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IAXO-101 (CD14/TLR4 Antagonist) (synthetic)

IAX-600-001-M001 1 mg INQ
IAX-600-001-M005 5 mg INQ
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Additional Information

Product Data
Synonyms Methyl 6-deoxy-6-N-dimethyl-N-cyclopentylammonium-2,3-di-O-tetradecyl-α-D-glucopyranoside iodide
Properties
Formula C42H84INO5
MW 810.02g/mol (iodide salt)
CAS 1202388-64-4
Source/Host Synthetic.
Purity ≥98% (TLC)
Appearance White solid.
Solubility Soluble in Methanol, DMSO and Ethanol 1:1 (vol:vol): >10mM.
Biological Activity Described to interfere with human, rat and mouse TLR4/CD14 signaling, other species not tested. Optimal working concentration depends upon the type, purity and concentration and of TLR4 ligand, carrier protein such as LPS-binding protein (LBP), soluble and membrane-bound CD14, the presence of TLR4 co-receptors (e.g. CD36) as well as on type and time of read-out (e.g. cytokine measurement in cell culture supernatant) or the biological outcome of in vivo experiments and therefore needs to be determined for each application. Recommended starting concentration: in vitro: 5μM, in vivo (rodent): 3mg/kg. Control compound: IAXO-202 (Cat. No.: IAX-600-005).
Identity Determined by NMR and MS.
Origin Manufactured by Innaxon.
Other Product Data Reconstitution: For a 2mM stock solution, dissolve total vial content in 617μl (1mg size) or 3,085μl (5mg size) DMSO/Ethanol (1:1) (vol:vol).

Click here for Original Manufacturer Product Datasheet: Our product description may differ slightly from the original manufacturers product datasheet.
InChi Key InChI=1/C42H84NO5.HI/c1-6-8-10-12-14-16-18-20-22-24-26-30-34-46-40-39(44)38(36-43(3,4)37-32-28-29-33-37)48-42(45-5)41(40)47-35-31-27-25-23-21-19-17-15-13-11-9-7-2;/h37-42,44H,6-36H2,1-5H3;1H/q+1;/p-1/fC42H84NO5.I/h;1h/qm;-1
Product Type Chemical
Shipping and Handling
Shipping AMBIENT
Short Term Storage +4°C
Long Term Storage +4°C
Use/Stability Stable for at least 1 year after receipt when stored at +4°C.
Documents
MSDS Download Document Download

Product Description

  • CD14/TLR4 antagonist. Inhibitor of sterile inflammation.
  • Synthetic TLR4/CD14 ligand with TLR4 modulating activities in vitro, and conferring protection against TLR4/CD14-mediated tissue damage and inflammation in vivo. Useful to explore CD14- dependent and TLR4-independent pathways and TLR4 activation by endogenous ligands (e.g. hyaluronic acid oligosaccharides, oxLDL, HMGB1) in sterile inflammation. Shown to inhibit neuropathic pain, secondary necrosis of acute drug-induced liver failure and vascular inflammation, and abdominal aortic aneurysm by blocking non-hematopoietic TLR4 signaling. Useful tool, where inhibition of sterile (auto-) inflammation is desired, without compromising TLR4’s key role in the defense of pathogens.

Product References

  1. Inhibition of lipid a stimulated activation of human dendritic cells and macrophages by amino and hydroxylamino monosaccharides: F. Peri, et al.; Angew. Chem.46, 3308 (2007)
  2. TLR4 receptor as new target to treat neuropathic pain: efficacy of a new receptor antagonist in a model of peripheral nerve injury in mice: I. Bettoni, et al.; Glia 56, 1312 (2008)
  3. Glycolipids and benzylammonium lipids as novel antisepsis agents: synthesis and biological characterization: M. Piazza, et al.; J. Med. Chem. 52, 1209 (2009)
  4. Evidence of a specific interaction between new synthetic antisepsis agents and CD14: M. Piazza, et al.; Biochemistry 48, 12337 (2009)
  5. Exploring the LPS/TLR4 signal pathway with small molecules: F. Peri, et al.; Biochem. Soc. Trans. 38, 1390 (2010) (Review)
  6. Therapeutic targeting of innate immunity with Toll-like receptor 4 (TLR4) antagonists: F. Peri & M. Piazza; Biotechnol. Adv. 30, 251 (2012) (Review)
  7. Synthetic molecules and functionalized nanoparticles targeting the LPS-TLR4 signaling: A new generation of immunotherapeutics: F. Peri, et al.; Pure Appl. Chem. 84, 97 (2012) (Review)
  8. Toll like receptor 4 antagonist prevents acetaminophen induced acute liver failure in mice: a novel therapeutic strategy: N. Shah, et al.; Gut 61, A28 (2012)
  9. Multivalent glycoconjugates as anti-pathogenic agents. A. Bernardi, et al.; Chem. Soc. Rev. 42, 4709 (2013) (Review)
  10. Toll-like receptor 4 (TLR4) modulation by synthetic and natural compounds: an update: F. Peri & V. Calabrese; Med. Chem. 57, 3612 (2014) (Review)
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