On the correlation between the structure of lyotropic carriers and the delivery profiles of two common NSAIDs

Colloids and Surfaces B: Biointerfaces

Volumn 122, Issue , 2014, Pages 231-240

  Cohen Avrahami, Marganit ^a   Shames, Alexander I ^b   Ottaviani, M Francesca ^c   Aserin, Abraham ^a   Garti, Nissim ^a  

^a HEBREW UNIVERSITY OF JERUSALEM   (Israel)

^b BEN GURION UNIVERSITY OF THE NEGEV   (Israel)

^c UNIVERSITY OF URBINO   (Italy)

Author keywords

ATR FTIR; EPR; Liquid crystals; NSAID; SAXS; Transdermal drug delivery

Indexed keywords

LAMELLAR STRUCTURES; LIQUID CRYSTALS; PARAMAGNETIC RESONANCE; SODIUM; SOLUBILITY;

ATR FTIR; LAMELLAR MESOPHASES; NON-STEROIDAL ANTI-INFLAMMATORY DRUGS; NSAID; RELEASE EXPERIMENTS; SAXS; STRUCTURE-BREAKERS; TRANSDERMAL DRUG DELIVERY;

DRUG INTERACTIONS;

AMPHOPHILE; CELECOXIB; DICLOFENAC; DRUG CARRIER; NONSTEROID ANTIINFLAMMATORY AGENT;

ARTICLE; ATOM TRANSFER RADICAL POLYMERIZATION; DIFFUSION; DRUG DELIVERY SYSTEM; DRUG FORMULATION; DRUG RELEASE; DRUG STRUCTURE; ELECTRON SPIN RESONANCE; FOURIER TRANSFORM MASS SPECTROMETRY; GASTROINTESTINAL HEMORRHAGE; HUMAN; HYDROGEN BOND; HYDROPHOBICITY; KIDNEY INJURY; LIPOPHILICITY; NUCLEAR MAGNETIC RESONANCE; PRIORITY JOURNAL; SOLUBILIZATION; TRANSDERMAL DRUG ADMINISTRATION; ULCER; INFRARED SPECTROSCOPY; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; SMALL ANGLE SCATTERING; X RAY DIFFRACTION;

ANTI-INFLAMMATORY AGENTS, NON-STEROIDAL; DRUG CARRIERS; ELECTRON SPIN RESONANCE SPECTROSCOPY; MAGNETIC RESONANCE SPECTROSCOPY; SCATTERING, SMALL ANGLE; SPECTROSCOPY, FOURIER TRANSFORM INFRARED; X-RAY DIFFRACTION;

EID: 84904579876     PISSN: 09277765     EISSN: 18734367     Source Type: Journal    
DOI: 10.1016/j.colsurfb.2014.04.026     Document Type: Article

References (60)

1. Negrini R., Mezzenga R. pH-responsive lyotropic liquid crystals for controlled drug delivery. Langmuir 2011, 27:5296-5303.
2. Zabara A., Amar-Yuli I., Mezzenga R. Tuning in-meso-crystallized lysozyme polymorphism by lyotropic liquid crystal symmetry. Langmuir 2011, 27:6418-6425.
3. Chorilli M., Prestes P.S., Rigon R.B., Leonardi G.R., Chiavacci L.A., Sarmento V.H.V., Oliveira A.G., Scarpa M.V. Structural characterization and in vivo evaluation of retinyl palmitate in non-ionic lamellar liquid crystalline system. Colloids Surf. B 2011, 85:182-188.
4. El Maghraby G.M. Self-microemulsifying and microemulsion systems for transdermal delivery of indomethacin: effect of phase transition. Colloids Surf. B 2010, 75:595-600.
5. II mesophases. J. Phys. Chem. B 2011, 115:825-835.
6. Imberg A. On the microstructures of ethyl acetate/monoolein/water. Colloids Surf. B 2006, 53:233-240.
7. Tavano L., Gentile L., Rossi C.O., Muzzalupo R. Novel gel-niosomes formulations as multicomponent systems for transdermal drug delivery. Colloids Surf. B 2013, 110:281-288.
8. Rengstl D., Diat O., Klein R., Kunz W.W. Influence of chain length and double bond on the aqueous behavior of choline carboxylate soaps. Langmuir 2013, 29:2506-2519.
9. Zetzl A., Ollivon M., Marangoni A. A coupled differential scanning calorimetry and X-ray study of the mesomorphic phases of monostearin and stearic acid in water. Cryst. Growth Des. 2009, 9:3928-3933.
10. Larsson K. Lyotropic liquid crystals and their dispersions relevant in foods. Curr. Opin. Colloid Interface Sci. 2009, 14:16-20.
11. Domenici F., Castellano C., Dell'Unto F., Congiu A. Temperature-dependent structural changes on DDAB surfactant assemblies evidenced by energy dispersive X-ray diffraction and dynamic light scattering. Colloids Surf. B 2012, 95:170-177.
12. Hughes N.E., Marangoni A.G., Wright A.J., Rogers M.A., Rush J.W.E. Potential food applications of edible oil organogels. Trends Food Sci. Technol. 2009, 20:470-480.
13. Engblöm J. Bicontinuous cubic phase: a model for investigating the effects on a lipid bilayer due to a foreign substance. Chem. Phys. Lipids 1996, 84:155-164.
14. Zhen G.L., Hinton T.M., Muir B.W., Shi S.N., Tizard M., McLean K.M., Hartley P.G., Gunatillake P. Glycerol monooleate-based nanocarriers for siRNA delivery in vitro. Mol. Pharm. 2012, 9:2450-2457.
15. Gustafsson J., Oradd G., Nyden M., Hansson P., Almgren M. Defective lamellar phases and micellar polymorphism in mixtures of glycerol monooleate and cetyltrimethylammonium bromide in aqueous solution. Langmuir 1998, 14:4987-4996.
16. Fraser S., Separovic F., Polyzos A. Cubic phases of ternary amphiphile-water systems. Eur. Biophys. J. Biophys. 2009, 39:83-90.
17. Wang Z.N., Zheng L.Q. Progress in cubic phase of lipid liquid crystal as drug delivery system. Prog. Chem. 2005, 17:417-422.
18. Efrat R., Aserin A., Kesselman E., Danino D., Wachtel E.J., Garti N. Liquid micellar discontinuous cubic mesophase from ternary monoolein/ethanol/water mixtures. Colloids Surf. A 2007, 299:133-145.
19. Helledi L.S., Schubert L. Release kinetics of acyclovir from a suspension of acyclovir incorporated in a cubic phase delivery system. Drug Dev. Ind. Pharm. 2001, 27:1073-1081.
20. Angelova A., Angelov B., Mutafchieva R., Lesieur S., Couvreur P. Self-assembled multicompartment liquid crystalline lipid carriers for protein, peptide, and nucleic acid drug delivery. Acc. Chem. Res. 2011, 44:147-156.
21. Vandoolaeghe P., Barauskas J., Johnsson M., Tiberg F., Nylander T. Interaction between lamellar (vesicles) and nonlamellar lipid liquid-crystalline nanoparticles as studied by time-resolved small-angle X-ray diffraction. Langmuir 2009, 25:3999-4008.
22. Qiu H., Caffrey M. Lyotropic and thermotropic phase behavior of hydrated monoacylglycerols: structure characterization of monovaccenin. J. Phys. Chem. B 1998, 102:4819-4829.
23. Angelov B., Angelova A., Ollivon M., Bourgaux C., Campitelli A. Diamond type lipid cubic phase with large water channels. J. Am. Chem. Soc. 2003, 125:7188-7189.
24. II mesophases of sodium diclofenac. J. Control. Release 2012, 159:419-428.
25. II mesophase and peptide cell-penetrating enhancers for improved transdermal delivery of sodium diclofenac. Colloids Surf. B 2010, 77:131-138.
26. Bitan-Cherbakovsky L., Aserin A., Garti N. Structural characterization of lyotropic liquid crystals containing a dendrimer for solubilization and release of gallic acid. Colloids Surf. B 2013, 112:87-95.
27. II mesophases monitored by electron paramagnetic resonance (EPR), small angle X-ray spectroscopy (SAXS), and attenuated total reflection Fourier transform spectroscopy (ATR-FTIR). J. Phys. Chem. B 2011, 115:8054-8062.
28. Angelov B., Angelova A., Papahadjopoulos-Sternberg B., Lesieur S., Sadoc J.-F., Ollivon M., Couvreur P. Detailed structure of diamond-type lipid cubic nanoparticles. J. Am. Chem. Soc. 2006, 128:5813-5817.
29. Sagalowicz L., Leser M.E., Watzke H.J., Michel M. Monoglyceride self-assembly structures as delivery vehicles. Trends Food Sci. Technol. 2006, 17:204-214.
30. Angelov B., Angelova A., Garamus V.M., Le Bas G., Lesieur S., Ollivon M., Funari S.S., Willumeit R., Couvreur P. Small-angle neutron and X-ray scattering from amphiphilic stimuli-responsive diamond type bicontinuous cubic phase. J. Am. Chem. Soc. 2007, 129:13474-13479.
31. Angelov B., Angelova A., Filippov S., Karlsson G., Terrill N., Lesieur S., Stepanek P. Topology and internal structure of PEGylated lipid nanocarriers for neuronal transfection: synchrotron radiation SAXS and cryo-TEM studies. Soft Matter 2011, 7:9714-9720.
32. Zielinska K., van Leeuwen H.P., Thibault S., Town R.M. Speciation analysis of aqueous nanoparticulate diclofenac complexes by solid-phase microextraction. Langmuir 2012, 28:14672-14680.
33. Hochberg M.C. New directions in symptomatic therapy for patients with osteoarthritis and rheumatoid arthritis. Semin. Arthritis Rheum. 2002, 32:4-14.
34. Singh G., Fort J.G., Goldstein J.L., Levy R.A., Hanrahan P.S., Bello A.E., Andrade-Ortega L., Wallemark C., Agrawal N.M., Eisen G.M., Stenson W.F., Triadafilopoulos G. Celecoxib versus naproxen and diclofenac in osteoarthritis patients: Success-I study. Am. J. Med. 2006, 119:255-266.
35. Hawkey C.J. COX-1 and COX-2 inhibitors. Best Pract. Res. Clin. Gastroenterol. 2001, 15:801-820.
36. Goldenberg M.M. Celecoxib, a selective cyclooxygenase-2 inhibitor for the treatment of rheumatoid arthritis and osteoarthritis. Clin. Ther. 1999, 21:1497-1513.
37. Shakeel F., Baboota S., Ahuja A., Ali J., Shafiq S. Skin permeation mechanism and bioavailability enhancement of celecoxib from transdermally applied nanoemulsion. J. Nanobiotechnol. 2008, 6:8-18.
38. Efrat R., Aserin A., Garti N. On structural transitions in a discontinuous micellar cubic phase loaded with sodium diclofenac. J. Colloid Interface Sci. 2008, 321:166-176.
39. Mao G., VanWyck D., Xiao X., Correa M.C.M., Gunn E., Flach C.R., Mendelsohn R., Walters R.M. Oleic acid disorders stratum corneum lipids in Langmuir monolayers. Langmuir 2013, 29:4857-4865.
40. Rodriguez G., Barbosa-Barros L., Rubio L., Cocera M., Diez A., Estelrich J., Pons R., Caelles J., De la Maza A., Lopez O. Conformational changes in stratum corneum lipids by effect of bicellar systems. Langmuir 2009, 25:10595-10603.
41. Zeng J.M., Tikare V., Jacob K.I. Numerical study of a drug release profile in the transdermal drug delivery system. Langmuir 2006, 22:1333-1340.
42. Huang Z.L., Hong J.Y., Chang C.H., Yang Y.M. Gelation of charged catanionic vesicles prepared by a semispontaneous process. Langmuir 2010, 26:2374-2382.
43. Cui Z.-K., Bouisse A., Cottenye N., Lafleur M. Formation of pH-sensitive cationic liposomes from a binary mixture of monoalkylated primary amine and cholesterol. Langmuir 2012, 28:13668-13674.
44. Bitan-Cherbakovsky L., Libster D., Ottaviani M.F., Aserin A., Garti N. Structural behavior and interactions of dendrimer within lyotropic liquid crystals, monitored by EPR spectroscopy and rheology. J. Phys. Chem. B 2012, 116:2420-2429.
45. Kogan A., Rozner S., Mehta S., Somasundaran P., Aserin A., Garti N., Ottaviani M.F. Characterization of the nonionic microemulsions by EPR. I. Effect of solubilized drug on nanostructure. J. Phys. Chem. B 2009, 113:691-699.
46. Rozner S., Kogan A., Mehta S., Somasundaran P., Aserin A., Garti N., Ottaviani M.F. Characterization of nonionic microemulsions by EPR. Part II. The effect of competitive solubilization of cholesterol and phytosterols on the nanostructure. J. Phys. Chem. B 2009, 113:700-707.
47. Budil D.E., Lee S., Saxena S., Freed J.H. Nonlinear-least-squares analysis of slow-motion EPR spectra in one and two dimensions using a modified Levenberg-Marquardt algorithm. J. Magn. Reson. Ser. A 1996, 120:155-189.
48. II) mesophase. J. Phys. Chem. B 2007, 111:13544-13553.
49. II mesophases: physical characterization and delivery. J. Phys. Chem. B 2011, 115:10189-10197.
50. Tsai Y.S., Ma S.M., Nishimura S., Ueda I. Infrared spectra of phospholipid membranes-interfacial dehydration by volatile anestethics and phase transition. Biochim. Biophys. Acta 1990, 1022:245-250.
51. Inoue T., Kawamura H., Matsuda M., Misono Y., Suzuki M. FT-IR and ESR spin-label studies of mesomorphic phases formed in aqueous mixtures of heptaethylene glycol dodecyl ether. Langmuir 2001, 17:6915-6922.
52. Nilsson A., Holmgren A., Lindblom G. An FTIR study of the hydration and molecular ordering at phase-transitions in the monoglycerol water system. Chem. Phys. Lipids 1994, 17:119-131.
53. Xu Y.H., Jia Y.X., Wang Z., Wang Z.J. Mathematical modeling and finite element simulation of slow release of drugs using hydrogels as carriers with various drug concentration distributions. J. Pharm. Sci. 2013, 102:1532-1543.
54. Higuchi T. Mechanism of sustained-action medication. Theoretical analysis of rate of release of solid drugs dispersed in solid matrices. J. Pharm. Sci. 1963, 52:1145-1149.
55. Lee P.I. Novel-approach to zero-order drug delivery via immobilized nonuniform drug distribution in glassy hydrogels. J. Pharm. Sci. 1984, 73:1344-1347.
56. Fong W.K., Hanley T., Boyd B.J. Stimuli responsive liquid crystals provide 'on-demand' drug delivery in vitro and in vivo. J. Control. Release 2009, 135:218-226.
57. Lee K.W.Y., Nguyen T.H., Hanley T., Boyd B.J. Nanostructure of liquid crystalline matrix determines in vitro sustained release and in vivo oral absorption kinetics for hydrophilic model drugs. Int. J. Pharm. 2009, 365:190-199.
58. Chang C.M., Bodmeier R. Low viscosity monoglyceride-based drug delivery systems transforming into a highly viscous cubic phase. Int. J. Pharm. 1998, 173:51-60.
59. Kossena G.A., Charman W.N., Boyd B.J., Porter C.J.H. A novel cubic phase of medium chain lipid origin for the delivery of poorly water soluble drugs. J. Control. Release 2004, 99:217-229.
60. Kossena G.A., Charman W.N., Boyd B.J., Porter C.I.H. Influence of the intermediate digestion phases of common formulation lipids on the absorption of a poorly water-soluble drug. J. Pharm. Sci. 2005, 94:481-492.