DuP-697

• CAT Number: I006557
• CAS Number: 88149-94-4
• Molecular Formula: C17H12BrFO2S2
• Molecular Weight: 411.31
• Purity: ≥95%
• Synonyms: 5-bromo-2-(4-fluorophenyl)-3-(4-methylsulfonylphenyl)thiophene
• InChI: InChI=1S/C17H12BrFO2S2/c1-23(20,21)14-8-4-11(5-9-14)15-10-16(18)22-17(15)12-2-6-13(19)7-3-12/h2-10H,1H3
• InChIKey: AJFTZWGGHJXZOB-UHFFFAOYSA-N
• SMILES: CS(=O)(=O)C1=CC=C(C=C1)C2=C(SC(=C2)Br)C3=CC=C(C=C3)F

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].
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].
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].

Reference

[1]. Altun A, et al. Anticancer effect of COX-2 inhibitor DuP-697 alone and in combination with tyrosine kinase inhibitor (E7080) on colon cancer cell lines. Asian Pac J Cancer Prev. 2014;15(7):3113-21.
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[2]. Gans KR, et al. Anti-inflammatory and safety profile of DuP 697, a novel orally effective prostaglandin synthesis inhibitor. J Pharmacol Exp Ther. 1990 Jul;254(1):180-7.
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[3]. Gierse JK, et al. Expression and selective inhibition of the constitutive and inducible forms of human cyclo-oxygenase. Biochem J. 1995 Jan 15;305 ( Pt 2):479-84.
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