An antibiotic and LpxC inhibitor
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Information provided in the product description is from published literature. Due to the nature of scientific experimentation, your results (e.g., selectivity and effective concentrations) or specific application for this product may differ. If you have questions about how this product fits your application, please contact our technical support staff.

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CHIR090

Item No. 22256

Technical Information
Formal Name
N-[(1S,2R)-2-hydroxy-1-[(hydroxyamino)carbonyl]propyl]-4-[2-[4-(4-morpholinylmethyl)phenyl]ethynyl]-benzamide
CAS Number
728865-23-4
Molecular Formula
C24H27N3O5
Formula Weight
Purity
≥98%
A crystalline solid
DMF: 2 mg/mlDMSO: 2.5 mg/ml
λmax
299 nm
SMILES
O=C(N[C@H](C(NO)=O)[C@H](O)C)C1=CC=C(C#CC2=CC=C(CN3CCOCC3)C=C2)C=C1
InChi Code
InChI=1S/C24H27N3O5/c1-17(28)22(24(30)26-31)25-23(29)21-10-8-19(9-11-21)3-2-18-4-6-20(7-5-18)16-27-12-14-32-15-13-27/h4-11,17,22,28,31H,12-16H2,1H3,(H,25,29)(H,26,30)/t17-,22+/m1/s1
InChi Key
FQYBTYFKOHPWQT-VGSWGCGISA-N
Shipping & Storage Information
Storage
-20°C
Shipping
Room temperature in continental US; may vary elsewhere
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    Product Description

    CHIR090 is an antibiotic that inhibits LpxC, a deacetylase involved in the biosynthesis of LPS lipid A, with Ki values of 1-1.7 nM in A. aeolicus.1 It is active against Gram-negative bacteria with MIC values of 0.05, 0.78, and 0.10-6.25 mg/ml for E. coli, P. aeruginosa, and various B. multivorans (II) strains, respectively.2,3 It is comparable in strength to ciprofloxacin (Item No. 14286) in disc assays.1

    WARNING This product is not for human or veterinary use.

    References & Product Citations
    Product Description References

    1. McClerren, A.L., Endsley, S., Bowman, J.L., et alA slow, tight-binding inhibitor of the zinc-dependent deacetylase LpxC of lipid A biosynthesis with antibiotic activity comparable to ciprofloxacin. Biochemistry 44(50), 16574-16583 (2005).

    2. Barb, A.W., McClerren, A.L., Snehelatha, K., et alInhibition of lipid A biosynthesis as the primary mechanism of CHIR-090 antibiotic activity in Escherichia coli. Biochemistry 46(12), 3793-3802 (2007).

    3. Bodewits, K., Raetz, C.R., Govan, J.R., et alAntimicrobial activity of CHIR-090, an inhibitor of lipopolysaccharide biosynthesis, against the Burkholderia cepacia complex. Antimicrob. Agents Chemother. 54(8), 3531-3533 (2010).