Celecoxib
Celecoxib is a highly selective inhibitor of cyclooxygenase-2 (COX-2) with IC50 value of 40nM [1].
In vitro, celecoxib not only reduced the production of PGE2 but also inhibited the downstream effects of PGE2. Celecoxib?blocked migration and invasion of A549 cells increased by PGE2 in the wound healing and transwell assays. ?Additionally, celecoxib?reduced MMP9?mRNA expression which was increased by PGE2. Moreover, celecoxib enhanced E-cadherin mRNA expression which was inhibited by PGE2 [2].
In vivo, celecoxib inhibited the increase in metastases of A549 cells and significantly reduced the increase in PGE2 plasma level?in mice receiving unilateral pneumonectomy [2].
References:
[1] Penning TD1,?Talley JJ,?Bertenshaw SR,?Carter JS,?Collins PW,?Docter S,?Graneto MJ,?Lee LF,?Malecha JW,?Miyashiro JM,?Rogers RS,?Rogier DJ,?Yu SS,AndersonGD,?Burton EG,?Cogburn JN,?Gregory SA,?Koboldt CM,?Perkins WE,?Seibert K,?Veenhuizen AW,?Zhang YY,?Isakson PC. Synthesis?and?biological?evaluation?of the?1,5-diarylpyrazole?class?of?cyclooxygenase-2 inhibitors: identification of 4-[5-(4-methylphenyl)-3-(trifluoromethyl)-1H-pyrazol-1-yl]benze nesulfonamide (SC-58635, celecoxib). J Med Chem.?1997 Apr 25;40(9):1347-65.
[2] Zhang S1,?Da L1,?Yang X1,?Feng D1,?Yin R1,?Li M1,?Zhang Z1,?Jiang F2,?Xu L3. Celecoxib?potentially inhibits metastasis of lung cancer promoted by surgery in mice, via suppression of the PGE2-modulated β-catenin pathway.
Toxicol Lett.?2014 Mar 3;225(2):201-7.
| Physical Appearance | A solid |
| Storage | Store at -20°C |
| M.Wt | 381.37 |
| Cas No. | 169590-42-5 |
| Formula | C17H14F3N3O2S |
| Solubility | insoluble in H2O; ≥16.8 mg/mL in EtOH; ≥19.07 mg/mL in DMSO |
| Chemical Name | 4-[5-(4-methylphenyl)-3-(trifluoromethyl)pyrazol-1-yl]benzenesulfonamide |
| SDF | Download SDF |
| Canonical SMILES | CC1=CC=C(C=C1)C2=CC(=NN2C3=CC=C(C=C3)S(=O)(=O)N)C(F)(F)F |
| Shipping Condition | Small Molecules with Blue Ice, Modified Nucleotides with Dry Ice. |
| General tips | We do not recommend long-term storage for the solution, please use it up soon. |
| Kinase experiment [1]: | |
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COX enzyme assay in vitro |
Expression of COX protein in insect cells was determined by assessing PG-synthetic capability in homogenates from cells incubated for 3 days with COX-1 or COX-2 baculovirus. Cells expressing COX-1 or COX-2 were homogenized and incubated with arachidonic acid (10 μM). COX activity was determined by monitoring PG production. No COX activity was detected in mock-infected Sf9 cells. Celecoxib were preincubated with crude 1% CHAPS homogenates (2 ~ 10 μg of protein) for 10 mins before addition of arachidonic acid. PGE2 formed was detected by ELISA after 10 min incubation. |
| Cell experiment [2]: | |
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Cell lines |
A549 cells |
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Preparation method |
The solubility of this compound in DMSO is > 19.1 mg/mL. General tips for obtaining a higher concentration: Please warm the tube at 37 °C for 10 minutes and/or shake it in the ultrasonic bath for a while. Stock solution can be stored below - 20 °C for several months. |
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Reacting condition |
0 ~ 10 μM |
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Applications |
In A549 cells, Celecoxib (≤ 10 μM) and PGE2 (≤ 12.5 μM) showed no effect on cell viability. However, Celecoxib reversed PGE2 (10 μM) increased migration and invasion of A549 cells. |
| Animal experiment [2]: | |
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Animal models |
Mice received unilateral pneumonectomy |
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Dosage form |
100 mg/kg; p.o.; q.d. |
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Applications |
In mice received unilateral pneumonectomy, Celecoxib inhibited increased metastasis of A549 cells. Moreover, Celecoxib significantly inhibited the increase in PGE2 plasma level as well. |
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Other notes |
Please test the solubility of all compounds indoor, and the actual solubility may slightly differ with the theoretical value. This is caused by an experimental system error and it is normal. |
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References: [1]. Penning TD1, Talley JJ, Bertenshaw SR, Carter JS, Collins PW, Docter S, Graneto MJ, Lee LF, Malecha JW, Miyashiro JM, Rogers RS, Rogier DJ, Yu SS,AndersonGD, Burton EG, Cogburn JN, Gregory SA, Koboldt CM, Perkins WE, Seibert K, Veenhuizen AW, Zhang YY, Isakson PC. Synthesis and biological evaluation of the 1,5-diarylpyrazole class of cyclooxygenase-2 inhibitors: identification of 4-[5-(4-methylphenyl)-3-(trifluoromethyl)-1H-pyrazol-1-yl]benze nesulfonamide (SC-58635, celecoxib). J Med Chem. 1997 Apr 25;40(9):1347-65. [2]. Zhang S1, Da L1, Yang X1, Feng D1, Yin R1, Li M1, Zhang Z1, Jiang F2, Xu L3. Celecoxib potentially inhibits metastasis of lung cancer promoted by surgery in mice, via suppression of the PGE2-modulated β-catenin pathway. Toxicol Lett. 2014 Mar 3;225(2):201-7. | |
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