Tetramethylcurcumin

Names

[ Name ]:
Tetramethylcurcumin

[Synonym ]:
FLLL31
(E,E)-1,7-Bis(3,4-dimethoxyphenyl)-4,4-dimethyl-1,6-heptadiene-3,5-dione
Tetramethylcurcumin
(1E,6E)-1,7-Bis(3,4-dimethoxyphenyl)-4,4-dimethyl-1,6-heptadiene-3,5-dione
1,6-Heptadiene-3,5-dione, 1,7-bis(3,4-dimethoxyphenyl)-4,4-dimethyl-, (1E,6E)-

Biological Activity

[Description]:

Tetramethylcurcumin (FLLL31), derived from curcumin, specifically suppresses the phosphorylation of STAT3 by binding selectively to Janus kinase 2 and the STAT3 Src homology-2 domain. Tetramethylcurcumin exhibits anti-inflammatory and anti-cancer effects[1][2].

[Related Catalog]:

Signaling Pathways >> Stem Cell/Wnt >> STAT

Signaling Pathways >> Apoptosis >> Apoptosis

Research Areas >> Cancer

Signaling Pathways >> JAK/STAT Signaling >> STAT

Research Areas >> Inflammation/Immunology

[Target]

STAT3

[In Vitro]

Tetramethylcurcumin (FLLL31; 2.5 and 5 µM; for 24 hours) downregulats STAT3 phosphorylation and DNA-binding activity in MDA-MB-231 breast and PANC-1 pancreatic cancer cells[1]. Tetramethylcurcumin inhibits cell viability, cell invasion. Tetramethylcurcumin is a effective inhibitor of STAT3 phosphorylation, DNA-binding activity, and transactivation in vitro, leading to the impediment of multiple oncogenic processes and the induction of apoptosis in pancreatic and breast cancer cell lines[1].

[References]

[1]. Lin L, et al. Novel STAT3 phosphorylation inhibitors exhibit potent growth-suppressive activity in pancreatic and breast cancer cells. Cancer Res. 2010 Mar 15;70(6):2445-54.

[2]. Yuan S, et al. FLLL31, a derivative of curcumin, attenuates airway inflammation in a multi-allergen challenged mouse model. Int Immunopharmacol. 2014 Jul;21(1):128-36.

Chemical & Physical Properties

[ Density]:
1.1±0.1 g/cm3

[ Boiling Point ]:
594.5±50.0 °C at 760 mmHg

[ Molecular Formula ]:
C₂₅H₂₈O₆

[ Molecular Weight ]:
424.486

[ Flash Point ]:
255.1±30.2 °C

[ Exact Mass ]:
424.188599

[ PSA ]:
71.06000

[ LogP ]:
4.81

[ Vapour Pressure ]:
0.0±1.7 mmHg at 25°C

[ Index of Refraction ]:
1.575

MSDS

Click to get detail MSDS

Safety Information

[ Hazard Statements ]:
H413

[ Hazard Codes ]:
N

[ RIDADR ]:
NONH for all modes of transport

Synthetic Route

Click to get detail synthetic route

Precursor & DownStream

Precursor

DownStream

Articles

Interleukin-17 Stimulates STAT3-Mediated Endothelial Cell Activation for Neutrophil Recruitment.

Cell Physiol. Biochem. 36 , 2340-56, (2015)

Interleukin-17 (IL-17) is a major pro-inflammatory cytokine that initiates and maintains inflammation. However, the molecular mechanisms as to how IL-17 influences endothelial cells to promote neutrop...

Modulation of cell metabolic pathways and oxidative stress signaling contribute to acquired melphalan resistance in multiple myeloma cells.

PLoS ONE 10(3) , e0119857, (2015)

Alkylating agents are widely used chemotherapeutics in the treatment of many cancers, including leukemia, lymphoma, multiple myeloma, sarcoma, lung, breast and ovarian cancer. Melphalan is the most co...

Effect of LIF-withdrawal on acetylcholine synthesis in the embryonic stem cell line CGR8 is not mediated by STAT3, PI3Ks or cAMP/PKA pathways.

Int. Immunopharmacol. 29 , 115-8, (2015)

Acetylcholine (ACh) acts as a local cellular signaling molecule and is widely expressed in nature, including mammalian cells and embryonic stem cells. The murine embryonic stem cell line CGR8 synthesi...