Supramolecular organization of neutral and ionic forms of pharmaceutically relevant glycyrrhizic acid-amphiphile self-assembly and inclusion of small drug molecules

Crystal Growth and Design

Volumn 12, Issue 4, 2012, Pages 2133-2137

  Tykarska, Ewa ^a   Sobiak, Stanisław ^a   Gdaniec, Maria ^b  

^a POZNAN UNIVERSITY OF MEDICAL SCIENCES   (Poland)

^b ADAM MICKIEWICZ UNIVERSITY   (Poland)

Author keywords

[No Author keywords available]

Indexed keywords

AMPHIPHILICS; CATION BINDING; DRUG MOLECULES; GLYCYRRHIZIC ACID; GUEST MOLECULES; INTEGRAL PART; IONIC FORMS; P-AMINOBENZOIC ACID; SOLVENT MOLECULES; STRUCTURAL CHARACTERIZATION; SUPRAMOLECULAR ORGANIZATIONS; WATER MOLECULE;

POSITIVE IONS; SELF ASSEMBLY; SUGARS; SUPRAMOLECULAR CHEMISTRY; X RAY CRYSTALLOGRAPHY;

MOLECULES;

EID: 84859417542     PISSN: 15287483     EISSN: 15287505     Source Type: Journal    
DOI: 10.1021/cg300160c     Document Type: Article

References (36)

1. Yoon, H.-J.; Jang, W.-D. J. Mater. Chem. 2010, 20, 211-222
2. Ajazuddin, S. S. Fitoterapia 2010, 81, 680-689
3. Nishiyama, N.; Kataoka, K. Pharmacol. Therapeut. 2006, 112, 630-648
4. Malmsten, M. Soft Matter 2006, 2, 760-769
5. Müller-Goymann, C. C. Eur. J. Pharm. Biopharm. 2004, 58, 343-356
6. Müller, R. H.; Mäder, K.; Gohla, S. Eur. J. Pharm. Biopharm. 2000, 50, 161-177
7. Zhou, J.; Ritter, H. Polym. Chem. 2010, 1, 1552-1559
8. Brewster, M. E.; Loftsson, T. Adv. Drug Delivery Rev. 2007, 59, 645-666
9. Loftson, T.; Duchene, D. Int. J. Pharm. 2007, 329, 1-11
10. Uekama, K.; Hirayama, F.; Irie, T. Chem. Rev. 1998, 98, 2045-2076
11. Walker, S.; Oun, R.; McInnes, F. J.; Wheate, N. J. Isr. J. Chem. 2011, 51, 616-624
12. Danylyuk, O.; Suwinska, K. Chem. Commun. 2009, 5799-5813
13. Makha, M.; McKinnon, I. R.; Raston, C. L. J. Chem. Soc., Perkin Trans. 2 2002, 1801-1806
14. Kornievskaja, V. S.; Kruppa, A. I.; Leshina, T. V. J. Inclusion Phenom. Macrocyclic Chem. 2008, 60, 123
15. Saito, S.; Furumoto, T.; Ochiai, M.; Hosono, A.; Hoshino, H.; Haraguchi, U.; Ikeda, R.; Shimada, N. Eur. J. Med. Chem. 1996, 31, 365-381
16. Polyakov, N. E.; Leshina, T. V. Open Conf. Proc. J. 2011, 2, 64-72
17. Polyakov, N. E.; Khan, V. K.; Taraban, M. B.; Leshina, T. V. J. Phys. Chem. B 2008, 112, 4435-4440
18. Polyakov, N. E.; Leshina, T. V.; Salakhutdinov, N. F.; Kispert, L. D. J. Phys. Chem. B 2006, 110, 6991-6998
19. Polyakov, N. E.; Leshina, T. V.; Salakhutdinov, N. F.; Konovalova, T. A.; Kispert, L. D. Free Radical Biol. Med. 2006, 40, 1804-1809
20. Polyakov, N. E.; Khan, V. K.; Taraban, M. B.; Leshina, T. V.; Salakhutdinov, N. F.; Tolstikov, G. A. J. Phys. Chem. B 2005, 109, 24526-24530
21. Kondratenko, R. M.; Baltina, L. A.; Mustafina, S. R.; Ismagilova, A. F.; Zarudii, F. S.; Davydova, V. A.; Bazekin, G. V.; Suleimanova, G. F.; Tolstikov, G. A. Pharm. Chem. J. 2003, 37, 485-488
22. Dalimov, D. N.; Isaev, Yu. T.; Saiitkulov, A. M. Chem. Nat. Compd. 2001, 37, 151-153
23. Baltina, L. A.; Murinov, Yu. I.; Ismagilova, A. F.; Davydova, V. A.; Zarudii, F. S.; Tolstikov, G. A. Pharm. Chem. J. 2001, 35, 585-587
24. Sui, X.; Yin, J.; Ren, X. Antiviral Res. 2010, 85, 346-353
25. Wolkerstorfer, A.; Kurz, H.; Bachhofner, N.; Szolar, O. H. J. Antiviral Res. 2009, 83, 171
26. Baltina, L. A.; Kondratenko, R. M.; Baltina, L. A., Jr.; Plyasunova, O. A.; Pokrovskii, A. G.; Tolstikov, G. A. Pharm. Chem. J. 2009, 43, 539-547
27. Lin, J.-C.; Cherng, J.-M.; Hung, M.-S.; Baltina, L. A. Antiviral Res. 2008, 79, 6-11
28. Fiore, C.; Eisenhut, M.; Krausse, R.; Ragazzi, E.; Pelatti, D.; Armanini, D.; Bielenberg, J. Phytother. Res. 2008, 22, 141-148
29. Pompei, R.; Flore, O.; Marccialis, M. A.; Pani, A.; Loddo, B. Nature 1979, 281, 689-690
30. Kimura, M.; Moro, T.; Motegi, H.; Maruyama, H.; Sekine, M.; Okamoto, H.; Inoue, H.; Sato, T.; Ogihara, M. Eur. J. Pharmacol. 2008, 579, 357-364
31. Ram, A.; Mabalirajan, U.; Das, M.; Battacharya, I.; Dinda, A. K.; Gangal, S. V.; Ghosh, B. Int. Immunopharmacol. 2006, 6, 1468-1477
32. Oxford Diffraction 2009; CrysAlis PRO Software. Oxford Diffraction Ltd.: Yarnton, Oxfordshire, England.
33. Sheldrick, G. M. Acta Crystallogr. 2008, A64, 112-122
34. Despite the fact that the correct β-configuration at the two anomeric carbon atoms of the diglucuronic unit has been known since 1956 (Marsh, C. A.; Levy, G. A. Biochem. J. 1956, 63, 9-14.) many authors continue to publish incorrect chemical schemes of GA with the α-configuration of the glycosidic bond to the aglycon.
35. Koide, M.; Ukawa, J.; Tagaki, W.; Tamagaki, S. J. Am. Oil Chem. Soc. 1997, 74, 49-54
36. Mollica, L.; De Marchis, F.; Spitaleri, A.; Dallacosta, C.; Pennacchini, D.; Zamai, M.; Agresti, A.; Trisciuoglio, L.; Musco, G.; Bianchi, M. E. Chem. Biol. 2007, 14, 431-441