An affinity probe for NAAA
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ARN14686

Item No. 24261

Product Insert (PDF)Safety Data Sheet (SDS) (PDF)
Technical Information
Formal Name
N-[(3S)-2-oxo-3-azetidinyl]-carbamic acid, 10-undecyn-1-yl ester
CAS Number
1628345-10-7
Synonyms
  • Click Tag™ ARN14686
Molecular Formula
C15H24N2O3
Formula Weight
280.4
Purity
≥98%
Formulation (Request formulation change)
A crystalline solid
Solubility(Learn about Variance in Solubility)
DMF: 30 mg/mlDMSO: 30 mg/mlEthanol: 1 mg/ml
SMILES
O=C(N[C@H]1CNC1=O)OCCCCCCCCCC#C
InChi Code
InChI=1S/C15H24N2O3/c1-2-3-4-5-6-7-8-9-10-11-20-15(19)17-13-12-16-14(13)18/h1,13H,3-12H2,(H,16,18)(H,17,19)/t13-/m0/s1
InChi Key
XEXRAYPXQNELAS-ZDUSSCGKSA-N
Shipping & Storage Information
Storage
-20°C
Shipping
Wet ice in continental US; may vary elsewhere
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    1 mg

    $54

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    5 mg

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    10 mg

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    25 mg

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    Product Description

    ARN14686 is an activity-based affinity probe for the detection of N-acylethanolamine acid amidase (NAAA) using click chemistry.1 It binds covalently to the N-terminal cysteine of catalytically active NAAA to form a thioester adduct. ARN14686 inhibits the hydrolysis of the NAAA substrate PAMCA in HEK293 cells (IC50s = 6 and 13 nM for human and rat recombinant enzymes, respectively) and is selective for NAAA over acid ceramidase (IC50 = 1,200 nM for the rat enzyme). It labels NAAA in HEK293 cells overexpressing human or rat recombinant NAAA and, when used at concentrations of 1 and 10 µM, in rat lung lysosomal fractions in vitro. It also detects NAAA in lung lysosomal fractions following intravenous administration at a dose of 10 mg/kg in rats. ARN14686 (3 mg/kg) has been used to determine that catalytically active NAAA is present in inflamed rat paw in a complete Freund’s adjuvant model of inflammation.2

    WARNING This product is not for human or veterinary use.

    References & Product Citations
    Product Description References

    1. Romeo, E., Ponzano, S., Armirotti, A., et al. Activity-based probe for N-acylethanolamine acid Amidase. ACS Chem Biol. 10(9), 2057-2064 (2015).

    2. Bonezzi, F.T., Sasso, O., Pontis, S., et al. An important role for N-acylethanolamine acid amidase in the complete Freund’s adjuvant rat model of arthritis. J. Pharmacol. Exp. Ther. 356(3), 656-663 (2016).