A 1:4 inclusion complex of 11-deoxymisoprostol (II) with glycyrrhizic acid (complex III) was synthesized and exhibited high anti-ulcer activity in experimental models of gastric mucosal ulcers (GMUs) inWistar rats induced by indomethacin and diclofenac. Complex III at a dose of 1 mg/kg (0.1 mg of II) reduced the number of indomethacin gastric ulcers by 46.4% (p < 0.012) as compared with the control group and by 39.2% as compared with II at the same dose. The anti-ulcer activity of complex III at a dose of 1 mg/kg was 5.8 times higher than that of the initial prostaglandin at an equivalent dose (0.1 mg/kg) in a model of gastric ulcers caused by diclofenac.
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References
D. P. Patel and B. G. Chaudhari, J. Curr. Pharma Res., 9, 1 – 5 (2012).
Th. Loftsson and D. Duchene, Int. J. Pharm., 329, 1 – 11 (2007).
I. E. Apanasenko, O. Yu. Selyutina, N. E. Polyakov, et al., Arch. Biochem. Biophys., 572, 58 – 65 (2015).
L. A. Yakovishin and V. I. Grishkovets, Stud. Nat. Prod. Chem., 55, 351 – 383 (2018).
T. G. Tolstikova, M. V. Khvostov, and A. O. Bryzgalov, Mini-Rev. Med. Chem., 9, 1317 – 1328 (2009).
T. G. Tolstikova, A. G. Tolstikov, and G. A. Tolstikov, Vestn. Ross. Akad. Nauk, 77(10), 867 – 874 (2007).
O. Yu. Selyutina and N. E. Polyakov, Int. J. Pharm., 559, 271 – 279 (2019).
G. A. Tolstikov, L. A. Baltina, V. P. Grankina, et al., Licorice: Biodiversity, Chemistry and Use in Medicine [in Russian], Geo, Novosibirsk (2007).
G. A. Tolstikov, L. A. Baltina, Y. I. Murinov, et al., Pharm. Chem. J., 25(2), 105 – 109 (1991).
G. A. Tolstikov, Yu. I. Murinov, L. A. Baltina, et al., Pharm. Chem. J., 25(3), 197 – 200 (1991).
G. A. Tolstikov, V. A. Myshkin, L. A. Baltina, et al., Pharm. Chem. J., 30(5), 320 – 322 (1996).
L. A. Baltina, Yu. I. Murinov, A. F. Ismagilova, et al., Pharm. Chem. J., 35(11), 585 – 587 (2001).
R. M. Kondratenko, L. A. Baltina, S. R. Mustafina, et al., Pharm. Chem. J., 37(9), 485 – 488 (2003).
A. I. Bondarev, S. A. Bashkatov, V. A. Davydova, et al., Farmakol. Toksikol., 54(5), 47 – 50 (1991).
A. O. Bryzgalov, T. G. Tolstikova, I. V. Sorokina, et al., Exp. Clin. Pharmacol., 68(4), 24 – 28 (2005).
N. E. Polyakov, V. K. Khan, M. B. Taraban, et al., J. Phys. Chem. B, 109(51), 24526 – 24530 (2005).
T. G. Tolstikova, M. V. Khvostov, A. O. Bryzgalov, et al., Lett. Drug Des. Discovery, 6, 155 – 158 (2009).
T. G. Tolstikova, I. V. Sorokina, I. L. Kovalenko, and A. G. Tolstikov, Dokl. Akad. Nauk, 394(5), 707 – 709 (2004).
N. E. Polyakov, T. V. Leshina, N. F. Salakhutdinov, and L. D. Kispert, J. Phys. Chem., 110, 6991 – 6998 (2006).
N. E. Polyakov, T. V. Leshina, N. F. Salakhutdinov, et al., Free Radical Biol. Med., 40, 1804 – 1809 (2006).
O. Y. Selyutina, I. E. Apanasenko, A. G. Shilov, et al., Russ. Chem. Bull., 66(1), 129 – 135 (2017).
O. Y. Selyutina, N. E. Polyakov, D. V. Korneev, and B. N. Zaitsev, Drug Delivery, 23(3), 858 – 865 (2016).
R. M. Kondratenko, L. A. Baltina, S. R. Mustafina, et al., Pharm. Chem. J., 35(2), 101 – 104 (2001).
N. A. Ivanova, A. M. Shainurova, and M. S. Miftakhov, Khim.-farm. Zh., No. 6, 39 – 40 (1998).
Da.-Ae. Kwon, Y. S. Kim, S. H. Baek, et al., Pharm. Biol., 57(1), 543 – 549 (2019).
J. Peter, K. Basha, R. Giridharan, et al., Biomed. Pharmacother., 88, 11 – 18 (2017).
F. Pauls, A. M. Wick and E. M. MacKey, Gastroenterology, 8(6), 774 – 780 (1947).
Ya. S. Tsimmerman, Klin. Farmakol. Ter., 27(1), 14 – 21 (2018).
N. Zh. Baschenko, T. A. Sapozhnikova, S. F. Gabdrakhmanova, et al., Bull. Exp. Biol. Med., 142(4), 467 – 469 (2006).
T. A. Sapozhnikova, F. S. Zarudii, L. T. Karachurina, et al., Eksp. Klin. Farmakol., 66(1), 34 – 36 (2003).
L. A. Baltina, R. M. Kondratenko, S. R. Mustafina, et al., Pharm. Chem. J., 35(1), 40 – 44 (2001).
L. A. Baltina, O. Kunert, A. A. Fatykhov, et al., Chem. Nat. Compd., 41(4), 432 – 435 (2005).
ACKNOWLEDGMENTS
The work was performed on State Task topics 1021062311395-6-1.4.1, AAAA-A17-117011910032-4, AAAA-A20-120012090021-4, and 1021062311386-8-1.4.1.
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Translated from Khimiko-Farmatsevticheskii Zhurnal, Vol. 56, No. 5, pp. 34 – 39, May, 2022.
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Baltina, L.A., Ivanova, N.A., Sapozhnikova, T.A. et al. Inclusion Complex of 11-deoxymisoprostol and Glycyrrhizic Acid with Improved Anti-Ulcer Activity. Pharm Chem J 56, 607–613 (2022). https://doi.org/10.1007/s11094-022-02684-1
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DOI: https://doi.org/10.1007/s11094-022-02684-1