Unknown

Dataset Information

0

A Potent Tyrosinase Inhibitor, (E)-3-(2,4-Dihydroxyphenyl)-1-(thiophen-2-yl)prop-2-en-1-one, with Anti-Melanogenesis Properties in ?-MSH and IBMX-Induced B16F10 Melanoma Cells.

ABSTRACT: In this study, we designed and synthesized eight thiophene chalcone derivatives (1a?h) as tyrosinase inhibitors and evaluated their mushroom tyrosinase inhibitory activities. Of these eight compounds, (E)-3-(2,4-dihydroxyphenyl)-1-(thiophen-2-yl)prop-2-en-1-one (1c) showed strong competitive inhibition activity against mushroom tyrosinase with IC50 values of 0.013 ?M for tyrosine hydroxylase and 0.93 ?M for dopa oxidase. In addition, we used enzyme kinetics study and docking program to further evaluate the inhibitory mechanism of 1c toward tyrosinase. As an underlying mechanism of 1c mediated anti-melanogenic effect, we investigated the inhibitory activity against melanin contents and cellular tyrosinase in B16F10 melanoma cells. As the results, the enzyme kinetics and docking results supports that 1c highly interacts with tyrosinase residues in the tyrosinase active site and it can directly inhibit tyrosinase as competitive inhibitor. In addition, 1c exhibited dose-dependent inhibitory effects in melanin contents and intracellular tyrosinase on ?-MSH and IBMX-induced B16F10 cells. Overall, our results suggested that 1c might be considered potent tyrosinase inhibitor for use in the development of therapeutic agents for diseases associated with hyperpigment disorders.

SUBMITTER: Kim CS 

PROVIDER: S-EPMC6222382 | biostudies-literature | 2018 Oct

REPOSITORIES: biostudies-literature

Json Xml
altmetric image

Publications

A Potent Tyrosinase Inhibitor, (<i>E</i>)-3-(2,4-Dihydroxyphenyl)-1-(thiophen-2-yl)prop-2-en-1-one, with Anti-Melanogenesis Properties in α-MSH and IBMX-Induced B16F10 Melanoma Cells.

Kim Chang Seok CS   Noh Sang Gyun SG   Park Yujin Y   Kang Dongwan D   Chun Pusoon P   Chung Hae Young HY   Jung Hee Jin HJ   Moon Hyung Ryong HR  

Molecules (Basel, Switzerland) 20181022 10

In this study, we designed and synthesized eight thiophene chalcone derivatives (<b>1a</b>⁻<b>h</b>) as tyrosinase inhibitors and evaluated their mushroom tyrosinase inhibitory activities. Of these eight compounds, (<i>E</i>)-3-(2,4-dihydroxyphenyl)-1-(thiophen-2-yl)prop-2-en-1-one (<b>1c</b>) showed strong competitive inhibition activity against mushroom tyrosinase with IC<sub>50</sub> values of 0.013 μM for tyrosine hydroxylase and 0.93 μM for dopa oxidase. In addition, we used enzyme kinetics  ...[more]

Similar Datasets

Unknown Catechin-7-<i>O</i>-α-L-rhamnopyranoside can reduce α-MSH-induced melanogenesis in B16F10 melanoma cells through competitive inhibition of tyrosinase.
| S-EPMC9339418 | biostudies-literature
Unknown Grape Extract Promoted α-MSH-Induced Melanogenesis in B16F10 Melanoma Cells, Which Was Inverse to Resveratrol.
| S-EPMC8512250 | biostudies-literature
Unknown Soyasaponin Ag inhibits α‑MSH‑induced melanogenesis in B16F10 melanoma cells via the downregulation of TRP‑2.
| S-EPMC5548002 | biostudies-other
Unknown Protocatechuic Aldehyde Inhibits α-MSH-Induced Melanogenesis in B16F10 Melanoma Cells via PKA/CREB-Associated MITF Downregulation.
| S-EPMC8068260 | biostudies-literature
Unknown (E)-1-(Furan-2-yl)-(substituted phenyl)prop-2-en-1-one Derivatives as Tyrosinase Inhibitors and Melanogenesis Inhibition: An In Vitro and In Silico Study.
| S-EPMC7700175 | biostudies-literature
Unknown 1-{(1Z)-1-[3-(2,4-Dichloro-phen-oxy)prop-oxy]-1-(2,4-difluoro-phen-yl)prop-1-en-2-yl}-1H-1,2,4-triazole.
| S-EPMC3379359 | biostudies-literature
Unknown Diarylpropionitrile inhibits melanogenesis via protein kinase A/cAMP-response element-binding protein/microphthalmia-associated transcription factor signaling pathway in α-MSH-stimulated B16F10 melanoma cells.
| S-EPMC8890945 | biostudies-literature
Unknown 2-Meth-oxy-4-(prop-2-en-1-yl)phenyl 2,4-di-chloro-benzoate.
| S-EPMC3770367 | biostudies-literature
Unknown (2E)-1-(2,4-Dimethyl-quinolin-3-yl)-3-phenyl-prop-2-en-1-one.
| S-EPMC3588443 | biostudies-literature
Unknown Inhibitory Effect of Avenanthramides (Avn) on Tyrosinase Activity and Melanogenesis in α-MSH-Activated SK-MEL-2 Cells: In Vitro and In Silico Analysis.
| S-EPMC8345984 | biostudies-literature