Funct. Mater. 2021; 28 (4): 773-783
Supramolecular inclusion complexes of 2-hydroxypropyl-β-cyclodextrin with mefenamic acid: preparation and characterization
1Institute for Scintillation Materials, STC "Institute for Single Crystals", National Academy of Sciences of Ukraine, 60 Nauky Ave., 61072 Kharkiv, Ukraine
2Institute for Single Crystals, STC "Institute for Single Crystals", National Academy of Sciences of Ukraine, 60 Nauky Ave., 61072 Kharkiv, Ukraine
3SSI "Institute for Single Crystals", National Academy of Sciences of Ukraine, 60 Nauky Ave., 61072 Kharkiv, Ukraine
We report the synthesis and evaluation of inclusion complexes between mefenamic acid (MFA) and 2-hydroxypropyl-β-cyclodextrin (HP-β-CD). The phase solubility studies reveal that MFA forms a complex with the HP-β-CD at a 1:1 molar ratio that was also confirmed by UV-vis spectral data (Job's plots). Characterizations of the prepared host-guest type solid complexes using a reliable spectroscopic and calorimetric methods indicate that MFA is found inside the cavity of the HP-β-CD. Obtained thermodynamic parameters for MFA/HP-β-CD complex formation show that MFA inclusion in HP-β-CD cavities is favorable, spontaneous exothermic and enthalpy-driven process. The stability constant Ks for MFA/HP-β-CD complexes determined from the Benesi-Hildebrand equation using fluorescence spectral data is adequate for the formation of an inclusion complex indicates that a fast MFA drug release from MFA/HP-β-CD complex should be expected. The presented results show the MFA/HP-β-CD complex as an effective new approach to design a novel formulation for pharmaceutical applications.
1. G.C.Seuanes, M.B.Moreira, T.Petta et al., J. Inorg. Biochem., 153, 178 (2015). https://doi.org/10.1016/j.jinorgbio.2015.08.004 |
||||
2. G.Ribeiro, M.Benadiba, A.Colquhoun, D.D.Silva, Polyhedron, 27, 1131 (2008). https://doi.org/10.1016/j.poly.2007.12.011 |
||||
3. S.Bindu, S.Mazumder, U.Bandyopadhyay, Biochem. Pharmacol., 180, 11447 (2020). https://doi.org/10.1016/j.bcp.2020.114147 |
||||
4. V.R.Cunha, C.M.Izumi, P.A.Petersen et al., J. Phys. Chem. B, 118, 4333 (2014). https://doi.org/10.1021/jp500988k |
||||
5. D.K.Demertzi, D.H.Litina, M.Staninska et al., J. Enzyme Inhib. Med. Chem., 24, 742 (2009). https://doi.org/10.1080/14756360802361589 |
||||
6. A.D.S.Hernandez, H.R.G.Salazar, D.A.M.Galindo et al., Int. Urol. Nephrol., 44, 471 (2012). https://doi.org/10.1007/s11255-011-0012-0 |
||||
7. D.H.Woo, I.S.Han, G.Jung, Life Sci., 24, 2439 (2004). https://doi.org/10.1016/j.lfs.2004.04.042 |
||||
8. M.Asanuma, S.Nishibayashi-Asanuma, I.Miyazaki et al., J. Neurochem., 76, 1895 (2001). https://doi.org/10.1046/j.1471-4159.2001.00205.x |
||||
9. O.Bekers, E.V, Uijtendaal, D.A.Beijnen et al., Drug Dev. Ind. Pharm., 17, 1503 (2008). https://doi.org/10.3109/03639049109026630 |
||||
10. K.Lobmann, H.Grohganz, R.Laitinen et al., Eur. J. Pharm, Biopharm., 85, 873 (2013). https://doi.org/10.1016/j.ejpb.2013.03.014 |
||||
11. G.L.Amidon, H.Lennernas, V.P.Shah, J.R.Crison, Pharm. Res., 12, 413 (1995). https://doi.org/10.1023/A:1016212804288 |
||||
12. M.N.Anjana, J.Joseph, S.C.Nair, Int. J. Pharm. Sci. Rev. Res., 20, 127 (2013). | ||||
13. A.R.Hedges, Chem. Rev., 98, 2035 (1998). https://doi.org/10.1021/cr970014w |
||||
14. K.A.Connors, Chem. Rev., 9, 1325 (1997). https://doi.org/10.1021/cr960371r |
||||
15. E.M.M.Del Valle, Process. Biochem., 39, 1088 (2004). https://doi.org/10.1016/S0032-9592(03)00258-9 |
||||
16. J.Szejtli, Chem. Rev., 98, 1743 (1998). https://doi.org/10.1021/cr970022c |
||||
17. N.Qiu, X.B.Li, J.D.Liu, J. Incl. Phenom. Macrocycl. Chem., 89, 229 (2017). https://doi.org/10.1007/s10847-017-0752-2 |
||||
18. M.E.Brewster, T.Loftsson, Adv. Drug Deliv, Rev., 59, 645 (2007). https://doi.org/10.1016/j.addr.2007.05.012 |
||||
19. S.Gould, R.C.Scott, Food Chem. Toxicol., 43, 1451 (2005). https://doi.org/10.1016/j.fct.2005.03.007 |
||||
20. J.Szejtli, Pure Appl. Chem., 76, 1825 (2004). https://doi.org/10.1351/pac200476101825 |
||||
21. L.Liu, Q.Guo, J. Incl. Phenom. Macrocycl. Chem., 42, 1 (2002). https://doi.org/10.1023/A:1014520830813 |
||||
22. T.Yousef, N.Hassan, J. Incl. Phenom. Macrocycl. Chem., 87, 105 (2017). https://doi.org/10.1007/s10847-016-0682-4 |
||||
23. C.T.Chang, L.C.Chen, C.C.Chang et al., J. Clin. Pharm. Ther., 33, 495 (2008). https://doi.org/10.1111/j.1365-2710.2008.00946.x |
||||
24. V.R.Sinha, Amita, R.Chadha et al., Cent. Eur, J, Chem., 8, 953 (2010). https://doi.org/10.2478/s11532-010-0066-3 |
||||
25. T.Higuchi, K.A.Connors, Phase Solubility Techniques, Interscience, New York (1965). | ||||
26. T.Loftsson, D.Hreinsdottir, M.Masson, J. Incl., Phenom. Macrocycl. Chem., 57, 545 (2007). https://doi.org/10.1007/s10847-006-9247-2 |
||||
27. P.Job, Ann. Chim., 9, 113 (1928). | ||||
28. J.S.Renny, L.L.Tomasevich, E.H.Tallmadge, D.B.Collum, Angew. Chem. Int. Ed., 52, 11998 (2013). https://doi.org/10.1002/anie.201304157 |
||||
29. H.Bouzit, M.Stiti, M.Abdaoui, J. Incl. Phenom. Macrocycl. Chem., 86, 121 (2016). https://doi.org/10.1007/s10847-016-0647-7 |
||||
30. W.Misiuk, M.Zalewska, J. Mol. Liq., 159, 220 (2011). https://doi.org/10.1016/j.molliq.2011.01.014 |
||||
31. J.V.Caso, L.Russo, M.Palmieri et al., Amino Acids, 47, 2215 (2015). https://doi.org/10.1007/s00726-015-2003-4 |
||||
32. H.A.Benesi, J.H.Hildebrand, J. Am. Chem. Soc., 89, 2703 (1949). https://doi.org/10.1021/ja01176a030 |
||||
33. S.Hamai, Bull. Chem. Soc. Jpn., 55, 2721 (1982). https://doi.org/10.1246/bcsj.55.2721 |
||||
34. U.Domanska, A.Pelczarska, A.Pobudkowska, Int. J. Mol. Sci., 12, 2383 (2011). https://doi.org/10.3390/ijms12042383 |
||||
35. D.Sid, M.Baitiche, Z.Elbahri et al., J. Enzyme Inhib. Med. Chem., 36, 605 (2021). https://doi.org/10.1080/14756366.2020.1869225 |
||||
36. R.Arun, K.C.K.Ashok, V.V.N.S.S.Sravanthi, Scientia Pharmaceutica, 76, 567 (2008). https://doi.org/10.3797/scipharm.0808-05 |
||||
37. R.Periasamy, S.Kothainayaki, K.Sivakumar, J. Mol. Struct., 1080, 69 (2015). https://doi.org/10.1016/j.molstruc.2014.09.046 |
||||
38. R.Rajamohan, S.Kothai Nayaki, M.Swaminathan, J. Mol. Liq., 220, 918 (2016). https://doi.org/10.1016/j.molliq.2016.04.118 |
||||
39. P.Padhan, A.Sethy, P.K.Behera, J. Photochem. Photobiol. A, 337, 165 (2017). https://doi.org/10.1016/j.jphotochem.2017.01.015 |
||||
40. A.M.Stalcup, S.S.Chang, D.W.Armstrong, J.Pitha, J. Chromatogr., 513, 181 (1990). https://doi.org/10.1016/S0021-9673(01)89435-8 |
||||
41. M.C.Chervenak, E.J.Toone, J. Am. Chem. Soc., 116, 10533 (1994). https://doi.org/10.1021/ja00102a021 |
||||
42. C.Alvariza, R.Usero, F.Mendicuti, Spectrochim. Acta A, 67, 420 (2007). https://doi.org/10.1016/j.saa.2006.07.039 |
||||
43. R.Singh, N.Bharti, J.Madan, S.N.Hiremath, J. Pharm. Sci. Technol., 2, 171 (2010). | ||||
44. L.Liu, S.Zhu, J. Pharm. Biomed. Anal., 40, 122 (2006). https://doi.org/10.1016/j.jpba.2005.06.022 |
||||
45. S.Siva, S.Kothai Nayaki, N.Rajendirana, Spectrochim. Acta Part A., 174, 349 (2017). https://doi.org/10.1016/j.saa.2014.12.002 |
||||
46. A.Celebioglu, T.Uyar, J. Agric. Food Chem., 65, 5404 (2017). https://doi.org/10.1021/acs.jafc.7b01562 |
||||
47. N.Qiu, X.Zhao, Q.Liu et al., J. Mol. Liq., 289, 111151 (2019). https://doi.org/10.1016/j.molliq.2019.111151 |
||||
48. S.Romero, B.Escalera, P.Bustamante, Int. J. Pharm., 178, 193 (1999). https://doi.org/10.1016/S0378-5173(98)00375-5 |
||||