58 JOURNAL OF COSMETIC SCIENCE REFERENCES (1) S. Briganti, E. Camera, and M. Picardo, Chemical and instrumental approaches to treat hyperpig mentation, Pigment Cell Res., 16, 101-110 (2003). (2) K. 0. Adebowale, B. I. Olu-Owolabi, E. K. Olawumi, and 0. S. Lawal, Functional properties of native, physically and chemically modified breadfruit (Artocarpus artifis) starch, Ind. Crops Prod., 21, 343-351 (2005). (3) K. Shimizu, R. Kondo, K. Sakai, S.-H. Lee, and H. Sato, The inhibitory components from Artocarpus incisus on melanin biosynthesis, Planta Med. 64, 408--412 (1998). (4) K. Shimizu, R. Kondo, and K. Sakai, The skin-lightening effects of artocarpin on DVB-induced pigmentation, Pfanta Med. 68, 79-81 (2002). (5) K. Likhitwitayawuid and B. Sritularak, A new dimeric stilbene with tyrosinase inhibitory activity from Artocarpus gomezianus,]. Nat. Prod., 64, 1457-1459 (2001). (6) Y. Masamoto, S. Iida, and M. Kubo, Inhibitory effect of Chinese crude drugs on tyrosinase, Pfanta Med., 40, 361-365 (1980). (7) C. Juliano, M. Cossu, M. C. Alamanni, and L. Piu, Antioxidant activity of gamma-oryzanol: Mecha nism of action and its effect on oxidative stability of pharmaceutical oils, Int.]. Pharm., 299, 146-154 (2005). (8) R. Amarowicz, R. B. Pegg, P. Rahimi-Moghddam, B. Barl, and J. A. Weil, Free-radical scavenging capacity and antioxidant activity of selected plant species from the Canadian prairies, Food Chem., 85, 551-562 (2004). (9) Y. J. Mun, S. W. Lee, H. W. Jeong, K. G. Lee, J. H. Kim, and W. H. Woo, Inhibitory effect of miconazole on melanogenesis, Biol. Pharm. Buff., 27, 806-809 (2004). (10) K. F. Huang, Y. W. Chen, C. T. Chang, and S. T. Chou, Studies on the inhibitory effect of Grapto petafum paraguayense E. Walther extracts on mushroom tyrosinase, Food Chem., 89, 583-587 (2005). (11) H. S. Lee, Tyrosinase inhibitors of Pufsatiffa cernua root-derived materials,]. Agr. Food Chem., 50, 1400-1403 (2002). (12) S. B. Potterf, J. Muller, I. Bernardini, F. Tietze, T. Kobayashi, V. J. Hearing, and W. A. Gahl, Characterization of a melanosomal transport system in murine melanocytes mediating entry of the melanogenic substrate tyrosine,]. Biol. Chem., 271, 4002--4008 (1996). (13) W. A. Gahl, Lysosomal membrane transport in cellular nutrition. Annu. Rev. Nutr., 9, 39-61 (1989). (14) G. Battaini, E. Monzani, L. Casella, L. Santagostini, and R. Pagliarin, Inhibition of the catecholase activity of biomimetic dinuclear copper complexes by kojic acid,]. Biol. Inorg. Chem., 5, 262-268 (2000). (15) Y. Hira, S. Hatae, T. Inoue, and Y. Ohyama, Inhibitory effects of kojic acid on melanin formation: In vitro and in vivo studies in black goldfish,]. Jap. Cosmet. Sci. Soc., 6, 193-194 (1982). (16) K. Shimizu, R. Kondo, and K. Sakai, Inhibition of tyrosinase by flavonoids, stilbenes and related 4-substituted resorcinols: Structure-activity investigations, Planta Med., 66, 11-15 (2001). (17) T. C. Lei, V. M. Virador, W. D. Vieira, and V. J. Hearing, A melanocyte-keratinocyte coculture model to assess regulators of pigmentation in vitro, Anal. Chem., 305, 260-268 (2002). (18) E. V. Curto, C. Kwong, H. Hermersdorfer, H. Glatt, C. Santis, V. Virador, V. J. Hearing, Jr., and T. P. Dooley, Inhibitor of mammalian melanocyte tyrosinase: In vitro comparisons of alkyl esters of gentisic acid with other putative inhibitors, Biochem. Pharmacof., 57, 663-672 (1999). (19) S. Y. Choi, S. Kim, H. Kim, K. Suk, J. S. Hwang, B. G. Lee, A. J. Kim, and S. Y. Kim, (4-methoxy benzylidene)-(3-methoxy-phenyl)-amine, a nitrogen analog of stilbene as a potent inhibitor of melanin production, Chem. Pharm. Bull., 50, 450--452 (2002). (20) H. S. Lee, Tyrosinase inhibitors of Pulsatilla cernua root-derived materials,]. Agr. Food Chem., 50, 1400-1403 (2002). (21) S. Khatib, 0. Nerya, R. Musa, M. Shmuel, S. Tamir, and J. Vaya, Chalcones as potent tyrosinase inhibitors: The importance of a 2,4-substitute resorcinol moiety, Bioorgan. Med. Chem., 13, 433--441 (2005). (22) K. H. Wang, R. D. Lin, F. L. Hsu, Y. H. Huang, H. C. Chang, C. Y. Huang, and M. H. Lee, Cosmetic applications of selected traditional Chinese herbal medicines,] Ethnopharmacof., 106, 353-359 (2006).
]. Cosmet. Sci., 59, 59-69 Qanuary/February 2008) Biological activities of selected peptides: Skin penetration ability of copper complexes with peptides LENAMAZUROWSKA and MIROSLAW MOJSKI, Warsaw University of Technology, Faculty of Chemistry, Noakowskiego 3, 01-664 Warsaw, Poland. Accepted for publication August 15, 2007. Synopsis This study concerning the permeability through skin barriers of copper complexes with peptides is an important part of the research on their biological activity. The transport of copper complexes through the skin is essential in treatment of dermatological dysfunctions connected to the deficiency of these elements in the skin. During the last several years, a special interest in transepidermal copper delivery has been observed. This is the reason why copper compounds have been used as active compounds in care cosmetics. Yet, the transport process of copper complexes with tripeptides, glycyl-histidyl-lysine GHK, or )'-glutamyl cysteinyl-glycine GSH through the stratum corneum has received very little attention in the literature so far. The penetration ability of GHK-Cu and GSH-Cu through the stratum corneum and the influence of the complexes with tripeptide on the copper ion transport process is the key factor in their cosmetic and pharmaceutical activity. The in vitro penetration process was studied in the model system, a Franz diffusion cell with a liposome membrane, where liquid crystalline systems of physicochemical properties similar to the ones of the intercellular cement of stratum corneum were used as a standard model of a skin barrier. The results obtained demonstrated that copper complexes permeate through the membranes modeling the horny lipid layer and showed the influence of peptides on the dynamics of copper ion diffusion. INTRODUCTION The existence of metal ions is essential for all living organisms because they are con stituents of a large group of enzymes responsible for different physiological processes. Thus, they determine the proper functioning of the whole body, including the skin tissue. One of these essential metals is copper, which, according to its antiradical activity, the potential of regulating the melanogenesis process, and the synthesis of collagen, elastine, and GAGs (1,2), is widely used as a cosmetic ingredient. Despite the fact that copper is one of the most important metals for normal skin activity and growth, not all of the copper compounds, because of their toxicity, may be used as Address all correspondence to Lena Mazurowska. 59
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