Abstract
The solubilization and solvatochromic behavior of piroxicam (PRX) were analyzed using UV-vis spectroscopy in neat (protic and aprotic) and binary solvent mixtures. The effects of solvent dipolarity/polarizability and solvent–solute hydrogen bonding interactions on the absorption maxima were evaluated by means of the linear solvation energy relationship concept of Kamlet and Taft. This analysis indicated that both interactions play an important role in the position of the absorption maxima in neat solvents. While, the PRX solubility depends on the solute–solvent specific interactions, polarizability and the cohesive forces of the solvent, manifested mainly by means of the Hildebrand’s solubility parameter. Preferential solvation (PS) was studied in 10 binary mixtures. A non-ideal behavior of the wavenumber curve as the function of analytical mole fraction of co-solvent was detected. Index of preferential solvation, as well as the influence of solvent parameters were calculated. The process of dissolution was analyzed in aqueous binary mixtures of ethanol, ethylene glycol and propylene glycol. They were not spontaneous in all proportions, but when water concentration decreases in the mixtures, the process becomes more spontaneous.
Acknowledgments
Financial support from the National University of San Luis (Argentine Republic) gratefully acknowledged.
References
1. S. Xu, C. A. Rouzer, L. J. Marnett, Int. Union Biochem. Mol. Biol. 66 (2014) 803.10.1002/iub.1334Search in Google Scholar
2. P. Bustamante, M. Peña, J. Barra, Int. J. Pharm. 174 (1998) 141.10.1016/S0378-5173(98)00263-4Search in Google Scholar
3. F. Bouchal, M. Skiba, N. Chaffai, F. Hallouard, S. Fatmi, M. Lahiani-Skiba, Int. J. Pharm. 478 (2015) 625.10.1016/j.ijpharm.2014.12.019Search in Google Scholar PubMed
4. R. G. Brito, A. A. S. Araújo, J. S. S. Quintans, K. A. Sluka, L. J. Quintans, Expert Opin. Drug Del. 12 (2015) 1677.10.1517/17425247.2015.1046835Search in Google Scholar PubMed
5. J. S. Patil, D. V. Kadam, S. C. Marapur, M. V. Kamalapur, Int. J. Pharm. Sci. Rev. Res. 2 (2010) 29.Search in Google Scholar
6. H. Valizadeh, P. Zakeri-Milani, M. Barzegar-Jalali, G. Mohammadi, M. A. Danesh-Bahreini, K. Adibkia, A. Nokhodchi, Drug Dev. Ind. Pharm. 33 (2007) 45.10.1080/03639040600814965Search in Google Scholar PubMed
7. R. G. Sotomayor, A. R. Holguín, A. Romdhani, F. Martınez, A. Jouyban, J Solution Chem. 42 (2013) 358.10.1007/s10953-013-9959-zSearch in Google Scholar
8. D. M. Cristancho, A. Jouyban, F. Martínez, J. Mol. Liq. 221 (2016) 72.10.1016/j.molliq.2016.05.056Search in Google Scholar
9. R. G. Sotomayor, A. R. Holguín, D. M. Cristancho, R. Delgado, F. Martínez, J. Mol. Liq. 180 (2013) 34.10.1016/j.molliq.2012.12.028Search in Google Scholar
10. S. Vieira Pereira, F. Belotti Colombo, L. A. P. de Freitas, Ultrason. Sonochem. 29 (2016) 461.10.1016/j.ultsonch.2015.10.022Search in Google Scholar PubMed
11. K. Wu, J. Li, W. Wang, D. A. Winstead, J. Pharm. Sci. 98 (2009) 2422.10.1002/jps.21598Search in Google Scholar PubMed
12. S. A. Swidan, H. M. Ghonaim, M. M. Ghorab, A. M. Samy, Br. J. Pharm. Res. 3 (2013) 108.10.9734/BJPR/2013/2534Search in Google Scholar
13. A. Karatas, N. Yüksel, T. Baykara, Il Farmaco 60 (2005) 777.10.1016/j.farmac.2005.04.014Search in Google Scholar PubMed
14. A. V. Marenich, C. J. Cramer, D. G. Truhlar, J. Phys. Chem. B 119 (2015) 958.10.1021/jp506293wSearch in Google Scholar PubMed
15. J. P. Graham, M. A. Rauf, S. Hisaindee, M. Nawaz, J. Mol. Struct. 1040 (2013) 1.10.1016/j.molstruc.2013.02.015Search in Google Scholar
16. M. Homocianu, A. Airinei, J. Mol. Liq. 209 (2015) 549.10.1016/j.molliq.2015.06.042Search in Google Scholar
17. V. Sasirekha, M. Umadevi, V. Ramakrishnan, Spectrochim. Acta, Part A 69 (2008) 148.10.1016/j.saa.2007.03.021Search in Google Scholar PubMed
18. S. Sanli, Y. Altun, G. Guven, J. Chem. Eng. Data, 59 (2014) 4015.10.1021/je500595wSearch in Google Scholar
19. M. Jabbari, J. Mol. Liq. 208 (2015) 5.10.1016/j.molliq.2015.03.055Search in Google Scholar
20. M. A. Filippa, E. I. Gasull, J. Mol. Liq. 198 (2014) 78.10.1016/j.molliq.2014.06.031Search in Google Scholar
21. M. A. Filippa, E. I. Gasull, Fluid Phase Equilib. 354 (2013) 185.10.1016/j.fluid.2013.06.032Search in Google Scholar
22. M. A. Filippa, G. M. Melo, E. I. Gasull, J. Pharm. Chem. Biol. Sci. 3 (2016) 440.Search in Google Scholar
23. M. C. Almandoz, M. I. Sancho, S. E. Blanco, Spectrochim. Acta, Part A 118 (2014) 112.10.1016/j.saa.2013.08.060Search in Google Scholar
24. M. C. Almandoz, M. I. Sancho, P. R. Duchowicz, S. E. Blanco, Spectrochim. Acta, Part A 129 (2014) 52.10.1016/j.saa.2014.02.191Search in Google Scholar
25. M. I. Sancho, M. C. Almandoz, S. E. Blanco, E. A. Castro, Int. J. Mol. Sci. 12 (2011) 8895.10.3390/ijms12128895Search in Google Scholar PubMed
26. D. Ivanova, V. Deneva, D. Nedeltcheva, F. S. Kamounah, G. Gergov, P. E. Hansen, S. Kawauchi, L. Antonov, RSC Adv. 5 (2015) 31852.10.1039/C5RA03653DSearch in Google Scholar
27. G. Angulo, G. Grampp, A. Rosspeintner, Spectrochim. Acta, Part A 65 (2006) 727.10.1016/j.saa.2006.01.007Search in Google Scholar
28. Y. Marcus, Chem. Soc. Rev. 22 (1993) 4094.10.1039/cs9932200409Search in Google Scholar
29. M. Gil, A. Douhal, J. Phys. Chem. A 112 (2008) 8231.10.1021/jp803457eSearch in Google Scholar PubMed
30. J. Bordner, P. D. Hammen, E. B. Whippie, J. Am. Chem. Soc. 111 (1989) 6572.10.1021/ja00199a015Search in Google Scholar
31. Y. H. Kim, D. W. Cho, S. G. Kang, M. Yoon, D. Kim, J. Lumin. 59 (1994) 209.10.1016/0022-2313(94)90043-4Search in Google Scholar
32. S. M. Andrade, S. M. B. Costa, Phys. Chem. Chem. Phys. 1 (1999) 4213.10.1039/a906213kSearch in Google Scholar
33. M. J. Kamlet, J. M. Abboud, R. W. Taft, Prog. Phys. Org. Chem. 13 (1981) 485.Search in Google Scholar
34. V. Sasirekha, V. Ramakrishnan, Spectrochim. Acta, Part A 70 (2008) 626.10.1016/j.saa.2007.08.013Search in Google Scholar PubMed
35. Y. Marcus, J. Chem. Soc., Perkin Trans. 2 8 (1994) 1751.10.1039/p29940001751Search in Google Scholar
36. T. Bevilaqua, T. F. Gonçalves, C. G. Venturini, V. G. Machado, Spectrochim. Acta, Part A 65 (2006) 535.10.1016/j.saa.2005.12.005Search in Google Scholar PubMed
37. R. D. Skwierczynski, K. A. Connors, J. Chem. Soc. Perkin Trans. 2 2 (1994) 467.10.1039/P29940000467Search in Google Scholar
38. M. A. R. Silva, D. C. Silva, V. G. Machado, E. Longhinotti, V. L. A. Frescura, J. Phys. Chem. A 106 (2002) 8820.10.1021/jp0145964Search in Google Scholar
39. D. Rácz, M. Nagya, A. Mándi, M. Zsuga, S. Kéki, J. Photochem. Photobiol. A 270 (2013) 19.10.1016/j.jphotochem.2013.07.007Search in Google Scholar
40. M. L. Moita, R. A. Teodoro, L. M. Pinheiro, J. Mol. Liq. 136 (2007) 15.10.1016/j.molliq.2006.12.023Search in Google Scholar
41. M. Rosés, C. Ràfols, J. Ortega, E. Bosch, J. Chem. Soc. Perkin Trans. 2 8 (1995) 1607.10.1039/P29950001607Search in Google Scholar
42. J. Ortega, C. Ràfols, E. Bosch, M. Rosés, J. Chem. Soc. Perkin Trans. 2 7 (1996) 1497.10.1039/P29960001497Search in Google Scholar
43. N. Nunes, C. Ventura, F. Martins, R. E. Leitão, J. Phys. Chem. B 113 (2009) 3071.10.1021/jp804157bSearch in Google Scholar PubMed
44. A. Martin, Physical Pharmacy and Pharmaceutical Sciences, Lippincott Williams & Wilkins, Baltimore, USA (2011), P. 54.Search in Google Scholar
45. D. Pacheco, Y. Manrique, F. Martínez, Fluid Phase Equilib. 262 (2007) 23.10.1016/j.fluid.2007.07.076Search in Google Scholar
46. R. R. Krug, W. G. Hunter, R. A. Grieger, J. Phys. Chem. 80 (1976) 2335.10.1021/j100562a006Search in Google Scholar
47. R. R. Krug, W. G. Hunter, R. A. Grieger, J. Phys. Chem. 80 (1976) 2341.10.1021/j100562a007Search in Google Scholar
48. P. Bustamante, J. Pharm. Sci. 87 (1998) 1590.10.1021/js980149xSearch in Google Scholar PubMed
49. G. L. Perlovich, S. Kurkov, A. Kinchin, AAPS J. 6 (2004) 22.10.1208/ps060103Search in Google Scholar PubMed PubMed Central
50. G. L. Perlovich, S. Kurkov, A. Kinchin, A. Bauer-Brandl, Eur. J. Pharm. Biopharm. 57 (2004) 411.10.1016/j.ejpb.2003.10.021Search in Google Scholar PubMed
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The online version of this article offers supplementary material (https://doi.org/10.1515/zpch-2017-0946).
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