3-Ethoxy-5,6-dibromosalicylaldehyde
Based on 1 Customer Validation
3-Ethoxy-5,6-dibromosalicylaldehyde is an IRE1/ERN1 inhibitor, with an IC50 of 0.12 μM, a Ki of 71-88 nM, and a Kd of 100 nM against the ribonuclease activity of hIRE1α, as well as an IC50 of 4.8 μM against yeast Ire1. It shows selectivity toward IRE1 ribonuclease. 3-Ethoxy-5,6-dibromosalicylaldehyde blocks the IRE1/ERN1-mediated unfolded protein response (UPR) signaling pathway, including XBP-1 mRNA splicing, induction of XBP1 target genes, and activation of MAPK8/9/10, but does not alter the phosphorylation level of IRE1α or the PERK/ATF6 pathway. 3-Ethoxy-5,6-dibromosalicylaldehyde inhibits chikungunya virus replication, induces growth arrest, apoptosis and clonogenic inhibition in pancreatic cancer cells, reduces FB1 (Fumonisin B1) (HY-N6719)-induced autophagy and cell death, regulates PGG-induced senescence and apoptosis, and alleviates Sorafenib (HY-10201)-induced vacuolization and damage in hepatic stellate cells. 3-Ethoxy-5,6-dibromosalicylaldehyde can be used in research related to chikungunya virus infection, pancreatic cancer, FB1-induced nephrotoxicity, liver cancer, breast cancer, lung cancer and liver fibrosis.
For research use only. We do not sell to patients.
- Purity: 99.97%
- CAS No.: 20041-64-9
- Formula: C9H8Br2O3
- Molecular Weight:323.97
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Storage:
4°C, sealed storage, away from moisture and light
* In solvent : -80°C, 6 months; -20°C, 1 month (sealed storage, away from moisture and light)
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Biological Activity
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Chemical Information
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Solvent & Solubility
- Purity & Documentation
- References
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Biological Activity
Description
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IRE1α 0.12 μM (IC50) |
IRE1α 71-88 nM (Ki) |
IRE1α 100 nM (Kd) |
yeast Ire1 4.8 μM (IC50) |
ERN1 |
XBP-1 |
p38 MAPK |
Cellular Effect
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Cell Line
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Type | Value | Description | References |
|---|---|---|---|---|
| MIA PaCa-2 | IC50 |
0.4 μM
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Antiproliferative activity against human MiaPaCa2 pancreatic cancer cells assessed as reduction in cell viability by MTT assay.
Antiproliferative activity against human MiaPaCa2 pancreatic cancer cells assessed as reduction in cell viability by MTT assay.
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24952679 |
| Panc1005 | IC50 |
76.2 μM
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Antiproliferative activity against human Panc1005 pancreatic cancer cells assessed as reduction in cell viability by MTT assay.
Antiproliferative activity against human Panc1005 pancreatic cancer cells assessed as reduction in cell viability by MTT assay.
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24952679 |
| Panc203 | IC50 |
1.5 μM
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Antiproliferative activity against human Panc0203 pancreatic cancer cells assessed as reduction in cell viability by MTT assay.
Antiproliferative activity against human Panc0203 pancreatic cancer cells assessed as reduction in cell viability by MTT assay.
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24952679 |
| SU.86.86 | IC50 |
9.8 μM
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Antiproliferative activity against human SU8686 pancreatic cancer cells assessed as reduction in cell viability by MTT assay.
Antiproliferative activity against human SU8686 pancreatic cancer cells assessed as reduction in cell viability by MTT assay.
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24952679 |
| PANC-03-27 | IC50 |
25.6 μM
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Antiproliferative activity against human Panc0327 pancreatic cancer cells assessed as reduction in cell viability by MTT assay.
Antiproliferative activity against human Panc0327 pancreatic cancer cells assessed as reduction in cell viability by MTT assay.
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24952679 |
| PANC-1 | IC50 |
23.5 μM
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Antiproliferative activity against human Panc1 pancreatic cancer cells assessed as reduction in cell viability by MTT assay.
Antiproliferative activity against human Panc1 pancreatic cancer cells assessed as reduction in cell viability by MTT assay.
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24952679 |
| ASPC1 | IC50 |
6.3 μM
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Antiproliferative activity against human AsPc1 pancreatic cancer cells assessed as reduction in cell viability by MTT assay.
Antiproliferative activity against human AsPc1 pancreatic cancer cells assessed as reduction in cell viability by MTT assay.
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24952679 |
| BXPC-3 | IC50 |
1.1 μM
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Antiproliferative activity against human BxPc3 pancreatic cancer cells assessed as reduction in cell viability by MTT assay.
Antiproliferative activity against human BxPc3 pancreatic cancer cells assessed as reduction in cell viability by MTT assay.
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24952679 |
In Vitro
3-Ethoxy-5,6-dibromosalicylaldehyde (DBSA) (30 μM; 4-48 h) inhibits the IRE1 pathway in HEK293 cells, as shown by reduced Xbp1s gene expression and phospho-IRE1 protein levels when used at 30 μM for 4 h (with Tunicamycin (HY-A0098)) or 48 h (with chikungunya virus)[1].
3-Ethoxy-5,6-dibromosalicylaldehyde (30 μM; 48 h post-infection) suppresses chikungunya virus replication in HEK293 cells when used at 30 μM for 48 h post-infection, as shown by reduced viral E1 gene and protein expression[1].
3-Ethoxy-5,6-dibromosalicylaldehyde (3ETH) (1 nM-100 μM) inhibits proliferation of a panel of human pancreatic cancer cell lines with IC50 values ranging from 0.4 μM to 76.2 μM, and is active against HNA-resistant cell lines including AsPc1, BxPc3, and PL45[2].
3-Ethoxy-5,6-dibromosalicylaldehyde (1-10 μM; 14 days) inhibits clonogenic growth of MiaPaCa2 and Panc0403 human pancreatic cancer cells in soft agar[2].
3-Ethoxy-5,6-dibromosalicylaldehyde (1 μM; 24 hours) up-regulates TXNIP mRNA and down-regulates TXN mRNA in Panc0403 and MiaPaCa2 human pancreatic cancer cells[2].
3-Ethoxy-5,6-dibromosalicylaldehyde (60 μM; 24 h) suppresses PGG-induced senescence-like growth arrest in HepG2, MCF-7, and A549 cells, as shown by reduced SA-β-gal-positive cell percentages[5].
3-Ethoxy-5,6-dibromosalicylaldehyde (100 nM-20 μM; 3 min) binds directly and selectively to purified human IRE1α-cyto with a Kd of ~100 nM, and does not bind to RNase A[6].
Pre-treatment of LX2 and HSC-T6 hepatic stellate cells with 3-Ethoxy-5,6-dibromosalicylaldehyde (10 μM; 60 min pre-incubation prior to 12-24 h Sorafenib treatment) reduces and delays Sorafenib-induced cytoplasmic vacuolation[7].
3-Ethoxy-5,6-dibromosalicylaldehyde potently and selectively inhibits the endoribonuclease activity of human and yeast IRE1α without affecting autophosphorylation, blocks chemically induced XBP1 splicing and XBP1 target gene induction in cultured cell lines, and binds specifically, reversibly, and dose-dependently to IRE1α[3].
3-Ethoxy-5,6-dibromosalicylaldehyde potently inhibits the endoribonuclease activity of purified human IRE1α-cyto with an IC50 of ~0.12 μM via a non-competitive mechanism relative to the mini-XBP-1 RNA substrate[6].
3-Ethoxy-5,6-dibromosalicylaldehyde (0.48-60 μM; 1 h) inhibits yeast Ire1 endoribonuclease activity with an IC50 of 6 μM, which is 50-fold less potent than its activity against human IRE1α-cyto[6].
3-Ethoxy-5,6-dibromosalicylaldehyde (5-120 μM; 2 h) dose-dependently inhibits DTT (DL-Dithiothreitol) (HY-15917)-induced XBP-1 splicing in human MM1.s myeloma cells, with complete inhibition at high concentrations[6].
Pre-treatment of LX2 and HSC-T6 hepatic stellate cells with 3-Ethoxy-5,6-dibromosalicylaldehyde (EDBS) (10 μM; 60 min pre-incubation prior to 12-24 h Sorafenib treatment) suppresses Sorafenib-induced activation of the IRE1α-XBP1s ER stress/UPR pathway by reducing protein expression of IRE1α, GRP78, XBP1s, and calreticulin[7].
3-Ethoxy-5,6-dibromosalicylaldehyde directly inhibits IRE1α endoribonuclease activity by covalently binding to lysine K907, dose-dependently reducing Xbp1 splicing in human cell lines without altering other UPR pathways[8].
3-Ethoxy-5,6-dibromosalicylaldehyde (DBS) (50 μM; 48 h) inhibits FB1-induced MAPK8/9/10 activation, autophagy, and subsequent cell death in MARC-145 monkey kidney cells[4].
3-Ethoxy-5,6-dibromosalicylaldehyde (60 μM; 24 h) inhibits PGG-induced autophagosome formation in HepG2 cells, as indicated by a reduced LC3-II/ACTB ratio of 0.08 compared to 0.36 with PGG alone[5].
3-Ethoxy-5,6-dibromosalicylaldehyde (24 h) enhances PGG-induced cell death in HepG2 and MCF-7 cells after 48 h of combined treatment[5].
Pre-treatment of LX2 hepatic stellate cells with 3-Ethoxy-5,6-dibromosalicylaldehyde (10 μM; 60 min pre-incubation prior to 12-24 h Sorafenib treatment) drastically reduces Sorafenib-induced non-apoptotic cell death at 12 h and 24 h post-treatment[7].
MedChemExpress (MCE) has not independently confirmed the accuracy of these methods. They are for reference only.
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Cell Line:Panc0403, MiaPaCa2
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Concentration:1 μM
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Incubation Time:24 hours
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Result:Up-regulated TXNIP mRNA expression by 13-fold in Panc0403 cells.
Up-regulated TXNIP mRNA expression by 7-fold in MiaPaCa2 cells.
Down-regulated TXN mRNA expression to 50% of control levels in Panc0403 cells.
Down-regulated TXN mRNA expression to 45% of control levels in MiaPaCa2 cells.
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Cell Line:African green monkey kidney MARC-145 cells
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Concentration:50 μM (co-treated with 20 μM FB1)
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Incubation Time:48 h
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Result:Significantly decreased FB1-induced MAPK8/9/10 phosphorylation.
Reduced the FB1-induced conversion of LC3-I to LC3-II, with LC3-II/ACTB ratio dropping from 0.58 to 0.18.
Dramatically reduced FB1-induced cell death.
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Cell Line:HepG2
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Concentration:60 μM (in combination with 25 μM PGG)
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Incubation Time:24 h
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Result:Significantly reduced the PGG-induced conversion of LC3-I to LC3-II.
Decreased the LC3-II/ACTB ratio from 0.36 to 0.08.
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Cell Line:activated human hepatic stellate cell line LX2, activated rat hepatic stellate cell line HSC-T6
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Concentration:10 μM (pre-incubated for 60 min prior to 10 μM Sorafenib treatment for 12 h); 10 μM (pre-incubated for 60 min prior to 10 μM Sorafenib treatment for 24 h)
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Incubation Time:12 h (post-Sorafenib treatment); 24 h (post-Sorafenib treatment)
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Result:Significantly reduced Sorafenib-induced upregulation of IRE1α, GRP78 (BiP), XBP1s, and calreticulin proteins in LX2 cells at 12 h post-Sorafenib treatment.
Suppressed Sorafenib-induced expression of IRE1α, GRP78 (BiP), XBP1s, and calreticulin proteins in LX2 cells at 24 h post-Sorafenib treatment.
Suppressed Sorafenib-induced IRE1α overexpression in HSC-T6 cells at 12 h and 24 h post-Sorafenib treatment.
Caused only a marginal reduction in basal phosphorylated IRE1α (pIRE1α) levels in LX2 cells at 12 h post-Sorafenib treatment.
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Cell Line:activated human hepatic stellate cell line LX2
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Concentration:10 μM (pre-incubated for 60 min prior to 10 μM Sorafenib treatment for 12 h); 10 μM (pre-incubated for 60 min prior to 10 μM Sorafenib treatment for 24 h)
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Incubation Time:12 h (post-Sorafenib treatment); 24 h (post-Sorafenib treatment)
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Result:Drastically reduced the PI-positive cell population in LX2 cells at both 12 h and 24 h post-Sorafenib treatment.
Reduced PI-positive cell population from 45.5% (Sorafenib alone) to 12.7% (Sorafenib plus target reagent) at 12 h post-Sorafenib treatment.
Reduced PI-positive cell population from 61.2% (Sorafenib alone) to 24.2% (Sorafenib plus target reagent) at 24 h post-Sorafenib treatment.
In Vivo
MedChemExpress (MCE) has not independently confirmed the accuracy of these methods. They are for reference only.
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Animal Model:NOD/SCID mice[2]
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Dosage:20 mg/kg
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Administration:i.p.; three times weekly; 4 weeks
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Result:Reduced mean tumor weight to 70% of control tumors.
Chemical Information
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CAS No. 20041-64-9
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Appearance Solid
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Molecular Weight 323.97
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Formula C9H8Br2O3
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Color White to yellow
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SMILES
O=CC1=C(O)C(OCC)=CC(Br)=C1Br
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Shipping
Room temperature in continental US; may vary elsewhere.
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Storage
4°C, sealed storage, away from moisture and light
* In solvent : -80°C, 6 months; -20°C, 1 month (sealed storage, away from moisture and light)
Solvent & Solubility
In Vitro:
DMSO : 100 mg/mL (308.67 mM; Need ultrasonic; Hygroscopic DMSO has a significant impact on the solubility of product, please use newly opened DMSO)
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 (sealed storage, away from moisture and light). When stored at -80°C, please use it within 6 months. When stored at -20°C, please use it within 1 month.
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 (sealed storage, away from moisture and light). When stored at -80°C, please use it within 6 months. When stored at -20°C, please use it within 1 month.
Concentration (start) × Volume (start) = Concentration (final) × Volume (final)
Purity & Documentation
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Data Sheet (298 KB)
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SDS (393 KB)
- English - EN (393 KB)
- Français - FR (393 KB)
- Deutsch - DE (393 KB)
- Norwegian - NO (393 KB)
- Español - ES (393 KB)
- Swedish - SV (393 KB)
- Italian - IT (393 KB)
- Korean - KR (393 KB)
- Portuguese - PT (393 KB)
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Handling Instructions (2659 KB)
References
[1]. Agrawal N, et al. Pharmacological Manipulation of UPR: Potential Antiviral Strategy Against Chikungunya Virus. Indian journal of microbiology. 2022 Dec;62(4):634-640. [Content Brief]
[2]. Chien W, et al. Selective inhibition of unfolded protein response induces apoptosis in pancreatic cancer cells. Oncotarget. 2014 Jul 15;5(13):4881-94. [Content Brief]
[6]. Volkmann K, et al. Potent and selective inhibitors of the inositol-requiring enzyme 1 endoribonuclease. The Journal of biological chemistry. 2011 Apr 08;286(14):12743-55. [Content Brief]
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 (sealed storage, away from moisture and light). 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 |
|---|---|---|---|---|---|
| DMSO | 1 mM | 3.0867 mL | 15.4335 mL | 30.8671 mL | 77.1676 mL |
| 5 mM | 0.6173 mL | 3.0867 mL | 6.1734 mL | 15.4335 mL | |
| 10 mM | 0.3087 mL | 1.5434 mL | 3.0867 mL | 7.7168 mL | |
| 15 mM | 0.2058 mL | 1.0289 mL | 2.0578 mL | 5.1445 mL | |
| 20 mM | 0.1543 mL | 0.7717 mL | 1.5434 mL | 3.8584 mL | |
| 25 mM | 0.1235 mL | 0.6173 mL | 1.2347 mL | 3.0867 mL | |
| 30 mM | 0.1029 mL | 0.5145 mL | 1.0289 mL | 2.5723 mL | |
| 40 mM | 0.0772 mL | 0.3858 mL | 0.7717 mL | 1.9292 mL | |
| 50 mM | 0.0617 mL | 0.3087 mL | 0.6173 mL | 1.5434 mL | |
| 60 mM | 0.0514 mL | 0.2572 mL | 0.5145 mL | 1.2861 mL | |
| 80 mM | 0.0386 mL | 0.1929 mL | 0.3858 mL | 0.9646 mL | |
| 100 mM | 0.0309 mL | 0.1543 mL | 0.3087 mL | 0.7717 mL |
3-Ethoxy-5,6-dibromosalicylaldehyde Related Classifications
HY-123996 Related Classifications
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