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

Innaxon
Product Code: IAX-600-001
Supplier: Innaxon

CodeSizePrice
IAX-600-001-M0011 mg£236.00
Quantity:
Prices exclude any Taxes / VAT

Overview

Regulatory Status: RUO
Shipping:
Ambient
Storage:
+4°C

Images

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Chemical Structure

Chemical Structure

Further Information

Alternate Names/Synonyms:
Methyl 6-deoxy-6-N-dimethyl-N-cyclopentylammonium-2,3-di-O-tetradecyl-alpha-D-glucopyranoside iodide
Appearance:
White solid.
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.
CAS:
1202388-64-4
EClass:
32160000
Form (Short):
solid
InChi:
BEFLBKFGGQBVHS-QITXJEEXCR
InChiKey:
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
Long Description:
Chemical. CAS: 1202388-64-4. Formula: C42H84INO5. MW: 810.02g/mol (iodide salt). Synthetic. 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.
MDL:
N/A
Molecular Formula:
C42H84INO5
Molecular Weight:
810.02g/mol (iodide salt)
Other 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).
Package Type:
Plastic Vial
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.
Purity:
>98% (TLC)
SMILES:
O[C@H]1[C@H](OCCCCCCCCCCCCCC)[C@@H](OCCCCCCCCCCCCCC)[C@@H](OC)O[C@@H]1C[N+](C)(C2CCCC2)C.[I-]
Solubility Chemicals:
Soluble in Methanol, DMSO and Ethanol 1:1 (vol:vol): >10mM.
Source / Host:
Synthetic.
Transportation:
Non-Hazardous
UNSPSC Category:
Biochemical Reagents
UNSPSC Number:
12352200
Use & Stability:
Stable for at least 1 year after receipt when stored at +4°C.

References

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) | 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) | Glycolipids and benzylammonium lipids as novel antisepsis agents: synthesis and biological characterization: M. Piazza, et al.; J. Med. Chem. 52, 1209 (2009) | Evidence of a specific interaction between new synthetic antisepsis agents and CD14: M. Piazza, et al.; Biochemistry 48, 12337 (2009) | Exploring the LPS/TLR4 signal pathway with small molecules: F. Peri, et al.; Biochem. Soc. Trans. 38, 1390 (2010) (Review) | Therapeutic targeting of innate immunity with Toll-like receptor 4 (TLR4) antagonists: F. Peri & M. Piazza; Biotechnol. Adv. 30, 251 (2012) (Review) | 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) | 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) | Multivalent glycoconjugates as anti-pathogenic agents. A. Bernardi, et al.; Chem. Soc. Rev. 42, 4709 (2013) (Review) | Toll-like receptor 4 (TLR4) modulation by synthetic and natural compounds: an update: F. Peri & V. Calabrese; Med. Chem. 57, 3612 (2014) (Review) | TLR4-mediated placental pathology and pregnancy outcome in experimental Malaria: R. Barboza, et al.; Sci. Rep. 7, 8623 (2017) | TLR4/NF-kB axis induces fludarabine resistance by suppressing TXNIP expression in acute myeloid leukemia cells: H. Huy, et al.; BBRC 506, 33 (2018) | Targeting CD14 on blood derived cells improves intracortical microelectrode performance: H.W. Bedell, et al.; Biomaterials 163, 163 (2018) | Inhibition of the cluster of differentiation 14 innate immunity pathway with IAXO-101 improves chronic microelectrode performance: J.K. Hermann, et al.; J. Neural Eng. 15, 025002 (2018) | Effect of CD14/TLR4 antagonist on GnRH/LH secretion in ewe during central inflammation induced by intracerebroventricular administration of LPS: K. Haziak, et al.; J. Animal Sci. Biotech. 9, 52 (2018) | Identification of hepatic NPC1L1 as an NAFLD risk factor evidenced by ezetimibe-mediated steatosis prevention and recovery: Y. Toyoda, et al.; FASEB Bioadv. 1, 283 (2019) | Increasing the chemical variety of small-molecule-based TLR4 modulators: An Overview: A. Romerio & F. Peri; Front. Immunol. 11, 1210 (2020)