Fluorescent penetration enhancers for transdermal applications

Journal of Controlled Release

Volumn 158, Issue 1, 2012, Pages 85-92

  Seto, Jennifer E ^a   Polat, Baris E ^a   Vanveller, Brett ^b   Lopez, Renata F V ^a,c   Langer, Robert ^a   Blankschtein, Daniel ^a  

^a Massachusetts Institute of Technology Cambridge   (United States)

^b MASSACHUSETTS INSTITUTE OF TECHNOLOGY   (United States)

^c UNIVERSITY OF SÃO PAULO   (Brazil)

Author keywords

Fluorescent amphiphiles; Lipid membrane fluorescent probe; Skin permeation enhancer; Surface active fluorescent dyes; Transdermal drug delivery; Two photon fluorescence microscopy

Indexed keywords

FLUORESCENT DYES; LIPID MEMBRANE FLUORESCENT PROBE; SKIN PERMEATION ENHANCER; TRANSDERMAL DRUG DELIVERY; TWO-PHOTON FLUORESCENCE MICROSCOPY;

AMPHIPHILES; GLYCEROL; LIPIDS; SKIN; VISUALIZATION;

FLUORESCENCE;

2 [3 CYANO 4 [4 (DODECYL METHYL AMINO)PHENYL] 5,5 DIMETHYL 5H FURAN 2 YLIDENE]MALONONITRILE; 5 CARBOXYTETRAMETHYLRHODAMINE; 5 DODECANOYLAMINOFLUORESCEIN; ACRIDINE ORANGE; AMPHOPHILE; FLUORESCENT DYE; GLYCEROL; METHYL ORANGE; PENETRATION ENHANCING AGENT; RHODAMINE 110; RHODAMINE 6G; RHODAMINE B; SULFORHODAMINE B; SULFORHODAMINE G; UNCLASSIFIED DRUG;

ANIMAL TISSUE; ARTICLE; AUTOFLUORESCENCE; CONTROLLED STUDY; DRUG ACTIVITY; DRUG SCREENING; FLUORESCENCE; FLUORESCENCE MICROSCOPY; HUMAN; HUMAN TISSUE; HYDROPHILICITY; IONIZATION; MOLECULAR WEIGHT; NONHUMAN; PRIORITY JOURNAL; SKIN; SKIN PENETRATION; STRUCTURE ACTIVITY RELATION; ULTRASOUND;

ADMINISTRATION, CUTANEOUS; ANIMALS; FLUORESCENT DYES; HUMANS; MICROSCOPY, FLUORESCENCE, MULTIPHOTON; SKIN; SKIN ABSORPTION; SWINE; ULTRASONICS;

EID: 84857923669     PISSN: 01683659     EISSN: 18734995     Source Type: Journal    
DOI: 10.1016/j.jconrel.2011.10.018     Document Type: Article

References (88)

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10. B.E. Polat, J.E. Seto, D. Blankschtein, and R. Langer Application of the aqueous porous pathway model to quantify the effect of sodium lauryl sulfate on ultrasound-induced skin structural perturbation J. Pharm. Sci. 100 4 2011 1387 1397
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17. B.E. Polat, S. Lin, J.D. Mendenhall, B. VanVeller, R. Langer, and D. Blankschtein Experimental and molecular dynamics investigation into the amphiphilic nature of sulforhodamine B J. Phys. Chem. B 115 6 2011 1394 1402
18. J.E. Seto, B.E. Polat, R.F.V. Lopez, D. Blankschtein, and R. Langer Effects of ultrasound and sodium lauryl sulfate on the transdermal delivery of hydrophilic permeants: comparative in vitro studies with full-thickness and split-thickness pig and human skin J. Control. Release 145 1 2010 26 32
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20. V.K. Rachakonda, K.M. Yerramsetty, S.V. Madihally, R.L. Robinson Jr., and K.A. Gasem Screening of chemical penetration enhancers for transdermal drug delivery using electrical resistance of skin Pharm. Res. 25 11 2008 2697 2704
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24. S. Ghosh, and D. Blankschtein The role of sodium dodecyl sulfate (SDS) micelles in inducing skin barrier perturbation in the presence of glycerol J. Cosmet. Sci. 58 2 2007 109 133
25. B.E. Polat, P.L. Figueroa, D. Blankschtein, and R. Langer Transport pathways and enhancement mechanisms within localized and non-localized transport regions in skin treated with low-frequency sonophoresis and sodium lauryl sulfate J. Pharm. Sci. 100 2 2011 512 529
26. J. Kushner, D. Blankschtein, and R. Langer Heterogeneity in skin treated with low-frequency ultrasound J. Pharm. Sci. 97 10 2008 4119 4128
27. E. Drakaki, E. Borisova, M. Makropoulou, L. Avramov, A.A. Serafetinides, and I. Angelov Laser induced autofluorescence studies of animal skin used in modeling of human cutaneous tissue spectroscopic measurements Skin Res. Technol. 13 4 2007 350 359 (Pubitemid 47506397)
28. B. Yu, C.-Y. Dong, P.T.C. So, D. Blankschtein, and R. Langer In vitro visualization and quantification of oleic acid induced changes in transdermal transport using two-photon fluorescence microscopy J. Invest. Dermatol. 117 1 2001 16 25 (Pubitemid 32652435)
29. R.H. Na, I.M. Stender, L.X. Ma, and H.C. Wulf Autofluorescence spectrum of skin: component bands and body site variations Skin Res. Technol. 6 3 2000 112 117 (Pubitemid 30459937)
30. M.R. Prausnitz, and R. Langer Transdermal drug delivery Nat. Biotechnol. 26 11 2008 1261 1268
31. D.M. Bagley, J.R. Gardner, G. Holland, R.W. Lewis, J.F. Regnier, D.A. Stringer, and A.P. Walker Skin irritation: reference chemicals data bank Toxicol. In Vitro 10 1 1996 1 6 (Pubitemid 26077098)
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33. H. Wang, Z. Lu, S.J. Lord, W.E. Moerner, and R.J. Twieg Modifications of DCDHF single molecule fluorophores to impart water solubility Tetrahedron Lett. 48 19 2007 3471 3474 (Pubitemid 46574777)
34. N. Kanikkannan, R.J. Babu, and M. Singh E.W. Smith, H.I. Maibach, Percutaneous Penetration Enhancers 2006 CRC Press Boca Raton, FL 17 33
35. 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 (Pubitemid 30396419)
36. K.S. Warner, S.K. Li, N. He, T.M. Suhonen, D. Chantasart, D. Bolikal, and W.I. Higuchi Structure-activity relationship for chemical skin permeation enhancers: probing the chemical microenvironment of the site of action J. Pharm. Sci. 92 6 2003 1305 1322 (Pubitemid 36676475)
37. 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
38. S. Ghosh, S. Hornby, G. Grove, C. Zerwick, Y. Appa, and D. Blankschtein Ranking of aqueous surfactant-humectant systems based on an analysis of in vitro and in vivo skin barrier perturbation measurements J. Cosmet. Sci. 58 6 2007 599 620
39. J. Kushner, D. Blankschtein, and R. Langer Experimental demonstration of the existence of highly permeable localized transport regions in low-frequency sonophoresis J. Pharm. Sci. 93 11 2004 2733 2745 (Pubitemid 39506624)
40. R. Alvarez-Roman, A. Naik, Y.N. Kalia, H. Fessi, and R.H. Guy Visualization of skin penetration using confocal laser scanning microscopy Eur. J. Pharm. Biopharm. 58 2 2004 301 316 (Pubitemid 39037237)
41. K.A. Walters M.S. Roberts K.A. Walters, Dermatological and Transdermal Formulations Vol. 119 2002 Marcel Dekker, Inc. New York 1 39
42. G.M. Golden, J.E. McKie, and R.O. Potts Role of stratum corneum lipid fluidity in transdermal drug flux J. Pharm. Sci. 76 1 1987 25 28 (Pubitemid 17023047)
43. E. Bodner, M. Afri, and A.A. Frimer Determining radical penetration into membranes using ESR splitting constants Free Radic. Biol. Med. 49 3 2010 427 436
44. A.C. Benniston, and G. Copley Lighting the way ahead with boron dipyrromethene (BODIPY) dyes Phys. Chem. Chem. Phys. 11 21 2009 4124 4131
45. A.C. Williams, and B.W. Barry Penetration enhancers Adv. Drug Deliv. Rev. 56 5 2004 603 618 (Pubitemid 38326936)
46. J.A. Nicolazzo, B.L. Reed, and B.C. Finnin Buccal penetration enhancers-how do they really work? J. Control. Release 105 1-2 2005 1 15 (Pubitemid 40805471)
47. Y. Sultana, M. Aqil, A. Ali, and A. Samad Advances in the topical ocular drug delivery Expert Rev. Ophthalmol. 2 2 2007 309 323
48. 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 (Pubitemid 40471515)
49. P. Karande, A. Jain, and S. Mitragotri Discovery of transdermal penetration enhancers by high-throughput screening Nat. Biotechnol. 22 2 2004 192 197 (Pubitemid 38160534)
50. A.P. Demchenko Introduction to Fluorescence Sensing 2009 Springer Dordrecht, Netherlands
51. J.W. Fluhr, R. Darlenski, and C. Surber Glycerol and the skin: holistic approach to its origin and functions Br. J. Dermatol. 159 1 2008 23 34 (Pubitemid 351874509)
52. B.E. Polat, D. Hart, R. Langer, and D. Blankschtein Ultrasound-mediated transdermal drug delivery: mechanisms, scope, and emerging trends J. Control. Release 152 3 2011 330 348
53. B.E. Polat, D. Blankschtein, and R. Langer Low-frequency sonophoresis: application to the transdermal delivery of macromolecules and hydrophilic drugs Expert Opin. Drug Deliv. 7 12 2010 1415 1432
54. B.E. Polat, J.E. Seto, D. Blankschtein, and R. Langer Application of the aqueous porous pathway model to quantify the effect of sodium lauryl sulfate on ultrasound-induced skin structural perturbation J. Pharm. Sci. 100 4 2011 1387 1397
55. A. Tezel, A. Sens, J. Tuchscherer, and S. Mitragotri Synergistic effect of low-frequency ultrasound and surfactants on skin permeability J. Pharm. Sci. 91 1 2002 91 100 (Pubitemid 34074469)
56. S. Ghosh, D. Kim, P. So, and D. Blankschtein Visualization and quantification of skin barrier perturbation induced by surfactant-humectant systems using two-photon fluorescence microscopy J. Cosmet. Sci. 59 4 2008 263 289
57. J. Kushner, D. Kim, P.T. So, D. Blankschtein, and R.S. Langer Dual-channel two-photon microscopy study of transdermal transport in skin treated with low-frequency ultrasound and a chemical enhancer J. Invest. Dermatol. 127 12 2007 2832 2846 (Pubitemid 350134811)
58. B. Yu, K.H. Kim, P.T.C. So, D. Blankschtein, and R. Langer Visualization of oleic acid-induced transdermal diffusion pathways using two-photon fluorescence microscopy J. Invest. Dermatol. 120 3 2003 448 455 (Pubitemid 36298432)
59. J.L. Zatz, and B. Lee M.M. Rieger, L.D. Rhein, Surfactants in Cosmetics 1997 Marcel Dekker New York, NY 501 517
60. J.D. Bos, and M.M.H.M. Meinardi The 500 Dalton rule for the skin penetration of chemical compounds and drugs Exp. Dermatol. 9 3 2000 165 169 (Pubitemid 30255378)
61. B.E. Polat, S. Lin, J.D. Mendenhall, B. VanVeller, R. Langer, and D. Blankschtein Experimental and molecular dynamics investigation into the amphiphilic nature of sulforhodamine B J. Phys. Chem. B 115 6 2011 1394 1402
62. J.E. Seto, B.E. Polat, R.F.V. Lopez, D. Blankschtein, and R. Langer Effects of ultrasound and sodium lauryl sulfate on the transdermal delivery of hydrophilic permeants: comparative in vitro studies with full-thickness and split-thickness pig and human skin J. Control. Release 145 1 2010 26 32
63. 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 (Pubitemid 41827484)
64. V.K. Rachakonda, K.M. Yerramsetty, S.V. Madihally, R.L. Robinson Jr., and K.A. Gasem Screening of chemical penetration enhancers for transdermal drug delivery using electrical resistance of skin Pharm. Res. 25 11 2008 2697 2704
65. I.H. Pitman, S.J. Rostas, and L.M. Downes Effects of breed, season, temperature, and solvents on the permeability of frozen and reconstituted cattle skin to levamisole J. Pharm. Sci. 72 3 1983 218 221 (Pubitemid 13159606)
66. W. Magerl, R.A. Westerman, B. Mohner, and H.O. Handwerker Properties of transdermal histamine iontophoresis: differential effects of season, gender, and body region J. Invest. Dermatol. 94 3 1990 347 352 (Pubitemid 20061645)
67. J. Schroder Cutaneous absorption of chemicals J. S. Afr. Vet. Assoc. 57 3 1986 169 176 (Pubitemid 17003569)
68. S. Ghosh, and D. Blankschtein The role of sodium dodecyl sulfate (SDS) micelles in inducing skin barrier perturbation in the presence of glycerol J. Cosmet. Sci. 58 2 2007 109 133
69. B.E. Polat, P.L. Figueroa, D. Blankschtein, and R. Langer Transport pathways and enhancement mechanisms within localized and non-localized transport regions in skin treated with low-frequency sonophoresis and sodium lauryl sulfate J. Pharm. Sci. 100 2 2011 512 529
70. J. Kushner, D. Blankschtein, and R. Langer Heterogeneity in skin treated with low-frequency ultrasound J. Pharm. Sci. 97 10 2008 4119 4128
71. E. Drakaki, E. Borisova, M. Makropoulou, L. Avramov, A.A. Serafetinides, and I. Angelov Laser induced autofluorescence studies of animal skin used in modeling of human cutaneous tissue spectroscopic measurements Skin Res. Technol. 13 4 2007 350 359 (Pubitemid 47506397)
72. B. Yu, C.-Y. Dong, P.T.C. So, D. Blankschtein, and R. Langer In vitro visualization and quantification of oleic acid induced changes in transdermal transport using two-photon fluorescence microscopy J. Invest. Dermatol. 117 1 2001 16 25 (Pubitemid 32652435)
73. R.H. Na, I.M. Stender, L.X. Ma, and H.C. Wulf Autofluorescence spectrum of skin: component bands and body site variations Skin Res. Technol. 6 3 2000 112 117 (Pubitemid 30459937)
74. M.R. Prausnitz, and R. Langer Transdermal drug delivery Nat. Biotechnol. 26 11 2008 1261 1268
75. D.M. Bagley, J.R. Gardner, G. Holland, R.W. Lewis, J.F. Regnier, D.A. Stringer, and A.P. Walker Skin irritation: reference chemicals data bank Toxicol. In Vitro 10 1 1996 1 6 (Pubitemid 26077098)
76. S.J. Lord, N.R. Conley, H.-L.D. Lee, S.Y. Nishimura, A.K. Pomerantz, K.A. Willets, Z. Lu, H. Wang, N. Liu, R. Samuel, R. Weber, A. Semyonov, M. He, R.J. Twieg, and W.E. Moerner DCDHF fluorophores for single-molecule imaging in cells ChemPhysChem 10 1 2009 55 65
77. H. Wang, Z. Lu, S.J. Lord, W.E. Moerner, and R.J. Twieg Modifications of DCDHF single molecule fluorophores to impart water solubility Tetrahedron Lett. 48 19 2007 3471 3474 (Pubitemid 46574777)
78. N. Kanikkannan, R.J. Babu, and M. Singh E.W. Smith, H.I. Maibach, Percutaneous Penetration Enhancers 2006 CRC Press Boca Raton, FL 17 33
79. 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 (Pubitemid 30396419)
80. K.S. Warner, S.K. Li, N. He, T.M. Suhonen, D. Chantasart, D. Bolikal, and W.I. Higuchi Structure-activity relationship for chemical skin permeation enhancers: probing the chemical microenvironment of the site of action J. Pharm. Sci. 92 6 2003 1305 1322 (Pubitemid 36676475)
81. 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
82. S. Ghosh, S. Hornby, G. Grove, C. Zerwick, Y. Appa, and D. Blankschtein Ranking of aqueous surfactant-humectant systems based on an analysis of in vitro and in vivo skin barrier perturbation measurements J. Cosmet. Sci. 58 6 2007 599 620
83. J. Kushner, D. Blankschtein, and R. Langer Experimental demonstration of the existence of highly permeable localized transport regions in low-frequency sonophoresis J. Pharm. Sci. 93 11 2004 2733 2745 (Pubitemid 39506624)
84. R. Alvarez-Roman, A. Naik, Y.N. Kalia, H. Fessi, and R.H. Guy Visualization of skin penetration using confocal laser scanning microscopy Eur. J. Pharm. Biopharm. 58 2 2004 301 316 (Pubitemid 39037237)
85. K.A. Walters M.S. Roberts K.A. Walters, Dermatological and Transdermal Formulations Vol. 119 2002 Marcel Dekker, Inc. New York 1 39
86. G.M. Golden, J.E. McKie, and R.O. Potts Role of stratum corneum lipid fluidity in transdermal drug flux J. Pharm. Sci. 76 1 1987 25 28 (Pubitemid 17023047)
87. E. Bodner, M. Afri, and A.A. Frimer Determining radical penetration into membranes using ESR splitting constants Free Radic. Biol. Med. 49 3 2010 427 436
88. A.C. Benniston, and G. Copley Lighting the way ahead with boron dipyrromethene (BODIPY) dyes Phys. Chem. Chem. Phys. 11 21 2009 4124 4131