88149-94-4
88149-94-4 structure
- Name: DuP 697
- Chemical Name: 5-bromo-2-(4-fluorophenyl)-3-(4-methylsulfonylphenyl)thiophene
- CAS Number: 88149-94-4
- Molecular Formula: C17H12BrFO2S2
- Molecular Weight: 411.308
- Catalog: Signaling Pathways Apoptosis Apoptosis
- Create Date: 2018-12-21 11:27:55
- Modify Date: 2024-01-20 17:30:37
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DuP-697 is a member of the vicinal diaryl heterocycles and a potent, irreversible, selective and orally active COX-2 inhibitor (IC50 of 10 nM and 800 nM for human COX-2 and COX-1, respectively). DuP-697 exerts antiproliferative (IC50 of 42.8 nM), antiangiogenic and apoptotic effects on HT29 colorectal cancer cells. DuP-697 inhibits prostaglandin synthesis and has anti-inflammatory, anticancer and antipyretic effects[1][2][3].
| Name | 5-bromo-2-(4-fluorophenyl)-3-(4-methylsulfonylphenyl)thiophene |
|---|---|
| Synonyms |
dup-697
4-[5-bromo-2-(4-fluorophenyl)-3-thienyl]phenyl methyl sulfone Thiophene, 5-bromo-2-(4-fluorophenyl)-3-[4-(methylsulfonyl)phenyl]- 5-Bromo-2-(4-fluorophenyl)-3-[4-(methylsulfonyl)phenyl]thiophene |
| Description | DuP-697 is a member of the vicinal diaryl heterocycles and a potent, irreversible, selective and orally active COX-2 inhibitor (IC50 of 10 nM and 800 nM for human COX-2 and COX-1, respectively). DuP-697 exerts antiproliferative (IC50 of 42.8 nM), antiangiogenic and apoptotic effects on HT29 colorectal cancer cells. DuP-697 inhibits prostaglandin synthesis and has anti-inflammatory, anticancer and antipyretic effects[1][2][3]. |
|---|---|
| Related Catalog | |
| Target |
hCOX-2:10 nM (IC50) hCOX-1:800 nM (IC50) |
| In Vitro | DuP-697 (0-100 nM; 24 hours; HT29 cells) treatment shows antiproliferative with an IC50 value of 42.8 nM[1]. DuP-697 (25-100 nM; 72 hours; HT29 cells) treatment causes concentration dependent apoptosis in HT29 cells. The percentage of UR (apoptosis portion) area increases gradually according to the concentration of DuP-697 from 7% in control group to 52% in 100 nM DuP-697[1]. DuP-697 in 100, 10 and 1 nM concentrations cause antiangiogenic effect. Antiangiogenic scores of DuP-697 are 1.2, 0.8 and 0.5, respectively[1]. Cell Proliferation Assay[1] Cell Line: HT29 cells Concentration: 0 nM, 12.5 nM, 25 nM, 50 nM, 100 nM Incubation Time: 24 hours Result: Exhibited decreasing CI values in a concentration dependent manner. Showed statistically significant cytotoxic effect. Apoptosis Analysis[1] Cell Line: HT29 cells Concentration: 25 nM, 50 nM, 100 nM Incubation Time: 72 hours Result: Caused concentration dependent apoptosis in HT29 cells. |
| In Vivo | DuP-697 is a potent inhibitor of paw swelling in nonestablished and established adjuvant arthritis in rats (ED50 = 0.03 and 0.18 mg/kg/day, respectively). DuP-697 has no effect on phenylquinone writhing in rats (ED50 greater than 100 mg/kg), but is analgetic against inflammation-related pain in the Randall-Selitto assay (ED50 = 3.5 mg/kg) and is a very potent antipyretic agent (ED50 = 0.05 mg/kg). DuP-697 (5 mg/kg i.v.) does not alter renal blood flow or the renal vascular response to angiotensin II in furosemide-pretreated, volume-depleted rats[2]. DuP-697 is a moderate inhibitor of bull seminal vesicle prostaglandin (PG) synthesis (IC50 of 24 μM) and a potent inhibitor of rat brain PG synthesis (IC50 of 4.5 μM) but was ineffective against rat kidney PG synthesis (IC50 of 75 μM)[2]. |
| References |
| Density | 1.5±0.1 g/cm3 |
|---|---|
| Boiling Point | 454.1±45.0 °C at 760 mmHg |
| Molecular Formula | C17H12BrFO2S2 |
| Molecular Weight | 411.308 |
| Flash Point | 228.4±28.7 °C |
| Exact Mass | 409.944611 |
| PSA | 70.76000 |
| LogP | 3.85 |
| Vapour Pressure | 0.0±1.1 mmHg at 25°C |
| Index of Refraction | 1.621 |
| Hazard Codes | Xi: Irritant; |
|---|---|
| Risk Phrases | 36/37/38 |
| Safety Phrases | 26-36 |
| HS Code | 2934999090 |
| Precursor 1 | |
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| DownStream 1 | |
| HS Code | 2934999090 |
|---|---|
| Summary | 2934999090. other heterocyclic compounds. VAT:17.0%. Tax rebate rate:13.0%. . MFN tariff:6.5%. General tariff:20.0% |