5-BDBD

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Cat.No. 3579 - 5-BDBD | C17H11BrN2O2 | CAS No. 768404-03-1
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)
Datasheet
Citations (17)
Reviews (1)
Literature (5)

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.

Compound Libraries for 5-BDBD

5-BDBD is also offered as part of the Tocriscreen 2.0 Max. Find out more about compound libraries available from Tocris.

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.

Select a batch to recalculate based on the batch molecular weight:
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

Certificate of Analysis / Product Datasheet
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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

17 Citations for 5-BDBD

Citations are publications that use Tocris products. Selected citations for 5-BDBD include:

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

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

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

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

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

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

Dosch et al (2019) Connexin-43-dependent ATP release mediates macrophage activation during sepsis. Elife 8 PMID: 30735126

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

Mascanfroni et al (2015) Metabolic control of type 1 regulatory T cell differentiation by AHR and HIF1-α. Circulation 21 638 PMID: 26005855

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

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


Do you know of a great paper that uses 5-BDBD from Tocris? Please let us know.

Reviews for 5-BDBD

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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

review image

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