2,5-Dimethyl-celecoxib

AdipoGen Life Sciences
Product Code: AG-CR1-3599

CodeSizePrice
AG-CR1-3599-M0055 mg£60.00
Quantity:
AG-CR1-3599-M02525 mg£160.00
Quantity:
Prices exclude any Taxes / VAT

Overview

Regulatory Status: RUO
Shipping:
-20°C
Storage:
-20°C

Images

1 / 1
Chemical Structure

Chemical Structure

Further Information

Alternate Names/Synonyms:
DMC; 2,5-Dimethylcelecoxib
Appearance:
White solid.
CAS:
457639-26-8
Class:
6.1
EClass:
32160000
Form (Short):
liquid
GHS Symbol:
GHS06
Handling Advice:
Keep cool and dry.
Hazards:
H301
InChi:
InChI=1S/C18H16F3N3O2S/c1-11-3-4-12(2)15(9-11)16-10-17(18(19,20)21)23-24(16)13-5-7-14(8-6-13)27(22,25)26/h3-10H,1-2H3,(H2,22,25,26)
InChiKey:
NTFOSUUWGCDXEF-UHFFFAOYSA-N
Long Description:
Chemical. CAS: 457639-26-8. Formula: C18H16F3N3O2S. MW: 395.4. Close structural analog of the selective cyclooxygenase-2 (COX-2) inhibitor celecoxib, that lacks COX-2 inhibitory function. Anti-proliferative, anti-tumorigenic and anti-angiogenic. Potent apoptosis inducer in many cancer cell lines. Down-regulates the expression of survivin, cyclins, MMPs and inhibits cyclin-dependent kinase activity. Modulates PDK-1, AKT, GSK3beta, p70 S6K, PKA and MAPKAP-K1alpha. Reduces phosphorylation of ERK1/2 but not AKT T-308 or AKT S-473. Increases intracellular free calcium levels and potently triggers the endoplasmatic reticulum stress response (ESR), activating ER stress-associated proteins GRP78/BiP, CHOP/GADD153 and caspase-4.
MDL:
MFCD19443858
Molecular Formula:
C18H16F3N3O2S
Molecular Weight:
395.4
Package Type:
Vial
PG:
III
Precautions:
P264, P301, P310, P330
Product Description:
Close structural analog of the selective cyclooxygenase-2 (COX-2) inhibitor celecoxib, that lacks COX-2 inhibitory function. Anti-proliferative, anti-tumorigenic and anti-angiogenic. Potent apoptosis inducer in many cancer cell lines. Down-regulates the expression of survivin, cyclins, MMPs and inhibits cyclin-dependent kinase activity. Modulates PDK-1, AKT, GSK3beta, p70 S6K, PKA and MAPKAP-K1alpha. Reduces phosphorylation of ERK1/2 but not AKT T-308 or AKT S-473. Increases intracellular free calcium levels and potently triggers the endoplasmatic reticulum stress response (ESR), activating ER stress-associated proteins GRP78/BiP, CHOP/GADD153 and caspase-4.
Purity:
>99% (HPLC)
Signal word:
Danger
SMILES:
CC1=CC=C(C)C(=C1)C1=CC(=NN1C1=CC=C(C=C1)S(N)(=O)=O)C(F)(F)F
Solubility Chemicals:
Soluble in DMSO, methanol or dichloromethane.
Transportation:
Excepted Quantity
UN Nummer:
UN 2811
UNSPSC Category:
Biochemical Reagents
UNSPSC Number:
12352200
Use & Stability:
Stable for at least 2 years after receipt when stored at -20°C.

References

Dimethyl-celecoxib (DMC), a derivative of celecoxib that lacks cyclooxygenase-2-inhibitory function, potently mimics the anti-tumor effects of celecoxib on Burkitt's lymphoma in vitro and in vivo: A. Kardosh, et al.; Cancer Biol. Ther. 4, 571 (2005) | DMC: novel celecoxib derivatives to rap cancer: P. Dent, et al.; Cancer Biol. Ther. 4, 583 (2005) | Multitarget inhibition of drug-resistant multiple myeloma cell lines by dimethyl-celecoxib (DMC), a non-COX-2 inhibitory analog of celecoxib: A. Kardosh, et al.; Blood 106, 4330 (2005) | Calcium-activated endoplasmic reticulum stress as a major component of tumor cell death induced by 2,5-dimethyl-celecoxib, a non-coxib analogue of celecoxib: P. Pyrko, et al.; Mol. Cancer Ther. 6, 1262 (2007) | Aggravated endoplasmic reticulum stress as a basis for enhanced glioblastoma cell killing by bortezomib in combination with celecoxib or its non-coxib analogue, 2,5-dimethyl-celecoxib: A. Kardosh, et al.; Cancer Res. 68, 843 (2008) | Dimethylcelecoxib inhibits mPGES-1 promoter activity by influencing EGR1 and NF-kappaB: K. Deckmann, et al.; Biochem. Pharmacol. 80, 1365 (2010) | Antiangiogenic activities of 2,5-dimethyl-celecoxib on the tumor vasculature: J.J. Virrey, et al.; Mol. Cancer Ther. 9, 631 (2010)

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