DuP-697
DuP-697, also known as S-6907 and BFMT, is a cyclooxygenase 2 (COX-2) inhibitor potentially for the treatment of rheumatoid arthritis (RA) and osteoarthritis. DuP-697 alone exerted antiproliferative, antiangiogenic and apoptotic effects on HT29 colorectal cancer cells. DuP-697 significantly suppressed K562 cells and primary CML cells growth and induced apoptosis in a concentration-dependent manner and the growth-inhibiting effect was independent on Philadelphia chromosome. DuP-697, at concentrations ranges which do not inhibit PGHS-1 activity, significantly attenuated the inhibition of PGHS-1 that was caused by aspirin and indomethacin.
1: Kaya TT, Altun A, Turgut NH, Ataseven H, Koyluoglu G. Effects of a Multikinase Inhibitor Motesanib (AMG 706) Alone and Combined with the Selective DuP-697 COX-2 Inhibitor on Colorectal Cancer Cells. Asian Pac J Cancer Prev. 2016;17(3):1103-10. PubMed PMID: 27039732.
2: Altun A, Turgut NH, Kaya TT. 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. PubMed PMID: 24815456.
3: Peng HL, Zhang GS, Liu JH, Gong FJ, Li RJ. Dup-697, a specific COX-2 inhibitor, suppresses growth and induces apoptosis on K562 leukemia cells by cell-cycle arrest and caspase-8 activation. Ann Hematol. 2008 Feb;87(2):121-9. PubMed PMID: 17999062.
4: Agarwal V, Hodgkinson VC, Eagle GL, Scaife L, Lind MJ, Cawkwell L. Proteomic (antibody microarray) exploration of the molecular mechanism of action of the specific COX-2 inhibitor DuP 697. Int J Oncol. 2013 Mar;42(3):1088-92. doi: 10.3892/ijo.2013.1784. PubMed PMID: 23338544.
5: Churchman A, Baydoun AR, Hoffman R. Inhibition of angiogenic tubule formation and induction of apoptosis in human endothelial cells by the selective cyclooxygenase-2 inhibitor 5-bromo-2-(4-fluorophenyl)-3-(methylsulfonyl) thiophene (DuP-697). Eur J Pharmacol. 2007 Nov 14;573(1-3):176-83. PubMed PMID: 17643408.
6: de Vries EF, van Waarde A, Buursma AR, Vaalburg W. Synthesis and in vivo evaluation of 18F-desbromo-DuP-697 as a PET tracer for cyclooxygenase-2 expression. J Nucl Med. 2003 Oct;44(10):1700-6. PubMed PMID: 14530489.
7: Burdan F, Dudka J, Szumilo J, Korobowicz A, Klepacz L. Prenatal effects of DuP-697-the irreversible, highly selective cyclooxygenase-2 inhibitor. Reprod Toxicol. 2003 Jul-Aug;17(4):413-9. PubMed PMID: 12849852.
8: Rosenstock M, Danon A, Rimon G. PGHS-2 inhibitors, NS-398 and DuP-697, attenuate the inhibition of PGHS-1 by aspirin and indomethacin without altering its activity. Biochim Biophys Acta. 1999 Aug 25;1440(1):127-37. PubMed PMID: 10477832.
9: Virdis A, Bacca A, Colucci R, Duranti E, Fornai M, Materazzi G, Ippolito C, Bernardini N, Blandizzi C, Bernini G, Taddei S. Endothelial dysfunction in small arteries of essential hypertensive patients: role of cyclooxygenase-2 in oxidative stress generation. Hypertension. 2013 Aug;62(2):337-44. doi: 10.1161/HYPERTENSIONAHA.111.00995. PubMed PMID: 23734008.
10: Xu X, Chen X, Li Y, Cao H, Shi C, Guan S, Zhang S, He B, Wang J. Cyclooxygenase-2 regulated by the nuclear factor-κB pathway plays an important role in endometrial breakdown in a female mouse menstrual-like model. Endocrinology. 2013 Aug;154(8):2900-11. doi: 10.1210/en.2012-1993. PubMed PMID: 23720426.
11: Jeong HJ, Lee SH, Cho SY, Lee CS, Jeong CW, Yoon MH, Kim WM. Roles of serotonergic and adrenergic receptors in the antinociception of selective cyclooxygenase-2 inhibitor in the rat spinal cord. Korean J Pain. 2011 Dec;24(4):179-84. doi: 10.3344/kjp.2011.24.4.179. PubMed PMID: 22220238; PubMed Central PMCID: PMC3248580.
12: Choi CH, Kim WM, Lee HG, Jeong CW, Kim CM, Lee SH, Yoon MH. Roles of opioid receptor subtype in the spinal antinociception of selective cyclooxygenase 2 inhibitor. Korean J Pain. 2010 Dec;23(4):236-41. doi: 10.3344/kjp.2010.23.4.236. PubMed PMID: 21217886; PubMed Central PMCID: PMC3000619.
13: Virdis A, Colucci R, Versari D, Ghisu N, Fornai M, Antonioli L, Duranti E, Daghini E, Giannarelli C, Blandizzi C, Taddei S, Del Tacca M. Atorvastatin prevents endothelial dysfunction in mesenteric arteries from spontaneously hypertensive rats: role of cyclooxygenase 2-derived contracting prostanoids. Hypertension. 2009 Jun;53(6):1008-16. doi: 10.1161/HYPERTENSIONAHA.109.132258. PubMed PMID: 19380610.
14: Joshi AS, Raghavan N, Williams RM, Takahashi K, Shingu H, King SY. Simultaneous quantification of an anti-inflammatory compound (DuP 697) and a potential metabolite (X6882) in human plasma and urine by high-performance liquid chromatography. J Chromatogr B Biomed Appl. 1994 Oct 3;660(1):143-50. PubMed PMID: 7858707.
15: Kim WM, Lee SH, Jeong HJ, Lee HG, Choi JI, Yoon MH. The analgesic activity of intrathecal tianeptine, an atypical antidepressant, in a rat model of inflammatory pain. Anesth Analg. 2012 Mar;114(3):683-9. doi: 10.1213/ANE.0b013e31824181e7. PubMed PMID: 22253265.
16: O'Kane SL, Eagle GL, Greenman J, Lind MJ, Cawkwell L. COX-2 specific inhibitors enhance the cytotoxic effects of pemetrexed in mesothelioma cell lines. Lung Cancer. 2010 Feb;67(2):160-5. doi: 10.1016/j.lungcan.2009.04.008. PubMed PMID: 19450893.
17: Yang C, Chen ZY, Wong SL, Liu J, Liang YT, Lau CW, Lee HK, Huang Y, Tsang SY. β-Sitosterol oxidation products attenuate vasorelaxation by increasing reactive oxygen species and cyclooxygenase-2. Cardiovasc Res. 2013 Mar 1;97(3):520-32. doi: 10.1093/cvr/cvs370. PubMed PMID: 23250922.
18: Rosenstock M, Danon A, Rubin M, Rimon G. Prostaglandin H synthase-2 inhibitors interfere with prostaglandin H synthase-1 inhibition by nonsteroidal anti-inflammatory drugs. Eur J Pharmacol. 2001 Jan 19;412(1):101-8. PubMed PMID: 11166741.
19: Gans KR, Galbraith W, Roman RJ, Haber SB, Kerr JS, Schmidt WK, Smith C, Hewes WE, Ackerman NR. 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. PubMed PMID: 2366180.
20: Foudi N, Norel X, Rienzo M, Louedec L, Brink C, Michel JB, Bäck M. Altered reactivity to norepinephrine through COX-2 induction by vascular injury in hypercholesterolemic rabbits. Am J Physiol Heart Circ Physiol. 2009 Nov;297(5):H1882-8. doi: 10.1152/ajpheart.00092.2009. PubMed PMID: 19783781.
2: Altun A, Turgut NH, Kaya TT. 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. PubMed PMID: 24815456.
3: Peng HL, Zhang GS, Liu JH, Gong FJ, Li RJ. Dup-697, a specific COX-2 inhibitor, suppresses growth and induces apoptosis on K562 leukemia cells by cell-cycle arrest and caspase-8 activation. Ann Hematol. 2008 Feb;87(2):121-9. PubMed PMID: 17999062.
4: Agarwal V, Hodgkinson VC, Eagle GL, Scaife L, Lind MJ, Cawkwell L. Proteomic (antibody microarray) exploration of the molecular mechanism of action of the specific COX-2 inhibitor DuP 697. Int J Oncol. 2013 Mar;42(3):1088-92. doi: 10.3892/ijo.2013.1784. PubMed PMID: 23338544.
5: Churchman A, Baydoun AR, Hoffman R. Inhibition of angiogenic tubule formation and induction of apoptosis in human endothelial cells by the selective cyclooxygenase-2 inhibitor 5-bromo-2-(4-fluorophenyl)-3-(methylsulfonyl) thiophene (DuP-697). Eur J Pharmacol. 2007 Nov 14;573(1-3):176-83. PubMed PMID: 17643408.
6: de Vries EF, van Waarde A, Buursma AR, Vaalburg W. Synthesis and in vivo evaluation of 18F-desbromo-DuP-697 as a PET tracer for cyclooxygenase-2 expression. J Nucl Med. 2003 Oct;44(10):1700-6. PubMed PMID: 14530489.
7: Burdan F, Dudka J, Szumilo J, Korobowicz A, Klepacz L. Prenatal effects of DuP-697-the irreversible, highly selective cyclooxygenase-2 inhibitor. Reprod Toxicol. 2003 Jul-Aug;17(4):413-9. PubMed PMID: 12849852.
8: Rosenstock M, Danon A, Rimon G. PGHS-2 inhibitors, NS-398 and DuP-697, attenuate the inhibition of PGHS-1 by aspirin and indomethacin without altering its activity. Biochim Biophys Acta. 1999 Aug 25;1440(1):127-37. PubMed PMID: 10477832.
9: Virdis A, Bacca A, Colucci R, Duranti E, Fornai M, Materazzi G, Ippolito C, Bernardini N, Blandizzi C, Bernini G, Taddei S. Endothelial dysfunction in small arteries of essential hypertensive patients: role of cyclooxygenase-2 in oxidative stress generation. Hypertension. 2013 Aug;62(2):337-44. doi: 10.1161/HYPERTENSIONAHA.111.00995. PubMed PMID: 23734008.
10: Xu X, Chen X, Li Y, Cao H, Shi C, Guan S, Zhang S, He B, Wang J. Cyclooxygenase-2 regulated by the nuclear factor-κB pathway plays an important role in endometrial breakdown in a female mouse menstrual-like model. Endocrinology. 2013 Aug;154(8):2900-11. doi: 10.1210/en.2012-1993. PubMed PMID: 23720426.
11: Jeong HJ, Lee SH, Cho SY, Lee CS, Jeong CW, Yoon MH, Kim WM. Roles of serotonergic and adrenergic receptors in the antinociception of selective cyclooxygenase-2 inhibitor in the rat spinal cord. Korean J Pain. 2011 Dec;24(4):179-84. doi: 10.3344/kjp.2011.24.4.179. PubMed PMID: 22220238; PubMed Central PMCID: PMC3248580.
12: Choi CH, Kim WM, Lee HG, Jeong CW, Kim CM, Lee SH, Yoon MH. Roles of opioid receptor subtype in the spinal antinociception of selective cyclooxygenase 2 inhibitor. Korean J Pain. 2010 Dec;23(4):236-41. doi: 10.3344/kjp.2010.23.4.236. PubMed PMID: 21217886; PubMed Central PMCID: PMC3000619.
13: Virdis A, Colucci R, Versari D, Ghisu N, Fornai M, Antonioli L, Duranti E, Daghini E, Giannarelli C, Blandizzi C, Taddei S, Del Tacca M. Atorvastatin prevents endothelial dysfunction in mesenteric arteries from spontaneously hypertensive rats: role of cyclooxygenase 2-derived contracting prostanoids. Hypertension. 2009 Jun;53(6):1008-16. doi: 10.1161/HYPERTENSIONAHA.109.132258. PubMed PMID: 19380610.
14: Joshi AS, Raghavan N, Williams RM, Takahashi K, Shingu H, King SY. Simultaneous quantification of an anti-inflammatory compound (DuP 697) and a potential metabolite (X6882) in human plasma and urine by high-performance liquid chromatography. J Chromatogr B Biomed Appl. 1994 Oct 3;660(1):143-50. PubMed PMID: 7858707.
15: Kim WM, Lee SH, Jeong HJ, Lee HG, Choi JI, Yoon MH. The analgesic activity of intrathecal tianeptine, an atypical antidepressant, in a rat model of inflammatory pain. Anesth Analg. 2012 Mar;114(3):683-9. doi: 10.1213/ANE.0b013e31824181e7. PubMed PMID: 22253265.
16: O'Kane SL, Eagle GL, Greenman J, Lind MJ, Cawkwell L. COX-2 specific inhibitors enhance the cytotoxic effects of pemetrexed in mesothelioma cell lines. Lung Cancer. 2010 Feb;67(2):160-5. doi: 10.1016/j.lungcan.2009.04.008. PubMed PMID: 19450893.
17: Yang C, Chen ZY, Wong SL, Liu J, Liang YT, Lau CW, Lee HK, Huang Y, Tsang SY. β-Sitosterol oxidation products attenuate vasorelaxation by increasing reactive oxygen species and cyclooxygenase-2. Cardiovasc Res. 2013 Mar 1;97(3):520-32. doi: 10.1093/cvr/cvs370. PubMed PMID: 23250922.
18: Rosenstock M, Danon A, Rubin M, Rimon G. Prostaglandin H synthase-2 inhibitors interfere with prostaglandin H synthase-1 inhibition by nonsteroidal anti-inflammatory drugs. Eur J Pharmacol. 2001 Jan 19;412(1):101-8. PubMed PMID: 11166741.
19: Gans KR, Galbraith W, Roman RJ, Haber SB, Kerr JS, Schmidt WK, Smith C, Hewes WE, Ackerman NR. 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. PubMed PMID: 2366180.
20: Foudi N, Norel X, Rienzo M, Louedec L, Brink C, Michel JB, Bäck M. Altered reactivity to norepinephrine through COX-2 induction by vascular injury in hypercholesterolemic rabbits. Am J Physiol Heart Circ Physiol. 2009 Nov;297(5):H1882-8. doi: 10.1152/ajpheart.00092.2009. PubMed PMID: 19783781.
| Chemical | |
|---|---|
| CAS Num | 88149-94-4 |
| Chemical Formula | C17H12BrFO2S2 |
| Molecular Weight | 411.3034 |
| IUPAC Chemical Name | 5-bromo-2-(4-fluorophenyl)-3-(4-(methylsulfonyl)phenyl)thiophene |
| Exact Mass | 409.9446 |
| Elemental Analysis | C, 49.64; H, 2.94; Br, 19.43; F, 4.62; O, 7.78; S, 15.59 |
| Synonym | DuP-697; DuP 697; DuP697; S-6907; S 6907; S6907; BFMT |
| Solubility | Soluble in DMSO |
| SMILES Code | O=S(C1=CC=C(C2=C(C3=CC=C(F)C=C3)SC(Br)=C2)C=C1)(C)=O |
| Biological | |
| Targets and Effects | COX-2 inhibitor |
| Pathways | Apoptosis |
| Physical | |
| Appearance | Solid powder |
| Purity | >98% (or refer to the Certificate of Analysis) |
| Shipping Condition | Shipped under ambient temperature as non-hazardous chemical. This product is stable enough for a few weeks during ordinary shipping and time spent in Customs. |
| Storage Condition | Dry, dark and at 0 - 4 C for short term (days to weeks) or -20 C for long term (months to years). |
| Shelf Life | >2 years if stored properly |
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