1. Immunology/Inflammation Apoptosis
  2. COX Apoptosis
  3. DuP-697

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.

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DuP-697

DuP-697 Chemical Structure

CAS No. : 88149-94-4

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Based on 1 publication(s) in Google Scholar

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1 Publications Citing Use of MCE DuP-697

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  • Purity & Documentation

  • References

  • Customer Review

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].

IC50 & Target[3]

hCOX-2

10 nM (IC50)

hCOX-1

800 nM (IC50)

Cellular Effect
Cell Line Type Value Description References
CHO IC50
0.002 μM
Compound: DuP-697
In vitro inhibition of the production of PGE-2 in arachidonic acid stimulated chinese hamster ovary (CHO) cells transfected with human cyclooxygenase-2
In vitro inhibition of the production of PGE-2 in arachidonic acid stimulated chinese hamster ovary (CHO) cells transfected with human cyclooxygenase-2
10.1016/S0960-894X(96)00580-X
CHO IC50
0.002 μM
Compound: DuP-697
Tested in vitro for the ability to inhibit Prostaglandin G/H synthase 2 in chinese hamster ovary (CHO) cells
Tested in vitro for the ability to inhibit Prostaglandin G/H synthase 2 in chinese hamster ovary (CHO) cells
10.1016/S0960-894X(96)00582-3
CHO IC50
0.002 μM
Compound: DuP-697
In vitro inhibition of PGE-2 produced by arachidonic acid-stimulated CHO cells stably expressing human Prostaglandin G/H synthase 2
In vitro inhibition of PGE-2 produced by arachidonic acid-stimulated CHO cells stably expressing human Prostaglandin G/H synthase 2
[PMID: 9873621]
CHO IC50
0.0021 μM
Compound: DuP-697
Inhibition of PGE-2 production by arachidonic acid-stimulated CHO cells expressing human Prostaglandin G/H synthase 2
Inhibition of PGE-2 production by arachidonic acid-stimulated CHO cells expressing human Prostaglandin G/H synthase 2
10.1016/S0960-894X(96)00501-X
CHO IC50
0.059 μM
Compound: DuP-697
Inhibition of PGE-2 production in arachidonic acid-stimulated CHO cells expressing human Prostaglandin G/H synthase 1
Inhibition of PGE-2 production in arachidonic acid-stimulated CHO cells expressing human Prostaglandin G/H synthase 1
10.1016/S0960-894X(96)00501-X
CHO IC50
0.059 μM
Compound: DuP-697
In vitro inhibition of the production of PGE-2 in arachidonic acid stimulated chinese hamster ovary (CHO) cells transfected with human cyclooxygenase-1
In vitro inhibition of the production of PGE-2 in arachidonic acid stimulated chinese hamster ovary (CHO) cells transfected with human cyclooxygenase-1
10.1016/S0960-894X(96)00580-X
CHO IC50
0.059 μM
Compound: DuP-697
Tested in vitro for the ability to inhibit Prostaglandin G/H synthase 1 in chinese hamster ovary (CHO) cells
Tested in vitro for the ability to inhibit Prostaglandin G/H synthase 1 in chinese hamster ovary (CHO) cells
10.1016/S0960-894X(96)00582-3
Sf21 IC50
126.32 μM
Compound: Dup-697
Inhibition of human recombinant COX2 expressed in baculovirus infected SF21 cell
Inhibition of human recombinant COX2 expressed in baculovirus infected SF21 cell
[PMID: 20974503]
Sf9 IC50
0.005 μM
Compound: 1 (DuP-697)
Inhibitory activity against human COX-2 expressed in baculovirus infected Sf9 cells
Inhibitory activity against human COX-2 expressed in baculovirus infected Sf9 cells
10.1016/0960-894X(95)00359-2
Sf9 IC50
0.007 μM
Compound: DuP-697
Inhibitory activity against human recombinant Prostaglandin G/H synthase 2 expressed in microsomes taken from baculovirus infected Sf9 cells
Inhibitory activity against human recombinant Prostaglandin G/H synthase 2 expressed in microsomes taken from baculovirus infected Sf9 cells
10.1016/0960-894X(95)00564-A
Sf9 IC50
0.6 μM
Compound: 1 (DuP-697)
Inhibitory activity against human COX-1 expressed in baculovirus infected Sf9 cells
Inhibitory activity against human COX-1 expressed in baculovirus infected Sf9 cells
10.1016/0960-894X(95)00359-2
Sf9 IC50
0.6 μM
Compound: DuP-697
Inhibitory activity against human recombinant Prostaglandin G/H synthase 1 expressed in microsomes taken from baculovirus infected Sf9 cells
Inhibitory activity against human recombinant Prostaglandin G/H synthase 1 expressed in microsomes taken from baculovirus infected Sf9 cells
10.1016/0960-894X(95)00564-A
U-937 IC50
0.007 μM
Compound: DuP-697
Inhibition of Prostaglandin G/H synthase 1 was measured by the inhibition of PGE-2 produced by microsomes from U937 cells at subsaturating arachidonic acid conc.
Inhibition of Prostaglandin G/H synthase 1 was measured by the inhibition of PGE-2 produced by microsomes from U937 cells at subsaturating arachidonic acid conc.
[PMID: 9873621]
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].

MedChemExpress (MCE) has not independently confirmed the accuracy of these methods. They are for reference only.

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].

MedChemExpress (MCE) has not independently confirmed the accuracy of these methods. They are for reference only.

Molecular Weight

411.31

Formula

C17H12BrFO2S2

CAS No.
Appearance

Solid

Color

White to off-white

SMILES

O=S(C1=CC=C(C2=C(C3=CC=C(F)C=C3)SC(Br)=C2)C=C1)(C)=O

Shipping

Room temperature in continental US; may vary elsewhere.

Storage
Powder -20°C 3 years
In solvent -80°C 6 months
-20°C 1 month
Solvent & Solubility
In Vitro: 

DMSO : 100 mg/mL (243.13 mM; Need ultrasonic; Hygroscopic DMSO has a significant impact on the solubility of product, please use newly opened DMSO)

DMF : ≥ 54 mg/mL (131.29 mM)

Ethanol : ≥ 7 mg/mL (17.02 mM)

*"≥" means soluble, but saturation unknown.

Preparing
Stock Solutions
Concentration Solvent Mass 1 mg 5 mg 10 mg
1 mM 2.4313 mL 12.1563 mL 24.3126 mL
5 mM 0.4863 mL 2.4313 mL 4.8625 mL
View the Complete Stock Solution Preparation Table

* Please refer to the solubility information to select the appropriate solvent. Once prepared, please aliquot and store the solution to prevent product inactivation from repeated freeze-thaw cycles.
Storage method and period of stock solution: -80°C, 6 months; -20°C, 1 month. When stored at -80°C, please use it within 6 months. When stored at -20°C, please use it within 1 month.

  • Molarity Calculator

  • Dilution Calculator

Mass (g) = Concentration (mol/L) × Volume (L) × Molecular Weight (g/mol)

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Molecular Weight *

Concentration (start) × Volume (start) = Concentration (final) × Volume (final)

This equation is commonly abbreviated as: C1V1 = C2V2

Concentration (start)

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C2

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V2

In Vivo:

Select the appropriate dissolution method based on your experimental animal and administration route.

For the following dissolution methods, please ensure to first prepare a clear stock solution using an In Vitro approach and then sequentially add co-solvents:
To ensure reliable experimental results, the clarified stock solution can be appropriately stored based on storage conditions. As for the working solution for in vivo experiments, it is recommended to prepare freshly and use it on the same day.
The percentages shown for the solvents indicate their volumetric ratio in the final prepared solution. If precipitation or phase separation occurs during preparation, heat and/or sonication can be used to aid dissolution.

  • Protocol 1

    Add each solvent one by one:  10% DMSO    90% Corn Oil

    Solubility: ≥ 2.5 mg/mL (6.08 mM); Clear solution

    This protocol yields a clear solution of ≥ 2.5 mg/mL (saturation unknown). If the continuous dosing period exceeds half a month, please choose this protocol carefully.

    Taking 1 mL working solution as an example, add 100 μL DMSO stock solution (25.0 mg/mL) to 900 μL Corn oil, and mix evenly.

In Vivo Dissolution Calculator
Please enter the basic information of animal experiments:

Dosage

mg/kg

Animal weight
(per animal)

g

Dosing volume
(per animal)

μL

Number of animals

Recommended: Prepare an additional quantity of animals to account for potential losses during experiments.
Please enter your animal formula composition:
%
DMSO +
+
%
Tween-80 +
%
Saline
Recommended: Keep the proportion of DMSO in working solution below 2% if your animal is weak.
The co-solvents required include: DMSO, . All of co-solvents are available by MedChemExpress (MCE). , Tween 80. All of co-solvents are available by MedChemExpress (MCE).
Calculation results:
Working solution concentration: mg/mL
Method for preparing stock solution: mg drug dissolved in μL  DMSO (Stock solution concentration: mg/mL).
The concentration of the stock solution you require exceeds the measured solubility. The following solution is for reference only. If necessary, please contact MedChemExpress (MCE).
Method for preparing in vivo working solution for animal experiments: Take μL DMSO stock solution, add μL . μL , mix evenly, next add μL Tween 80, mix evenly, then add μL Saline.
 If the continuous dosing period exceeds half a month, please choose this protocol carefully.
Please ensure that the stock solution in the first step is dissolved to a clear state, and add co-solvents in sequence. You can use ultrasonic heating (ultrasonic cleaner, recommended frequency 20-40 kHz), vortexing, etc. to assist dissolution.
Purity & Documentation

Purity: 99.79%

References

Complete Stock Solution Preparation Table

* Please refer to the solubility information to select the appropriate solvent. Once prepared, please aliquot and store the solution to prevent product inactivation from repeated freeze-thaw cycles.
Storage method and period of stock solution: -80°C, 6 months; -20°C, 1 month. When stored at -80°C, please use it within 6 months. When stored at -20°C, please use it within 1 month.

Optional Solvent Concentration Solvent Mass 1 mg 5 mg 10 mg 25 mg
Ethanol / DMF / DMSO 1 mM 2.4313 mL 12.1563 mL 24.3126 mL 60.7814 mL
5 mM 0.4863 mL 2.4313 mL 4.8625 mL 12.1563 mL
10 mM 0.2431 mL 1.2156 mL 2.4313 mL 6.0781 mL
15 mM 0.1621 mL 0.8104 mL 1.6208 mL 4.0521 mL
DMF / DMSO 20 mM 0.1216 mL 0.6078 mL 1.2156 mL 3.0391 mL
25 mM 0.0973 mL 0.4863 mL 0.9725 mL 2.4313 mL
30 mM 0.0810 mL 0.4052 mL 0.8104 mL 2.0260 mL
40 mM 0.0608 mL 0.3039 mL 0.6078 mL 1.5195 mL
50 mM 0.0486 mL 0.2431 mL 0.4863 mL 1.2156 mL
60 mM 0.0405 mL 0.2026 mL 0.4052 mL 1.0130 mL
80 mM 0.0304 mL 0.1520 mL 0.3039 mL 0.7598 mL
100 mM 0.0243 mL 0.1216 mL 0.2431 mL 0.6078 mL
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Product Name:
DuP-697
Cat. No.:
HY-103387
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