Penetratin-induced transdermal delivery from H II mesophases of sodium diclofenac

Journal of Controlled Release

Volumn 159, Issue 3, 2012, Pages 419-428

  Cohen Avrahami, Marganit ^a   Libster, Dima ^a   Aserin, Abraham ^a   Garti, Nissim ^a  

^a HEBREW UNIVERSITY OF JERUSALEM   (Israel)

Author keywords

Cell penetrating peptides; Hexagonal liquid crystals; Penetratin; SD NMR; Skin FTIR spectroscopy; Transdermal delivery systems

Indexed keywords

CELL-PENETRATING PEPTIDE; FTIR SPECTROSCOPY; PENETRATIN; SD-NMR; TRANSDERMAL DELIVERY;

FOURIER TRANSFORM INFRARED SPECTROSCOPY; GLYCEROL; LIQUID CRYSTALS; PEPTIDES; RESERVOIRS (WATER);

SODIUM;

DICLOFENAC; GLYCEROL OLEATE; PENETRATIN; SKIN LIPID; WATER;

ARTICLE; CONTROLLED STUDY; DEHYDRATION; DRUG DIFFUSION; FOURIER TRANSFORM INFRARED PHOTOACOUSTIC SPECTROSCOPY; GEL; HUMAN; INFRARED SPECTROSCOPY; NUCLEAR MAGNETIC RESONANCE; PRIORITY JOURNAL; STRATUM CORNEUM;

ADMINISTRATION, CUTANEOUS; ANIMALS; ANTI-INFLAMMATORY AGENTS, NON-STEROIDAL; CARRIER PROTEINS; DICLOFENAC; DIFFUSION; DRUG CARRIERS; GLYCERIDES; HYDROPHOBIC AND HYDROPHILIC INTERACTIONS; LIQUID CRYSTALS; MAGNETIC RESONANCE SPECTROSCOPY; MICROSCOPY, POLARIZATION; MODELS, CHEMICAL; OCTANOIC ACIDS; SKIN; SOLUBILITY; SPECTROSCOPY, FOURIER TRANSFORM INFRARED; SUS SCROFA; TRIGLYCERIDES;

EID: 84860666078     PISSN: 01683659     EISSN: 18734995     Source Type: Journal    
DOI: 10.1016/j.jconrel.2012.01.025     Document Type: Article

References (71)

1. A. Zabara, I. Amar-Yuli, and R. Mezzenga Tuning in-meso-crystallized lysozyme polymorphism by lyotropic liquid crystal symmetry Langmuir 27 2011 6418 6425
2. R. Negrini, and R. Mezzenga pH-responsive lyotropic liquid crystals for controlled drug delivery Langmuir 27 2011 5296 5303
3. P.B. Geraghty, D. Attwood, J.H. Collett, and Y. Dandiker The in vitro release of some antimuscarinic drugs from monoolein/water lyotropic liquid crystalline gels Pharm. Res. 13 1996 1265 1271
4. II mesophases J. Phys. Chem. B 115 2011 825 835
5. T. Mishraki, D. Libster, A. Aserin, and N. Garti Temperature-dependent behavior of lysozyme within the reverse hexagonal mesophases Colloids Surf. B Biointerfaces 75 2010 391 397
6. II) mesophase J. Phys. Chem. B 111 2007 13544 13553
7. D. Libster, D. Yariv, A. Aserin, and N. Garti Concentration- and temperature-induced effects of incorporated desmopressin on the properties of reverse hexagonal mesophase J. Phys. Chem. B 113 2009 6336 6346
8. D. Libster, P. Ben Ishai, A. Aserin, and N. Garti Molecular interactions in reverse hexagonal mesophase in the presence of cyclosporin A Int. J. Pharm. 367 2009 115 126
9. G. Cevc, and U. Vierl Nanotechnology and the transdermal route: a state of the art review and critical appraisal J. Control. Release 141 2010 277 299
10. M. Novotný, J. Klimentová, B. Janůšová, K. Palát, A. Hrabálek, and K. Vávrová Ammonium carbamates as highly active transdermal permeation enhancers with a dual mechanism of action J. Control. Release 150 2011 164 170
11. S. Hatziantoniou, S. Rallis, C. Demetzos, and G.T. Papaionnou Pharmacological activity of natural lipids on skin barrier disruption model Pharmacol. Res. 42 2000 55 59
12. I.T. Degim, D.J. Burgess, and F. Papadimitrakopoulos Carbon nanotubes for transdermal drug delivery J. Microencapsul. 27 2010 669 681
13. B.E. Polat, D. Hart, R. Langer, and D. Blankschtein Ultrasound-mediated transdermal drug delivery: mechanisms, scope, and emerging trends J. Control. Release 152 2011 330 348
14. Y.W. Chien, P. Lelawongs, O. Siddiqui, Y. Sun, and W.M. Shi Facilitated transdermal delivery of therapeutic peptides and proteins by iontophoretic delivery devices J. Control. Release 13 1990 263 278
15. Y. Henchoz, N. Abla, J.-L. Veuthey, and P.-A. Carrupt A fast screening strategy for characterizing peptide delivery by transdermal iontophoresis J. Control. Release 137 2009 123 129
16. S.N. Murthy, S.M. Sammeta, and C. Bowers Magnetophoresis for enhancing transdermal drug delivery: mechanistic studies and patch design J. Control. Release 148 2010 197 203
17. R. Vanbever, G. Langers, S. Montmayeur, and V. Préat Transdermal delivery of fentanyl: rapid onset of analgesia using skin electroporation J. Control. Release 50 1998 225 235
18. H. Chen, H. Zhu, J. Zheng, D. Mou, J. Wan, J. Zhang, T. Shi, Y. Zhao, H. Xu, and X. Yang Iontophoresis-driven penetration of nanovesicles through microneedle-induced skin microchannels for enhancing transdermal delivery of insulin J. Control. Release 139 2009 63 72
19. A.C. Sintov, I. Krymberk, D. Daniel, T. Hannan, Z. Sohn, and G. Levin Radiofrequency-driven skin microchanneling as a new way for electrically assisted transdermal delivery of hydrophilic drugs J. Control. Release 89 2003 311 320
20. W.-R. Lee, T.-L. Pan, P.-W. Wang, R.-Z. Zhuo, C.-M. Huang, and J.-Y. Fang Erbium: YAG laser enhances transdermal peptide delivery and skin vaccination J. Control. Release 128 2008 200 208
21. J.W. Lee, P. Gadiraju, J.-H. Park, M.G. Allen, and M.R. Prausnitz Microsecond thermal ablation of skin for transdermal drug delivery J. Control. Release 154 2011 58 68
22. K. Kigasawa, K. Kajimoto, T. Nakamura, S. Hama, K. Kanamura, H. Hideyoshi, and K. Kogure Noninvasive and efficient transdermal delivery of CpG-oligodeoxynucleotide for cancer immunotherapy J. Control. Release 150 2011 256 265
23. P. Säälik, A. Niinep, J. Pae, M. Hansen, D. Lubenets, Ü. Langel, and M. Pooga Penetration without cells: membrane translocation of cell-penetrating peptides in the model giant plasma membrane vesicles J. Control. Release 153 2011 117 125
24. E.-S. Khafagy, M. Morishita, K. Isowa, J. Imai, and K. Takayama Effect of cell-penetrating peptides on the nasal absorption of insulin J. Control. Release 133 2009 103 108
25. A. Takahashi, S. Suzuki, N. Kawasaki, W. Kubo, S. Miyazaki, R. Loebenberg, J. Bachynsky, and D. Attwood Percutaneous absorption of non-steroidal anti-inflammatory drugs from in situ gelling xyloglucan formulations in rats Int. J. Pharm. 246 2002 179 186
26. II mesophase and peptide cell-penetrating enhancers for improved transdermal delivery of sodium diclofenac Colloids Surf. B Biointerfaces 77 2010 131 138
27. T. Letoha, S. Gaal, C. Somlai, A. Czajlik, A. Perczel, and B. Penke Membrane translocation of penetratin and its derivatives in different cell lines J. Mol. Recognit. 16 2003 272 279
28. S. Deshayes, M.C. Morris, G. Divita, and F. Heitz Cell-penetrating peptides: tools for intracellular delivery of therapeutics Cell. Mol. Life Sci. 62 2005 1839 1849
29. A. Czajlik, E. Mesko, B. Penke, and A. Perczel Investigation of penetratin peptides. Part 1. The environment dependent conformational properties of penetratin and two of its derivatives J. Pept. Sci. 8 2002 151 171
30. E.-S. Khafagy, M. Morishita, N. Ida, R. Nishio, K. Isowa, and K. Takayama Structural requirements of penetratin absorption enhancement efficiency for insulin delivery J. Control. Release 143 2010 302 310
31. H. Binder, and G. Lindblom Charge-dependent translocation of the Trojan peptide penetratin across lipid membranes Biophys. J. 85 2003 982 995
32. H. Binder, and G. Lindblom A molecular view on the interaction of the Trojan peptide penetratin with the polar interface of lipid bilayers Biophys. J. 87 2004 332 343
33. J. Lee, E. Jung, J. Park, and D. Park Transdermal delivery of interferon-gamma (IFN-gamma) mediated by penetratin, a cell-permeable peptide Biotechnol. Appl. Biochem. 42 2005 169 173
34. A.C. Sintov, and S. Botner Transdermal drug delivery using microemulsion and aqueous systems: influence of skin storage conditions on the in vitro permeability of diclofenac from aqueous vehicle systems Int. J. Pharm. 311 2006 55 62
35. A. Llinas, J.C. Burley, K.J. Box, R.C. Glen, and J.M. Goodman Diclofenac solubility: independent determination of the intrinsic solubility of three crystal forms J. Med. Chem. 50 2007 979 983
36. II mesophases: physical characterization and delivery J. Phys. Chem. B 115 2011 10189 10197
37. R. Efrat, D.E. Shalev, R.E. Hoffman, A. Aserin, and N. Garti Effect of sodium diclofenac loads on mesophase components and structure Langmuir 24 2008 7590 7595
38. M. Magzoub, K. Kilk, L.E. Göran Eriksson, Ü. Langel, and A. Gräslund Interaction and structure induction of cell-penetrating peptides in the presence of phospholipid vesicles Biochim. Biophys. Acta 1512 2001 77 89
39. M. Magzoub, L.E. Eriksson, and A. Gräslund Conformational states of the cell-penetrating peptide penetratin when interacting with phospholipid vesicles: effects of surface charge and peptide concentration Biochim. Biophys. Acta 1563 2002 53 63
40. L. Coppola, C. Oliviero, L. Pogliani, G.A. Ranieri, and M. Terenzi A self-diffusion study in aqueous solution and lyotropic mesophases of amphiphilic block copolymers Colloid Polym. Sci. 5 2000 434 442
41. L. Coppola, C. Oliviero, U. Olsson, and G.A. Ranieri Characterization of a reverse hexagonal lyomesophase by a PGSE NMR water self-diffusion study Langmuir 16 2000 4180 4184
42. Y. Maitani, M. Kugo, M. Nakagaki, and T. Nagai Ionic size and behavior of diclofenac salts in water and ethanol/water mixtures by conductivity at 25 degrees C J. Pharm. Sci. 82 1993 1245 1249
43. W.J. Xu, and Y.Q. Yang Drug release and its relationship with kinetic and thermodynamic parameters of drug sorption onto starch acetate fibers Biotechnol. Bioeng. 105 2010 814 822
44. K.I. Momot, and P.W. Kuchel PFG NMR diffusion experiments for complex systems Concepts Magnetic Resonance A 28A 2006 249 269
45. A. Andersson, J. Almqvist, F. Hagn, and L. Mäler Diffusion and dynamics of penetratin in different membrane mimicking media Biochim. Biophys. Acta, Biomembr. 1661 2004 18 25
46. B.S. Zolnik, P.E. Leary, and D.J. Burgess Elevated temperature accelerated release testing of PLGA microspheres J. Control. Release 112 2006 293 300
47. E.M. Renkin Filtration, diffusion, and molecular sieving through porous cellulose membranes J. Gen. Physiol. 38 1954 225 243
48. A. Pluen, P.A. Netti, R.K. Jain, and D.A. Berk Diffusion of macromolecules in agarose gels: comparison of linear and globular configurations Biophys. J. 77 1999 542 552
49. R. Efrat, A. Aserin, and N. Garti On structural transitions in a discontinuous micellar cubic phase loaded with sodium diclofenac J. Colloid Interface Sci. 321 2008 166 176
50. V. Razumas, K. Larsson, Y. Miezis, and T. Nylander A cubic monoolein cytochrome c water phase: X-ray diffraction, FT-IR, differential scanning calorimetric, and electrochemical studies J. Phys. Chem. 100 1996 11766 11774
51. W. Hübner, and H.H. Mantsch Orientation of specifically C-13O labelled phosphatidylcholine multilayers from polarized attenuated total reflection FT-IR spectroscopy Biophys. J. 59 1996 1261 1272
52. N.A. Monteiro-Riviere, and J. Riviere The pig as a model for human skin research, swine in biomedical research: update on animal models The 56th AALAS National Meeting, St. Louis, MO Sep 2005 17 22
53. N.A. Monteiro-Riviere, and J. Riviere Advances in Swine in Biomedical Research 1996 Plenum Press New York 425 458
54. E.J. Calabrese Gastrointestinal and dermal absorption: interspecies differences Drug Metab. Rev. 15 1984 1013 1032
55. L.B. Lopes, J.L.C. Lopes, D.C.R. Oliveira, J.A. Thomazini, M.T.J. Garcia, M.C.A. Fantini, J.H. Collett, and M.V.L.B. Bentley Liquid crystalline phases of monoolein and water for topical delivery of cyclosporin A: characterization and study of in vitro and in vivo delivery Eur. J. Pharm. Biopharm. 63 2006 146 155
56. R. Mendelsohn, C.R. Flach, and D.J. Moore Determination of molecular conformation and permeation in skin via IR spectroscopy, microscopy, and imaging Biochim. Biophys. Acta 1758 2006 923 933
57. M. Boncheva, F. Damien, and V. Normand Molecular organization of the lipid matrix in intact stratum corneum using ATR-FTIR spectroscopy Biochim. Biophys. Acta 1778 2008 1344 1355
58. B. Forslind A domain mosaic model of the skin barrier Acta Derm. Venereol. 74 1994 1 6
59. B. Forslind, S. Engström, J. Engblom, and L. Norlén A novel approach to the understanding of human skin barrier function J. Dermatol. Sci. 14 1997 115 125
60. M. Lafleur Phase behaviour of model stratum corneum lipid mixtures: an infrared spectroscopy investigation Can. J. Chem. 76 1998 1501 1511
61. 2 + modulate the mixing properties of lipids in stratum corneum model mixtures Biophys. J. 92 2007 99 114
62. D.J. Moore, and M.E. Rerek Insights into the molecular organization of lipids in the skin barrier from infrared spectroscopy studies of stratum corneum lipid models Acta Derm. Venereol. Suppl. 208 2000 16 22
63. D.J. Moore, M.E. Rerek, and R. Mendelsohn FTIR spectroscopy studies of the conformational order and phase behavior of ceramides J. Phys. Chem. B 101 1997 8933 8940
64. J.A. Bouwstra, G.S. Gooris, W. Bras, and D.T. Downing Lipid organization in pig stratum corneum J. Lipid Res. 36 1995 685 695
65. J.A. Bouwstra, G.S. Gooris, F.E.R. Dubbelaar, and M. Ponec Phase behavior of lipid mixtures based on human ceramides: coexistence of crystalline and liquid phases J. Lipid Res. 42 2001 1759 1770
66. R.A. Dluhy, B.Z. Chowdhry, and D.G. Cameron Infrared characterization of conformational differences in the lamellar phases of 1,3-dipalmytoyl-sn-glycero- 2-phosphocholine Biochim. Biophys. Acta 821 1985 437 444
67. R.N.A.H. Lewis, and R.N. McElhaney FTIR spectroscopy in the study of hydrated lipids and lipid bilayer membranes H.H. Mantsch, D. Chapman, Infrared Spectroscopy of Biomolecules 1996 Wiley-Liss, Inc. 159 202
68. J. Umemura, D.G. Cameron, and H.H. Mantsch A Fourier-transform infrared spectroscopic study of the molecular interaction of cholesterol with 1,2-dipalmitoyl-sn-glycero-3-phosphocholine Biochim. Biophys. Acta 602 1980 32 44
69. H. Kandarova, M. Liebsch, I. Gerner, E. Schmidt, E. Genschow, D. Traue, and H. Spielmann The EpiDerm test protocol for the upcoming ECVAM validation study on in vitro skin irritation tests - an assessment of the performance of the optimised test Altern. Lab. Anim. 33 2005 351 367
70. M. Schäfer-Korting, U. Bock, W. Diembeck, H.J. Düsing, A. Gamer, E. Haltner-Ukomadu, C. Hoffmann, M. Kaca, H. Kamp, S. Kersen, M. Kietzmann, H.C. Korting, H.U. Krächter, C.M. Lehr, M. Liebsch, A. Mehling, C. Müller-Goymann, F. Netzlaff, F. Niedorf, M.K. Rübbelke, U. Schafer, E. Schmidt, S. Schreiber, H. Spielmann, A. Vuia, and M. Weimer The use of reconstructed human epidermis for skin absorption testing: results of the validation study Altern. Lab. Anim. 36 2008 161 187
71. H. Spielmann, S. Hoffmann, M. Liebsch, P. Botham, J.H. Fentem, C. Eskes, R. Roguet, J. Cotovio, T. Cole, A. Worth, J. Heylings, P. Jones, C. Robles, H. Kandarova, A. Gamer, M. Remmele, R. Curren, H. Raabe, A. Cockshott, I. Gerner, and V. Zuang The ECVAM international validation study on in vitro tests for acute skin irritation: report on the validity of the EPISKIN and EpiDerm assays and on the skin integrity function test Altern. Lab. Anim. 35 2007 559 601