Bulletin of the Korean Chemical Society

Korean Chemical Society (대한화학회)
권호 표지
DOI QR코드

DOI QR Code

Synthesis and Evaluation of Coumaroyl Dipeptide Amide as Potential Whitening Agents

  • Lee, Hye-Suk (Central Research Laboratories, Aekyung Co., Ltd.) ;
  • Shin, Kyong-Hoon (Central Research Laboratories, Aekyung Co., Ltd.) ;
  • Ryu, Geun-Seog (Central Research Laboratories, Aekyung Co., Ltd.) ;
  • Cho, In-Shik (Central Research Laboratories, Aekyung Co., Ltd.) ;
  • Kim, Jae-Il (Department of Life Science, Gwangju Institute of Science and Technology (GIST)) ;
  • Lee, Jae-Ho (Department of Life Science, Gwangju Institute of Science and Technology (GIST)) ;
  • Kim, Han-Young (Central Research Laboratories, Aekyung Co., Ltd.)
  • Received : 2013.06.25
  • Accepted : 2013.07.22
  • Published : 2013.10.20
Download PDF
⟨ Previous Next ⟩

Abstract

Coumaroyl dipeptide amide, Coumaric acid-LG-$NH_2$, was prepared successfully using the solid-phase method, and its efficacy as a skin whitening agent was studied. Coumaric acid-LG-$NH_2$ was prepared with Rink-amide resin, and 96.354% of purity was obtained. Using MTT assay and LDH release assay, we found that it exhibited very low cytotoxicity. And, we found that Coumaric acid-LG-$NH_2$ inhibited tyrosinase activity dose-dependently and showed superior tyrosinase inhibitory activity to well-known whitening agent, arbutin. $IC_{50}$ value of Coumaric acid-LG-$NH_2$ was 182.4 ${\mu}M$, and $IC_{50}$ value of arbutin was 384.6 ${\mu}M$. Also, in measurement of melanin contents using B16F1 melanoma cell lines, Coumaric acid-LG-$NH_2$ reduced melanin production induced by ${\alpha}$-MSH statistically significant, and showed superior melanin inhibitory activity to p-coumaric acid or arbutin. In addition, Coumaric acid-LG-$NH_2$ reduced MC1R mRNA expression level. Thus, we concluded that MC1R pathway is the significant pathway of Coumaric acid-LG-$NH_2$, and Coumaric acid-LG-$NH_2$ has great potential to be used as novel whitening agents.

Keywords

References

  1. Schallreuter, K.; Slominski, A.; Pawelek, J. M.; Jimbow, K.; Gilchrest, B. A. Exp. Dermatol. 1998, 7, 143. https://doi.org/10.1111/j.1600-0625.1998.tb00315.x
  2. Perez-Bernal A.; Munoz-Perez M. A.; Camacho F. Am. J. Clin. Dermatol. 2000, 1(5), 261. https://doi.org/10.2165/00128071-200001050-00001
  3. Briganti, S.; Camera, E.; Picardo, M. Pigment Cell Res. 2003, 16, 101. https://doi.org/10.1034/j.1600-0749.2003.00029.x
  4. Rescigno, A.; Sollai, F.; Pisu, B.; Rinaldi, A.; Sanjust, E. J. Enzym. Inhib. Med. Chem. 2002, 17, 207. https://doi.org/10.1080/14756360210000010923
  5. Cone, R. D.; Lu, D.; Koppula, S.; Vage, D. I.; Klungland, H.; Boston, B.; Chen, W.; Orth, D. N.; Pouton, C.; Kesterson, R. A. Recent Prog. Horm. Res. 1996, 51, 287.
  6. Powell, M. F.; Stewart, T.; Otvos, L.; Urge, L.; Gaeta, F. C. A.; Sette, A.; Arrhenius, T.; Thomson, D.; Soda, K.; Colon, S. M. Pharm. Res. 1993, 10, 1268. https://doi.org/10.1023/A:1018953309913
  7. Celis M. E.; Taleisnik S.; Walter R. Proc. Nat. Acad. Sci. 1971, 68(7), 1428. https://doi.org/10.1073/pnas.68.7.1428
  8. Scimonelli, T.; Celis, M. E. Peptides 1982, 3(6), 885. https://doi.org/10.1016/0196-9781(82)90055-9
  9. Shin, K. H.; Lee, J. H.; Ryu, G. S.; Jee, K. Y.; Park, S. N.; Kim, J. I.; Cho, I. S.; Kim, H.-Y. J. Soc. Cosmet. Scientists Korea 2010, 36(3), 233.
  10. Froidevaux, S.; Eberle, A. N. J. Recept. Signal. Transduct. Res. 2002, 22(1-4), 111. https://doi.org/10.1081/RRS-120014590
  11. Jang, D. I.; Lee, B. G.; Jeon, C. O.; Jo, N. S.; Koh, J. S. Cosmet. Toiletries 1997, 112(3), 59.
  12. Andrawis, A.; Kahn, V. Biochem. J. 1986, 235, 91.
  13. Mosmann T. Journal of Immunological Methods 1983, 65(1-2), 55. https://doi.org/10.1016/0022-1759(83)90303-4

Cited by

  1. Synthesis and Biological Evaluation of the Anti-Melanogenesis Effect of Coumaric and Caffeic Acid-Conjugated Peptides in Human Melanocytes vol.11, pp.None, 2013, https://doi.org/10.3389/fphar.2020.00922