Terrein

Modify Date: 2024-01-05 18:29:17

Terrein Structure
Terrein structure
Common Name Terrein
CAS Number 582-46-7 Molecular Weight 154.16300
Density 1.449g/cm3 Boiling Point 327.2ºC at 760mmHg
Molecular Formula C8H10O3 Melting Point N/A
MSDS Chinese USA Flash Point 165.9ºC

 Use of Terrein


Terrein is a melanogenesis inhibitor[1]. Terrein induces apoptosis in breast cancer cell lines [2]. Terrein is an inhibitor of quorum sensing and c-di-GMP in Pseudomonas aeruginosa[3].

 Names

Name 2-Cyclopenten-1-one, 4,5-dihydroxy-3-(1-propenyl)
Synonym More Synonyms

 Terrein Biological Activity

Description Terrein is a melanogenesis inhibitor[1]. Terrein induces apoptosis in breast cancer cell lines [2]. Terrein is an inhibitor of quorum sensing and c-di-GMP in Pseudomonas aeruginosa[3].
Related Catalog
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[1]. Terrein (5-500 µM; 24 and 48 hours) reduces the viability of these cells in concentration- and time-dependent manners[2]. 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[2]. 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[2]. 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[2]. 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[3]. Cell Viability Assay[2] Cell Line: MCF-7 and MDA-MB-231 cells Concentration: 5, 25, 50, 75, 100, 150, 250, 500 µM Incubation Time: 24 and 48 hours Result: The IC50s for MCF-7 and MDA-MB-231 cells after 24 h of incubation were 2.34 mM and 700 µM, respectively. After 48 h of incubation, the IC50s are 244.3 µM for MCF-7 and 244.5 µM for MDA-MB-231 cells. Apoptosis Analysis[2] Cell Line: MCF-7 and MDA-MB-231 cells Concentration: 25, 75, 150, 250, 500 µM Incubation Time: 24 hours Result: The percentages of apoptotic cells after 25 and 75 µM treatment were 7.52 and 5.82%, respectively for MCF-7 cells (9.94% for the control), and 15.77 and 15.82%, respectively for MDA-MB-231 cells (8.79% for the control). RT-PCR[2] Cell Line: MCF-7 and MDA-MB-231 cells Concentration: 25, 75 µM Incubation Time: Result: Decreased the mRNA levels of both MMP-2 and MMP-9 in a concentration-dependent manner. Western Blot Analysis[2] Cell Line: MCF-7 and MDA-MB-231 cells Concentration: 75 µM Incubation Time: 6, 12 and 24 hours Result: RhoA and RhoB protein levels were significantly decreased after 6 h of 75 µM treatment in MCF-7 cells. Phosphorylated (p)-Rac1 was also slightly decreased at 12 h. However, RhoC and Cdc42 levels remained unchanged. RhoB protein levels and Rac1 phosphorylation were also decreased in MDA-MB-231 cells at 12 and 24 h, respectively.
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.

 Chemical & Physical Properties

Density 1.449g/cm3
Boiling Point 327.2ºC at 760mmHg
Molecular Formula C8H10O3
Molecular Weight 154.16300
Flash Point 165.9ºC
Exact Mass 154.06300
PSA 57.53000
Index of Refraction 1.713

 Safety Information

RIDADR NONH for all modes of transport

 Precursor & DownStream

Precursor  0

DownStream  1

 Synonyms

trans-(4S,5R)-4,5-dihydroxy-3-[(E)-1-propenyl]-2-cyclopenten-1-one
trans-4,5-dihydroxy-3-propenyl-2-cylopenten-1-one
(4S)-4r,5t-dihydroxy-3-trans-propenyl-cyclopent-2-enone
(4S,5R)-4,5-Dihydroxy-3-[(E)-1-propenyl]-2-cyclopenten-1-one
trans-2,3-dihydroxy-4-propenylcyclopent-4-enone
TERREIN