medicinal Chemistry, Russian Academy of Sciences
Email: uten@icp.ac.ru
ORCID iD: 0000-0002-4170-9951
Candidate of Chemical Sciences, Senior Researcher, Laboratory of Structural Chemistry
Russian Federation, Acad. Semenov Av. 1, Chernogolovka, 143432Alexander Vladimirovich Dzuban
Lomonosov Moscow State University
Email: dzubanav@my.msu.ru
ORCID iD: 0000-0003-3685-0528
SPIN-code: 7520-4915
Senior Teacher, Department of Physical Chemistry, Faculty of Chemistry
Russian Federation, Leninskiye gory, 1–3, Moscow, 119234Elizaveta Andreevna Krivosheeva
Sechenov First Moscow State Medical University (Sechenov University)
Email: krivosheeva_e_a@student.sechenov.ru
ORCID iD: 0009-0001-6639-9400
Student, Nelyubin Institute of Pharmacy
Russian Federation, Trubetskaya str., 8/2, Mosсow, 119048Gennadii Victorovich Shilov
Federal Research Center of Problems of Chemical Physics and Medicinal Chemistry, Russian Academy of Sciences
Email: genshil@icp.ac.ru
ORCID iD: 0000-0001-5279-7283
Candidate of Physical and Mathematical Sciences, Senior Researcher, Laboratory of Structural Chemistry, Department of Structure of Matter
Russian Federation, Acad. Semenov Av. 1, Chernogolovka, 143432Eduard Valer'evich Bocharov
State Scientific Center of the Russian Federation Institute of Bioorganic Chemistry named after academicians M.M. Shemyakin and Yu.A. Ovchinnikov of the Russian Academy of Sciences
Email: bon@nmr.ru
ORCID iD: 0000-0002-3635-1609
SPIN-code: 9295-6073
Doctor of Physical and Mathematical Sciences, Chief Researcher of the Laboratory of Biomolecular NMR Spectroscopy
Russian Federation, Miklukho-Maklaya str., 16/10, GSP-7, Moscow, 117997Roman Petrovich Terekhov
Sechenov First Moscow State Medical University (Sechenov University)
Email: terekhov_r_p@staff.sechenov.ru
ORCID iD: 0000-0001-9206-8632
SPIN-code: 3308-7478
Candidate of Pharmaceutical Sciences, Associate Professor of the Department of Chemistry of Nelyubin Institute of Pharmacy
Russian Federation, Trubetskaya str., 8/2, Mosсow, 119048Irina Anatolyevna Selivanova
Sechenov First Moscow State Medical University (Sechenov University)
Email: selivanova_i_a@staff.sechenov.ru
ORCID iD: 0000-0002-2244-445X
SPIN-code: 7929-8090
Doctor of Pharmaceutical Sciences, Professor, Professor at the Department of Chemistry of Nelyubin Institute of Pharmacy
Russian Federation, Trubetskaya str., 8/2, Mosсow, 119048References
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