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530613 IRAP Inhibitor, HFI-419 - CAS 1110650-72-0 - Calbiochem

A substrate competitive inhibitor of insulin-regulated aminopeptidase (IRAP) activity (Ki = 0.48 µM against 25 µM Leu-AMC).

FDS (Fiches de données de sécurité), certificats d’analyse (CoA) et de qualité (CoQ), dossiers, brochures et autres documents disponibles.

Synonymes: (±)-Ethyl-2-acetamido-7-hydroxy-4-(pyridin-3-yl)-4H-chromene-3-carboxylate, HFI419, Insulin-Regulated Aminopeptidase Inhibitor

Primary Target: IRAP
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530613
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Tableau de caractéristiques principal

CAS #Empirical Formula
1110650-72-0C₁₉H₁₈N₂O₅

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      Description
      OverviewThe racemic mixture of an aqueous soluble pyridinyl-4H-benzopyran compound that inhibits insulin-regulated aminopeptidase (IRAP) activity by competing against substrate for IRAP extracellular catalytic site binding (Ki = 0.48 µM against 25 µM Leu-AMC), while displaying little potency against glucose-6-phosphatase, aminopeptidae N, ACE1, leukotriene A4 hydrolase, or ER-associated aminopeptidases 1 & 2. Reported to boost 1 mM dibutyryl cAMP-evoked glucose uptake in cultured rat hippocampal slices (68% higher uptake with 100 nM HFI-419 than dbcAMP alone) in vitro and exhibit in vivo memory-enhancing efficacay in an object recognition test via direct cerebral lateral ventricle administration (0.1 or 1.0 nmol/2 µL/rat). HFI-419 is reported to hydrolyze into the less potent HFI-142 (Ki = 2.0 µM) after i.v. or i.p. injection in rats, although HFI-142 is more stable and likely exhibits better blood-brain permeability.
      Catalogue Number530613
      Brand Family Calbiochem®
      Synonyms(±)-Ethyl-2-acetamido-7-hydroxy-4-(pyridin-3-yl)-4H-chromene-3-carboxylate, HFI419, Insulin-Regulated Aminopeptidase Inhibitor
      References
      ReferencesMountford, S.J., et al. 2014. J. Med. Chem. 57, 1368.
      Albiston, A.L., et al. 2011. Br. J. Pharmacol. 164, 37.
      Albiston, A.L., et al. 2010. Mol. Pharmacol. 78, 600.
      Albiston, A.L., et al. 2008. FASEB J. 22, 4209.
      Product Information
      CAS number1110650-72-0
      FormOff-white powder
      Hill FormulaC₁₉H₁₈N₂O₅
      Chemical formulaC₁₉H₁₈N₂O₅
      ReversibleY
      Quality LevelMQ100
      Applications
      Biological Information
      Primary TargetIRAP
      Purity≥97% by HPLC
      Physicochemical Information
      Cell permeableY
      Dimensions
      Materials Information
      Toxicological Information
      Safety Information according to GHS
      Safety Information
      Product Usage Statements
      Storage and Shipping Information
      Ship Code Ambient Temperature Only
      Toxicity Standard Handling
      Storage +2°C to +8°C
      Protect from Light Protect from light
      Do not freeze Ok to freeze
      Special InstructionsFollowing reconstitution, aliquot and freeze (-20°C). Stock solutions are stable for up to 3 months at -20°C.
      Packaging Information
      Packaged under inert gas Packaged under inert gas
      Transport Information
      Supplemental Information
      Specifications
      Global Trade Item Number
      Référence GTIN
      5.30613.0001 04055977260946

      Documentation

      IRAP Inhibitor, HFI-419 - CAS 1110650-72-0 - Calbiochem FDS

      Titre

      Fiche de données de sécurité des matériaux (FDS) 

      Références bibliographiques

      Aperçu de la référence bibliographique
      Mountford, S.J., et al. 2014. J. Med. Chem. 57, 1368.
      Albiston, A.L., et al. 2011. Br. J. Pharmacol. 164, 37.
      Albiston, A.L., et al. 2010. Mol. Pharmacol. 78, 600.
      Albiston, A.L., et al. 2008. FASEB J. 22, 4209.
      Fiche technique

      Note that this data sheet is not lot-specific and is representative of the current specifications for this product. Please consult the vial label and the certificate of analysis for information on specific lots. Also note that shipping conditions may differ from storage conditions.

      Revision06-June-2014 JSW
      Synonyms(±)-Ethyl-2-acetamido-7-hydroxy-4-(pyridin-3-yl)-4H-chromene-3-carboxylate, HFI419, Insulin-Regulated Aminopeptidase Inhibitor
      DescriptionThe racemic mixture of an aqueous soluble (at least 50 µg/mL or 140 µM at pH 6.5) pyridinyl-4H-benzopyran compound that inhibits insulin-regulated (IRAP) aminopeptidase activity by competing against substrate for IRAP extracellular catalytic site binding (Ki = 0.48 µM; using 25 µM Leu-AMC as substrate) with concomitant interaction with active site zinc via its acetamide, while displaying little potency against glucose-6-phosphatase, aminopeptidase N, ACE1, leukotriene A4 hydrolase, or ER-associated aminopeptidases 1 & 2 (≤13% inhibition at 100 µM). Reported to boost 1 mM dibutyryl cAMP-evoked glucose uptake in cultured rat hippocampal slices (68% higher uptake in 5 min than dbcAMP alone without 100 nM HFI-419) in vitro and exhibit in vivo memory-enhancing efficacay in an object recognition test when administered directly into the cerebral lateral ventricle of rats via a cannula implant (0.1 or 1.0 nmol/2 µL/rat). HFI-419 is reported to hydrolyze into slightly less potent HFI-142 (Ki = 2.0 µM) after i.v. (plasma t1/2 = 11 min; 2 mg/kg) or i.p (plasma t1/2 = 4.6 h; 10 mg/kg) injection in rats, although HFI-142 is more stable and likely exhibits better blood-brain permeability (Blood:Brain HFI-142 ratio = 3.36 and 0.38, respectively, 0.5 and 4 h post single 3 mg HFI-419/kg i.v. injection).
      FormOff-white powder
      Intert gas (Yes/No) Packaged under inert gas
      CAS number1110650-72-0
      Chemical formulaC₁₉H₁₈N₂O₅
      Purity≥97% by HPLC
      SolubilityDMSO (100 mg/ml). Use only fresh DMSO for reconstitution.
      Storage Protect from light
      +2°C to +8°C
      Do Not Freeze Ok to freeze
      Special InstructionsFollowing reconstitution, aliquot and freeze (-20°C). Stock solutions are stable for up to 3 months at -20°C.
      Toxicity Standard Handling
      ReferencesMountford, S.J., et al. 2014. J. Med. Chem. 57, 1368.
      Albiston, A.L., et al. 2011. Br. J. Pharmacol. 164, 37.
      Albiston, A.L., et al. 2010. Mol. Pharmacol. 78, 600.
      Albiston, A.L., et al. 2008. FASEB J. 22, 4209.