Reactivity of a lipophilic ingredient solubilized in anionic or cationic surfactant micelles

Colloids and Surfaces A: Physicochemical and Engineering Aspects

Volumn 412, Issue , 2012, Pages 135-142

  Berton Carabin, Claire C ^a   Coupland, John N ^a   Qian, Cheng ^b   McClements, D Julian ^b   Elias, Ryan J ^a  

^a PENNSYLVANIA STATE UNIVERSITY   (United States)

^b UNIVERSITY OF MASSACHUSETTS   (United States)

Author keywords

Anionic surfactant; Cationic surfactant; Electron paramagnetic resonance; Micelle; Spin probe

Indexed keywords

ANIONIC SURFACTANTS; BROMINE COMPOUNDS; CATIONIC SURFACTANTS; ELECTRON RESONANCE; ELECTRON SPIN RESONANCE SPECTROSCOPY; MICELLES; MOLECULES; PARAMAGNETIC RESONANCE; PARAMAGNETISM; PROBES; SODIUM SULFATE;

AQUEOUS PHASE; CATIONIC SURFACTANT MICELLES; MICELLAR SYSTEMS; MOBILE FRACTIONS; NITROXIDES; PROBE MOLECULES; SDS MICELLES; SODIUM DODECYL SULFATE; SOLUBILIZATION CAPACITIES; SPIN PROBE; SURFACTANT CONCENTRATIONS; SURFACTANT MICELLES;

DYES;

4 PHENYL 2,2,5,5 TETRAMETHYL 3 IMIDAZOLINE 1 OXYLNITROXIDE; ANION; CATION; DODECYL SULFATE SODIUM; DODECYLTRIMETHYLAMMONIUM BROMIDE; NITROXIDE DERIVATIVE; PHOSPHATE BUFFERED SALINE; SURFACTANT; UNCLASSIFIED DRUG;

AQUEOUS SOLUTION; ARTICLE; CHEMICAL STRUCTURE; CONCENTRATION (PARAMETERS); ELECTRON SPIN RESONANCE; LIPOPHILICITY; MICELLE; PRIORITY JOURNAL; SOLUBILIZATION;

EID: 84865866354     PISSN: 09277757     EISSN: 18734359     Source Type: Journal    
DOI: 10.1016/j.colsurfa.2012.07.029     Document Type: Article

References (43)

1. McClements D.J., Decker E.A., Weiss J. Emulsion-based delivery systems for lipophilic bioactive components. J. Food Sci. 2007, 72(8):R109-R124.
2. McClements D.J., Li Y. Structured emulsion-based delivery systems: controlling the digestion and release of lipophilic food components. Adv. Colloid Interf. Sci. 2010, 159(2):213-228.
3. McClements D.J. Edible nanoemulsions: fabrication, properties, and functional performance. Soft Matter 2011, 7(6):2297-2316.
4. Fathi M., Mozafari M.R., Mohebbi M. Nanoencapsulation of food ingredients using lipid based delivery systems. Trends Food Sci. Technol. 2012, 23(1):13-27.
5. Mall S., Buckton G., Rawlins D.A. Dissolution behaviour of sulphonamides into sodium dodecyl sulfate micelles: a thermodynamic approach. J. Pharm. Sci. 1996, 85(1):75-78.
6. Stephenson B.C., Rangel-Yagui C.O., Junior A.P., Tavares L.C., Beers K., Blankschtein D. Experimental and theoretical investigation of the micellar-assisted solubilization of ibuprofen in aqueous media. Langmuir 2006, 22(4):1514-1525.
7. Narang A., Delmarre D., Gao D. Stable drug encapsulation in micelles and microemulsions. Int. J. Pharm. 2007, 345(1-2):9-25.
8. Richards M.P., Chaiyasit W., McClements D.J., Decker E.A. Ability of surfactant micelles to alter the partitioning of phenolic antioxidants in oil-in-water emulsions. J. Agric. Food Chem. 2002, 50(5):1254-1259.
9. Nuchi C.D., Hernandez P., McClements D.J., Decker E.A. Ability of lipid hydroperoxides to partition into surfactant micelles and alter lipid oxidation rates in emulsions. J. Agric. Food Chem. 2002, 50(19):5445-5449.
10. Panya A., Laguerre M., Bayrasy C., Lecomte J., Villeneuve P., McClements D.J., Decker E.A. An investigation of the versatile antioxidant mechanisms of action of rosmarinate alkyl esters in oil-in-water emulsions. J. Agric. Food Chem. 2012, 60(10):2692-2700.
11. Shinoda K., Hutchinson E. Pseudo-phase separation model for thermodynamic calculations on micellar solutions. J. Phys. Chem. 1962, 66(4):577-582.
12. Kandori K., McGreevy R.J., Schechter R.S. Solubilization of phenol and benzene in cationic micelles: binding sites and effect on structure. J. Phys. Chem. 1989, 93(4):1506-1510.
13. Ahmad N., Malik M.A., Al-Thabaiti S.A., Obaid A.Y., Khan Z. Effect of cetyltrimethylammonium bromide on the oxidation of phthalic acid by in aqueous medium. J. Disp. Sci. Technol. 2011, 32(1):35-40.
14. Abe M., Mizuguchi K., Kondo Y., Ogino K., Uchiyama H., Scamehorn J.F., Tucker E.E., Christian S.D. Solubilization of perfume compounds by pure and mixtures of surfactants. J. Colloid Interf. Sci. 1993, 160(1):16-23.
15. Christian S.D., Scamehorn J.F. Solubilization in Surfactant Aggregates 1995, Marcel Dekker, Inc., New York.
16. Leung M.H.M., Colangelo H., Kee T.W. Encapsulation of curcumin in cationic micelles suppresses alkaline hydrolysis. Langmuir 2008, 24(11):5672-5675.
17. Baglioni P., Ferroni E., Martini G., Ottaviani M.F. Micellar solutions of sulfate surfactants studied by ESR of nitroxide radicals. 2. Use of C8, C12, and C16 derivatives of piperidinyl-1-oxy. J. Phys. Chem. 1984, 88(21):5107-5113.
18. Ottaviani M.F., Baglioni P., Martini G. Micellar solutions of sulfate surfactants studied by electron spin resonance of nitroxide radicals. 1. Use of neutral and positively charged spin probes. J. Phys. Chem. 1983, 87(16):3146-3153.
19. Baglioni P., Francesca Ottaviani M., Martini G. Micellar solutions of sulfate surfactants studied by ESR of nitroxide radicals. 3. Effect of added electrolytes. J. Phys. Chem. 1986, 90(22):5878-5882.
20. Baglioni P., Kevan L. Structural effects of alcohol addition to sodium dodecyl sulfate micelles studied by electron spin-echo modulation of 5-doxylstearic acid spin probe. J. Phys. Chem. 1987, 91(6):1516-1518.
21. Baglioni P., Bongiovanni R., Rivara-Minten E., Kevan L. Electron spin-echo modulation of x-doxylstearic acid in nonionic surfactants. J. Phys. Chem. 1989, 93(14):5574-5578.
22. Baglioni P., Rivara-Minten E., Dei L., Ferroni E. ESR study of sodium dodecyl sulfate and dodecyltrimethylammonium bromide micellar solutions: effect of urea. J. Phys. Chem. 1990, 94(21):8218-8222.
23. Baglioni P., Dei L., Rivara-Minten E., Kevan L. Mixed micelles of SDS/C12E6 and DTAC/C12E6 surfactants. J. Am. Chem. Soc. 1993, 115(10):4286-4290.
24. Talsania S.K., Wang Y., Rajagopalan R., Mohanty K.K. Monte Carlo simulations for micellar encapsulation. J. Colloid Interf. Sci. 1997, 190(1):92-103.
25. Choi S.J., Decker E.A., Henson L., Popplewell L.M., McClements D.J. Inhibition of citral degradation in model beverage emulsions using micelles and reverse micelles. Food Chem. 2010, 122(1):111-116.
26. Bunton C.A., Carrasco N., Huang S.K., Paik C.H., Romsted L.S. Reagent distribution and micellar catalysis of carbocation reactions. J. Am. Chem. Soc. 1978, 100(17):5420-5425.
27. Bunton C.A., Gan L.H., Moffatt J.R., Romsted L.S., Savelli G. Reactions in micelles of cetyltrimethylammonium hydroxide. Test of the pseudophase model for kinetics. J. Phys. Chem. 1981, 85(26):4118-4125.
28. Bunton C.A., Nome F., Quina F.H., Romsted L.S. Ion binding and reactivity at charged aqueous interfaces. Acc. Chem. Res. 1991, 24(12):357-364.
29. Tonnesen H.H. Solubility, chemical and photochemical stability of curcumin in surfactant solutions: studies of curcumin and curcuminoids, XXVIII. Pharmazie 2002, 57(12):820-824.
30. Yucel U., Elias R.J., Coupland J.N. Solute distribution and stability in emulsion-based delivery systems: an EPR study. J. Colloid Interf. Sci. 2012, 377(1):105-113.
31. Mikhalev O.I., Karpov I.N., Kazarova E.B., Alfimov M.V. The effect of crystallization of the dispersion phase in emulsions on the rate of interfacial reactions. Chem. Phys. Lett. 1989, 164(1):96-100.
32. Fuchs J., Groth N., Herrling T., Zimmer G. Electron paramagnetic resonance studies on nitroxide radical 2,2,5,5-tetramethyl-4-piperidin-1-oxyl (TEMPO) redox reactions in human skin. Free Radic. Biol. Med. 1997, 22(6):967-976.
33. Pérez-Rodríguez M., Prieto G., Rega C., Varela L.M., Sarmiento F., Mosquera V. A comparative study of the determination of the critical micelle concentration by conductivity and dielectric constant measurements. Langmuir 1998, 14(16):4422-4426.
34. Thongngam M., McClements D.J. Influence of pH, ionic strength, and temperature on self-association and interactions of sodium dodecyl sulfate in the absence and presence of chitosan. Langmuir 2005, 21(1):79-86.
35. Bahri M.A., Hoebeke M., Grammenos A., Delanaye L., Vandewalle N., Seret A. Investigation of SDS, DTAB and CTAB micelle microviscosities by electron spin resonance. Colloids Surf. A 2006, 290(1-3):206-212.
36. Cabane B., Duplessix R. Neutron scattering study of water-soluble polymers adsorbed on surfactant micelles. Colloids Surf. 1985, 13:19-33.
37. Mazer N.A., Benedek G.B., Carey M.C. An investigation of the micellar phase of sodium dodecyl sulfate in aqueous sodium chloride solutions using quasielastic light scattering spectroscopy. J. Phys. Chem. 1976, 80(10):1075-1085.
38. Turro N.J., Yekta A. Luminescent probes for detergent solutions. A simple procedure for determination of the mean aggregation number of micelles. J. Am. Chem. Soc. 1978, 100(18):5951-5952.
39. Bergström M., Skov Pedersen J. Structure of pure SDS and DTAB micelles in brine determined by small-angle neutron scattering (SANS). Phys. Chem. Chem. Phys. 1999, 1(18):4437-4446.
40. Herrington K.L., Kaler E.W., Miller D.D., Zasadzinski J.A., Chiruvolu S. Phase behavior of aqueous mixtures of dodecyltrimethylammonium bromide (DTAB) and sodium dodecyl sulfate (SDS). J. Phys. Chem. 1993, 97(51):13792-13802.
41. Bartlett D., Church D.F., Bounds P.L., Koppenol W.H. The kinetics of the oxidation of l-ascorbic acid by peroxynitrite. Free Radic. Biol. Med. 1995, 18(1):85-92.
42. Buettner G.R., Jurkiewicz B.A. Catalytic metals, ascorbate and free radicals: combinations to avoid. Radiat. Res. 1996, 145(5):532-541.
43. Halliwell B. Commentary: vitamin C: antioxidant or pro-oxidant in vivo?. Free Radic. Res. 1996, 25(5):439-454.