CHIR-090

• CAT Number: I004713
• CAS Number: 728865-23-4
• Molecular Formula: C₂₄H₂₇N₃O5
• Molecular Weight: 437.5
• Purity: ≥95%
• Target: LpxC
• Solubility: DMSO: ≥ 30 mg/mL
• Storage: Store at -20°C
• IUPAC Name: N-[(2S,3R)-3-hydroxy-1-(hydroxyamino)-1-oxobutan-2-yl]-4-[2-[4-(morpholin-4-ylmethyl)phenyl]ethynyl]benzamide
• InChI: 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
• InChIKey: FQYBTYFKOHPWQT-VGSWGCGISA-N
• SMILES: CC(C(C(=O)NO)NC(=O)C1=CC=C(C=C1)C#CC2=CC=C(C=C2)CN3CCOCC3)O

CHIR-090（Cat No.:I004713） is a highly potent inhibitor of LpxC, an essential enzyme involved in the biosynthesis of lipid A, a component of Gram-negative bacterial cell walls. It exhibits a unique two-step time-dependent inhibition mechanism. Notably, CHIR-090 demonstrates remarkable efficacy in killing a diverse array of Gram-negative pathogens, comparable to the effectiveness of widely used antibiotics such as ciprofloxacin or tobramycin.

Reference

1:In-vitro and in-vivo efficacy of LpxC inhibitor, CHIR-090, alone or combined with colistin against Pseudomonas aeruginosa biofilm. Tan JH, Vidaillac C, Yam JKH, Chua SL, Givskov M, Yang L.Antimicrob Agents Chemother. 2017 May 1. pii: AAC.02223-16. doi: 10.1128/AAC.02223-16. [Epub ahead of print] PMID: 28461320 2:Design and stereoselective synthesis of a C-aryl furanoside as a conformationally constrained CHIR-090 analogue. Oddo A, Holl R.Carbohydr Res. 2012 Oct 1;359:59-64. doi: 10.1016/j.carres.2012.06.006. Epub 2012 Jun 18. PMID: 22925765 3:Mechanisms decreasing in vitro susceptibility to the LpxC inhibitor CHIR-090 in the gram-negative pathogen Pseudomonas aeruginosa. Caughlan RE, Jones AK, Delucia AM, Woods AL, Xie L, Ma B, Barnes SW, Walker JR, Sprague ER, Yang X, Dean CR.Antimicrob Agents Chemother. 2012 Jan;56(1):17-27. doi: 10.1128/AAC.05417-11. Epub 2011 Oct 24. PMID: 22024823 Free PMC Article4:Structure of the metal-dependent deacetylase LpxC from Yersinia enterocolitica complexed with the potent inhibitor CHIR-090 . Cole KE, Gattis SG, Angell HD, Fierke CA, Christianson DW.Biochemistry. 2011 Jan 18;50(2):258-65. Epub 2010 Dec 20. PMID: 21171638 Free PMC Article5:Antimicrobial activity of CHIR-090, an inhibitor of lipopolysaccharide biosynthesis, against the Burkholderia cepacia complex. Bodewits K, Raetz CR, Govan JR, Campopiano DJ.Antimicrob Agents Chemother. 2010 Aug;54(8):3531-3. doi: 10.1128/AAC.01600-09. Epub 2010 Jun 1. No abstract available. PMID: 20516283 Free PMC Article6:Structure of the deacetylase LpxC bound to the antibiotic CHIR-090: Time-dependent inhibition and specificity in ligand binding. Barb AW, Jiang L, Raetz CR, Zhou P.Proc Natl Acad Sci U S A. 2007 Nov 20;104(47):18433-8. Epub 2007 Nov 19. Erratum in: Proc Natl Acad Sci U S A. 2007 Dec 26;104(52):21020. PMID: 18025458 Free PMC Article7:Inhibition of lipid A biosynthesis as the primary mechanism of CHIR-090 antibiotic activity in Escherichia coli. Barb AW, McClerren AL, Snehelatha K, Reynolds CM, Zhou P, Raetz CR.Biochemistry. 2007 Mar 27;46(12):3793-802. Epub 2007 Mar 3. PMID: 17335290 Free PMC Article