Solubility of sulfacetamide in aqueous propylene glycol mixtures: Measurement, correlation, dissolution thermodynamics, preferential solvation and solute volumetric contribution at saturation

The equilibrium solubility at temperatures from (278.15 to 318.15) K, dissolution thermodynamics, preferential solvation, and apparent specific volume at saturation of sulfacetamide (SCM) in {propylene glycol (PG) (1) + water (2)} mixtures is reported. Mole fraction solubility of SCM (x3) increases...

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Autores:
Osorio, Irmis P
Martinez, Fleming
Delgado, Daniel Ricardo
Jouyban, Abolghasem
Acree Jr, William Eugene
Tipo de recurso:
Article of journal
Fecha de publicación:
2019
Institución:
Universidad Cooperativa de Colombia
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Repositorio UCC
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oai:repository.ucc.edu.co:20.500.12494/15631
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https://doi.org/10.1016/j.molliq.2019.111889
https://hdl.handle.net/20.500.12494/15631
Palabra clave:
Sulfacetamide
Propylene glycol + water mixtures
SolubilityJouyban-Acree model
Solution thermodynamics
Preferential solvation
Apparent specific volume
Sulfacetamide
Propylene glycol + water mixtures
SolubilityJouyban-Acree model
Solution thermodynamics
Preferential solvation
Apparent specific volume
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Atribución – No comercial – Compartir igual
id COOPER2_06c9e0c4eb601354fc914805e267688d
oai_identifier_str oai:repository.ucc.edu.co:20.500.12494/15631
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network_name_str Repositorio UCC
repository_id_str
dc.title.spa.fl_str_mv Solubility of sulfacetamide in aqueous propylene glycol mixtures: Measurement, correlation, dissolution thermodynamics, preferential solvation and solute volumetric contribution at saturation
title Solubility of sulfacetamide in aqueous propylene glycol mixtures: Measurement, correlation, dissolution thermodynamics, preferential solvation and solute volumetric contribution at saturation
spellingShingle Solubility of sulfacetamide in aqueous propylene glycol mixtures: Measurement, correlation, dissolution thermodynamics, preferential solvation and solute volumetric contribution at saturation
Sulfacetamide
Propylene glycol + water mixtures
SolubilityJouyban-Acree model
Solution thermodynamics
Preferential solvation
Apparent specific volume
Sulfacetamide
Propylene glycol + water mixtures
SolubilityJouyban-Acree model
Solution thermodynamics
Preferential solvation
Apparent specific volume
title_short Solubility of sulfacetamide in aqueous propylene glycol mixtures: Measurement, correlation, dissolution thermodynamics, preferential solvation and solute volumetric contribution at saturation
title_full Solubility of sulfacetamide in aqueous propylene glycol mixtures: Measurement, correlation, dissolution thermodynamics, preferential solvation and solute volumetric contribution at saturation
title_fullStr Solubility of sulfacetamide in aqueous propylene glycol mixtures: Measurement, correlation, dissolution thermodynamics, preferential solvation and solute volumetric contribution at saturation
title_full_unstemmed Solubility of sulfacetamide in aqueous propylene glycol mixtures: Measurement, correlation, dissolution thermodynamics, preferential solvation and solute volumetric contribution at saturation
title_sort Solubility of sulfacetamide in aqueous propylene glycol mixtures: Measurement, correlation, dissolution thermodynamics, preferential solvation and solute volumetric contribution at saturation
dc.creator.fl_str_mv Osorio, Irmis P
Martinez, Fleming
Delgado, Daniel Ricardo
Jouyban, Abolghasem
Acree Jr, William Eugene
dc.contributor.author.none.fl_str_mv Osorio, Irmis P
Martinez, Fleming
Delgado, Daniel Ricardo
Jouyban, Abolghasem
Acree Jr, William Eugene
dc.subject.spa.fl_str_mv Sulfacetamide
Propylene glycol + water mixtures
SolubilityJouyban-Acree model
Solution thermodynamics
Preferential solvation
Apparent specific volume
topic Sulfacetamide
Propylene glycol + water mixtures
SolubilityJouyban-Acree model
Solution thermodynamics
Preferential solvation
Apparent specific volume
Sulfacetamide
Propylene glycol + water mixtures
SolubilityJouyban-Acree model
Solution thermodynamics
Preferential solvation
Apparent specific volume
dc.subject.other.spa.fl_str_mv Sulfacetamide
Propylene glycol + water mixtures
SolubilityJouyban-Acree model
Solution thermodynamics
Preferential solvation
Apparent specific volume
description The equilibrium solubility at temperatures from (278.15 to 318.15) K, dissolution thermodynamics, preferential solvation, and apparent specific volume at saturation of sulfacetamide (SCM) in {propylene glycol (PG) (1) + water (2)} mixtures is reported. Mole fraction solubility of SCM (x3) increases when temperature arises and also increases with the PG proportion arising. Solubility behavior was adequately correlated and/or predicted by the Jouyban-Acree and Jouyban-Acree-van't Hoff models and the obtained mean percentage deviations (MPD) are varied between 6.5 and 11.5%. Apparent thermodynamic analysis of dissolution and mixing was performed in all the mixtures and neat solvents. Based on the inverse Kirkwood-Buff integrals (IKBI) is observed that SCM is preferentially solvated by water molecules in water-rich mixtures but preferentially solvated by PG in the other mixtures. Further, the apparent specific volumes of SCM at saturation were also calculated.
publishDate 2019
dc.date.accessioned.none.fl_str_mv 2019-12-13T17:39:10Z
dc.date.available.none.fl_str_mv 2019-12-13T17:39:10Z
dc.date.issued.none.fl_str_mv 2019-11-18
dc.type.none.fl_str_mv Artículo
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dc.identifier.issn.spa.fl_str_mv 01677322
dc.identifier.uri.spa.fl_str_mv https://doi.org/10.1016/j.molliq.2019.111889
dc.identifier.uri.none.fl_str_mv https://hdl.handle.net/20.500.12494/15631
dc.identifier.bibliographicCitation.spa.fl_str_mv Irmis P Osorio, Fleming Martínez, Daniel R Delgado, Abolghasem Jouyban, William E Acree Jr, Solubility of sulfacetamide in aqueous propylene glycol mixtures: Measurement, correlation, dissolution thermodynamics, preferential solvation and solute volumetric contribution at saturation, Journal of Molecular Liquids Available online 18 November 2019, 111889
identifier_str_mv 01677322
Irmis P Osorio, Fleming Martínez, Daniel R Delgado, Abolghasem Jouyban, William E Acree Jr, Solubility of sulfacetamide in aqueous propylene glycol mixtures: Measurement, correlation, dissolution thermodynamics, preferential solvation and solute volumetric contribution at saturation, Journal of Molecular Liquids Available online 18 November 2019, 111889
url https://doi.org/10.1016/j.molliq.2019.111889
https://hdl.handle.net/20.500.12494/15631
dc.relation.isversionof.spa.fl_str_mv https://www.sciencedirect.com/science/article/abs/pii/S0167732219345325#!
dc.relation.ispartofjournal.spa.fl_str_mv Journal of Molecular Liquids
dc.relation.references.spa.fl_str_mv S. Budavari, M.J. O’Neil, A. Smith, P.E. Heckelman, J.R. Obenchain Jr., J.A.R. Gallipeau, M.A. D’Arecea, The Merck Index, an Encyclopedia of Chemicals, Drugs, and Biologicals, 13th ed. Merck & Co., Inc, Whitehouse Station, NJ, 2001.
F. Martínez, A. Gómez, Thermodynamics of partitioning of some sulfonamides in 1- octanol/buffer and liposome systems, J. Phys. Org. Chem. 15 (2002) 874–880.
S. Gelone, J.A. O’Donell, Anti-infectives, in: A.R. Gennaro (Ed.), Remington: The Science and Practice of Pharmacy, 21st ed.Lippincott Williams & Wilkins, Philadelphia, 2005
F. Martínez, A. Gómez, Thermodynamic study of the solubility of some sulfonamides in octanol, water, and the mutually saturated solvents, J. Solut. Chem. 30 (2001) 909–923.
] S.C. Sweetman (Ed.), Martindale: The Complete Drug Reference, 36th ed.Pharmaceutical Press, London, 2009
S.H. Yalkowsky, Y. He, P. Jain, Handbook of Aqueous Solubility Data, 2nd ed. CRC Press, Boca Raton (FL), 2010.
A. Romdhani, F. Martínez, O.A. Almanza, M.A. Peña, A. Jouyban, W.E. Acree Jr., Solubility of sulfacetamide in (ethanol + water) mixtures: measurement, correlation, thermodynamics, preferential solvation and volumetric contribution at saturation, J. Mol. Liq. 290 (2019) 111219.
J.T. Rubino, Cosolvents and cosolvency, in: J. Swarbrick, J.C. Boylan (Eds.), Encyclopedia of Pharmaceutical Technology, vol 3, Marcel Dekker, Inc, New York, 1988.
S.H. Yalkowsky, Solubility and Solubilization in Aqueous Media, American Chemical Society and Oxford University Press, New York, 1999
A. Jouyban, Handbook of Solubility Data for Pharmaceuticals, CRC Press, Boca Raton, FL, 2010.
Y. Marcus, On the preferential solvation of drugs and PAHs in binary solvent mixtures, J. Mol. Liq. 140 (2008) 61–67.
Y. Marcus, Preferential solvation of ibuprofen and naproxen in aqueous 1,2– propanediol, Acta Chim. Slov. 56 (2009) 40–44.
F. Martinez, A. Jouyban, W.E. Acree Jr., Pharmaceuticals solubility is still nowadays widely studied everywhere (editorial), Pharm. Sci. (Tabriz) 23 (2017) 1–2.
A. Avdeef, Absorption and Drug Development, Solubility, Permeability and Charge State, Wiley-Interscience, Hoboken, NJ, 2003
J.W. Mauger, Thermodynamics of Sulfonamide Solutions, Ph.D. thesis University of Rhode Island, 1971.
R.C. Rowe, P.J. Sheskey, M.E. Quinn (Eds.), Handbook of Pharmaceutical Excipients, 6th editionPharmaceutical Press, London, 2009.
D.R. Delgado, A. Romdhani, F. Martínez, Thermodynamics of sulfanilamide solubility in propylene glycol + water mixtures, Lat. Am. J. Pharm. 30 (2011) 2024–2030.
D.R. Delgado, A. Romdhani, F. Martínez, Solubility of sulfamethizole in some propylene glycol + water mixtures at several temperatures, Fluid Phase Equilib. 322–323 (2012) 113–119
D.R. Delgado, G.A. Rodríguez, A.R. Holguín, F. Martínez, A. Jouyban, Solubility of sulfapyridine in propylene glycol + water mixtures and correlation with the Jouyban–Acree model, Fluid Phase Equilib. 341 (2013) 86–95.
M.M. Muñoz, D.R. Delgado, M.Á. Peña, A. Jouyban, F. Martínez, Solubility and preferential solvation of sulfadiazine, sulfamerazine and sulfamethazine in propylene glycol + water mixtures at 298.15 K, J. Mol. Liq. 204 (2015) 132–136.
A. Martin, P. Bustamante, A.H.C. Chun, Physical Chemical Principles in the Pharmaceutical Sciences, 4th ed. Lea & Febiger, Philadelphia, 1993.
K.A. Connors, Thermodynamics of Pharmaceutical Systems: An Introduction for Students of Pharmacy, Wiley–Interscience, Hoboken, NJ, 2002.
A.F.M. Barton, Handbook of Solubility Parameters and Other Cohesion Parameters, 2nd ed. CRC Press, New York, 1991.
R.F. Fedors, A method for estimating both the solubility parameters and molar volumes of liquids, Polym. Eng. Sci. 14 (1974) 147–154.
A. Kristl, G. Vesnaver, Thermodynamic investigation of the effect of octanol–water mutual miscibility on the partitioning and solubility of some guanine derivatives, J. Chem. Soc. Faraday Trans. 91 (1995) 995–998.
S.H. Yalkowsky, T.J. Roseman, Solubilization of drugs by cosolvents, in: S.H. Yalkowsky (Ed.), Techniques of Solubilization of Drugs, Marcel Dekker, New York, 1981
W.E. Acree, Mathematical representation of thermodynamic properties: part 2: derivation of the combined nearly solvent (NIBS)/Redlich-Kister mathematical representation from a two-body and three-body interactional mixing model, Thermochim. Acta 198 (1992) 71–79.
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S.G. Machatha, P. Bustamante, S.H. Yalkowsky, Deviation from linearity of drug solubility in ethanol/water mixtures, Int. J. Pharm. 283 (2004) 83–88.
S. Dadmand, F. Kamari, W.E. Acree Jr., A. Jouyban, Solubility prediction of drugs in binary solvent mixtures at various temperatures using a minimum number of experimental data points, AAPS PharmSciTech 20 (2018) 10
A. Jouyban, Review of the cosolvency models for predicting drug solubility in solvent mixtures: an update, J. Pharm. Pharm. Sci. 22 (2019) 466–485.
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A. Jouyban, W.E. Acree Jr., Mathematical derivation of the Jouyban-Acree model to represent solute solubility data in mixed solvents at various temperatures, J. Mol. Liq. 256 (2018) 541–547.
A. Jouyban, M. Khoubnasabjafari, H.K. Chan, W.E. Acree Jr., Mathematical representation of solubility of amino acids in binary aqueous-organic solvent mixtures at various temperatures using the Jouyban-Acree model, Pharmazie 61 (2006) 789–792.
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M.A. Ruidiaz, D.R. Delgado, F. Martínez, Y. Marcus, Solubility and preferential solvation of indomethacin in 1,4–dioxane + water solvent mixtures, Fluid Phase Equilib. 299 (2010) 259–265.
G.L. Perlovich, S.V. Kurkov, A.N. Kinchin, A. Bauer-Brandl, Thermodynamics of solutions III: comparison of the solvation of (+)-naproxen with other NSAIDs, Eur. J. Pharm. Biopharm. 57 (2004) 411–420.
D.R. Delgado, O.A. Almanza, F. Martínez, M.A. Peña, A. Jouyban, W.E. Acree Jr., Solution thermodynamics and preferential solvation of sulfamethazine in (methanol + water) mixtures, J. Chem. Thermodyn. 97 (2016) 264–276.
C.P. Mora, F. Martínez, Thermodynamic quantities relative to solution processes of naproxen in aqueous media at pH 1.2 and 7.4, Phys. Chem. Liq. 44 (2006) 585–596
S. Romero, A. Reillo, B. Escalera, P. Bustamante, The behaviour of paracetamol in mixtures of aprotic and amphiprotic-aprotic solvents. Relationship of solubility curves to specific and nonspecific interactions, Chem. Pharm. Bull. (Tokyo) 44 (1996) 1061–1066.
P. Bustamante, S. Romero, A. Peña, B. Escalera, A. Reillo, Nonlinear enthalpy-entropy compensation for the solubility of drugs in solvent mixtures: paracetamol, acetanilide and nalidixic acid in dioxane-water, J. Pharm. Sci. 87 (1998) 1590–1596.
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D.M. Jiménez, Z.J. Cárdenas, D.R. Delgado, F. Martínez, A. Jouyban, Preferential solvation of methocarbamol in aqueous binary cosolvent mixtures at 298.15 K, Phys. Chem. Liq. 52 (2014) 726–737
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Z.J. Cárdenas, D.M. Jiménez, F. Martínez, Preferential solvation of ketoprofen in some co-solvent binary mixtures, J. Solut. Chem. 43 (2014) 1904–1915.
] M.Á. Peña, D.R. Delgado, F. Martínez, Preferential solvation of acetaminophen in propylene glycol + water co-solvent mixtures, J. Appl. Sol. Chem. Model. 3 (2014) 65–73.
D.M. Jiménez, Z.J. Cárdenas, D.R. Delgado, M.Á. Peña, F. Martínez, Preferential solvation of the antioxidant agent daidzein in some aqueous co-solvent mixtures according to IKBI and QLQC methods, J. Appl. Sol. Chem. Mod. 4 (2015) 110–118.
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spelling Osorio, Irmis PMartinez, FlemingDelgado, Daniel RicardoJouyban, AbolghasemAcree Jr, William Eugene2019-12-13T17:39:10Z2019-12-13T17:39:10Z2019-11-1801677322https://doi.org/10.1016/j.molliq.2019.111889https://hdl.handle.net/20.500.12494/15631Irmis P Osorio, Fleming Martínez, Daniel R Delgado, Abolghasem Jouyban, William E Acree Jr, Solubility of sulfacetamide in aqueous propylene glycol mixtures: Measurement, correlation, dissolution thermodynamics, preferential solvation and solute volumetric contribution at saturation, Journal of Molecular Liquids Available online 18 November 2019, 111889The equilibrium solubility at temperatures from (278.15 to 318.15) K, dissolution thermodynamics, preferential solvation, and apparent specific volume at saturation of sulfacetamide (SCM) in {propylene glycol (PG) (1) + water (2)} mixtures is reported. Mole fraction solubility of SCM (x3) increases when temperature arises and also increases with the PG proportion arising. Solubility behavior was adequately correlated and/or predicted by the Jouyban-Acree and Jouyban-Acree-van't Hoff models and the obtained mean percentage deviations (MPD) are varied between 6.5 and 11.5%. Apparent thermodynamic analysis of dissolution and mixing was performed in all the mixtures and neat solvents. Based on the inverse Kirkwood-Buff integrals (IKBI) is observed that SCM is preferentially solvated by water molecules in water-rich mixtures but preferentially solvated by PG in the other mixtures. Further, the apparent specific volumes of SCM at saturation were also calculated.The equilibrium solubility at temperatures from (278.15 to 318.15) K, dissolution thermodynamics, preferential solvation, and apparent specific volume at saturation of sulfacetamide (SCM) in {propylene glycol (PG) (1) + water (2)} mixtures is reported. Mole fraction solubility of SCM (x3) increases when temperature arises and also increases with the PG proportion arising. Solubility behavior was adequately correlated and/or predicted by the Jouyban-Acree and Jouyban-Acree-van't Hoff models and the obtained mean percentage deviations (MPD) are varied between 6.5 and 11.5%. Apparent thermodynamic analysis of dissolution and mixing was performed in all the mixtures and neat solvents. Based on the inverse Kirkwood-Buff integrals (IKBI) is observed that SCM is preferentially solvated by water molecules in water-rich mixtures but preferentially solvated by PG in the other mixtures. Further, the apparent specific volumes of SCM at saturation were also calculated.Highlights. -- Abstract. -- Keywords. -- 1. Introduction. -- 2. Experimental. -- 3. Results and discussion. -- 4. Conclusions. -- Acknowledgements. -- Declaration of competing interest. -- References.http://scienti.colciencias.gov.co:8081/cvlac/visualizador/generarCurriculoCv.do?cod_rh=0001402116https://orcid.org/0000-0002-4835-9739https://scienti.colciencias.gov.co/gruplac/jsp/visualiza/visualizagr.jsp?nro=00000000004151danielr.delgado@campusucc.edu.cohttps://scholar.google.com/citations?hl=es&user=OW0mejcAAAAJ&view_op=list_worksUniversidad Cooperativa de Colombia, Facultad de Ingenierías, Ingeniería Industrial, NeivaEl sevierIngeniería IndustrialNeivahttps://www.sciencedirect.com/science/article/abs/pii/S0167732219345325#!Journal of Molecular LiquidsS. Budavari, M.J. O’Neil, A. Smith, P.E. Heckelman, J.R. Obenchain Jr., J.A.R. Gallipeau, M.A. D’Arecea, The Merck Index, an Encyclopedia of Chemicals, Drugs, and Biologicals, 13th ed. Merck & Co., Inc, Whitehouse Station, NJ, 2001.F. Martínez, A. Gómez, Thermodynamics of partitioning of some sulfonamides in 1- octanol/buffer and liposome systems, J. Phys. Org. Chem. 15 (2002) 874–880.S. Gelone, J.A. O’Donell, Anti-infectives, in: A.R. Gennaro (Ed.), Remington: The Science and Practice of Pharmacy, 21st ed.Lippincott Williams & Wilkins, Philadelphia, 2005F. Martínez, A. Gómez, Thermodynamic study of the solubility of some sulfonamides in octanol, water, and the mutually saturated solvents, J. Solut. Chem. 30 (2001) 909–923.] S.C. Sweetman (Ed.), Martindale: The Complete Drug Reference, 36th ed.Pharmaceutical Press, London, 2009S.H. Yalkowsky, Y. He, P. Jain, Handbook of Aqueous Solubility Data, 2nd ed. CRC Press, Boca Raton (FL), 2010.A. Romdhani, F. Martínez, O.A. Almanza, M.A. Peña, A. Jouyban, W.E. Acree Jr., Solubility of sulfacetamide in (ethanol + water) mixtures: measurement, correlation, thermodynamics, preferential solvation and volumetric contribution at saturation, J. Mol. Liq. 290 (2019) 111219.J.T. Rubino, Cosolvents and cosolvency, in: J. Swarbrick, J.C. Boylan (Eds.), Encyclopedia of Pharmaceutical Technology, vol 3, Marcel Dekker, Inc, New York, 1988.S.H. Yalkowsky, Solubility and Solubilization in Aqueous Media, American Chemical Society and Oxford University Press, New York, 1999A. Jouyban, Handbook of Solubility Data for Pharmaceuticals, CRC Press, Boca Raton, FL, 2010.Y. Marcus, On the preferential solvation of drugs and PAHs in binary solvent mixtures, J. Mol. Liq. 140 (2008) 61–67.Y. Marcus, Preferential solvation of ibuprofen and naproxen in aqueous 1,2– propanediol, Acta Chim. Slov. 56 (2009) 40–44.F. Martinez, A. Jouyban, W.E. Acree Jr., Pharmaceuticals solubility is still nowadays widely studied everywhere (editorial), Pharm. Sci. (Tabriz) 23 (2017) 1–2.A. Avdeef, Absorption and Drug Development, Solubility, Permeability and Charge State, Wiley-Interscience, Hoboken, NJ, 2003J.W. Mauger, Thermodynamics of Sulfonamide Solutions, Ph.D. thesis University of Rhode Island, 1971.R.C. Rowe, P.J. Sheskey, M.E. Quinn (Eds.), Handbook of Pharmaceutical Excipients, 6th editionPharmaceutical Press, London, 2009.D.R. Delgado, A. Romdhani, F. Martínez, Thermodynamics of sulfanilamide solubility in propylene glycol + water mixtures, Lat. Am. J. Pharm. 30 (2011) 2024–2030.D.R. Delgado, A. Romdhani, F. Martínez, Solubility of sulfamethizole in some propylene glycol + water mixtures at several temperatures, Fluid Phase Equilib. 322–323 (2012) 113–119D.R. Delgado, G.A. Rodríguez, A.R. Holguín, F. Martínez, A. Jouyban, Solubility of sulfapyridine in propylene glycol + water mixtures and correlation with the Jouyban–Acree model, Fluid Phase Equilib. 341 (2013) 86–95.M.M. Muñoz, D.R. Delgado, M.Á. Peña, A. Jouyban, F. Martínez, Solubility and preferential solvation of sulfadiazine, sulfamerazine and sulfamethazine in propylene glycol + water mixtures at 298.15 K, J. Mol. Liq. 204 (2015) 132–136.A. Martin, P. Bustamante, A.H.C. Chun, Physical Chemical Principles in the Pharmaceutical Sciences, 4th ed. Lea & Febiger, Philadelphia, 1993.K.A. Connors, Thermodynamics of Pharmaceutical Systems: An Introduction for Students of Pharmacy, Wiley–Interscience, Hoboken, NJ, 2002.A.F.M. Barton, Handbook of Solubility Parameters and Other Cohesion Parameters, 2nd ed. CRC Press, New York, 1991.R.F. Fedors, A method for estimating both the solubility parameters and molar volumes of liquids, Polym. Eng. Sci. 14 (1974) 147–154.A. Kristl, G. Vesnaver, Thermodynamic investigation of the effect of octanol–water mutual miscibility on the partitioning and solubility of some guanine derivatives, J. Chem. Soc. Faraday Trans. 91 (1995) 995–998.S.H. Yalkowsky, T.J. Roseman, Solubilization of drugs by cosolvents, in: S.H. Yalkowsky (Ed.), Techniques of Solubilization of Drugs, Marcel Dekker, New York, 1981W.E. 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Commun. 203 (2016) 619–627.SulfacetamidePropylene glycol + water mixturesSolubilityJouyban-Acree modelSolution thermodynamicsPreferential solvationApparent specific volumeSulfacetamidePropylene glycol + water mixturesSolubilityJouyban-Acree modelSolution thermodynamicsPreferential solvationApparent specific volumeSolubility of sulfacetamide in aqueous propylene glycol mixtures: Measurement, correlation, dissolution thermodynamics, preferential solvation and solute volumetric contribution at saturationArtículohttp://purl.org/coar/resource_type/c_6501http://purl.org/coar/resource_type/c_2df8fbb1http://purl.org/coar/version/c_970fb48d4fbd8a85info:eu-repo/semantics/articleinfo:eu-repo/semantics/publishedVersionAtribución – No comercial – Compartir igualinfo:eu-repo/semantics/closedAccesshttp://purl.org/coar/access_right/c_14cbPublicationLICENSElicense.txtlicense.txttext/plain; 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