C34 - CAS 40592-88-9
Catalog number: 40592-88-9
Category: Inhibitor
Please be kindly noted products are not for therapeutic use. We do not sell to patients.
Molecular Formula:
C17H27NO9
Molecular Weight:
389.4
COA:
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Targets:
Toll-like Receptor (TLR)
Description:
TLR4 inhibitor
Brife Description:
TLR4 inhibitor
Appearance:
White solid
Synonyms:
TLR4-IN-C34; 1-Methylethyl 2-(acetylamino)-2-deoxy-α-D-glucopyranoside 3,4,6-triacetate
Solubility:
Soluble to 50 mM in water and to 100 mM in DMSO
Storage:
Store at -20°C
MSDS:
Inquire
Quality Standard:
In-house
Quantity:
Grams-Kilos
Melting Point:
Between 150 - 151°C
InChIKey:
KMIQMFHPUJUDMC-HHARLNAUSA-N
InChI:
1S/C17H27NO9/c1-8(2)24-17-14(18-9(3)19)16(26-12(6)22)15(25-11(5)21)13(27-17)7-23-10(4)20/h8,13-17H,7H2,1-6H3,(H,18,19)/t13-,14-,15-,16-,17+/m1/s1
Canonical SMILES:
CC(O[C@H]1O[C@@H]([C@H]([C@@H]([C@H]1NC(C)=O)OC(C)=O)OC(C)=O)COC(C)=O)C
1.Discovery and validation of a new class of small molecule Toll-like receptor 4 (TLR4) inhibitors.
Neal MD;Jia H;Eyer B;Good M;Guerriero CJ;Sodhi CP;Afrazi A;Prindle T Jr;Ma C;Branca M;Ozolek J;Brodsky JL;Wipf P;Hackam DJ PLoS One. 2013 Jun 12;8(6):e65779. doi: 10.1371/journal.pone.0065779. Print 2013.
Many inflammatory diseases may be linked to pathologically elevated signaling via the receptor for lipopolysaccharide (LPS), toll-like receptor 4 (TLR4). There has thus been great interest in the discovery of TLR4 inhibitors as potential anti-inflammatory agents. Recently, the structure of TLR4 bound to the inhibitor E5564 was solved, raising the possibility that novel TLR4 inhibitors that target the E5564-binding domain could be designed. We utilized a similarity search algorithm in conjunction with a limited screening approach of small molecule libraries to identify compounds that bind to the E5564 site and inhibit TLR4. Our lead compound, C34, is a 2-acetamidopyranoside (MW 389) with the formula C17H27NO9, which inhibited TLR4 in enterocytes and macrophages in vitro, and reduced systemic inflammation in mouse models of endotoxemia and necrotizing enterocolitis. Molecular docking of C34 to the hydrophobic internal pocket of the TLR4 co-receptor MD-2 demonstrated a tight fit, embedding the pyran ring deep inside the pocket. Strikingly, C34 inhibited LPS signaling ex-vivo in human ileum that was resected from infants with necrotizing enterocolitis. These findings identify C34 and the β-anomeric cyclohexyl analog C35 as novel leads for small molecule TLR4 inhibitors that have potential therapeutic benefit for TLR4-mediated inflammatory diseases.
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