For research use only. Not for therapeutic Use.
CHIR-090（Cat No.:I004713）is a potent and selective inhibitor of the enzyme indoleamine 2,3-dioxygenase (IDO1), a key enzyme involved in tryptophan catabolism and immune regulation. By blocking IDO1, CHIR-090 modulates the immune system and has shown promise in cancer immunotherapy, enhancing T-cell activity and preventing immune evasion by tumors. It holds potential for treating various cancers, autoimmune disorders, and chronic inflammatory diseases. This compound provides researchers with valuable insights into immune checkpoint regulation and may contribute to novel therapeutic approaches targeting the IDO1 pathway.
| Catalog Number | I004713 |
| CAS Number | 728865-23-4 |
| Synonyms | N-[(2S,3R)-3-hydroxy-1-(hydroxyamino)-1-oxobutan-2-yl]-4-[2-[4-(morpholin-4-ylmethyl)phenyl]ethynyl]benzamide |
| Molecular Formula | C₂₄H₂₇N₃O5 |
| Purity | ≥95% |
| Target | Bacterial; Antibiotic |
| 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 | C[C@H]([C@@H](C(=O)NO)NC(=O)C1=CC=C(C=C1)C#CC2=CC=C(C=C2)CN3CCOCC3)O |
| Reference | </br>1:<i>In-vitro</i> and <i>in-vivo</i> efficacy of LpxC inhibitor, CHIR-090, alone or combined with colistin against <i>Pseudomonas aeruginosa biofilm</i>. 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 </br>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 </br>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 Article</br>4: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 Article</br>5: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 Article</br>6: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 Article</br>7: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 |
