Journal of Integrative Natural Science (통합자연과학논문집)

The Basic Science Institute Chosun University (조선대학교 기초과학연구원)
권호 표지
DOI QR코드

DOI QR Code

Biological Activity of Multifunctional Oligopeptide Derivatives

  • Kim, Bo Mi (Department of BionanoChemistry, Wonkwang University)
  • Received : 2016.06.01
  • Accepted : 2016.06.25
  • Published : 2016.06.30
Download PDF
⟨ Previous Next ⟩

Abstract

The peptide sequences, GHK(Gly-His-Lys) and KTTKS(Lys-Thr-Thr-Lys-Ser), using a collagen stimulator recently were manipulated at N-terminal as a multifunctional peptide derivative with PEG(polyethyleneglycol) linker connected to gallic acid which presents anti-inflammatory activity. The multifunctional peptide derivatives were obtained in a normal peptide preparation method through SPPS(solid phase peptide synthesis) using Fmoc chemistry and a carboxyl group insertion reaction of PEG-3,4,5-triacetoxy benzoate by using potassium tert-butoxide and ethyl bromoacetate, which was separated by Sephadex DEAE. It gave a good compromise to a cosmetic application for cell cytotoxicity, anti-wrinkle, and anti-inflammation.

Keywords

References

  1. The National Institute of The Korean Language: Korean Language Dictionary, Seoul: Doosan Dong-A Co., Ltd, 2013.
  2. J. K. Kim, J. H. Lee, M. S. Yang, D. B. Seo, and S. J. Lee, "Beneficial effect of collagen peptide supplement on anti-aging against photodamage", Korean Journal of Food Science and Technology, Vol. 41, No. 4, pp. 441-445, 2009.
  3. A. F. Ahmed, K. Mohammad, K. Amal, A. Saeed, and N. Sami, "PEGylation enhances the oral bioavailability of $\gamma$-tocotrienol isomer of vitamin E", Southern Biomedical Engineering Conference (SBEC), Vol. 32, pp. 96, 2016.
  4. Y.-A. Jang and J.-T. Lee, "The evaluation of antioxidant, anti-inflammatory, and anti-aging of extract solvent and poria cocos by part", The Korean Society for Aesthetics and Cosmethology, Vol. 13, pp. 377-383, 2015.
  5. E. Matsumoto, Y. Fujita, Y. Okada, E. I. Kauppinen, H. Kamiya, and K. Chiba, "Hydrophobic benzyl amines as supports for liquid-phase C-terminal amidated peptide synthesis: application to the preparation of ABT-510", J. Pept. Sci., Vol 21, 9, pp. 691- 695, 2015. https://doi.org/10.1002/psc.2791
  6. F. M. Veronese, "Peptide and protein PEGylation: a review of problems and solutions", Biomaterials, Vol. 22, pp. 405-417, 2001. https://doi.org/10.1016/S0142-9612(00)00193-9
  7. K. Matsuzaki, "Control of cell selectivity of antimicrobial peptides", BBA-biomembranes, Vol. 1788, 8, pp. 1687-1692, 2009. https://doi.org/10.1016/j.bbamem.2008.09.013
  8. S. Namjoshi and H. A. E. Benson, "Cyclic peptides as potential therapeutic agents for skin disorders", Peptide Science, Vol. 94, pp. 673-680, 2010. https://doi.org/10.1002/bip.21476
  9. M. J. Kim, K. R. Im, and K. S. Yoon, "Effect of medicinal herb prepared through traditional antidiabetic prescription on $\alpha$-glucosidase activity and evaluation method for anti-melanogenesis agents using $\alpha$-glucosidase activity", Journal of the Korean Society of Food Science and Nutrition, Vol. 44, pp. 993-999, 2015. https://doi.org/10.3746/jkfn.2015.44.7.993
  10. J. Y. Lee, K. R. Lim, and K. S. Yoon, "The inhibitory effects of nelumbo nucifera gaertner extract on melanogenesis", Korean Society for Biotechnology and Bioengineering, Vol. 28, pp. 137-145, 2013.
  11. J. S. Suk, Q. Xu, N. Kim, J. Hanes, and L. M. Ensign, "PEGylation as a strategy for improving nanoparticle-based drug and gene delivery", Adv. Drug Deliver. Rev., Vol. 99, pp. 28-51, 2016. https://doi.org/10.1016/j.addr.2015.09.012
  12. S. Kitada, S. Fujita, Y. Okada, S. Kim, and K. Chiba,"Total synthesis of conotoxin MII using a soluble-tag-assisted method.", Tetrahedron, Vol. 69, pp. 2555-2559, 2013. https://doi.org/10.1016/j.tet.2013.01.068
  13. Y. Fujita, S. Fujita, Y. Okada, and K. Chiba, "Soluble tag-assisted peptide head-to-tail cyclization: total synthesis of mahafacyclin B", Org. Lett., Vol. 15, pp. 1155-1157, 2013. https://doi.org/10.1021/ol4003477
  14. X-D. Wang, H. Teng, J.-J. Hu, and Z.-L. Xiu "PEGylation of recombinant hirudin in mixed aqueous-organic solutions", Process biochem., Vol. 50, pp. 367-377, 2015. https://doi.org/10.1016/j.procbio.2015.01.007
  15. H. Y. Kweon, Y. Y. Jo, J.-H. Yeo, S. O. Woo, S. M. Han, and K.-G. Lee, "PEGylation of silk fibroin model peptide", International Journal of Industrial Entomology, Vol. 20, pp. 87-91, 2010.
  16. A. El-Sayed, S. Futaki, and H. Harashima, "Delivery of macromolecules using arginine-rich cell-penetrating peptides: Ways to overcome endosomal entrapment", AAPS J., Vol. 11, pp. 13-22, 2009. https://doi.org/10.1208/s12248-008-9071-2
  17. M. Dirin, E. Urban, C. R. Noe, and J. Winkler, "Fragment-based solid-phase assembly of oligonucleotide conjugates with peptide and polyethylene glycol ligands", Eur. J. Med. Chem., Vol. 121, pp. 132-142, 2016. https://doi.org/10.1016/j.ejmech.2016.05.001
  18. D. Yu and R. Ghosh,"Purification of PEGylated protein using membrane chromatography", J. Pharm. Sci-us., Vol. 99, pp. 3326-3333, 2010. https://doi.org/10.1002/jps.22103
  19. J. Chatterjee, F. Rechenmacher, and H. Kessler, "N-methylation of peptides and proteins: an important element for modulating biological functions.", Angew. Chem. Int. Edit., Vol. 52, pp. 254-269, 2013. https://doi.org/10.1002/anie.201205674
  20. R. B. Merrifield, "Solid phase peptide synthesis. I. The synthesis of a tetrapeptide", J. Am. Chem. Soc., Vol. 85, pp. 2149-2154, 1963. https://doi.org/10.1021/ja00897a025
  21. N. Shokrzadeh, A.-M. Winkler, M. Dirin, and J. Winkler, "Oligonucleotides conjugated with short chemically defined polyethylene glycol chains are efficient antisense agents", Bioorg. Med. Chem. Lett., Vol. 24, pp. 5758-5761, 2014. https://doi.org/10.1016/j.bmcl.2014.10.045
  22. B.-H. Kim, K.-W. Park, J.-Y. Kim, I.-Y. Jeong, G.-H. Yang, Y.-S. Cho, S.-T. Yee, and K.-I. Seo, "Purification and characterization of anticarcinogenic compound from corni fructus", Korean Journal of Food Science and Technology, Vol. 36, pp. 1001-1007, 2004.
  23. G. Tian, T. Zhang, F. Yang, and Y. Ito,"Separation of gallic acid from Cornus officinalis Sieb. et Zucc by high-speed counter-current chromatography", J. Chromatogr. A, Vol. 886, pp. 309-312, 2000. https://doi.org/10.1016/S0021-9673(00)00480-5