Physicochemical characterization of native glycyl-l-histidyl-l-lysine tripeptide for wound healing and anti-aging: a preformulation study for dermal delivery

References

• Mazurowska L, Mojski M. ESI-MS study of the mechanism of glycyl-l-histidyl-l-lysine-Cu(II) complex transport through model membrane of stratum corneum. Talanta 2007;72:650–654
   PubMed Web of Science ®Google Scholar
• Pickart L, Freedman JH, Loker WJ, et al. Growth-modulating plasma tripeptide may function by facilitating copper uptake into cells. Nat 1980;288:715–717
   Web of Science ®Google Scholar
• Rucker RB, Kosonen T, Clegg MS, et al. Copper, lysyl oxidase, and extracellular matrix protein cross-linking. Am J Clin Nutr 1998;67:996–1002
   PubMed Web of Science ®Google Scholar
• Siddikuzzaman, Grace VMB, Guruvayoorappan C. Lysyl oxidase: a potential target for cancer therapy. Inflammopharmacol 2011;19:117–129
   PubMedGoogle Scholar
• Leyden J, Stevens T, Finkey M, Barkovic S, eds. Skin care benefits of copper peptide containing facial cream. American Academy of Dermatology 60th Annual Meeting; 2002; New Orleans, Louisiana, USA
   Google Scholar
• Appa Y, Stephens T, Barkovic S, Finkey M, eds. A clinical evaluation of a copper-peptide-containing liquid foundation and cream concealer designed for improving skin condition. American Academy of Dermatology 60th Annual Meeting; 2002; New Orleans, Louisiana, USA
   Google Scholar
• Abdulghani A, Sherr A, Shirin S, et al. Effects of topical creams containing vitamin C, a copper-binding peptide cream and melatonin compared with tretinoin on the ultrastructure of normal skin-A pilot clinical, histologic, and ultrastructural study. Dis Manag Clin Outcome 1998;1:136–141
   Google Scholar
• Maquart F, Bellon G, Chaqour B, et al. In vivo stimulation of connective tissue accumulation by the tripeptide-copper complex glycyl-l-histidyl-l-lysine-Cu2 + in rat experimental wounds. J Clin Inv 1993;92:2368–2376
   PubMed Web of Science ®Google Scholar
• Maquart FX, Siméon A, Pasco S, Monboisse JC. Regulation of cell activity by the extracellular matrix: the concept of matrikines. J Soc Biol 1999;193:423–428
   PubMedGoogle Scholar
• Simeon A, Emonard H, Hornebeck W, Maquart FX. The tripeptide-copper complex glycyl-l-histidyl-l-lysine-Cu2 + stimulates matrix metalloproteinase-2 expression by fibroblast cultures. Life Sci 2000;67:2257–2265
   PubMed Web of Science ®Google Scholar
• Gorouhi F, Maibach HI. Role of topical peptides in preventing or treating aged skin. Int J Cosmet Sci 2009;31:327–345
   PubMedGoogle Scholar
• Mitragotri S, Anissimov YG, Bunge AL, et al. Mathematical models of skin permeability: an overview. Int J Pharm 2011;418:115–129
   PubMed Web of Science ®Google Scholar
• Conato C, Gavioli R, Guerrini R, et al. Copper complexes of glycyl-histidyl-lysine and two of its synthetic analogues: chemical behaviour and biological activity. Biochim Biophys Acta 2001;1526:199–210
   PubMed Web of Science ®Google Scholar
• Bakshi M, Singh S. Development of validated stability-indicating assay methods‚ a critical review. J Pharm Biomed Anal 2002;28:1011–1040
   PubMed Web of Science ®Google Scholar
• Mura S, Pirot F, Manconi M, et al. Liposomes and niosomes as potential carriers for dermal delivery of minoxidil. J Drug Target 2007;15:101–108
   PubMed Web of Science ®Google Scholar
• ICH. Guidance for Industry: Q2B Validation for Analytical Procedures. Rockville (MD): US Department of Health and Human Services Food and Drug Administration, Centre for Evaluation and Research; 1996
   Google Scholar
• Goetz H, Schulenberg-schell H. Intra- and interday precision of molecular weight data determined by GPC. Int J Polym Anal Char 2001;6:565–580
   Web of Science ®Google Scholar
• Reynolds DW, Facchine KL, Mullaney JF, et al. Available guidance and best practices for conducting forced degradation studies. Pharm Tech 2002;26:48
   Google Scholar
• Alsante KM, Martin L, Baertschi SW. A stress testing benchmarking study. Pharm Tech 2003;27:60–71
   Google Scholar
• Jain R, Wu Z, Tucker IG. A stability-indicating HPLC assay with diode array detection for the determination of a benzylpenicillin prodrug in aqueous solutions. J Pharm Biomed Anal 2009;50:841–846
   PubMed Web of Science ®Google Scholar
• Lachman L, Lieberman H. Kinetic principles and stability testing In: Kanig J, ed. The theory and practice of industrial pharmacy. 3rd ed. Philadelphia (PA): Lea & Febiger; 1987:32–89
   Google Scholar
• Paschke A, Neitzel PL, Walther W, Schuurmann G. Octanol/water partition coefficient of selected herbicides: determination using shake-flask method and reversed-phase high-performance liquid chromatography. J Chem Eng Data 2004;49:1639–1642
   Web of Science ®Google Scholar
• Zlotogorski A. Distribution of skin surface pH on the forehead and cheek of adults. Arch Dermatol Res 1987;279:398–401
   PubMed Web of Science ®Google Scholar
• Gerweck LE. Modification of cell lethality at elevated temperatures the pH effect. Rad Res 1977;70:224–235
   PubMed Web of Science ®Google Scholar
• Wu Z, Razzak M, Tucker IG, Medlicott NJ. Physicochemical characterization of ricobendazole: I. solubility, lipophilicity, and ionization characteristics. J Pharm Sci 2005;94:983–993
   PubMed Web of Science ®Google Scholar
• Azmin MN, Florence AT, Handjani-Vila RM, et al. The effect of non-ionic surfactant vesicle (niosome) entrapment on the absorption and distribution of methotrexate in mice. J Pharm Pharmacol 1985;37:237–242
   PubMed Web of Science ®Google Scholar
• Snyder LR, Kirkland JJ, Glajch JL. Detection sensitivity and selectivity. Practical HPLC method development. Danvers (MA): John Wiley & Sons, Inc.; 1997:59–99
   Google Scholar
• Sanchez-Ruiz JM. Protein kinetic stability. Biophys Chem 2010;148:1–15
   PubMed Web of Science ®Google Scholar
• Street TO, Courtemanche N, Barrick D. Protein folding and stability using denaturants. Methods Cell Biol 2008;84:295–325
   PubMed Web of Science ®Google Scholar
• Bummer P. Chemical considerations in protein and peptide stability. Protein formulation and delivery. New York, USA: Taylor and Francis; 2007:7–42
   Google Scholar
• Kafka AP, Rades T, McDowell A. Rapid and specific high-performance liquid chromatography for the in vitro quantification of d-Lys6–GnRH in a microemulsion-type formulation in the presence of peptide oxidation products. Biomed Chromatogr 2010;24:132–139
   PubMed Web of Science ®Google Scholar
• Woods DJ, Otago H. Formulation in pharmacy practice. Otago: Health Care; 1993
   Google Scholar
• Benson HAE, Namjoshi S. Proteins and peptides: strategies for delivery to and across the skin. J Pharm Sci 2008;97:3591–3610
   PubMed Web of Science ®Google Scholar
• Almeida AJ, Souto E. Solid lipid nanoparticles as a drug delivery system for peptides and proteins. Adv Drug Deliv Rev 2007;59:478–490
   PubMed Web of Science ®Google Scholar
• Eicher T, Hauptmann S, Speicher A. Five-membered heterocycles: sections 5.22–5.36. The chemistry of heterocycles. Weinheim, Germany: Wiley-VCH Verlag GmbH & Co. KGaA; 2004:122–184
   Google Scholar
• Orgován G, Noszál B. NMR analysis and site-specific protonation constants of streptomycin. J Pharm Biomed Anal 2012;59:78–82
   PubMed Web of Science ®Google Scholar
• Guy RH. Current status and future prospects of transdermal drug delivery. Pharm Res 1996;13:1765–1769
   PubMed Web of Science ®Google Scholar
• Yeh M-I, Huang H-C, Liaw J-H, et al. Dermal delivery by niosomes of black tea extract as a sunscreen agent. Int J Dermatol 2013;52:239–245
   PubMed Web of Science ®Google Scholar