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Submit Review5-BDBD
Description: Potent and selective P2X4 antagonist
Chemical Name: 5-(3-Bromophenyl)-1,3-dihydro-2H-benzofuro[3,2-e]-1,4-diazepin-2-one
Purity: ≥99% (HPLC)
Biological Activity for 5-BDBD
5-BDBD is a potent and selective P2X4 receptor antagonist. Blocks P2X4-mediated currents in Chinese hamster ovary cells (IC50 = 0.50 μM). Exhibits no significant antagonist effects at other P2X receptors. Reduces long-term potentiation (LTP) in rat hippocampal slices.
Technical Data for 5-BDBD
| M. Wt | 355.19 |
| Formula | C17H11BrN2O2 |
| Storage | Store at RT |
| Purity | ≥99% (HPLC) |
| CAS Number | 768404-03-1 |
| PubChem ID | 9841560 |
| InChI Key | NKYMVQPXXTZHSF-UHFFFAOYSA-N |
| Smiles | BrC1=CC(C(C3=C4C2=C(O3)C=CC=C2)=NCC(N4)=O)=CC=C1 |
The technical data provided above is for guidance only. For batch specific data refer to the Certificate of Analysis.
Tocris products are intended for laboratory research use only, unless stated otherwise.
Solubility Data for 5-BDBD
| Solvent | Max Conc. mg/mL | Max Conc. mM | |
|---|---|---|---|
| Solubility | |||
| DMSO | 35.52 | 100 |
Preparing Stock Solutions for 5-BDBD
The following data is based on the product molecular weight 355.19. Batch specific molecular weights may vary from batch to batch due to the degree of hydration, which will affect the solvent volumes required to prepare stock solutions.
| Concentration / Solvent Volume / Mass | 1 mg | 5 mg | 10 mg |
|---|---|---|---|
| 1 mM | 2.82 mL | 14.08 mL | 28.15 mL |
| 5 mM | 0.56 mL | 2.82 mL | 5.63 mL |
| 10 mM | 0.28 mL | 1.41 mL | 2.82 mL |
| 50 mM | 0.06 mL | 0.28 mL | 0.56 mL |
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Product Datasheets for 5-BDBD
References for 5-BDBD
References are publications that support the biological activity of the product.
Donnelly-Roberts et al (2008) Painful purinergic receptors. J.Pharmacol.Exp.Ther. 324 409 PMID: 18042830
Casati et al (2011) Cell-autonomous regulation of hematopoietic stem cell cycling activity by ATP. Cell Death Differ. 18 396 PMID: 20798687
Coddou et al (2018) Characterization of the antagonist actions of 5-BDBD at the rat P2X4 receptor. Neurosci Lett. 690 219 PMID: 30366010
If you know of a relevant reference for 5-BDBD, please let us know.
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Keywords: 5-BDBD, 5-BDBD supplier, potent, P2X4, antagonists, purinergic, receptors, BDBD, selective, P2X, Receptors, 3579, Tocris Bioscience
26 Citations for 5-BDBD
Citations are publications that use Tocris products. Selected citations for 5-BDBD include:
Belinda L et al (2020) Pharmacological and genetic characterisation of the canine P2X4 receptor. Br J Pharmacol 177 2812-2829 PMID: 32017039
Chen et al (2016) Effect of P2X4R on airway inflammation and airway remodeling in allergic airway challenge in mice. Mol Med Rep 13 697 PMID: 26648454
Ledderose et al (2016) Mitochondrial Dysfunction, Depleted Purinergic Signaling, and Defective T Cell Vigilance and Immune Defense. J Infect Dis 213 456 PMID: 26150546
Gofman et al (2016) Relative Role of Akt, ERK and CREB in Alcohol-Induced Microglia P2X4R Receptor Expression. Alcohol Alcohol 51 647 PMID: 26946194
Maslieieva and Thompson (2014) A critical role for pannexin-1 in activation of innate immune cells of the choroid plexus. Channels (Austin) 8 131 PMID: 24418937
Wu et al (2011) Functional expression of P2X4 receptor in capillary endothelial cells of the cochlear spiral ligament and its role in regulating the capillary diameter. Am J Physiol Heart Circ Physiol 301 H69 PMID: 21460192
Mascanfroni et al (2015) Metabolic control of type 1 regulatory T cell differentiation by AHR and HIF1-α. Circulation 21 638 PMID: 26005855
Miguel Cruz & Beall (2020) Extracellular ATP Increases Glucose Metabolism in Skeletal Muscle Cells in a P2 Receptor Dependent Manner but Does Not Contribute to Palmitate-Induced Insulin Resistance. Front Physiol 11 PMID: 33101053
Dhuna et al (2019) Ginsenosides Act As Positive Modulators of P2X4 Receptors. Mol Pharmacol 95 210 PMID: 30545933
Kawano et al (2015) Autocrine Regulation of UVA-Induced IL-6 Production via Release of ATP and Activation of P2Y Receptors. PLoS One 10 e0127919 PMID: 26030257
Dosch et al (2019) Connexin-43-dependent ATP release mediates macrophage activation during sepsis. Elife 8 PMID: 30735126
Trabanelli et al (2012) Extracellular ATP exerts opposite effects on activated and regulatory CD4+ T cells via purinergic P2 receptor activation. J Immunol 189 1303 PMID: 22753942
Nörenberg et al (2012) Positive allosteric modulation by iverm. of human but not murine P2X7 receptors. Br J Pharmacol 167 48 PMID: 22506590
Vladislav et al (2021) Characterization of purinergic receptor 2 signaling in podocytes from diabetic kidneys. iScience 24 102528 PMID: 34142040
Timothy S et al (2021) Differential Regulation of ATP- and UTP-Evoked Prostaglandin E2 and IL-6 Production from Human Airway Epithelial Cells. J Immunol 207 1275-1287 PMID: 34389624
Rui et al (2021) Astragalin Alleviates Neuropathic Pain by Suppressing P2X4-Mediated Signaling in the Dorsal Root Ganglia of Rats. Front Neurosci 14 570831 PMID: 33505232
Aron M et al (2018) Keratinocytes mediate innocuous and noxious touch via ATP-P2X4 signaling. Elife 7 PMID: 29336303
László et al (2022) Motoneuronal inflammasome activation triggers excessive neuroinflammation and impedes regeneration after sciatic nerve injury. J Neuroinflammation 19 68 PMID: 35305649
Vladislav et al (2022) Modulation of P2X4 receptor activity by ivermectin and 5-BDBD has no effect on the development of ARPKD in PCK rats. Physiol Rep 10 e15510 PMID: 36353932
Zumerle et al (2019) Intercellular Calcium Signaling Induced by ATP Potentiates Macrophage Phagocytosis. Cell Rep 27 1 PMID: 30943393
Uderhardt et al (2019) Resident Macrophages Cloak Tissue Microlesions to Prevent Neutrophil-Driven Inflammatory Damage. Cell 177 541 PMID: 30955887
Peng et al (2016) Purinergic and store-operated Ca(2+) signaling mechanisms in mesenchymal stem cells and their roles in ATP-induced stimulation of cell migration. Stem Cells 34 2102 PMID: 27038239
Ilatovskaya et al (2013) Pharmacological characterization of the P2 receptors profile in the podocytes of the freshly isolated rat glomeruli. Am J Physiol Cell Physiol 305 C1050 PMID: 24048730
Raghava et al (2014) P2X4 receptor regulates alcohol-induced responses in microglia. J Neuroimmune Pharmacol 9 668-78 PMID: 25135400
Shabir et al (2013) Functional expression of purinergic P2 receptors and transient receptor potential channels by the human urothelium. Nat Med 305 F396 PMID: 23720349
Vergani et al (2013) Long-term heart transplant survival by targeting the ionotropic purinergic receptor P2X7. J Biol Chem 127 463 PMID: 23250993
Do you know of a great paper that uses 5-BDBD from Tocris? Please let us know.
Reviews for 5-BDBD
Average Rating: 5 (Based on 1 Review.)
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Good inhibitor.
By
Stefan Uderhardt on 06/06/2020
Assay Type: In Vivo
Species: Mouse
Cell Line/Tissue: phagocyte
DMSO dilution 10 μM
Literature in this Area
Tocris offers the following scientific literature in this area to showcase our products. We invite you to request* your copy today!
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P2X and P2Y Receptors Scientific Review
Written by Kenneth Jacobson, this review provides an overview of the different subtypes and structures of the P2 receptor families, as well as the pharmacological probes used to study them; compounds available from Tocris are listed.