Amino acid derivatives as transdermal permeation enhancers

Journal of Controlled Release

Volumn 165, Issue 2, 2013, Pages 91-100

  Janůšová, Barbora ^a   Školová, Barbora ^a   Tükörová, Katarína ^a   Wojnarová, Lea ^a   Šimůnek, Tomáš ^a   Mladěnka, Přemysl ^a   Filipský, Tomáš ^a   Říha, Michal ^a   Roh, Jaroslav ^a   Palát, Karel ^a   Hrabálek, Alexandr ^a   Vávrová, Kateřina ^a  

^a Charles University in Prague Faculty of Pharmacy   (Czech Republic)

Author keywords

Amino acid; in vitro in vivo skin absorption; Penetration enhancer; Stratum corneum; Transdermal drug delivery

Indexed keywords

AMINO ACID DERIVATIVES; BARRIER PROPERTIES; CELL LINES; CLINICAL USE; DOUBLE CHAIN; ELECTRICAL IMPEDANCE; ENHANCEMENT RATIOS; ENHANCING EFFECT; ESTER LINKS; HYDROPHOBIC CHAINS; IN-VIVO; KERATINOCYTES; LIQUID-ORDERED PHASE; MINIMAL EFFECTS; PENETRATION ENHANCERS; PROLINE DERIVATIVES; PROPYLENE GLYCOLS; SARCOSINE; SKIN ABSORPTION; SKIN PERMEABILITY; SKIN TOXICITY; STRATUM CORNEUM; STRATUM CORNEUM LIPIDS; TRANSDERMAL ABSORPTIONS; TRANSDERMAL DRUG DELIVERY; TRANSDERMAL PERMEATION; TRANSEPIDERMAL WATER LOSS;

CELL CULTURE; CONTROLLED DRUG DELIVERY; SKIN; TOXICITY;

AMINO ACIDS;

2 (DIMETHYLAMINO)PROPANOATE; ALANINE; AMINO ACID DERIVATIVE; BETA ALANINE; DODECYL 6 (DIMETHYLAMINO)HEXANOATE; GLYCINE; HYDROCORTISONE; LAUROCAPRAM; PENETRATION ENHANCING AGENT; PROLINE; PROLINE 2; PROPYLENE GLYCOL; SARCOSINE; THEOPHYLLINE; TRANSKARBAM 12; UNCLASSIFIED DRUG;

ANIMAL TISSUE; ARTICLE; CELL VIABILITY; CONTROLLED STUDY; DRUG PENETRATION; FIBROBLAST; HUMAN; HUMAN CELL; HYDROPHILICITY; HYDROPHOBICITY; IC 50; KERATINOCYTE; NONHUMAN; PRIORITY JOURNAL; RAT; SKIN TOXICITY; SKIN WATER LOSS; STEREOCHEMISTRY; STRATUM CORNEUM; TRANSDERMAL DRUG ADMINISTRATION;

3T3 CELLS; ADMINISTRATION, CUTANEOUS; AMINO ACIDS; ANIMALS; CELL LINE; DRUG STABILITY; HUMANS; KERATINOCYTES; MICE; PERMEABILITY; PLASMA; PROLINE; RATS; SKIN; SKIN ABSORPTION; SWINE;

EID: 84870663917     PISSN: 01683659     EISSN: 18734995     Source Type: Journal    
DOI: 10.1016/j.jconrel.2012.11.003     Document Type: Article

References (70)

1. T.M. Suhonen, J.A. Bouwstra, and A. Urtti Chemical enhancement of percutaneous absorption in relation to stratum corneum structural alterations J. Control. Release 59 2 1999 149 161
2. B.W. Barry Novel mechanisms and devices to enable successful transdermal drug delivery Eur. J. Pharm. Sci. 14 2 2001 101 114
3. A.C. Williams, and B.W. Barry Penetration enhancers Adv. Drug Deliv. Rev. 56 5 2004 603 618
4. D. Kaushik, P. Batheja, B. Kilfoyle, V. Rai, and B. Michniak-Kohn Percutaneous permeation modifiers: enhancement versus retardation Expert Opin. Drug Deliv. 5 5 2008 517 529
5. M.R. Prausnitz, and R. Langer Transdermal drug delivery Nat. Biotechnol. 26 11 2008 1261 1268
6. K. Vavrova, J. Zbytovska, and A. Hrabalek Amphiphilic transdermal permeation enhancers: structure-activity relationships Curr. Med. Chem. 12 19 2005 2273 2291
7. E.R. Cooper, Penetrating topical pharmaceutical compositions containing N-(2-hydroxyethyl)pyrrolidone. US 4,537,776 (1985).
8. E.R. Cooper Increased skin permeability for lipophilic molecules J. Pharm. Sci. 73 8 1984 1153 1156
9. M.L. Francoeur, R.O. Potts, Topical compositions of lipophilic pharmaceutical agents. US 4,959,365 (1990).
10. E.R. Cooper, Penetrating topical pharmaceutical compositions containing 9-(2-hydroxyethoxymethyl)guanine. EP 0,095,813 (1983).
11. E.R. Cooper, Penetrating topical pharmaceutical compositions containing 1-dodecyl-azacycloheptan-2-one. US 4,557,934 (1985).
12. M.L. Francoeur, R.O. Potts, Transdermal flux enhancing compositions to treat hypertension, diabetes and angina pectoris. US 5,391,548 (1995).
13. M.L. Francoeur, R.O. Potts, Transdermal flux enhancing compositions. US 5,196,410 (1993).
14. S. Andega, N. Kanikkannan, and M. Singh Comparison of the effect of fatty alcohols on the permeation of melatonin between porcine and human skin J. Control. Release 77 1-2 2001 17 25
15. N. Kanikkannan, K. Kandimalla, S.S. Lamba, and M. Singh Structure-activity relationship of chemical penetration enhancers in transdermal drug delivery Curr. Med. Chem. 7 6 2000 593 608
16. S. Buyuktimkin, N. Buyuktimkin, and J.H. Rytting Synthesis and enhancing effect of dodecyl 2-(N, N-dimethylamino)propionate on the transepidermal delivery of indomethacin, clonidine, and hydrocortisone Pharm. Res. 10 11 1993 1632 1637
17. P. Karande, A. Jain, K. Ergun, V. Kispersky, and S. Mitragotri Design principles of chemical penetration enhancers for transdermal drug delivery Proc. Natl. Acad. Sci. U. S. A. 102 13 2005 4688 4693
18. P. Karande, A. Jain, and S. Mitragotri Discovery of transdermal penetration enhancers by high-throughput screening Nat. Biotechnol. 22 2 2004 192 197
19. P. Karande, and S. Mitragotri High throughput screening of transdermal formulations Pharm. Res. 19 5 2002 655 660
20. A. Arora, E. Kisak, P. Karande, J. Newsam, and S. Mitragotri Multicomponent chemical enhancer formulations for transdermal drug delivery: more is not always better J. Control. Release 144 2 2010 175 180
21. P. Karande, A. Jain, A. Arora, M.J. Ho, and S. Mitragotri Synergistic effects of chemical enhancers on skin permeability: a case study of sodium lauroylsarcosinate and sorbitan monolaurate Eur. J. Pharm. Sci. 31 1 2007 1 7
22. P. Karande, A. Jain, and S. Mitragotri Insights into synergistic interactions in binary mixtures of chemical permeation enhancers for transdermal drug delivery J. Control. Release 115 1 2006 85 93
23. A. Hrabalek, P. Dolezal, K. Vavrova, J. Zbytovska, T. Holas, J. Klimentova, and J. Novotny Synthesis and enhancing effect of transkarbam 12 on the transdermal delivery of theophylline, clotrimazole, flobufen, and griseofulvin Pharm. Res. 23 5 2006 912 919
24. M. Novotny, J. Klimentova, B. Janusova, K. Palat, A. Hrabalek, and K. Vavrova Ammonium carbamates as highly active transdermal permeation enhancers with a dual mechanism of action J. Control. Release 150 2 2011 164 170
25. K. Vavrova, A. Hrabalek, P. Dolezal, T. Holas, and J. Klimentova Biodegradable derivatives of tranexamic acid as transdermal permeation enhancers J. Control. Release 104 1 2005 41 49
26. J. Novotny, P. Kovarikova, M. Novotny, B. Janusova, A. Hrabalek, and K. Vavrova Dimethylamino acid esters as biodegradable and reversible transdermal permeation enhancers: effects of linking chain length, chirality and polyfluorination Pharm. Res. 26 4 2009 811 821
27. K. Vavrova, P. Kovarikova, B. Skolova, M. Libalova, J. Roh, R. Cap, A. Holy, and A. Hrabalek Enhanced topical and transdermal delivery of antineoplastic and antiviral acyclic nucleoside phosphonate cPr-PMEDAP Pharm. Res. 28 12 2011 3105 3115
28. K. Vavrova, K. Lorencova, J. Novotny, A. Holy, and A. Hrabalek Permeation enhancer dodecyl 6-(dimethylamino)hexanoate increases transdermal and topical delivery of adefovir: influence of pH, ion-pairing and skin species Eur. J. Pharm. Biopharm. 70 3 2008 901 907
29. K. Vavrova, A. Hrabalek, P. Dolezal, T. Holas, and J. Zbytovska l-Serine and glycine based ceramide analogues as transdermal permeation enhancers: polar head size and hydrogen bonding Bioorg. Med. Chem. Lett. 13 14 2003 2351 2353
30. K. Vavrova, A. Hrabalek, P. Dolezal, L. Samalova, K. Palat, J. Zbytovska, T. Holas, and J. Klimentova Synthetic ceramide analogues as skin permeation enhancers: structure-activity relationships Bioorg. Med. Chem. 11 24 2003 5381 5390
31. K. Vávrová, A. Hrabálek, S. Mac-Mary, P. Humbert, and P. Muret Ceramide analogue 14S24 selectively recovers perturbed human skin barrier Br. J. Dermatol. 157 4 2007 704 712
32. K. Vávrová, J. Zbytovská, K. Palát, T. Holas, J. Klimentová, A. Hrabálek, and P. Doležal Ceramide analogue 14S24 ((S)-2-tetracosanoylamino-3-hydroxypropionic acid tetradecyl ester) is effective in skin barrier repair in vitro Eur. J. Pharm. Sci. 21 5 2004 581 587
33. W.T. Harris, S.N. Tenjarla, J.M. Holbrook, J. Smith, C. Mead, and J. Entrekin n-pentyl N-acetylprolinate. A new skin penetration enhancer J. Pharm. Sci. 84 5 1995 640 642
34. S.N. Tenjarla, R. Kasina, P. Puranajoti, M.S. Omar, and W.T. Harris Synthesis and evaluation of N-acetylprolinate esters - novel skin penetration enhancers Int. J. Pharm. 192 2 1999 147 158
35. Y.C. Kim, J.H. Park, P.J. Ludovice, and M.R. Prausnitz Synergistic enhancement of skin permeability by N-lauroylsarcosine and ethanol Int. J. Pharm. 352 1-2 2008 129 138
36. O.W. Ackaert, J. De Graan, R. Capancioni, O.E. Della Pasqua, D. Dijkstra, B.H. Westerink, M. Danhof, and J.A. Bouwstra The in vitro and in vivo evaluation of new synthesized prodrugs of 5-OH-DPAT for iontophoretic delivery J. Control. Release 144 3 2010 296 305
37. R.B. Stoughton Enhanced percutaneous penetration with 1-dodecylazacycloheptan-2-one Arch. Dermatol. 118 7 1982 474 477
38. W.J. Fasano, and P.M. Hinderliter The Tinsley LCR Databridge Model 6401 and electrical impedance measurements to evaluate skin integrity in vitro Toxicol. in Vitro 18 5 2004 725 729
39. A.M. Kligman, and E. Christophers Preparation of isolated sheets of human stratum corneum Arch. Dermatol. 88 1963 702 705
40. E.G. Bligh, and W.J. Dyer A rapid method of total lipid extraction and purification Can. J. Biochem. Physiol. 37 8 1959 911 917
41. E.R. Cooper, E.W. Merritt, and R.L. Smith Effect of fatty acids and alcohols on the penetration of acyclovir across human skin in vitro J. Pharm. Sci. 74 6 1985 688 689
42. V.H. Mak, R.O. Potts, and R.H. Guy Percutaneous penetration enhancement in vivo measured by attenuated total reflectance infrared spectroscopy Pharm. Res. 7 8 1990 835 841
43. I.H. Blank, and J.E. Finesinger Electrical resistance of the skin; effect of size of electrodes, exercise and cutaneous hydration Arch. Neurol. Psychiatry 56 5 1946 544 557
44. G. Bernard, M. Auger, J. Soucy, and R. Pouliot Physical characterization of the stratum corneum of an in vitro psoriatic skin model by ATR-FTIR and Raman spectroscopies Biochim. Biophys. Acta 1770 9 2007 1317 1323
45. A. Naik, L.A.R.M. Pechtold, R.O. Potts, and R.H. Guy Mechanism of oleic acid-induced skin penetration enhancement in vivo in humans J. Control. Release 37 3 1995 299 306
46. B. Ongpipattanakul, R.R. Burnette, R.O. Potts, and M.L. Francoeur Evidence that oleic acid exists in a separate phase within stratum corneum lipids Pharm. Res. 8 3 1991 350 354
47. E. Brief, S. Kwak, J.T. Cheng, N. Kitson, J. Thewalt, and M. Lafleur Phase behavior of an equimolar mixture of N-palmitoyl-d-erythro-sphingosine, cholesterol, and palmitic acid, a mixture with optimized hydrophobic matching Langmuir 25 13 2009 7523 7532
48. C. Pare, M. Lafleur, F. Liu, R.N. Lewis, and R.N. McElhaney Differential scanning calorimetry and (2)H nuclear magnetic resonance and Fourier transform infrared spectroscopy studies of the effects of transmembrane alpha-helical peptides on the organization of phosphatidylcholine bilayers Biochim. Biophys. Acta 1511 1 2001 60 73
49. V. Velkova, and M. Lafleur Influence of the lipid composition on the organization of skin lipid model mixtures: an infrared spectroscopy investigation Chem. Phys. Lipids 117 1-2 2002 63 74
50. J. Pinnagoda, R.A. Tupker, T. Agner, and J. Serup Guidelines for transepidermal water loss (TEWL) measurement. A report from the Standardization Group of the European Society of Contact Dermatitis Contact Dermatitis 22 3 1990 164 178
51. J. Novotny, A. Hrabalek, and K. Vavrova Synthesis and structure-activity relationships of skin ceramides Curr. Med. Chem. 17 21 2010 2301 2324
52. J. van Smeden, L. Hoppel, R. van der Heijden, T. Hankemeier, R.J. Vreeken, and J.A. Bouwstra LC/MS analysis of stratum corneum lipids: ceramide profiling and discovery J. Lipid Res. 52 6 2011 1211 1221
53. M. Novotny, A. Hrabalek, B. Janusova, J. Novotny, and K. Vavrova Dicarboxylic acid esters as transdermal permeation enhancers: effects of chain number and geometric isomers Bioorg. Med. Chem. Lett. 19 2 2009 344 347
54. J. Novotny, B. Janusova, M. Novotny, A. Hrabalek, and K. Vavrova Short-chain ceramides decrease skin barrier properties Skin Pharmacol. Physiol. 22 1 2009 22 30
55. J. Novotny, K. Pospechova, A. Hrabalek, R. Cap, and K. Vavrova Synthesis of fluorescent C24-ceramide: evidence for acyl chain length dependent differences in penetration of exogenous NBD-ceramides into human skin Bioorg. Med. Chem. Lett. 19 24 2009 6975 6977
56. K. Vavrova, A. Hrabalek, and P. Dolezal Enhancement effects of (R) and (S) enantiomers and the racemate of a model enhancer on permeation of theophylline through human skin Arch. Dermatol. Res. 294 8 2002 383 385
57. S. Mitragotri Modeling skin permeability to hydrophilic and hydrophobic solutes based on four permeation pathways J. Control. Release 86 1 2003 69 92
58. J.E. Seto, B.E. Polat, B. Vanveller, R.F. Lopez, R. Langer, and D. Blankschtein Fluorescent penetration enhancers for transdermal applications J. Control. Release 158 1 2012 85 92
59. P. Karande, A. Jain, and S. Mitragotri Relationships between skin's electrical impedance and permeability in the presence of chemical enhancers J. Control. Release 110 2 2006 307 313
60. S.Y. Oh, L. Leung, D. Bommannan, R.H. Guy, and R.O. Potts Effect of current, ionic strength and temperature on the electrical properties of skin J. Control. Release 27 1993 115 125
61. R.O. Potts, R.H. Guy, and M.L. Francoeur Routes of ionic permeability through mammalian skin Solid State Ionics 53-56 1992 165 169
62. N.G. Turner, Y.N. Kalia, and R.H. Guy The effect of current on skin barrier function in vivo: recovery kinetics post-iontophoresis Pharm. Res. 14 9 1997 1252 1257
63. C. Curdy, Y.N. Kalia, and R.H. Guy Post-iontophoresis recovery of human skin impedance in vivo Eur. J. Pharm. Biopharm. 53 1 2002 15 21
64. Y.N. Kalia, and R.H. Guy Interaction between penetration enhancers and iontophoresis: effect on human skin impedance in vivo J. Control. Release 44 1 1997 33 42
65. S.Y. Lin, K.J. Duan, and T.C. Lin Simultaneous determination of the protein conversion process in porcine stratum corneum after pretreatment with skin enhancers by a combined microscopic FT-IR/DSC system Spectrochim. Acta A 52 12 1996 1671 1678
66. F.P. Schmook, J.G. Meingassner, and A. Billich Comparison of human skin or epidermis models with human and animal skin in in-vitro percutaneous absorption Int. J. Pharm. 215 1-2 2001 51 56
67. M.J. Bartek, J.A. LaBudde, and H.I. Maibach Skin permeability in vivo: comparison in rat, rabbit, pig and man J. Invest. Dermatol. 58 3 1972 114 123
68. E.M. Niazy Differences in penetration-enhancing effect of Azone through excised rabbit, rat, hailess mouse, guinea pig and human skins Int. J. Pharm. 130 1996 225 230
69. A. Ahad, M. Aqil, K. Kohli, Y. Sultana, M. Mujeeb, and A. Ali Role of novel terpenes in transcutaneous permeation of valsartan: effectiveness and mechanism of action Drug Dev. Ind. Pharm. 37 5 2011 583 596
70. A. Ahad, M. Aqil, K. Kohli, Y. Sultana, M. Mujeeb, and A. Ali Interactions between novel terpenes and main components of rat and human skin: mechanistic view for transdermal delivery of propranolol hydrochloride Curr. Drug Deliv. 8 2 2011 213 224