Structural requirement of phenylthiourea analogs for their inhibitory activity of melanogenesis and tyrosinase

Pillaiyar Thanigaimalai, Ki Cheul Lee, Vinay K. Sharma, Cheonik Joo, Won Jea Cho, Eunmiri Roh, Youngsoo Kim, Sang Hun Jung

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23 Scopus citations

Abstract

Effect of a series of 1-phenylthioureas 1a-k and 1,3-disubstituted thioureas 2a-k were evaluated against melanin formation in melanoma B16 cell line and mushroom tyrosinase. Inhibitory activity of tyrosinase of 1-phenylthioureas 1a-k is parallel to their melanogenic inhibition. Thus, the melanogenic inhibition in melanoma B16 cells of 1-phenylthioureas could be the result of inhibition of tyrosinase. However, 1,3-diaryl or 1-phenyl-3- alkylthioureas, 2a-k, appears as melanogenic inhibitor without inhibition of tyrosinase. The molecular docking study of 1e and 2b to binding pocket of tyrosinase provided convincing explanation regarding the necessity of direct connection of planar phenyl to thiourea unit without N′-substitution of phenylthioureas 1 as tyrosinase inhibitor and 2 as non-tyrosinase inhibitor.

Original languageEnglish (US)
Pages (from-to)6824-6828
Number of pages5
JournalBioorganic and Medicinal Chemistry Letters
Volume21
Issue number22
DOIs
StatePublished - Nov 15 2011

Bibliographical note

Funding Information:
This work was supported by a Priority Research Centers Program (2009-0093815) through the National Research Foundation of Korea (NRF) funded by the Ministry of Education, Science and Technology.

Keywords

  • 1,3-Disubstituted thioureas
  • 1-Phenylthioureas
  • Docking study
  • Melaninogenic inhibitor
  • Tyrosinase inhibitor

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