Bulletin of the Korean Chemical Society

Korean Chemical Society (대한화학회)
권호 표지
DOI QR코드

DOI QR Code

Synthesis of Small Molecule-Peptide Conjugates as Potential Whitening Agents

  • Received : 2012.05.09
  • Accepted : 2012.06.18
  • Published : 2012.09.20
Download PDF
⟨ Previous Next ⟩

Abstract

Small molecule conjugated peptides were prepared by solid-phase synthesis as potential novel whitening agents, and their melanogenesis inhibitory activities were investigated. The conjugated small molecules were well-known materials as tyrosinase inhibitors, and peptides were selected from the sequences that are known to antagonize melanocortin receptor 1 (MC1R). Most of small molecules-peptide conjugates showed superior melanin inhibition activity to kojic acid and arbutin. Among these, almost all compounds have -AR- sequence. From this study, we concluded that the small molecule conjugated peptides containing -AR- sequence have melanogenesis inhibitory activities and have 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. Buscà, R.; Ballotti, R. Pigment Cell Res. 2000, 13(2), 60. https://doi.org/10.1034/j.1600-0749.2000.130203.x
  3. Penalver, M. J.; Hiner, A. N. P.; Rodriguez-Lopez, J. N.; Garcia Canovas, F.; Tudela, J. J. Biochim. Biophys. Acta 2002, 1597, 140. https://doi.org/10.1016/S0167-4838(02)00264-9
  4. 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
  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. Froidevaux, S.; Eberle, A. N. J. Recept. Signal. Transduct. Res. 2002, 22(1-4), 111. https://doi.org/10.1081/RRS-120014590
  7. Suzuki, I.; Tada, A.; Ollmann, M. M.; Barsh, G. S.; Im, S.; Lamoreux, M. L.; Hearing, V. J.; Nordlund, J. J.; Abdel-Malek, Z. A. Journal of Investigative Dermatology 1997, 108, 838. https://doi.org/10.1111/1523-1747.ep12292572
  8. Kwon, H. Y.; Bultman, S. J.; Löffler, C.; Chen, W.-J.; Furdon, P. J.; Powell, J. G.; Usala, A.-L.; Wilkison, W.; Hansmann, I.; Woychik, R. P. Proc. Natl. Acad Sci. USA 1994, 91, 9760. https://doi.org/10.1073/pnas.91.21.9760
  9. Virador, V. M.; Santis, C.; Furumura, M.; Kalbacher, H.; Hearing, V. J. J. Experimental Cell Research 2000, 259, 54. https://doi.org/10.1006/excr.2000.4975
  10. King, D. S.; Fields, C. G.; Fields, G. B. A. Int. J. Pept. Protein Res. 1990, 36, 255.
  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. 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.

Cited by

  1. Natural, semisynthetic and synthetic tyrosinase inhibitors vol.31, pp.1, 2016, https://doi.org/10.3109/14756366.2015.1004058
  2. Anti-melanogenesis and anti-tyrosinase properties of Pistacia atlantica subsp. mutica extracts on B16F10 murine melanoma cells vol.13, pp.6, 2012, https://doi.org/10.4103/1735-5362.245965
  3. Scenedesmus obliquus: A Potential Natural Source for Cosmetic Industry vol.6, pp.2, 2012, https://doi.org/10.21448/ijsm.545771
  4. Synthesis and Biological Evaluation of the Anti-Melanogenesis Effect of Coumaric and Caffeic Acid-Conjugated Peptides in Human Melanocytes vol.11, pp.None, 2012, https://doi.org/10.3389/fphar.2020.00922