Solid–in–Oil化技術を利用したアスコルビン酸誘導体の経皮デリバリーシステム
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1 Solid in Oil , 2 1, 2, ASPION A transdermal Delivery System of an Ascorbic Acid Derivative Utilizing Solid in Oil Technique Aiko Okuma 1, Hongyu Piao 3, Yoshiro Tahara 1, Noriho Kamiya1, 2, and Masahiro Goto1, 2, 3 1 Department of Applied Chemistry, Graduate School of Engineering, Kyushu University, 744 Moto oka, Fukuoka , Japan 2 Center for Future Chemistry, Kushu University, 744 Moto oka, Fukuoka , Japan 3 ASPION Corporation, Minatojima minamimachi, Kobe , Japan A solid in oil (S/O) solution containing L ascorbic acid phosphate magnesium salt (VC) was prepared to investigate the permeation behavior of VC into epidermis and dermis. The VC was coated with hydrophobic surfactant molecules. Therefore, the coated VC was well dispersed in an oil phase. Using a Yucatan micropig skin as a model skin, we validated if the S/O technique is applicable to carry a hydrophilic biomolecules into the cutaneous tissue. The observation of the cross-sectional skin by a fluorescent microscope confirmed that VC is present inside the skin tissue. The results indicated that the S/O solution can deliver VC into the skin. Since VC works as an inhibitor against melanin formation at epidermis and dermis, it is suggested that the VC S/O solution can be applied to a whitening agent and a cosmetic ingredient. Keywords : transdermal delivery ascorbic acid derivative solid in oil solution yucatan micropig skin melanin 1. 1 C Fig. 1 Corresponding author Tel : Fax : m-goto@mail.cstm.kyushu-u.ac.jp
2 Skin structure and a synthetic pathway leading to melanin pigment in melanocytes. sketch of the skin structure, stratum corneum, epidermis, and dermis were shown. pathway of melanocytes, tyrosinase was involved in the production of melanin. In a In a 4 5 water in oil W/O 6 A E 7 nm VC S/O, L 2. VC VC 2.1 L solid in oil S/O VC n VC S/O ER 290, IPM Type Candida rugosa 819 units/mg S/O Fig. 1 PVDF Nihon Millipore K.K m 13 mm m Yucatan micropig skin YMP skin Charles River Laboratories Japan, Inc. 2.2 VC S/O ER mg 20 ml S/O 50 ml Fig. 2 8, 9 10 VC 25 mg Milli Q 10 ml 11 S/O 5
3 Preparation scheme of a solid in oil (S/O) solution. (1) Homogenization of organic phase containing surfactants and aqueous phase dissolving VC. The volume of organic phase is two times as much as that of aqueous solution. (2) After freeze drying, IPM or olive oil was added rpm W/O 2 ml W/O 1 ml VC S/O VC 2.5 mg/g S/O VC IPM VC HPLC : high performance liquid 2.3 VC S/O chromatography S/O HPLC Inertsil ODS DLS : dynamic light scattering Nano ZS / 5 VC S/O mmol / 20 mmol 2.0 L S/O TEM 20 l S/O VC 2.5 mg/g 20 TEM : transmission electron 2.4 S/O microscopy H YMP skin S/O 2 cm 2 Franz VC S/O cm 2, 40 S/O ph ml VC S/O VC 0.5 L 0.95 ml/min VC S/O Table 1 No.#1, 250 mg 24 S/O. VC VC 40 mg 1 control 1 VC 2.5 mg/g ER 290 VC mm ph 7.0, 3 ml control 2 VC 2.5 mg/g S/O 50 mg S/O
4 Particle sizes of VC S/O solutions by DLS measurement (n 3 TEM images of VC S/O solution. Particle sizes of VC S/O solutions by DLS measurement and the recovery yields of VC included in S/O solutions YMP skin Franz S/O 80 / 20 S/O 560 nm m mm IPM 50 M Table 1 ph 7 VC S/O 13 OLYM- IPM PUS IX70 10 ex 490 nm S/O Fig YMP skin VC S/O YMP skin 14 S/O TEM S/O 1 mm HCl 0.5 ml Fig nm VC HPLC VC S/O VC S/O 700 nm Table 1 IPM IPM / VC S/O VC IPM S/O VC VC S/O DLS S/O S/O S/O IPM S/O 150 nm
5 Fluorescence microscopy of the YMP skin sections treated with the samples containing VC visualized through a 10 objective (scale bar : 10 m). Samples to which a aqueous solution (A), a VC and ER 290 physical mixture (B), and a S/O solution (C) were applied at 24 h. At the left side of the sections, the skin surface is displayed. VC S/O VC VC S/O Table 2 VC S/O S/O VC S/O VC S/O S/O S/O VC Table 2 VC S/O 30 In vitro cumulative amount time profiles of transdermal VC delivery from various additives ; VC S/O solution ( ), aqueous solution ( : control 1), and a 3.2 S/O mixture ( : control 2). After all samples 250 mg were administered to YMP skin, transcutaneous VC S/O YMP skin 24 delivery started. The S/O solution concentration is VC 2.5 mg/g. S/O 10 m VC VC Fig. 5 S/O 6 12 VC control 1 18 VC S/O VC Fig. 4 control YMP skin VC VC Fig. 4 S/O VC VC S/O VC VC VC Fig. 4 VC VC control 1
6 VC 162 (2006) S/O VC S/O 12) Kishimoto K, Nagashima M, Shigeoka S, Minowa K, Kadoi H, Moriyasu T, Seto T, Masuda H : Ann. Rep. Tokyo Metr. Inst. P. H.,, (2006) VC 13) Fei N, Jiuru L : Anal. Chim. Acta.,, (2007) 14) Boinpally RR, Zhou S-L, Poondru S, Devraj G, Jasti RB : Fig. 5 VC Eur. J. Pharm. Biopharm.,, (2003) VC VC (Received 14 January 2009 ; Accepted 18 May 2009) 4. VC S/O VC S/O S/O 1 VC VC S/O VC VC VC S/O 1), :,, (2008) 2) Ito S, Wakamatsu K : Photochem. Photobiol.,, (2008) 3) Parvez S, Kang M, Chung HS, Bae H : Phytother Res.,, (2007) 4) Ebihara M, Akiyama M, Ohnishi Y, Tajima S, Komata K, Mitsui Y : J. Dermatol. Sci.,, (2003) 5) Shibayama H, Hisama M, Matsuda S, Ohtsuki M : Skin Pharmacol. Physiol.,, (2008) 6) Ochiai Y, Kaburagi S, Obayashi K, Ujiie N, Hashimoto S, Okano Y, Masaki H, Ichihashi M, Saurai H : J. Dermatol. Sci.,, (2006) 7) Segall AI, Moyano MA : Int. J. Cosmet. Sci.,, (2008) 8) Piao H, Kamiya N, Hirata A, Yokoyama H, Fujii T, Shimizu I, Ito S, Goto M : Pharm. Dev. Technol.,, (2007) 9) Piao H, Kamiya N, Hirata A, Fujii T, Shimizu I, Ito S, Goto M : Pharm. Res.,, (2008) 10) Tahara Y, Honda S, Kamiya N, Piao H, Hirata A, Hayakawa E, Fujii T, Goto M : J. Control. Release,, (2008) 11) Piao H, Kamiya N, Watanabe J, Yokoyama H, Hirata A, Fujii T, Shimizu I, Ito S, Goto M : Int. J. Pharm.,, 159-
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