The Effect of Various Penetration Enhancers on the Octyl Methoxycinnamate Permeability: Mechanisms of Action Study

Document Type : Research Paper

Authors

1 Nanotechnology Research Center, Ahvaz Jundishapur University of Medical Sciences, Ahvaz, Iran ;Department of Pharmaceutics, Ahvaz Jundishapur University of Medical Sciences, Ahvaz, Iran

2 Student Research Committee, Ahvaz Jundishapur University of Medical Sciences, Ahvaz, IR Iran

3 Department of Clinical Pharmacy, Faculty of Pharmacy, Shahid Beheshti University of Medical Sciences, Tehran, Iran

10.22034/ijps.2019.103550.1531

Abstract

Octyl methoxycinnamate is one of the ingredients in sunscreen products. The main aim of this study was to investigate the effect of different enhancers of in vitro skin permeability of Octyl methoxycinnamate.
Octyl methoxycinnamate permeability parameters were evaluated through the whole skin of the rat with and without chemical enhancers including eucalyptus oil, urea, menthol and olive oil by Franz cell diffusion. The effects of enhancers on skin structure were also studied using DSC and FT-IR techniques.
The skin prevented the permeability of Octyl methoxycinnamate so that after 24 hours less than 3% of the substance passed through the skin. The results of this study showed that by increasing the time, it is possible to increase the skin permeation and the highest rate of skin absorption were corresponded to olive oil (ERflux=63.074), eucalyptus oil (ERflux=48.78) and menthol (ERflux=33.5), respectively while the least amount of skin absorption was related to urea (ERflux=29.53). Chemical penetration enhancers are substances that interfere with the complex structure of the skin and protein lipids. Two endothermic transitions were obtained at about 67 (Tm1) and 112 ° C (Tm2) in thermogram of the hydrated whole rat skin. Tm1 and Tm2 seems to be due to the melting of the lipids and the irreversible intracellular keratin or melting of the lipid-protein (keratin) complex, respectively. The amount of Tm1, ΔH1 and ΔH2 were decreased by all penetration enhancers compared to the hydrated skin. The FT-IR results suggested the mechanism of increasing absorption effect by lipid fluidization and lipid extraction.
All of penetration enhancers used in this study significantly increased the skin permeability of Octyl methoxycinnamate.

Keywords

References

[1] Janjua NR, Mogensen B, Andersson A-M, Petersen JH, Henriksen M, Skakkebæk NE, et al. Systemic absorption of the sunscreens benzophenone-3, octyl-methoxycinnamate, and 3-(4-methyl-benzylidene) camphor after whole-body topical application and reproductive hormone levels in humans. J. Invest. Dermatol. (2004) 123 (1): 57-61.
[2] Pattanaargson S, Munhapol T, Hirunsupachot P, Luangthongaram P. Photoisomerization of octyl methoxycinnamate. J. Photochem. Photobiol. A. Chem. (2004) 161 (2): 269-274.
[3] Serpone N, Salinaro A, Emeline AV, Horikoshi S, Hidaka H, Zhao J. An in vitro systematic spectroscopic examination of the photostabilities of a random set of commercial sunscreen lotions and their chemical uvb/uva active agents. Photochem. Photobiol. Sci. (2002) 1 (12): 970-981.
[4] Tsakovska I, Pajeva I, Al Sharif M, Alov P, Fioravanzo E, Kovarich S, et al. Quantitative structure-skin permeability relationships. Toxicology. (2017) 387: 27-42.
[5] Scheuplein RJ, Blank IH. Permeability of the skin. Physiol. Rev. (1971) 51 (4): 702-747.
[6] S Shete A, V Yadav A, A.P D, S. Sakhare S. Formulation and evaluation of hydrotropic solublization based suspensions of griseofulvin (2010).
[7] Pham QD, Björklund S, Engblom J, Topgaard D, Sparr E. Chemical penetration enhancers in stratum corneum — relation between molecular effects and barrier function. J. Control Release. (2016) 232: 175-187.
[8] Feher J. 2.5 - passive transport and facilitated diffusion. In: Feher J, editor. Quantitative human physiology. Boston: Academic Press; (2012). 126-133.
[9] Salimi A, Hedayatipour N, Moghimipour E. The effect of various vehicles on the naproxen permeability through rat skin: A mechanistic study by dsc and ft-ir techniques. Adv. Pharm. Bull. (2016) 6 (1): 9-16.
[10] Ogiso T, Shintani M. Mechanism for the enhancement effect of fatty acids on the percutaneous absorption of propranolol. J. Pharm. Sci. (1990) 79 (12): 1065-1071.
[11] Zaid Alkilani A, McCrudden MTC, Donnelly RF. Transdermal drug delivery: Innovative pharmaceutical developments based on disruption of the barrier properties of the stratum corneum. Pharmaceutics (2015) 7 (4): 438-470.
[12] Dreher F, Walde P, Walther P, Wehrli E. Interaction of a lecithin microemulsion gel with human stratum corneum and its effect on transdermal transport. J. Control Release (1997) 45 (2): 131-140.
[13] Hoar TP, Schulman JH. Transparent water-in-oil dispersions: The oleopathic hydro-micelle. Nature (1943) 152: 102.
[14] Obata Y, Utsumi S, Watanabe H, Suda M, Tokudome Y, Otsuka M, et al. Infrared spectroscopic study of lipid interaction in stratum corneum treated with transdermal absorption enhancers. Int. J. Pharm. (2010) 389 (1): 18-23.
[15] Constantinides PP, Lancaster CM, Marcello J, Chiossone DC, Orner D, Hidalgo I, et al. Enhanced intestinal absorption of an rgd peptide from water-in-oil microemulsions of different composition and particle size. J. Control Release (1995) 34 (2): 109-116.
[16] Constantinides P, Welzel G, Ellens H, L. Smith P, Sturgis S, H. Yiv S, et al. Water-in-oil microemulsions containing medium-chain fatty acids/salts: Formulation and intestinal absorption enhancement evaluation (1996) 210-215.
[17] Kawakami K, Yoshikawa T, Moroto Y, Kanaoka E, Takahashi K, Nishihara Y, et al. Microemulsion formulation for enhanced absorption of poorly soluble drugs. I. Prescription design. J. Control Release (2002) 81 (1-2): 65-74.
[18] Jain TK, Varshney M, Maitra A. Structural studies of aerosol ot reverse micellar aggregates by ft-ir spectroscopy. J. Phys. Chem. (1989) 93 (21): 7409-7416.
[19] Goh CF, Moffat JG, Craig DQM, Hadgraft J, Lane ME. Nano-thermal imaging of the stratum corneum and its potential use for understanding of the mechanism of skin penetration enhancer. Thermochim. Acta. (2017) 655: 278-283.
[20] Aoyagi T, Terashima O, Suzuki N, Matsui K, Nagase Y. Polymerization of benzalkonium chloride-type monomer and application to percutaneous drug absorption enhancer. J. Control Release (1990) 13 (1): 63-71.
[21] Salimi A, Kazem Hajiani M. Enhanced stability and dermal delivery of hydroquinone using microemulsion-based system (2018).
[22] Zhao K, Singh S, Singh J. Effect of menthone on the in vitro percutaneous absorption of tamoxifen and skin reversibility. Int. J. Pharm. (2001) 219 (1-2): 177-181.
[23] Kanlayavattanakul M, Kasikawatana N, Lourith N. Analysis of octyl methoxycinnamate in sunscreen products by a validated uv-spectrophotometric method. J. Cosmet. Sci. (2016) 67 (3): 167-173.
[24] Ng S-F, Rouse JJ, Sanderson FD, Meidan V, Eccleston GM. Validation of a static franz diffusion cell system for in vitro permeation studies. AAPS Pharm. Sci. Tech. (2010) 11 (3): 1432-1441.
[25] Salimi A, Moghimipour E, Rahmani F. Effects of the various solvents on the in vitro permeability of indomethacin through whole abdominal rat skin (2015) 335-346.
[26] Salimi A, Sharif Makhmal Zadeh B, Hemati Aa, Akbari Birgani S. Design and evaluation of self-emulsifying drug delivery system (sedds) of carvedilol to improve the oral absorption. Jundishapur J. Nat. Pharm. Prod. (2014) 9 (3): e16125.
[27] Salimi A, Sharif Makhmal Zadeh B, Moghimipour E. Preparation and characterization of cyanocobalamin (vit b12) microemulsion properties and structure for topical and transdermal application. Iran. J. Basic Med. Sci. (2013) 16 (7): 865-872.
[28] Gee GW, Bauder JW. Particle-size analysis1. In: Klute A, editor. Methods of soil analysis: Part 1—physical and mineralogical methods. Madison, WI: Soil Science Society of America, American Society of Agronomy; (1986). p. 383-411.
[29] Garti N, Aserin A, Ezrahi S, Tiunova I, Berkovic G. Water behavior in nonionic surfactant systems i: Subzero temperature behavior of water in nonionic microemulsions studied by dsc. J. Colloid. Interface Sci. (1996) 178 (1): 60-68.
[30] Sharif B, Yazdani a, Rezai a, Salimi A. The effect of chemical enhancers on tacrolimus permeation through rat skin (2012) 1309-1312.
[31] Spicer PT, Small WB, Small WB, Lynch ML, Burns JL. Dry powder precursors of cubic liquid crystalline nanoparticles (cubosomes). Journal of Nanoparticle Research. (2002) 4 (4): 297-311.
[32] Krauel K, Girvan L, Hook S, Rades T. Characterisation of colloidal drug delivery systems from the naked eye to cryo-fesem. Micron. (2007) 38 (8): 796-803.
[33] Kaushik D, Batheja P, Kilfoyle B, Rai V, Michniak-Kohn B. Percutaneous permeation modifiers: Enhancement versus retardation. Expert Opin. Drug Deliv. (2008) 5 (5): 517-529.
Iranian Journal of Pharmaceutical Sciences
Volume 16, Issue 2
April 2020
Pages 87-104

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