Quercetin topical application, from conventional dosage forms to nanodosage forms

European Journal of Pharmaceutics and Biopharmaceutics

Volumn 108, Issue , 2016, Pages 41-53

  Hatahet, T ^a   Morille, M ^a   Hommoss, A ^b   Devoisselle, J M ^a   Muller R H ^b   Begu S ^a  

^a UNIVERSITÉ DE MONTPELLIER   (France)

^b FREIE UNIVERSITÄT BERLIN   (Germany)

Author keywords

Antiinflammatory activity; Antioxidant activity; Franz cells; In vitro skin penetration; In vivo skin penetration; Quercetin; Skin antiaging; Wound healing

Indexed keywords

QUERCETIN; ANTIINFLAMMATORY AGENT; ANTIOXIDANT; EMULSION; NANOPARTICLE; REACTIVE OXYGEN METABOLITE; WATER;

ANTIINFLAMMATORY ACTIVITY; ANTIOXIDANT ACTIVITY; ANTIOXIDANT ASSAY; CLINICAL EVALUATION; CUTANEOUS PARAMETERS; DRUG DELIVERY SYSTEM; DRUG DOSAGE FORM; DRUG FORMULATION; DRUG STABILITY; HUMAN; IN VITRO STUDY; IN VIVO STUDY; NONHUMAN; PIG; REVIEW; RODENT; SKIN; SKIN PENETRATION; SKIN PROTECTION; WOUND HEALING; ANIMAL; CELL LINE; CHEMISTRY; CUTANEOUS DRUG ADMINISTRATION; CYTOLOGY; DRUG EFFECTS; EMULSION; FEMALE; KERATINOCYTE; MALE; MOUSE; NANOMEDICINE; PARTICLE SIZE; PROCEDURES; RAT; SKIN ABSORPTION; SOLUBILITY;

ADMINISTRATION, CUTANEOUS; ANIMALS; ANTI-INFLAMMATORY AGENTS; ANTIOXIDANTS; CELL LINE; EMULSIONS; FEMALE; HUMANS; KERATINOCYTES; MALE; MICE; NANOMEDICINE; NANOPARTICLES; PARTICLE SIZE; QUERCETIN; RATS; REACTIVE OXYGEN SPECIES; SKIN; SKIN ABSORPTION; SOLUBILITY; SWINE; WATER; WOUND HEALING;

EID: 84984596197     PISSN: 09396411     EISSN: 18733441     Source Type: Journal    
DOI: 10.1016/j.ejpb.2016.08.011     Document Type: Review

References (106)

1. [1] Wysocki, A.B., Skin anatomy, physiology, and pathophysiology. Nurs. Clin. North Am. 34 (1999), 777–797 v.
2. [2] Sander, C.S., Chang, H., Salzmann, S., Muller, C.S.L., Ekanayake-Mudiyanselage, S., Elsner, P., Thiele, J.J., Photoaging is associated with protein oxidation in human skin in vivo. J. Investigat. Dermatol. 118 (2002), 618–625.
3. [3] Hoppe, U., Bergemann, J., Diembeck, W., Ennen, J., Gohla, S., Harris, I., Jacob, J., Kielholz, J., Mei, W., Pollet, D., Schachtschabel, D., Sauermann, G., Schreiner, V., Stab, F., Steckel, F., Coenzyme Q10, a cutaneous antioxidant and energizer. BioFactors 9 (1999), 371–378.
4. [4] Pardeike, J., Schwabe, K., Müller, R.H., Influence of nanostructured lipid carriers (NLC) on the physical properties of the Cutanova Nanorepair Q10 cream and the in vivo skin hydration effect. Int. J. Pharm. 396 (2010), 166–173.
5. [5] Shibuya, S., Nojiri, H., Morikawa, D., Koyama, H., Shimizu, T., Chapter 14 - Protective Effects of Vitamin C on Age-Related Bone and Skin Phenotypes Caused by Intracellular Reactive Oxygen Species. Preedy, V.R., (eds.) Aging, 2014, Academic Press, San Diego, 137–144.
6. [6] Freitas, J.V., Lopes, N.P., Gaspar, L.R., Photostability evaluation of five UV-filters, trans-resveratrol and beta-carotene in sunscreens. Eur. J. Pharm. Sci. 78 (2015), 79–89.
7. [7] Offord, E.A., Gautier, J.-C., Avanti, O., Scaletta, C., Runge, F., Krämer, K., Applegate, L.A., Photoprotective potential of lycopene, β-carotene, vitamin E, vitamin C and carnosic acid in UVA-irradiated human skin fibroblasts. Free Radical Biol. Med. 32 (2002), 1293–1303.
8. [8] Vayalil, P.K., Mittal, A., Hara, Y., Elmets, C.A., Katiyar, S.K., Green tea polyphenols prevent ultraviolet light-induced oxidative damage and matrix metalloproteinases expression in mouse skin. J. Investig. Dermatol. 122 (2004), 1480–1487.
9. [9] Nichols, J., Katiyar, S., Skin photoprotection by natural polyphenols: anti-inflammatory, antioxidant and DNA repair mechanisms. Arch. Dermatol. Res. 302 (2010), 71–83.
10. [10] Veeriah, S., Kautenburger, T., Habermann, N., Sauer, J., Dietrich, H., Will, F., Pool-Zobel, B.L., Apple flavonoids inhibit growth of HT29 human colon cancer cells and modulate expression of genes involved in the biotransformation of xenobiotics. Mol. Carcinog. 45 (2006), 164–174.
11. [11] Slimestad, R., Fossen, T., Vagen, I.M., Onions: a source of unique dietary flavonoids. J. Agric. Food Chem. 55 (2007), 10067–10080.
12. [12] Ewald, C., Fjelkner-Modig, S., Johansson, K., Sjöholm, I., Åkesson, B., Effect of processing on major flavonoids in processed onions, green beans, and peas. Food Chem. 64 (1999), 231–235.
13. [13] Bonina, F., Lanza, M., Montenegro, L., Puglisi, C., Tomaino, A., Trombetta, D., Castelli, F., Saija, A., Flavonoids as potential protective agents against photo-oxidative skin damage. Int. J. Pharm. 145 (1996), 87–94.
14. [14] Kim, H., Namgoong, S., Kim, H., Antiinflammatory activity of flavonoids: mouse ear edema inhibition. Arch. Pharmacal Res. 16 (1993), 18–24.
15. [15] Saija, A., Tomaino, A., Trombetta, D., Luisa Pellegrino, M., Tita, B., Messina, C., Bonina, F.P., Rocco, C., Nicolosi, G., Castelli, F., ‘In vitro’ antioxidant and photoprotective properties and interaction with model membranes of three new quercetin esters. Eur. J. Pharm. Biopharm. 56 (2003), 167–174.
16. [16] Hatahet, T., Morille, M., Hommoss, A., Dorandeu, C., Muller, R.H., Begu, S., Dermal quercetin smartCrystals(R): formulation development, antioxidant activity and cellular safety. Eur. J. Pharm. Biopharm. 102 (2016), 51–63.
17. [17] Lh, Quercetin, CAS 117–39-5, Santa Cruz Biotech, 2016.
18. [18] Zheng, Y., Haworth, I.S., Zuo, Z., Chow, M.S., Chow, A.H., Physicochemical and structural characterization of quercetin-beta-cyclodextrin complexes. J. Pharm. Sci. 94 (2005), 1079–1089.
19. [19] Rothwell, J.A., Day, A.J., Morgan, M.R., Experimental determination of octanol-water partition coefficients of quercetin and related flavonoids. J. Agric. Food Chem. 53 (2005), 4355–4360.
20. [20] Celia, C., Cilurzo, F., Trapasso, E., Cosco, D., Fresta, M., Paolino, D., Ethosomes(R) and transfersomes(R) containing linoleic acid: physicochemical and technological features of topical drug delivery carriers for the potential treatment of melasma disorders. Biomed. Microdevices 14 (2012), 119–130.
21. [21] Paolino, D., Celia, C., Trapasso, E., Cilurzo, F., Fresta, M., Paclitaxel-loaded ethosomes(R): potential treatment of squamous cell carcinoma, a malignant transformation of actinic keratoses. Eur. J. Pharm. Biopharm. 81 (2012), 102–112.
22. [22] Paolino, D., Cosco, D., Cilurzo, F., Trapasso, E., Morittu, V.M., Celia, C., Fresta, M., Improved in vitro and in vivo collagen biosynthesis by asiaticoside-loaded ultradeformable vesicles. J. Control. Release 162 (2012), 143–151.
23. [23] Liu, D., Hu, H., Lin, Z., Chen, D., Zhu, Y., Hou, S., Shi, X., Quercetin deformable liposome: preparation and efficacy against ultraviolet B induced skin damages in vitro and in vivo. J. Photochem. Photobiol., B 127 (2013), 8–17.
24. [24] Tan, Q., Liu, W., Guo, C., Zhai, G., Preparation and evaluation of quercetin-loaded lecithin-chitosan nanoparticles for topical delivery. Int. J. Nanomed. 6 (2011), 1621–1630.
25. [25] Borghetti, G.S., Costa, I.M., Petrovick, P.R., Pereira, V.P., Bassani, V.L., Characterization of different samples of quercetin in solid-state: indication of polymorphism occurrence. Pharmazie 61 (2006), 802–804.
26. [26] Sies, H., Strategies of antioxidant defense. Eur. J. Biochem. 215 (1993), 213–219.
27. [27] Blois, M.S., Antioxidant determinations by the use of a stable free radical. Nature 181 (1958), 1199–1200.
28. [28] Fridovich, I., Quantitative aspects of the production of superoxide anion radical by milk xanthine oxidase. J. Biol. Chem. 245 (1970), 4053–4057.
29. [29] Majkic-Singh, N., Koprivica, M., Spasic, S., Stojanov, M., Berkes, I., Evaluation of bathophenanthroline method for serum iron assay. Clin. Chem., 26, 1980, 1360.
30. [30] Lefevre, G., Beljean-Leymarie, M., Beyerle, F., Bonnefont-Rousselot, D., Cristol, J.P., Therond, P., Torreilles, J., Evaluation of lipid peroxidation by measuring thiobarbituric acid reactive substances. Ann. Biol. Clin. (Paris) 56 (1998), 305–319.
31. [31] Casagrande, R., Georgetti, S.R., Verri, W.A., Jabor, J.R., Santos, A.C., Fonseca, M.J.V., Evaluation of functional stability of quercetin as a raw material and in different topical formulations by its antilipoperoxidative activity. AAPS PharmSciTech, 2006, E64–E71.
32. [32] Heim, K.E., Tagliaferro, A.R., Bobilya, D.J., Flavonoid antioxidants: chemistry, metabolism and structure-activity relationships. J. Nutr. Biochem. 13 (2002), 572–584.
33. [33] Casagrande, R., Georgetti, S.R., Verri, W.A. Jr., Borin, M.F., Lopez, R.F.V., Fonseca, M.J.V., In vitro evaluation of quercetin cutaneous absorption from topical formulations and its functional stability by antioxidant activity. Int. J. Pharm. 328 (2007), 183–190.
34. [34] Wu, T.-H., Yen, F.-L., Lin, L.-T., Tsai, T.-R., Lin, C.-C., Cham, T.-M., Preparation, physicochemical characterization, and antioxidant effects of quercetin nanoparticles. Int. J. Pharm. 346 (2008), 160–168.
35. [35] Wolfe, K.L., Liu, R.H., Cellular antioxidant activity (CAA) assay for assessing antioxidants, foods, and dietary supplements. J. Agri. Food Chem. 55 (2007), 8896–8907.
36. [36] López-Alarcón, C., Denicola, A., Evaluating the antioxidant capacity of natural products: a review on chemical and cellular-based assays. Anal. Chim. Acta 763 (2013), 1–10.
37. [37] Skaper, S.D., Fabris, M., Ferrari, V., Dalle Carbonare, M., Leon, A., Quercetin protects cutaneous tissue-associated cell types including sensory neurons from oxidative stress induced by glutathione depletion: cooperative effects of ascorbic acid. Free Radic. Biol. Med. 22 (1997), 669–678.
38. [38] Manca, M.L., Castangia, I., Caddeo, C., Pando, D., Escribano, E., Valenti, D., Lampis, S., Zaru, M., Fadda, A.M., Manconi, M., Improvement of quercetin protective effect against oxidative stress skin damages by incorporation in nanovesicles. Colloids Surf. B 123 (2014), 566–574.
39. [39] Düzgüneş, N., Nir, S., Mechanisms and kinetics of liposome–cell interactions. Adv. Drug Deliv. Rev. 40 (1999), 3–18.
40. [40] Torchilin, V.P., Recent advances with liposomes as pharmaceutical carriers. Nat. Rev. Drug Discov. 4 (2005), 145–160.
41. [41] Hung, C.-F., Fang, C.-L., Al-Suwayeh, S.A., Yang, S.-Y., Fang, J.-Y., Evaluation of drug and sunscreen permeation via skin irradiated with UVA and UVB: comparisons of normal skin and chronologically aged skin. J. Dermatol. Sci. 68 (2012), 135–148.
42. [42] Casagrande, R., Georgetti, S.R., Verri, W.A. Jr., Dorta, D.J., dos Santos, A.C., Fonseca, M.J.V., Protective effect of topical formulations containing quercetin against UVB-induced oxidative stress in hairless mice. J. Photochem. Photobiol., B 84 (2006), 21–27.
43. [43] Vicentini, F.T.M.C., Simi, T.R.M., Del Ciampo, J.O., Wolga, N.O., Pitol, D.L., Iyomasa, M.M., Bentley, M.V.L.B., Fonseca, M.J.V., Quercetin in w/o microemulsion: in vitro and in vivo skin penetration and efficacy against UVB-induced skin damages evaluated in vivo. Eur. J. Pharm. Biopharm. 69 (2008), 948–957.
44. [44] Singh Joshan, D., Singh, S.K., Investigational study of Juglans regia extract and quercetin against photoaging. Biomed. Ag. Pathol. 3 (2013), 193–200.
45. [45] Lin, C.F., Leu, Y.L., Al-Suwayeh, S.A., Ku, M.C., Hwang, T.L., Fang, J.Y., Anti-inflammatory activity and percutaneous absorption of quercetin and its polymethoxylated compound and glycosides: the relationships to chemical structures. Eur. J. Pharm. Sci. 47 (2012), 857–864.
46. [46] Gomathi, K., Gopinath, D., Rafiuddin Ahmed, M., Jayakumar, R., Quercetin incorporated collagen matrices for dermal wound healing processes in rat. Biomaterials 24 (2003), 2767–2772.
47. [47] Hamminga, E.A., van der Lely, A.J., Neumann, H.A.M., Thio, H.B., Chronic inflammation in psoriasis and obesity: implications for therapy. Med. Hypotheses 67 (2006), 768–773.
48. [48] Bickers, D.R., Athar, M., Oxidative stress in the pathogenesis of skin disease. J. Investigat. Dermatol. 126 (2006), 2565–2575.
49. [49] Cooper, S.J., Bowden, G.T., Ultraviolet B regulation of transcription factor families: roles of nuclear factor-kappa B (NF-kappaB) and activator protein-1 (AP-1) in UVB-induced skin carcinogenesis. Curr. Cancer Drug Targets 7 (2007), 325–334.
50. [50] Tak, P.P., Firestein, G.S., NF-κB: a key role in inflammatory diseases. J. Clin. Invest., 2001, 7–11.
51. [51] Ruiz, P.A., Braune, A., Holzlwimmer, G., Quintanilla-Fend, L., Haller, D., Quercetin inhibits TNF-induced NF-kappaB transcription factor recruitment to proinflammatory gene promoters in murine intestinal epithelial cells. J. Nutr. US, 2007, 1208–1215.
52. [52] Musonda, C.A., Chipman, J.K., Quercetin inhibits hydrogen peroxide (H2O2)-induced NF-kappaB DNA binding activity and DNA damage in HepG2 cells. Carcinogenesis 19 (1998), 1583–1589.
53. [53] Granado-Serrano, A.B., Martin, M.A., Bravo, L., Goya, L., Ramos, S., Quercetin modulates NF-kappa B and AP-1/JNK pathways to induce cell death in human hepatoma cells. Nutr. Cancer, Engl., 2010, 390–401.
54. [54] Vicentini, F.T., He, T., Shao, Y., Fonseca, M.J., Verri, W.A. Jr., Fisher, G.J., Xu, Y., Quercetin inhibits UV irradiation-induced inflammatory cytokine production in primary human keratinocytes by suppressing NF-kappaB pathway. J Dermatol Sci, 2011 Japanese Society for Investigative Dermatology, 2011, Elsevier Ireland Ltd., Netherlands, 162–168.
55. [55] Lin, C.-F., Leu, Y.-L., Al-Suwayeh, S.A., Ku, M.-C., Hwang, T.-L., Fang, J.-Y., Anti-inflammatory activity and percutaneous absorption of quercetin and its polymethoxylated compound and glycosides: the relationships to chemical structures. Eur. J. Pharm. Sci. 47 (2012), 857–864.
56. [56] Choquenet, B., Couteau, C., Paparis, E., Coiffard, L.J.M., Quercetin and rutin as potential sunscreen agents: determination of efficacy by an in vitro method. J. Nat. Prod. 71 (2008), 1117–1118.
57. [57] Vijayalakshmi, A., Ravichandiran, V., Malarkodi, V., Nirmala, S., Jayakumari, S., Screening of flavonoid “quercetin” from the rhizome of Smilax china Linn. for anti-psoriatic activity. Asian Pac. J. Trop. Biomed., 2012, 269–275.
58. [58] Caddeo, C., Diez-Sales, O., Pons, R., Fernandez-Busquets, X., Fadda, A.M., Manconi, M., Topical anti-inflammatory potential of quercetin in lipid-based nanosystems: in vivo and in vitro evaluation. Pharm. Res. 31 (2014), 959–968.
59. [59] Caddeo, C., Sales, O.D., Valenti, D., Sauri, A.R., Fadda, A.M., Manconi, M., Inhibition of skin inflammation in mice by diclofenac in vesicular carriers: liposomes, ethosomes and PEVs. Int. J. Pharm. 443 (2013), 128–136.
60. [60] Hunt, T.K., The physiology of wound healing. Ann. Emerg. Med. 17 (1988), 1265–1273.
61. [61] Cerimele, D., Celleno, L., Serri, F., Physiological changes in ageing skin. Br. J. Dermatol. 122 (1990), 13–20.
62. [62] Calleja-Agius, J., Muscat-Baron, Y., Brincat, M.P., Skin ageing. Menopause Int. 13 (2007), 60–64.
63. [63] Farage, M.A., Miller, K.W., Elsner, P., Maibach, H.I., Intrinsic and extrinsic factors in skin ageing: a review. Int. J. Cosmet. Sci. 30 (2008), 87–95.
64. [64] Hara, M., Verkman, A.S., Glycerol replacement corrects defective skin hydration, elasticity, and barrier function in aquaporin-3-deficient mice. Proc. Natl. Acad. Sci. 100 (2003), 7360–7365.
65. [65] Terao, J., Piskula, M., Yao, Q., Protective effect of epicatechin, epicatechin gallate, and quercetin on lipid peroxidation in phospholipid bilayers. Arch. Biochem. Biophys. 308 (1994), 278–284.
66. [66] Majtan, J., Bohova, J., Garcia-Villalba, R., Tomas-Barberan, F., Madakova, Z., Majtan, T., Majtan, V., Klaudiny, J., Fir honeydew honey flavonoids inhibit TNF-α-induced MMP-9 expression in human keratinocytes: a new action of honey in wound healing. Arch. Dermatol. Res. 305 (2013), 619–627.
67. [67] Chung, J.H., Seo, J.Y., Choi, H.R., Lee, M.K., Youn, C.S., Rhie, G.-E., Cho, K.H., Kim, K.H., Park, K.C., Eun, H.C., Modulation of skin collagen metabolism in aged and photoaged human skin in vivo. J. Investigat. Dermatol. 117 (2001), 1218–1224.
68. [68] Lock-Andersen, J., Therkildsen, P., de Fine Olivarius, F., Gniadecka, M., Dahlstrom, K., Poulsen, T., Wulf, H.C., Epidermal thickness, skin pigmentation and constitutive photosensitivity. Photodermatol. Photoimmunol. Photomed. 13 (1997), 153–158.
69. [69] Chondrogianni, N., Kapeta, S., Chinou, I., Vassilatou, K., Papassideri, I., Gonos, E.S., Anti-ageing and rejuvenating effects of quercetin. Exp. Gerontol. 45 (2010), 763–771.
70. [70] Debacq-Chainiaux, F., Erusalimsky, J.D., Campisi, J., Toussaint, O., Protocols to detect senescence-associated beta-galactosidase (SA-[beta]gal) activity, a biomarker of senescent cells in culture and in vivo. Nat. Prot. 4 (2009), 1798–1806.
71. [71] Agar, N., Young, A.R., Melanogenesis: a photoprotective response to DNA damage?. Mutat. Res./Fund. Molec. Mech. Mutagen. 571 (2005), 121–132.
72. [72] Ando, H., Kondoh, H., Ichihashi, M., Hearing, V.J., Approaches to identify inhibitors of melanin biosynthesis via the quality control of tyrosinase. J. Investig. Dermatol. 127 (2007), 751–761.
73. [73] Rothwell, J.A., Day, A.J., Morgan, M.R.A., Experimental determination of octanol-water partition coefficients of quercetin and related flavonoids. J. Agri. Food Chem. 53 (2005), 4355–4360.
74. [74] Fasolo, D., Bassani, V.L., Teixeira, H.F., Development of topical nanoemulsions containing quercetin and 3-O-methylquercetin. Pharmazie 64 (2009), 726–730.
75. [75] Chessa, M., Caddeo, C., Valenti, D., Manconi, M., Sinico, C., Fadda, A.M., Effect of penetration enhancer containing vesicles on the percutaneous delivery of quercetin through new born pig skin. Pharmaceutics 3 (2011), 497–509.
76. [76] Scalia, S., Franceschinis, E., Bertelli, D., Iannuccelli, V., Comparative evaluation of the effect of permeation enhancers, lipid nanoparticles and colloidal silica on in vivo human skin penetration of quercetin. Skin Pharmacol. Physiol. (Basel., Switzerland), 2013, 57–67.
77. [77] Bose, S., Du, Y., Takhistov, P., Michniak-Kohn, B., Formulation optimization and topical delivery of quercetin from solid lipid based nanosystems. Int. J. Pharm. 441 (2012), 56–66.
78. [78] Bose, S., Michniak-Kohn, B., Preparation and characterization of lipid based nanosystems for topical delivery of quercetin. Eur. J. Pharm. Sci. 48 (2013), 442–452.
79. [79] Sapino, S., Ugazio, E., Gastaldi, L., Miletto, I., Berlier, G., Zonari, D., Oliaro-Bosso, S., Mesoporous silica as topical nanocarriers for quercetin: characterization and in vitro studies. Eur. J. Pharm. Biopharm. 89 (2015), 116–125.
80. [80] Saija, A., Tomaino, A., Trombetta, D., Giacchi, M., Pasquale, A.D., Bonina, F., Influence of different penetration enhancers on in vitro skin permeation and in vivo photoprotective effect of flavonoids. Int. J. Pharm. 175 (1998), 85–94.
81. [81] Montenegro, L., Carbone, C., Maniscalco, C., Lambusta, D., Nicolosi, G., Ventura, C.A., Puglisi, G., In vitro evaluation of quercetin-3-O-acyl esters as topical prodrugs. Int. J. Pharm. 336 (2007), 257–262.
82. [82] Schmook, F.P., Meingassner, J.G., Billich, A., Comparison of human skin or epidermis models with human and animal skin in in-vitro percutaneous absorption. Int. J. Pharm. 215 (2001), 51–56.
83. [83] Bronaugh, R.L., Stewart, R.F., Congdon, E.R., Methods for in vitro percutaneous absorption studies II. Animal models for human skin. Toxicol. Appl. Pharm. 62 (1982), 481–488.
84. [84] Chantasart, D., Li, S.K., He, N., Warner, K.S., Prakongpan, S., Higuchi, W.I., Mechanistic studies of branched-chain alkanols as skin permeation enhancers. J. Pharm. Sci. 93 (2004), 762–779.
85. [85] Marianecci, C., Rinaldi, F., Mastriota, M., Pieretti, S., Trapasso, E., Paolino, D., Carafa, M., Anti-inflammatory activity of novel ammonium glycyrrhizinate/niosomes delivery system: human and murine models. J. Control. Release 164 (2012), 17–25.
86. [86] Durrheim, H., Flynn, G.L., Higuchi, W.I., Behl, C.R., Permeation of hairless mouse skin I: Experimental methods and comparison with human epidermal permeation by alkanols. J. Pharm. Sci. 69 (1980), 781–786.
87. [87] Jung, E.C., Maibach, H.I., Animal models for percutaneous absorption. J. Appl. Toxicol. 35 (2015), 1–10.
88. [88] Capt, A., Luzy, A.P., Esdaile, D., Blanck, O., Comparison of the human skin grafted onto nude mouse model with in vivo and in vitro models in the prediction of percutaneous penetration of three lipophilic pesticides. Regul. Toxicol. Pharmacol. 47 (2007), 274–287.
89. [89] Banerjee, P.S., Ritschel, W.A., Transdermal permeation of vasopressin. I. Influence of pH, concentration, shaving and surfactant on in vitro permeation. Int. J. Pharm. 49 (1989), 189–197.
90. [90] Dick, I.P., Scott, R.C., Pig ear skin as an in-vitro model for human skin permeability. J. Pharm. Pharmacol. 44 (1992), 640–645.
91. [91] Singh, S., Zhao, K., Singh, J., In vitro permeability and binding of hydrocarbons in pig ear and human abdominal skin. Drug Chem. Toxicol. 25 (2002), 83–92.
92. [92] Hoeller, S., Sperger, A., Valenta, C., Lecithin based nanoemulsions: a comparative study of the influence of non-ionic surfactants and the cationic phytosphingosine on physicochemical behaviour and skin permeation. Int. J. Pharm. 370 (2009), 181–186.
93. [93] Yilmaz, E., Borchert, H.-H., Design of a phytosphingosine-containing, positively-charged nanoemulsion as a colloidal carrier system for dermal application of ceramides. Eur. J. Pharm. Biopharm. 60 (2005), 91–98.
94. [94] Baspinar, Y., Borchert, H.-H., Penetration and release studies of positively and negatively charged nanoemulsions—is there a benefit of the positive charge?. Int. J. Pharm. 430 (2012), 247–252.
95. [95] Smith, E.W., Maibach, H.I., Percutaneous Penetration Enhancers. 1995, Taylor & Francis.
96. [96] Bartek, M.J., Labudde, J.A., Maibach, H.I., Skin permeability in vivo: comparison in rat, rabbit, pig and man. J. Investig. Dermatol. 58 (1972), 114–123.
97. [97] Cnubben, N.H.P., Elliott, G.R., Hakkert, B.C., Meuling, W.J.A., van de Sandt, J.J.M., Comparative in vitro–in vivo percutaneous penetration of the fungicide ortho-phenylphenol. Regul. Toxicol. Pharmacol. 35 (2002), 198–208.
98. [98] Lachenmeier, D.W., Safety evaluation of topical applications of ethanol on the skin and inside the oral cavity. J. Occupat. Med. Toxicol. (London, England), 3, 2008, 26.
99. [99] Aungst, B.J., Rogers, N.J., Shefter, E., Enhancement of naloxone penetration through human skin in vitro using fatty acids, fatty alcohols, surfactants, sulfoxides and amides. Int. J. Pharm. 33 (1986), 225–234.
100. [100] Valia, K.H., Chien, Y.W., Shinal, E.C., Long-term skin permeation kinetics of estradiol (I): Effect of drug solubilizer-polyethylene glycol 400. Drug Dev. Ind. Pharm. 10 (1984), 951–981.
101. [101] Catz, P., Friend, D.R., Transdermal delivery of levonorgestrel. VIII. Effect of enhancers on rat skin, hairless mouse skin, hairless guinea pig skin, and human skin. Int. J. Pharm. 58 (1990), 93–102.
102. [102] Suwanpidokkul, N., Thongnopnua, P., Umprayn, K., Transdermal delivery of zidovudine (AZT): the effects of vehicles, enhancers, and polymer membranes on permeation across cadaver pig skin. AAPS PharmSciTech 5 (2004), 82–89.
103. [103] Sarpotdar, P.P., Gaskill, J.L., Giannini, R.P., Effect of polyethylene glycol 400 on the penetration of drugs through human cadaver skin in vitro. J. Pharm. Sci. 75 (1986), 26–28.
104. [104] Pardeike, J., Hommoss, A., Müller, R.H., Lipid nanoparticles (SLN, NLC) in cosmetic and pharmaceutical dermal products. Int. J. Pharm. 366 (2009), 170–184.
105. [105] Patzelt, A., Richter, H., Knorr, F., Schäfer, U., Lehr, C.-M., Dähne, L., Sterry, W., Lademann, J., Selective follicular targeting by modification of the particle sizes. J. Control. Release 150 (2011), 45–48.
106. [106] Baroli, B., Penetration of nanoparticles and nanomaterials in the skin: fiction or reality?. J. Pharm. Sci. 99 (2010), 21–50.