Skip to main content
SpringerLink
Log in

Synthesis and Preliminary In Vitro Biological Evaluation of 5-Chloro-2-(Substituted Phenyl)Benzo[d]Thiazole Derivatives Designed As Novel Antimelanogenesis Agents

  • Published:
Applied Biochemistry and Biotechnology Aims and scope Submit manuscript

Abstract

We describe the design, synthesis, and biological activities of 5-chloro-2-(substituted phenyl)benzo[d]thiazole derivatives as novel tyrosinase inhibitors. Among them, 4-(5-chloro-2,3-dihydrobenzo[d]thiazol-2-yl)-2,6-dimethoxyphenol (MHY884) and 2-bromo-4-(5-chloro-benzo[d]thiazol-2-yl)phenol (MHY966) showed inhibitory activity higher than or similar to kojic acid, against mushroom tyrosinase. Therefore, we carried out kinetic studies on the two compounds with potent tyrosinase inhibitory effects. Kinetic analysis of tyrosinase inhibition revealed that all of these compounds are competitive inhibitors. MHY884 and MHY966 effectively inhibited tyrosinase activity and reduced melanin levels in B16 cells treated with α-melanocyte stimulating hormone (α-MSH). These data strongly suggest that the newly synthesized compounds MHY884 and MHY966 could suppress production of melanin via inhibition of tyrosinase activity.

This is a preview of subscription content, log in via an institution to check access.

Access this article

Log in via an institution

Price excludes VAT (USA)
Tax calculation will be finalised during checkout.

Instant access to the full article PDF.

Institutional subscriptions

Fig. 1
Scheme 1
Fig. 2
Fig. 3
Fig. 4
Fig. 5
Fig. 6

Similar content being viewed by others

References

  1. Strothkemp, K. G., Jolley, R. L., & Mason, H. S. (1976). Biochemical and Biophysical Research Communications, 70, 519–524.

    Article  Google Scholar 

  2. Halaban, R., Cheng, E., Svedine, S., Aron, R., & Hebert, D. N. (2001). Biological Chemistry, 276, 11933–11938.

    Article  CAS  Google Scholar 

  3. Halaban, R., Patton, R. S., Cheng, E., Svedine, S., Trombetta, E. S., Wahl, M. L., Ariyan, S., & Hebert, D. N. (2002). The Journal of Biological Chemistry, 277, 14821–14828.

    Article  CAS  Google Scholar 

  4. Raper, H. S. (1927). The Biochemical Journal, 21, 89–96.

    CAS  Google Scholar 

  5. Mason, H. S. (1948). The Journal of Biological Chemistry, 172, 83–99.

    CAS  Google Scholar 

  6. Lerner, A. B., Fitzpatrick, T. B., Calkins, E., & Summerson, W. H. (1949). The Journal of Biological Chemistry, 178, 185–195.

    CAS  Google Scholar 

  7. Iozumi, K., Hoganson, G. E., Pennella, R., Everett, M. A., & Fuller, B. B. J. (1993). The Journal of Investigative Dermatology, 100, 806–811.

    Article  CAS  Google Scholar 

  8. Fitzpatrick, T. B., Eisen, A. Z., Woff, K., Freedberg, I. M., & Austen, K. F. (1979). Dermatology in general medicine. New York: McGraw-Hill.

    Google Scholar 

  9. Cho, S. J., Roh, J. S., Sun, W. S., Kim, S. H., & Park, K. D. (2006). Bioorganic & Medicinal Chemistry Letters, 16, 2682–2684.

    Article  CAS  Google Scholar 

  10. Funayama, M., Arakawa, H., Yamamoto, R., & Nishino, T. (1995). Bioscience. Biotechnology and Biochemistry, 59, 143–144.

    Article  CAS  Google Scholar 

  11. Sugimoto, K., Nishmura, T., Nomura, K., Sugimoto, K., & Kuriki, T. (2003). Chemical & Pharmaceutical Bulletin, 51, 798–801.

    Article  CAS  Google Scholar 

  12. Yi, W., Cao, R. H., Wen, H., Yan, Q., & Zhou, B. H. (2008). Bioorganic & Medicinal Chemistry Letters, 18, 6490–6493.

    Article  CAS  Google Scholar 

  13. Liu, J. B., Cao, R. H., Yi, W., Ma, C. M., Wan, Y. Q., Zhou, B. H., Ma, L., & Song, H. C. (2009). European Journal of Medicinal Chemistry, 44, 1773–1778.

    Article  CAS  Google Scholar 

  14. Liu, J. B., Yi, W., Wan, Y. Q., Ma, L., & Song, H. C. (2008). Bioorganic & Medicinal Chemistry, 16, 1096–1102.

    Article  CAS  Google Scholar 

  15. Sabrina Okombi, S., Rival, D., Bonnet, S., Mariotte, A. M., & Perrier Boumendjel, A. (2006). Bioorganic & Medicinal Chemistry Letters, 16, 2252–2255.

    Article  Google Scholar 

  16. Okombi, S., Rival, D., Bonnet, S., Mariotte, A. M., Perrier, E., & Boumendjel, A. (2006). Journal of Medicinal Chemistry, 49, 329–333.

    Article  CAS  Google Scholar 

  17. Andrawis, A., & Kahn, V. (1986). The Biochemical Journal, 235, 91–96.

    CAS  Google Scholar 

  18. Chang, T. S. (2009). International Journal of Molecular Sciences, 10, 2440–2475.

    Article  CAS  Google Scholar 

  19. Parvez, S., Kang, M., Chung, H. S., & Bae, H. (2007). Phytotherapy Research, 21, 805–816.

    Article  CAS  Google Scholar 

  20. Tada, H., Shiho, O., Kuroshima, K., Koyama, M., & Tsukamoto, K. (1986). Journal of Immunological Methods, 93, 157–165.

    Article  CAS  Google Scholar 

  21. Morris, G. M., Goodsell, D. S., Halliday, R. S., Huey, R., Hart, W. E., Belew, R. K., & Olson, A. J. (1998). Journal of Computational Chemistry, 19, 1639–1662.

    Article  CAS  Google Scholar 

  22. Moustakas, D. T., Lang, P. T., Pegg, S., Pettersen, E., Kuntz, I. D., Brooijmans, N., & Rizzo, R. C. (2006). Journal of Computer-Aided Molecular Design, 20, 601–619.

    Article  CAS  Google Scholar 

  23. Wermuth, C. G., Ganellin, C. R., Lindberg, P., & Mitscher, L. A. (1998). Pure and Applied Chemistry, 70, 1129–1143.

    Article  CAS  Google Scholar 

  24. Wolber, G., & Langer, T. (2005). Journal of Chemical Information and Modeling, 45, 160–169.

    Article  CAS  Google Scholar 

  25. No, J. K., Soung, D. Y., Kim, Y. J., Shim, K. H., Jun, Y. S., Rhee, S. H., Yokozawa, T., & Chung, H. Y. (1999). Life Sciences, 65, PL241–PL246.

    Article  CAS  Google Scholar 

  26. Kim, D. S., Kim, S. Y., Chung, J. H., Kim, K. H. H., Eun, C., & Park, K. C. (2002). Cell Signaling, 14, 779–785.

    Article  CAS  Google Scholar 

  27. Bilodeau, M. L., Greulich, J. D., Hullinger, R. L., Bertolotto, C., Ballotti, R., & Andrisani, O. M., (2001). Pigmentation Cell Research, 14, 328–336.

    Article  CAS  Google Scholar 

  28. Ha, Y. M., Chung, S. W., Song, S., Lee, H., Suh, H., & Chung, H. Y. (2007). Biological & Pharmaceutical Bulletin, 30, 1711–1715.

    Article  CAS  Google Scholar 

  29. Takiwaki, H., Shirai, S., Kohno, H., Soh, H., & Arase, S. J. (1994). The Journal of Investigative Dermatology, 103, 642–646.

    Article  CAS  Google Scholar 

  30. Shin, N. H., Ryu, S. Y., Lee, H. S., Min, K. R., & Kim, Y. S. (1998). Planta Medica, 64, 283–284.

    Article  CAS  Google Scholar 

  31. Nimmanpisut, S., Chudapongse, P., & Ratanabanangkoon, K. (1976). Biochemical Pharmacology, 25, 1245–1248.

    Article  CAS  Google Scholar 

  32. Song, S. H., Lee, H. J., Jin, Y. G., Ha, Y. M., Bae, S. J., Chung, H. Y., & Suh, H. S. (2007). Bioorganic & Medicinal Chemistry Letters, 17, 461–464.

    Article  CAS  Google Scholar 

  33. Kim, Y. J., No, J. K., Lee, J. H., & Chung, H. Y. (2005). Biological & Pharmaceutical Bulletin, 28, 323–327.

    Article  CAS  Google Scholar 

  34. No, J. K., Kim, M. S., Kim, Y. J., Bae, S. J., Choi, J. S., & Chung, H. Y. (2004). The American Journal of Chinese Medicine, 32, 97–103.

    Article  CAS  Google Scholar 

  35. Lim, J. T. (1999). Dermatologic Surgery, 25, 282–284.

    Article  CAS  Google Scholar 

  36. Ha, Y. M., Park, J. Y., Park, Y. J., Park, D., Choi, Y. J., Kim, J. M., Lee, E. K., Han, Y. K., Kim, J. A., Lee, J. Y., Moon, H. R., & Chung, H. Y. (2011). Bioorganic & Medicinal Chemistry Letters, 21, 2445–2449.

    Article  CAS  Google Scholar 

  37. Ha, Y. M., Kim, J. A., Park, Y. J., Park, D., Kim, J. M., Chung, K. W., Lee, E. K., Park, J. Y., Lee, J. Y., Lee, H. J., Yoon, J. H., Moon, H. R., & Chung, H. Y. (2011). Biochimica et Biophysica Acta, 1810, 612–619.

    Article  CAS  Google Scholar 

  38. Ha, Y. M., Park, Y. J., Lee, J. Y., Park, D., Choi, Y. J., Lee, E. K., Kim, J. M., Kim, J. A., Park, J. Y., Lee, H. J., Moon, H. R., & Chung, H. Y. (2011). Biochimie, 94, 533–540.

    Article  Google Scholar 

  39. Criton, M., & Le Mellay-Hamon, V. (2008). Bioorganic & Medicinal Chemistry Letters, 18, 3607–3610.

    Article  CAS  Google Scholar 

  40. No, J. K., Soung, D. Y., Kim, Y. J., Shim, K. H., Jun, Y. S., Rhee, S. H., Yokozawa, T., & Chung, H. Y. (1999). Life Science, 65, PL241–PL246.

    Article  CAS  Google Scholar 

Download references

Acknowledgments

This work was supported by MRC program No. 2009–0083538 from the Medical Research Center program of the National Research Foundation of Korea. We thank the Aging Tissue Bank for providing research materials for the study.

Author information

Authors and Affiliations

  1. Molecular Inflammation Research Center for Aging Intervention (MRCA), College of Pharmacy, Pusan National University, Kumjeong-Gu, Busan, 609-735, Republic of Korea

    Young Mi Ha, Yohei Uehara, Daeui Park, Hyoung Oh Jeong & Hae Young Chung

  2. Laboratory of Medicinal Chemistry, College of Pharmacy, Pusan National University, Busan, 609-735, Republic of Korea

    Ji Young Park, Yun Jung Park, Ji Yeon Lee, Hye Jin Lee, Yu Min Song & Hyung Ryong Moon

Authors
  1. Young Mi Ha
    View author publications

    You can also search for this author in PubMed Google Scholar

  2. Yohei Uehara
    View author publications

    You can also search for this author in PubMed Google Scholar

  3. Daeui Park
    View author publications

    You can also search for this author in PubMed Google Scholar

  4. Hyoung Oh Jeong
    View author publications

    You can also search for this author in PubMed Google Scholar

  5. Ji Young Park
    View author publications

    You can also search for this author in PubMed Google Scholar

  6. Yun Jung Park
    View author publications

    You can also search for this author in PubMed Google Scholar

  7. Ji Yeon Lee
    View author publications

    You can also search for this author in PubMed Google Scholar

  8. Hye Jin Lee
    View author publications

    You can also search for this author in PubMed Google Scholar

  9. Yu Min Song
    View author publications

    You can also search for this author in PubMed Google Scholar

  10. Hyung Ryong Moon
    View author publications

    You can also search for this author in PubMed Google Scholar

  11. Hae Young Chung
    View author publications

    You can also search for this author in PubMed Google Scholar

Corresponding authors

Correspondence to Hyung Ryong Moon or Hae Young Chung.

Rights and permissions

Reprints and permissions

About this article

Cite this article

Ha, Y.M., Uehara, Y., Park, D. et al. Synthesis and Preliminary In Vitro Biological Evaluation of 5-Chloro-2-(Substituted Phenyl)Benzo[d]Thiazole Derivatives Designed As Novel Antimelanogenesis Agents. Appl Biochem Biotechnol 168, 1416–1433 (2012). https://doi.org/10.1007/s12010-012-9867-5

Download citation

  • Received:

  • Accepted:

  • Published:

  • Issue Date:

  • DOI: https://doi.org/10.1007/s12010-012-9867-5

Keywords

Search

Navigation