Terrein

Terrein is a melanogenesis inhibitor. Terrein induces apoptosis in breast cancer cell lines. Terrein is an inhibitor of quorum sensing and c-di-GMP in Pseudomonas aeruginosa.

Product information

CAS Number: 582-46-7

Molecular Weight: 154.16

Formula: C8H10O3

Synonym:

(+)Terrein

Terrain

NSC 291308

NSC-291308

NSC291308

Chemical Name: (4S, 5R)-4, 5-dihydroxy-3-[(1E)-prop-1-en-1-yl]cyclopent-2-en-1-one

Smiles: C/C=C/C1=CC(=O)[C@H](O)[C@H]1O

InChiKey: MHOOPNKRBMHHEC-HZIBQTDNSA-N

InChi: InChI=1S/C8H10O3/c1-2-3-5-4-6(9)8(11)7(5)10/h2-4,7-8,10-11H,1H3/b3-2+/t7-,8-/m0/s1

Technical Data

Appearance: Solid Power

Purity: ≥98% (or refer to the Certificate of Analysis)

Solubility: Soluble in DMSO

Shipping Condition: Shipped under ambient temperature as non-hazardous chemical or refer to Certificate of Analysis

Storage Condition: Dry, dark and -20 ^oC for 1 year or refer to the Certificate of Analysis.

Shelf Life: ≥360 days if stored properly.

Stock Solution Storage: 0 - 4 ^oC for 1 month or refer to the Certificate of Analysis.

Drug Formulation: To be determined

HS Tariff Code: 382200

How to use

In Vitro:

Treatment of Mel-Ab cells with Terrein (10-100 µM) for 4 days significantly reduces melanin levels in a dose-dependent manner. Terrein reduces melanin synthesis by reducing tyrosinase production via ERK activation. Terrein (5-500 µM; 24 and 48 hours) reduces the viability of these cells in concentration- and time-dependent manners. Terrein (150, 250, 500µM; 24 hours) induces programmed cell death in both invasive and non-invasive breast cancer cell lines. Thus, the optimal non-toxic concentrations of Terrein (25 and 75 µM) were used for subsequent experiments. Terrein (25 and 75 µM) significantly decrease the mRNA levels of both MMP-2 and MMP-9 in MDA-MB-231 cells. Terrein (75 µM) significantly decrease the mRNA levels of both MMP-2 and MMP-9 in MCF-7 cells. Terrein (75 µM) inhibits the expression of RhoA, RhoB, p-Rac1 in MCF-7 cells. Terrein (75 µM) inhibits the expression of RhoB, p-Rac1 in MDA-MB-231 cells. Terrein (10, 30, and 100 μM) inhibits the production of virulence factors such as elastase, pyocyanin, and rhamnolipid, as well as biofilm formation in P. aeruginosa PAO1 and PA14 strains.

References:

1. S-H Park, et al. Terrein: A New Melanogenesis Inhibitor and Its Mechanism. Cell Mol Life Sci. 2004 Nov;61(22):2878-85.
2. Anongnard Kasorn, et al. Terrein Inhibits Migration of Human Breast Cancer Cells via Inhibition of the Rho and Rac Signaling Pathways. Oncol Rep. 2018 Mar;39(3):1378-1386.
3. Bomin Kim, et al. Terrein Is an Inhibitor of Quorum Sensing and c-di-GMP in Pseudomonas Aeruginosa: A Connection Between Quorum Sensing and c-di-GMP. Sci Rep. 2018 Jun 5;8(1):8617.

Products are for research use only. Not for human use.