40592-88-9 Usage
Description
Isopropyl 2-(acetylamino)-2-deoxy á-D-glucopyranoside 3,4,6-triacetate is a complex organic compound with a unique structure that features an isopropyl group, an acetylamino group, and three acetate groups attached to a deoxy-glucopyranoside core. This molecule is characterized by its potential interactions with biological systems due to its structural features.
Uses
Used in Pharmaceutical Industry:
Isopropyl 2-(acetylamino)-2-deoxy á-D-glucopyranoside 3,4,6-triacetate is used as a potential therapeutic agent for various applications due to its ability to interact with biological molecules and receptors.
Used in Anti-inflammatory Applications:
As a new class of toll-like receptor 4 (TLR4) inhibitors, Isopropyl 2-(acetylamino)-2-deoxy á-D-glucopyranoside 3,4,6-triacetate is used as an anti-inflammatory agent. It has the potential to modulate the immune response by inhibiting TLR4, which plays a crucial role in the initiation and amplification of inflammatory responses.
Used in Drug Delivery Systems:
Isopropyl 2-(acetylamino)-2-deoxy á-D-glucopyranoside 3,4,6-triacetate can be employed in the development of novel drug delivery systems to improve the bioavailability and therapeutic outcomes of various drugs. Its unique structure may allow for targeted delivery and controlled release of pharmaceutical agents.
Used in Research and Development:
Due to its specific interactions with biological systems, Isopropyl 2-(acetylamino)-2-deoxy á-D-glucopyranoside 3,4,6-triacetate can be used in research and development for the discovery of new drugs and therapies, particularly in the fields of immunology and inflammation.
Biological Activity
c34 is a 2-acetamidopyranoside that inhibits tlr4 signaling in enterocytes and macrophages in vitro when used at 10 μm. it does not affect signaling through either tlr2 or tlr9[1,2].c34, used at 1 mg/kg can reduce systemic inflammation in mouse models of endotoxemia and necrotizing enterocolitis[1].c34 markedly decreases the basal expression of tnfα, as well as lps-induced inos and tnfα expression, in intestinal tissue isolated from patients with necrotizing enterocolitis[1].[1]. neal m d, jia h, eyer b, et al. discovery and validation of a new class of small molecule toll-like receptor 4 (tlr4) inhibitors. plos one, 2013, 8(6): e65779.[2]. wipf p, eyer b r, yamaguchi y, et al. synthesis of anti-inflammatory α-and β-linked acetamidopyranosides as inhibitors of toll-like receptor 4 (tlr4). tetrahedron letters, 2015, 56(23): 3097-3100.
Biochem/physiol Actions
TLR4-IN-C34 is a potent and specific inhibitor of toll-like receptor 4 (TLR4), which inhibits TLR4 signaling in vivo and in vitro. TLR4-IN-C34, also known as C34, is an aminomonosaccharide that inhibits TLR4 signaling by docking with the hydrophobic pocket of the TLR4 co-receptor, myeloid differentiation protein-2 (MD-2). C34 has been shown to diminish the severity of experimental necrotizing enterocolitis (NEC).
Check Digit Verification of cas no
The CAS Registry Mumber 40592-88-9 includes 8 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 5 digits, 4,0,5,9 and 2 respectively; the second part has 2 digits, 8 and 8 respectively.
Calculate Digit Verification of CAS Registry Number 40592-88:
(7*4)+(6*0)+(5*5)+(4*9)+(3*2)+(2*8)+(1*8)=119
119 % 10 = 9
So 40592-88-9 is a valid CAS Registry Number.
40592-88-9Relevant articles and documents
Synthesis of anti-inflammatory α-and β-linked acetamidopyranosides as inhibitors of toll-like receptor 4 (TLR4)
Wipf, Peter,Eyer, Benjamin R.,Yamaguchi, Yukihiro,Zhang, Feng,Neal, Matthew D.,Sodhi, Chhinder P.,Good, Misty,Branca, Maria,Prindle, Thomas,Lu, Peng,Brodsky, Jeffrey L.,Hackam, David J.
, p. 3097 - 3100 (2015/06/02)
Abstract The low-molecular weight isopropyl 2-acetamido-α-glucoside 16 (C34) inhibits toll-like receptor 4 (TLR4) in enterocytes and macrophages in vitro, and reduces systemic inflammation in mouse models of endotoxemia and necrotizing enterocolitis. We used a copper(II)-mediated solvolysis of anomeric oxazolines and an acid-mediated conversion of β-glucosamine and β-galactosamine pentaacetates to generate analogs of 16 at the anomeric carbon and at C-4 of the pyranose ring. These compounds were evaluated for their influence on TLR4-mediated inflammatory signaling in cultured enterocytes and monocytes. Their efficacy was confirmed using a NF-kB-luciferase reporter mouse, thus establishing the first structure-activity relationship (SAR) study in this series and identifying the more efficacious isopropyl 2-acetamido-α-galactoside 17.
