| Identification | Back Directory | [Name]
PD 146176 | [CAS]
4079-26-9 | [Synonyms]
6,11-dihydrothiochromeno[4,3-b]indole
[1]Benzothiopyrano[4,3-b]indole, 6,11-dihydro- | [Molecular Formula]
C15H11NS | [MDL Number]
MFCD05664738 | [MOL File]
4079-26-9.mol | [Molecular Weight]
237.32 |
| Chemical Properties | Back Directory | [Melting point ]
160 °C | [Boiling point ]
485.4±24.0 °C(Predicted) | [density ]
1.333±0.06 g/cm3(Predicted) | [storage temp. ]
Store at +4°C | [solubility ]
DMSO: 16 mg/mL, soluble
| [form ]
solid
| [pka]
16.17±0.20(Predicted) | [color ]
cream-colored
| [InChI]
1S/C15H11NS/c1-3-7-13-10(5-1)12-9-17-14-8-4-2-6-11(14)15(12)16-13/h1-8,16H,9H2 | [InChIKey]
ZGOOPZVQMLHPFM-UHFFFAOYSA-N | [SMILES]
C1Sc2ccccc2-c3[nH]c4ccccc4c13 |
| Hazard Information | Back Directory | [Description]
PD 146176 is a potent and selective inhibitor of reticulocyte 15-lipoxygenase-1.1 It limits hypercholesterolemia-induced atherosclerosis in New Zealand White rabbits and reduces oxidant stress-induced apoptosis in endothelial cells.1,2,3 PD 146176 inhibits amyloid β protein aggregate formation without changing total levels of amyloid β precursor protein (APP) in cells stably expressing APP.4 In addition, it lacks significant non-specific antioxidant properties.2 | [Uses]
PD 146176 has been used to study its influence on ex vivo leukotriene B4 (LTB4) and lipoxin A4 (LXA4) secretion in adipose tissue. | [Definition]
ChEBI: PD-146176 is an organic heterotetracyclic compound that is 1H-indole which is ortho-fused to a 2H-1-benzothiopyran group at positions 2-3. It is an inhibitor of 15-lipoxygenase that limits atherosclerotic lesion development in rabbits. It has a role as a ferroptosis inhibitor, an EC 1.13.11.33 (arachidonate 15-lipoxygenase) inhibitor and an antiatherogenic agent. It is an organic heterotetracyclic compound, an organosulfur heterocyclic compound and an organonitrogen heterocyclic compound. | [Biological Activity]
Specific, non-competitve 15-lipoxygenase (15-LOX) inhibitor (K i = 197nM) that has no demonstrable effect on 5-LOX, 12-LOX, COX-1 or COX-2 (IC 50 = 0.54 μ M for 15-LOX in rabbit reticulocytes). Lacks non-specific antioxidant properties and prevents atherogenesis via regulation of monocyte-macrophage enrichment in vivo . | [Biochem/physiol Actions]
PD 146176 blocks neuroprotectin D1 (NPD1) and eicosanoid synthesis by inhibiting the 5-lipoxygenase-1 (15-LOX-1) enzyme. | [storage]
Store at +4°C | [References]
[1] THOMAS M.A BOCAN . A specific 15-lipoxygenase inhibitor limits the progression and monocyte–macrophage enrichment of hypercholesterolemia-induced atherosclerosis in the rabbit[J]. Atherosclerosis, 1998, 136 2: Pages 203-216. DOI: 10.1016/s0021-9150(97)00204-9
[2] SANDRA M. SENDOBRY. Attenuation of diet-induced atherosclerosis in rabbits with a highly selective 15-lipoxygenase inhibitor lacking significant antioxidant properties[J]. British Journal of Pharmacology, 2009, 120 7: 1199-1206. DOI: 10.1038/sj.bjp.0701007
[3] LORRAINE M. SORDILLO . Enhanced 15-HPETE production during oxidant stress induces apoptosis of endothelial cells[J]. Prostaglandins & other lipid mediators, 2005, 76 1: Pages 19-34. DOI: 10.1016/j.prostaglandins.2004.10.007
[4] FRANCESCA SUCCOL Domenico P. A role for 12/15 lipoxygenase in the amyloid β precursor protein metabolism[J]. Journal of Neurochemistry, 2007, 103 1: 380-387. DOI: 10.1111/j.1471-4159.2007.04742.x
[5] RON SHAH . Beyond DPPH: Use of Fluorescence-Enabled Inhibited Autoxidation to Predict Oxidative Cell Death Rescue[J]. Cell Chemical Biology, 2019, 26 11: Pages 1594-1607.e7. DOI: 10.1016/j.chembiol.2019.09.007
[6] MARCUS CONRAD Derek A P. The chemical basis of ferroptosis[J]. Nature chemical biology, 2019, 15 12: 1137-1147. DOI: 10.1038/s41589-019-0408-1 |
|
| Company Name: |
Sigma-Aldrich
|
| Tel: |
021-61415566 800-8193336 |
| Website: |
https://www.sigmaaldrich.cn |
| Company Name: |
Rhawn Reagent
|
| Tel: |
400-400-1332688 18019345275 |
| Website: |
http://www.rhawn.cn |
|