AC-55541 - CAS 916170-19-9
Catalog number: B0084-271988
Category: Inhibitor
Please be kindly noted products are not for therapeutic use. We do not sell to patients.
Molecular Formula:
C25H20BrN5O3
Molecular Weight:
518.36
COA:
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Targets:
Protease-Activated Receptors (PARs)
Description:
AC-55541 is a novel small-molecule protease-activated receptor 2(PAR2) agonist which displays no activity at other PAR subtypes or at over 30 other receptors involved in nociception and inflammation. It activated PAR2 signaling in cellular proliferation assays, phosphatidylinositol hydrolysis assays, and Ca(2+) mobilization assays, with potencies ranging from 200 to 1000 nM. It was well absorbed when administered intraperitoneally to rats, reaching micromolar peak plasma concentrations. It was stable to metabolism by liver microsomes and maintained sustained exposure in rats.
Ordering Information
Catalog Number Size Price Stock Quantity
B0084-271988 300 mg $299 In stock
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Purity:
>97 %
Appearance:
Solid powder
Synonyms:
AC-55541; AC 55541; AC55541. (2E)-2-[1-(3-Bromophenyl)ethylidene]α-(benzoylamino)-3,4-dihydro-4-oxo-1-phthalazineaceticacidhydrazide;AC 55541;alpha-(Benzoylamino)-3,4-dihydro-4-oxo-1-phthalazineacetic acid (2E)-2-[1-(3-bromophenyl)ethylidene]hydrazide;N-[2-[(2E)-2-[1-(3-bromophenyl)ethylidene]hydrazinyl]-2-oxo-1-(4-oxo-3H-phthalazin-1-yl)ethyl]benzamide
Solubility:
DMSO: ≥ 51 mg/mL
Storage:
-20°C Freezer
MSDS:
Inquire
Application:
AC-55541 stimulates cell proliferation, phosphatidylinositol hydrolysis, and calcium mobilization.
Quality Standard:
In-house standard
Shelf Life:
2 month in rt, long time
Quantity:
Grams to Kilograms
Density:
1.49±0.1 g/cm3 | Condition: Temp: 20 °C Press: 760 Torr
InChIKey:
UCUHFWIFSHROPY-RWPZCVJISA-N
InChI:
InChI=1S/C25H20BrN5O3/c1-15(17-10-7-11-18(26)14-17)28-31-25(34)22(27-23(32)16-8-3-2-4-9-16)21-19-12-5-6-13-20(19)24(33)30-29-21/h2-14,22H,1H3,(H,27,32)(H,30,33)(H,31,34)/b28-15+
Canonical SMILES:
CC(=NNC(=O)C(C1=NNC(=O)C2=CC=CC=C21)NC(=O)C3=CC=CC=C3)C4=CC(=CC=C4)Br
1.Alterations in serotonin, transient receptor potential channels and protease-activated receptors in rats with irritable bowel syndrome attenuated by Shugan decoction.
Shi HL;Liu CH;Ding LL;Zheng Y;Fei XY;Lu L;Zhou XM;Yuan JY;Xie JQ World J Gastroenterol. 2015 Apr 28;21(16):4852-63. doi: 10.3748/wjg.v21.i16.4852.
AIM: ;To determine the molecular mechanisms of Shugan decoction (SGD) in the regulation of colonic motility and visceral hyperalgesia (VHL) in irritable bowel syndrome (IBS).;METHODS: ;The chemical compounds contained in SGD were measured by high-performance liquid chromatography. A rat model of IBS was induced by chronic water avoidance stress (WAS). The number of fecal pellets was counted after WAS and the pain pressure threshold was measured by colorectal distension. Morphological changes in colonic mucosa were detected by hematoxylin-eosin staining. The contents of tumor necrosis factor (TNF)-α in colonic tissue and calcitonin-gene-related peptide (CGRP) in serum were measured by ELISA. The protein expression of serotonin [5-hydroxytryptamide (5-HT)], serotonin transporter (SERT), chromogranin A (CgA) and CGRP in colon tissue was measured by immunohistochemistry.;RESULTS: ;SGD inhibited colonic motility dysfunction and VHL in rats with IBS. Blockers of transient receptor potential (TRP) vanilloid 1 (TRPV1) (Ruthenium Red) and TRP ankyrin-1 (TRPA1) (HC-030031) and activator of protease-activated receptor (PAR)4 increased the pain pressure threshold, whereas activators of PAR2 and TRPV4 decreased the pain pressure threshold in rats with IBS.
2.Identification and characterization of novel small-molecule protease-activated receptor 2 agonists.
Gardell LR;Ma JN;Seitzberg JG;Knapp AE;Schiffer HH;Tabatabaei A;Davis CN;Owens M;Clemons B;Wong KK;Lund B;Nash NR;Gao Y;Lameh J;Schmelzer K;Olsson R;Burstein ES J Pharmacol Exp Ther. 2008 Dec;327(3):799-808. doi: 10.1124/jpet.108.142570. Epub 2008 Sep 3.
We report the first small-molecule protease-activated receptor (PAR) 2 agonists, AC-55541 [N-[[1-(3-bromo-phenyl)-eth-(E)-ylidene-hydrazinocarbonyl]-(4-oxo-3,4-dihydro-phthalazin-1-yl)-methyl]-benzamide] and AC-264613 [2-oxo-4-phenylpyrrolidine-3-carboxylic acid [1-(3-bromo-phenyl)-(E/Z)-ethylidene]-hydrazide], each representing a distinct chemical series. AC-55541 and AC-264613 each activated PAR2 signaling in cellular proliferation assays, phosphatidylinositol hydrolysis assays, and Ca(2+) mobilization assays, with potencies ranging from 200 to 1000 nM for AC-55541 and 30 to 100 nM for AC-264613. In comparison, the PAR2-activating peptide 2-furoyl-LIGRLO-NH(2) had similar potency, whereas SLIGRL-NH(2) was 30 to 300 times less potent. Neither AC-55541 nor AC-264613 had activity at any of the other PAR receptor subtypes, nor did they have any significant affinity for over 30 other molecular targets involved in nociception. Visualization of EYFP-tagged PAR2 receptors showed that each compound stimulated internalization of PAR2 receptors. AC-55541 and AC-264613 were well absorbed when administered intraperitoneally to rats, each reaching micromolar peak plasma concentrations. AC-55541 and AC-264613 were each stable to metabolism by liver microsomes and maintained sustained exposure in rats, with elimination half-lives of 6.
3.Protease-activated receptor 2 (PAR2) is upregulated by Acanthamoeba plasminogen activator (aPA) and induces proinflammatory cytokine in human corneal epithelial cells.
Tripathi T;Abdi M;Alizadeh H Invest Ophthalmol Vis Sci. 2014 May 29;55(6):3912-21. doi: 10.1167/iovs.14-14486.
PURPOSE: ;Acanthamoeba plasminogen activator (aPA) is a serine protease elaborated by Acanthamoeba trophozoites that facilitates the invasion of trophozoites to the host and contributes to the pathogenesis of Acanthamoeba keratitis (AK). The aim of this study was to explore if aPA stimulates proinflammatory cytokine in human corneal epithelial (HCE) cells via the protease-activated receptors (PARs) pathway.;METHODS: ;Acanthamoeba castellanii trophozoites were grown in peptone-yeast extract glucose for 7 days, and the supernatants were collected and centrifuged. The aPA was purified using the fast protein liquid chromatography system, and aPA activity was determined by zymography assays. Human corneal epithelial cells were incubated with or without aPA (100 μg/mL), PAR1 agonists (thrombin, 10 μM; TRAP-6, 10 μM), and PAR2 agonists (SLIGRL-NH2, 100 μM; AC 55541, 10 μM) for 24 and 48 hours. Inhibition of PAR1 and PAR2 involved preincubating the HCE cells for 1 hour with the antagonist of PAR1 (SCH 79797, 60 μM) and PAR2 (FSLLRY-NH2, 100 μM) with or without aPA. Human corneal epithelial cells also were preincubated with PAR1 and PAR2 antagonists and then incubated with or without PAR1 agonists (thrombin and TRAP-6) and PAR2 agonists (SLIGRL-NH2 and AC 55541).
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