Abstract
Herein, we investigated the micelle formation of mixed systems of the antipsychotic drug, chlorpromazine hydrochloride (CPZ), and the bile salt, sodium deoxycholate (NaDC), both in the absence and presence of NaCl by tensiometry. To understand the aggregation behaviour of the mixture of these two amphiphiles, we calculated various micellar and interfacial parameters using the theories of Clint, Rubingh, Rosen and Motomura. The calculated interaction parameters indicate an attractive interaction between the two amphiphiles both in the absence and presence of salt. The results were discussed with regard to the use of bile salt as a promising drug carrier for CPZ and the improvement of its bioavailability.
Kurzfassung
Wir untersuchten die Mizellenbildung von Mischsystemen aus dem antipsychotischem Arzneiwirkstoff Chlorpromazinhydrochlorid (Chlorpromazin, CPZ) und dem Gallensalz Natriumdesoxycholat (NaDC) sowohl in Abwesenheit als auch in Anwesenheit von NaCl mittels Tensiometrie. Um das Aggregationsverhalten der Mischung aus diesen beiden Amphiphilen zu verstehen, berechneten wir verschiedene mizellare und grenzflächenbezogene Parameter unter Verwendung der Theorien von Clint, Rubingh, Rosen und Motomura. Die berechneten Wechselwirkungsparameter weisen auf eine attraktive Wechselwirkung zwischen den zwei Amphiphilen sowohl bei Abwesenheit als auch bei Anwesenheit von Salz hin. Die Ergebnisse wurden hinsichtlich der Verwendung des Gallensalzes als vielversprechender Wirkstoffträger für den Wirkstoff CPZ und der Verbesserung seiner Bioverfügbarkeit diskutiert.
References
1 E. R. Jones and C. R.Bury: The freezing-points of concentrated solutions. Part II. Solutions of formic, acetic, propionic, and butyric acids, The London, Edinburgh, and Dublin Philosophical Magazine and Journal of Sci.4 (1927), 841–848. 10.1080/14786441008564388Search in Google Scholar
2 M. A. Rub , N.Azum and A. M.Asiri: Self-association behavior of an amphiphilic drug nortriptyline hydrochloride under the influence of inorganic salts, Russ. J. Phys. Chem.10 (2016)1007–1013. 10.1134/S1990793116060257Search in Google Scholar
3 Q. Zhou and M. J.Rosen: Molecular interactions of surfactants in mixed monolayers at the air/aqueous solution interface and in mixed micelles in aqueous media: The regular solution approach, Langmuir, 19 (2003), 4555–4562. 10.1021/la020789 mSearch in Google Scholar
4 D. Kumar , N.Azum, M. A.Rub and A. M.Asiri: Aggregation behavior of sodium salt of ibuprofen with conventional and gemini surfactant, J. Mol. Liqs. 262 (2018) 86–96. 10.1016/j.molliq.2018.04.053Search in Google Scholar
5 M. A. Rub , F.Khan, M. S.Sheikh, N.Azum and A. M.Asiri: Tensiometric, fluorescence and 1H NMR study of mixed micellization of non-steroidal anti-inflammatory drug sodium salt of ibuprofen in the presence of non-ionic surfactant in aqueous/urea solutions, J. Chem. Therm. 96 (2016) 196–207. 10.1016/j.jct.2016.01.001Search in Google Scholar
6 F. Khan , M. A.Rub, N.Azum, D.Kumar and A. M.Asiri: Interaction of an amphiphilic drug and sodium bis(2-ethylhexyl) sulfosuccinate at low concentrations in the absence and presence of sodium chloride, J. Sol. Chem. 44 (2015) 1937–1961. 10.1007/s10953-015-0386-1Search in Google Scholar
7 N. Azum , M. A.Rub and A. M.Asiri: Bile salt–bile salt interaction in mixed monolayer and mixed micelle formation, The J. Chem. Therm. 128 (2019) 406–414. 10.1016/j.jct.2018.08.030Search in Google Scholar
8 N. Azum , M. A.Rub, A. M.Asiri and H. A.Kashmery: Synergistic effect of an antipsychotic drug chlorpromazine hydrochloride with pluronic triblock copolymer: A physicochemical study, J. Mol. Liqs.260 (2018) 159–165. 10.1016/j.molliq.2018.03.088Search in Google Scholar
9 M. A. Rub , N.Azum, F.Khan and A. M.Asiri: Aggregation of sodium salt of ibuprofen and sodium taurocholate mixture in different media: A tensiometry and fluorometry study, J. Chem. Therm. 121 (2018) 199–210. 10.1016/j.jct.2018.02.019Search in Google Scholar
10 P. Nair : The bile acids chemistry, physiology, and metabolism, Springer US, Boston, (1971), ISBN 978-1-4757-0647-5.Search in Google Scholar
11 M. C. Carey : Phospholipids and atherosclerosis, Raven Press, New York (1983).Search in Google Scholar
12 A. F. Hofmann : Bile Acids and Hepatobiliary Disease, Kluwer Academic Publishers, Boston, 1999, ISBN 0-7923-8755-4.Search in Google Scholar
13 H. Danielson : The bile acids: Chemistry, physiology and metabolism, Plenum Press, New York, 1971. 10.1007/978-1-4615-7563-4Search in Google Scholar
14 M. Mikov and J. P.Fawcett: Bile Acids, Medishet Publisher, Geneva, 2007.Search in Google Scholar
15 D. W. Martin ; P. A.Mayes and V. W.Rodwell: Harper's review of biochemistry, 18th ed., Maurzen Asia, Tokyo, 1981.Search in Google Scholar
16 R. T. Holzbach , M.Marsh, M.Olszewski and K.Holan: Cholesterol solubility in bile. Evidence that supersaturated bile is frequent in healthy man, J. Clin. Investigation, 52 (1973), 1467–1479. 4703231 10.1172/JCI107321Search in Google Scholar
17 L. R. S. Barbosa , R.Itri, W.Caetano, D.de Sousa Neto and M.Tabak: Self-assembling of phenothiazine compounds investigated by small-angle X-ray scattering and electron paramagnetic resonance spectroscopy, J. Phys. Chem. B, 112 (2008) 4261–4269. 18345659 10.1021/jp710332tSearch in Google Scholar
18 J. H. Clint : Surfactant aggregation, Springer, Netherlands (1992), ISBN: 978-94-011-2272-6.Search in Google Scholar
19 M. J. Rosen and S.Aronson: Standard free energies of adsorption of surfactants at the aqueous solution/air interface from surface tension data in the vicinity of the critical micelle concentration, Colloids and Surfaces3 (1981) 201–208. 10.1016/0166-6622(81)80037-6Search in Google Scholar
20 M. A. Rub , F.Khan, D.Kumar and A. M.Asiri: Study of mixed micelles of promethazine hydrochloride (PMT) and nonionic surfactant (TX-100) mixtures at different temperatures and compositions, Tenside Surfactants Detergents52 (2015) 236–244. 10.3139/113.110371Search in Google Scholar
21 H. Otmani , F.Bouanani and D.Bendedouch: Synergistic properties of a mixed micelle system consisting of a nonionic fluorinated surfactant and a cationic surfactant, Tenside Surfactants Detergents, 56 (2019) 61–67. 10.3139/113.110600Search in Google Scholar
22 W. M. Lee : Drug-induced acute liver failure, Clinics in Liver Disease, 17 (2013) 575–586. 24099019 10.1016/j.cld.2013.07.001Search in Google Scholar PubMed PubMed Central
23 S. Mahajan and R. K.Mahajan: Interactions of phenothiazine drugs with bile salts: Micellization and binding studies, J. Colloid and Interface Sci.387 (2012) 194–204. 22939256 10.1016/j.jcis.2012.07.085Search in Google Scholar PubMed
24 G. A. Kabir-ud-Din Al-dahbali , A. Z.Naqvi and M.Akram: Adsorption and micellization behavior of mixtures of amphiphilic drugs with small amounts of bile salts, Tenside Surfactants Detergents52 (2015) 271–279. 10.3139/113.110375Search in Google Scholar
25 S. C. A. Chen , E. G.Playford and T. C.Sorrell: Antifungal therapy in invasive fungal infections, Current Opinion in Pharmacology, 10 (2010) 522–530. 20598943 10.1016/j.coph.2010.06.002Search in Google Scholar PubMed
26 C. D. Klaassen and L. M.Aleksunes: Xenobiotic, Bile acid, and cholesterol transporters: Function and regulation, Pharmacological Reviews, 62 (2010) 1–96. 20103563 10.1124/pr.109.002014Search in Google Scholar PubMed PubMed Central
27 N. Azum , M. A.Rub and A. M.Asiri: Energetics of clouding phenomenon in amphiphilic drug imipramine hydrochloride with pharmaceutical excipients, Pharm. Chem. J.48 (2014) 201–208. 10.1007/s11094-014-1077-8Search in Google Scholar
28 M. K. Al-Muhanna , M. A.Rub, N.Azum, S. B.Khan and A. M.Asiri: Self-aggregation phenomenon of promazine hydrochloride under the influence of sodium cholate/sodium deoxycholate in aqueous medium, J. Disp. Sci. Techn.37 (2016) 450–463. 10.1080/01932691.2015.1045598Search in Google Scholar
29 M. A. Rub , N.Azum and A. M.Asiri: Binary mixtures of sodium salt of ibuprofen and selected bile salts: Interface, micellar, thermodynamic, and spectroscopic study, J. Chem. & Eng. Data62 (2017) 3216–3228. 10.1021/acs.jced.7b00298Search in Google Scholar
30 W. C. Bowman and M. J.Rand: Textbook of pharmacology, Blackwell Scientific Publications, UK (1980), ISBN 10: 0632099909.Search in Google Scholar
31 D. Kumar and M. A.Rub: Effect of sodium taurocholate on aggregation behavior of amphiphilic drug solution, Tenside Surfactants Detergents52 (2015) 464–472. 10.3139/113.110398Search in Google Scholar
32 E. M. Glaser and P. S. B.Newling: Side effects of chlorpromazine hydrochloride, British J. Pharm. and Chemotherapy10 (1955) 429–433. 13276597 10.1111/j.1476-5381.1955.tb00098.xSearch in Google Scholar
33 W. Halliwell : Cationic amphiphilic drug-induced phospholipidosis, Toxicologic Pathology25 (1997) 53–60. 9061852 10.1177/019262339702500111Search in Google Scholar
34 S. Tehrani , N.Brandstater, Y. D.Saito and P.Dea: Studies on the size and stability of chlorpromazine hydrochloride nanostructures in aqueous solution, Biophysical Chemistry94 (2001) 87–96. 10.1016/S0301-4622(01)00226-5Search in Google Scholar
35 S. Singh : Complex behaviour of bile salts at various temperatures under the influence of antidepressant drug (imipramine) in aqueous solution, Science Innovation4 (2016) 235. 10.11648/j.si.20160405.13Search in Google Scholar
36 A. Maestre , P.Guardado and M. L.Moyá: Thermodynamic study of bile salts micellization, J. Chem. & Eng. Data59 (2014) 433–438. 10.1021/je400903nSearch in Google Scholar
37 S. Schreier , S. V. P.Malheiros and E.de Paula: Surface active drugs: self-association and interaction with membranes and surfactants. Physicochemical and biological aspects, Biochimica et Biophysica Acta (BBA)–Biomembranes, 1508 (2000) 210–234. 10.1016/S0304-4157(00)00012-5Search in Google Scholar
38 D. N. Rubingh : Mixed micelle solutions, solution chemistry of surfactants, Springer New York, Boston, MA (1979) 337–354. 10.1007/978-1-4615-7880-2_15Search in Google Scholar
39 K. Motomura : Mixed surfactant systems, Marcel Dekker, New York (1993).Search in Google Scholar
40 M. J. Rosen : Surfactants and interfacial phenomena, John Wiley & Sons, Inc., Hoboken, NJ, USA (2004). 10.1002/0471670561Search in Google Scholar
41 N. Azum , M. A.Rub and A. M.Asiri: Self-association and micro-environmental properties of sodium salt of ibuprofen with BRIJ-56 under the influence of aqueous/urea solution, J. Disp. Sci. and Techn. 38 (2017) 96–104. 10.1080/01932691.2016.1144197Search in Google Scholar
42 N. Azum , M. A.Rub and A. M.Asiri: Interaction of triblock-copolymer with cationic gemini and conventional surfactants: A physicochemical study, Journal of Dispersion Science and Tech. 38 (2017) 1785–1791. 10.1080/01932691.2017.1283510Search in Google Scholar
43 N. Azum , S. B.Khan, M. A.Rub, A. M.Asiri, D.Kumar and Kabir-ud-Din: Effect of novel surfactant on the growth kinetics of cobalt nanoparticles, Tenside Surfactants Detergents54 (2017) 448–452. 10.3139/113.110515Search in Google Scholar
44 G. Sugihara , A.Miyazono, S.Nagadome, T.Oida, Y.Hayashi and J. S.Ko: Adsorption and micelle formation of mixed surfactant systems in water II: A combination of cationic gemini-type surfactant with MEGA-10, J. Oleo Sci.52 (2003) 449–461. 10.5650/jos.52.449Search in Google Scholar
45 K. Tsubone , Y.Arakawa and M. J.Rosen: Structural effects on surface and micellar properties of alkanediyl-α,ω-bis(sodium N-acyl-β-alaninate) gemini surfactants, J. Colloid and Interface Sci.262 (2003) 516–524. 10.1016/S0021-9797(03)00078-XSearch in Google Scholar
46 N. Azum , M. A.Rub, A. M.Asiri and W. A.Bawazeer: Micellar and interfacial properties of amphiphilic drug–non-ionic surfactants mixed systems: Surface tension, fluorescence and UV–vis studies, Colloids Surfaces A522 (2017) 183–192. 10.1016/j.colsurfa.2017.02.093Search in Google Scholar
47 D. Kumar , M. A.Rub, N.Azum and A. M.Asiri: Mixed micellization study of ibuprofen (sodium salt) and cationic surfactant (conventional as well as gemini), J. Phys. Org. Chem.31 (2018) e3730. 10.1002/poc.3730Search in Google Scholar
48 M. A. Rub , N.Azum, S. B.Khan, F.Khan and A. M.Asiri: Physicochemical properties of amphiphilic drug and anionic surfactant mixtures: experimental and theoretical approach, J. Disp. Sci. Techn.36 (2015) 521–531. 10.1080/01932691.2014.914443Search in Google Scholar
49 N. Azum , M. A.Rub and A. M.Asiri: Interaction of antipsychotic drug with novel surfactants: Micellization and binding studies, Chin. J. Chem. Eng. 26 (2018) 566–573. 10.1016/j.cjche.2017.09.009Search in Google Scholar
50 F. Khan , M. A.Rub, N.Azum and A. M.Asiri: Mixtures of antidepressant amphiphilic drug imipramine hydrochloride and anionic surfactant: Micellar and thermodynamic investigation, J. Phys. Org. Chem.31, (2018) e3812. 10.1002/poc.3812Search in Google Scholar
51 N. Azum , A. Z.Naqvi, M. A.Rub and A. M.Asiri: Multi-technique approach towards amphiphilic drug-surfactant interaction: A physicochemical study, J. Mol. Liqs. 240 (2017) 189–195. 10.1016/j.molliq.2017.05.066Search in Google Scholar
52 N. Azum , A. M.Asiri, M. A.Rub and A. O.Al-Youbi: Thermodynamic properties of ibuprofen sodium salt in aqueous/urea micellar solutions at 298.15 K, Russ. J. Phys. Chem. A91 (2017) 685–691. 10.1134/S0036024417040173Search in Google Scholar
© 2020, Carl Hanser Publisher, Munich