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About This Item
Empirical Formula (Hill Notation):
C7H9N3O
CAS Number:
Molecular Weight:
151.17
MDL number:
UNSPSC Code:
51111800
NACRES:
NA.77
description
RTECS - DG2580000
Quality Level
Assay
≥95% (HPLC)
form
solid
manufacturer/tradename
Calbiochem®
storage condition
OK to freeze
protect from light
color
beige
solubility
DMSO: 10 mg/mL
dilute acid: soluble
shipped in
ambient
storage temp.
−20°C
SMILES string
N(N)C(=O)c1ccc(cc1)N
InChI
1S/C7H9N3O/c8-6-3-1-5(2-4-6)7(11)10-9/h1-4H,8-9H2,(H,10,11)
InChI key
WPBZMCGPFHZRHJ-UHFFFAOYSA-N
Related Categories
General description
A benzoic acid hydrazide analog that acts as a potent, specific, and irreversible inhibitor of myeloperoxidase. ABAH is a mechanism-based inhibitor that is oxidized to radical intermediates that, in turn, promote the irreversible inactivation of myeloperoxidase. Reported to inhibit hypochlorous acid (HOCl) production by purified myeloperoxidase (IC50 = 300 nM). Has also been shown to inhibit HOCl production up to 90% in zymosan and phorbol myristate acetate stimulated neutrophils (IC50 = 16 µM and 2.2 µM, respectively). Does not affect superoxide radical production or degranulation of neutrophils and does not inhibit catalase or glutathione peroxidase. Shown to inhibit myeloperoxidase-mediated apoptosis in >90% of ras-expressing fibroblasts and glutathione-depleted, src-transformed cells. Also shown to inhibit apoptosis in H2O2-treated HL-60 promyelocytic leukemia cells.
Biochem/physiol Actions
Cell permeable: no
Primary Target
Myeloperoxidase
Myeloperoxidase
Product does not compete with ATP.
Reversible: no
Target IC50: 300 nM against myeloperoxidase (MPO)
Packaging
Packaged under inert gas
Preparation Note
Following reconstitution, aliquot and freeze (-20°C). Stock solutions are stable for up to 6 months at -20°C.
Other Notes
Engelmann, I., et al. 2000. Redox Report5, 207.
Wagner, B.A., et al. 2000. J. Biol. Chem.275, 22461.
Burner, U., et al. 1999. J. Biol. Chem.274, 9494.
Kettle, A.J., et al. 1997. Biochem. J.321, 503.
Kettle, A.J., et al. 1995. Biochem. J.308, 559.
Wagner, B.A., et al. 2000. J. Biol. Chem.275, 22461.
Burner, U., et al. 1999. J. Biol. Chem.274, 9494.
Kettle, A.J., et al. 1997. Biochem. J.321, 503.
Kettle, A.J., et al. 1995. Biochem. J.308, 559.
Legal Information
CALBIOCHEM is a registered trademark of Merck KGaA, Darmstadt, Germany
Disclaimer
Toxicity: Irritant (B)
Storage Class Code
11 - Combustible Solids
WGK
WGK 3
Flash Point(F)
Not applicable
Flash Point(C)
Not applicable
Certificates of Analysis (COA)
Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.
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