WARNING: This product is for research use only, not for human or veterinary use.
Hodoodo CAT#: H556151
CAS#: 216014-05-0 (CRX-547)
Description: CRX-547 is a member of the aminoalkyl glucosaminide 4-phosphate (AGP) class of lipid A mimetics possessing three (R)-3-decanoyloxytetradecanoyl groups and d-relative configuration in the aglycon, selectively reduces MyD88-dependent signaling resulting in TRIF-selective signaling. CRX-547 stimulated little or no activation of MyD88-dependent signaling molecules or cytokines, whereas its ability to activate the TRIF-dependent pathway was similar to that of a structurally related inflammatory AGP and of lipopolysaccharide from Salmonella minnesota.
Hodoodo Cat#: H556151
Name: CRX-547
CAS#: 216014-05-0 (CRX-547)
Chemical Formula: C81H151N2O19P
Exact Mass: 1,487.06
Molecular Weight: 1,488.068
Elemental Analysis: C, 65.38; H, 10.23; N, 1.88; O, 20.43; P, 2.08
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Related CAS #: 216014-14-1 (CRX-527) 216014-05-0 (CRX-547)
Synonym: CRX-547; CRX 547; CRX547;
IUPAC/Chemical Name: Decanoic acid, (1R)-1-[2-[[(1R)-1-carboxy-2-[[2-deoxy-3-O-[(3R)-1-oxo-3-[(1-oxodecyl)oxy]tetradecyl]-2-[[(3R)-1-oxo-3-[(1-oxodecyl)oxy]tetradecyl]amino]-4-O-phosphono-β-D-glucopyranosyl]oxy]ethyl]amino]-2-oxoethyl]dodecyl ester (9CI, ACI)
InChi Key: REEGNIYAMZUTIO-ARLDOHDRSA-N
InChi Code: InChI=1S/C81H151N2O19P/c1-7-13-19-25-31-34-40-43-49-55-66(97-73(87)58-52-46-37-28-22-16-10-4)61-71(85)82-69(80(91)92)65-96-81-77(83-72(86)62-67(56-50-44-41-35-32-26-20-14-8-2)98-74(88)59-53-47-38-29-23-17-11-5)79(78(70(64-84)100-81)102-103(93,94)95)101-76(90)63-68(57-51-45-42-36-33-27-21-15-9-3)99-75(89)60-54-48-39-30-24-18-12-6/h66-70,77-79,81,84H,7-65H2,1-6H3,(H,82,85)(H,83,86)(H,91,92)(H2,93,94,95)/t66-,67-,68-,69-,70-,77-,78-,79-,81-/m1/s1
SMILES Code: O(C(C[C@H](OC(CCCCCCCCC)=O)CCCCCCCCCCC)=O)[C@@H]1[C@@H](NC(C[C@H](OC(CCCCCCCCC)=O)CCCCCCCCCCC)=O)[C@H](OC[C@@H](NC(C[C@H](OC(CCCCCCCCC)=O)CCCCCCCCCCC)=O)C(O)=O)O[C@H](CO)[C@H]1OP(=O)(O)O
Appearance: To be determined
Purity: >98% (or refer to the Certificate of Analysis)
Shipping Condition: Shipped under ambient temperature as non-hazardous chemical. This product is stable enough for a few weeks during ordinary shipping and time spent in Customs.
Storage Condition: Dry, dark and at 0 - 4 C for short term (days to weeks) or -20 C for long term (months to years).
Solubility: To be determined
Shelf Life: >2 years if stored properly
Drug Formulation: To be determined
Stock Solution Storage: 0 - 4 C for short term (days to weeks), or -20 C for long term (months).
HS Tariff Code: 2934.99.9001
More Info:
| Biological target: | |
| In vitro activity: | |
| In vivo activity: |
The following data is based on the product molecular weight 1,488.07 Batch specific molecular weights may vary from batch to batch due to the degree of hydration, which will affect the solvent volumes required to prepare stock solutions.
| Concentration / Solvent Volume / Mass | 1 mg | 5 mg | 10 mg |
|---|---|---|---|
| 1 mM | 1.15 mL | 5.76 mL | 11.51 mL |
| 5 mM | 0.23 mL | 1.15 mL | 2.3 mL |
| 10 mM | 0.12 mL | 0.58 mL | 1.15 mL |
| 50 mM | 0.02 mL | 0.12 mL | 0.23 mL |
| Formulation protocol: | |
| In vitro protocol: | |
| In vivo protocol: |
1: Liu D, Dong S, Liu C, Du J, Wang S, Yu H, Li W, Chen Z, Peng R, Jiang Q, Zou M, Li F, Zhang R. CRX-527 induced differentiation of HSCs protecting the intestinal epithelium from radiation damage. Front Immunol. 2022 Aug 30;13:927213. doi: 10.3389/fimmu.2022.927213. PMID: 36110845; PMCID: PMC9468934.
2: Legat A, Thomas S, Hermand P, Van Mechelen M, Goldman M, De Wit D. CD14-independent responses induced by a synthetic lipid A mimetic. Eur J Immunol. 2010 Mar;40(3):797-802. doi: 10.1002/eji.200939992. PMID: 20039305.
3: Bowen WS, Minns LA, Johnson DA, Mitchell TC, Hutton MM, Evans JT. Selective TRIF-dependent signaling by a synthetic toll-like receptor 4 agonist. Sci Signal. 2012 Feb 14;5(211):ra13. doi: 10.1126/scisignal.2001963. PMID: 22337809; PMCID: PMC3684200.
4: Reintjens NRM, Tondini E, de Jong AR, Meeuwenoord NJ, Chiodo F, Peterse E, Overkleeft HS, Filippov DV, van der Marel GA, Ossendorp F, Codée JDC. Self- Adjuvanting Cancer Vaccines from Conjugation-Ready Lipid A Analogues and Synthetic Long Peptides. J Med Chem. 2020 Oct 22;63(20):11691-11706. doi: 10.1021/acs.jmedchem.0c00851. Epub 2020 Oct 6. PMID: 32960056; PMCID: PMC7586330.
5: Khalaf JK, Bowen WS, Bazin HG, Ryter KT, Livesay MT, Ward JR, Evans JT, Johnson DA. Characterization of TRIF selectivity in the AGP class of lipid A mimetics: role of secondary lipid chains. Bioorg Med Chem Lett. 2015 Feb 1;25(3):547-53. doi: 10.1016/j.bmcl.2014.12.024. Epub 2014 Dec 17. PMID: 25553892; PMCID: PMC4330088.
6: Lembo A, Pelletier M, Iyer R, Timko M, Dudda JC, West TE, Wilson CB, Hajjar AM, Skerrett SJ. Administration of a synthetic TLR4 agonist protects mice from pneumonic tularemia. J Immunol. 2008 Jun 1;180(11):7574-81. doi: 10.4049/jimmunol.180.11.7574. PMID: 18490759; PMCID: PMC3063511.
7: Airhart CL, Rohde HN, Bohach GA, Hovde CJ, Deobald CF, Lee SS, Minnich SA. Induction of innate immunity by lipid A mimetics increases survival from pneumonic plague. Microbiology (Reading). 2008 Jul;154(Pt 7):2131-2138. doi: 10.1099/mic.0.2008/017566-0. PMID: 18599840.
8: Royer CM, Rudolph K, Barrett EG. The neonatal susceptibility window for inhalant allergen sensitization in the atopically predisposed canine asthma model. Immunology. 2013 Apr;138(4):361-9. doi: 10.1111/imm.12043. PMID: 23181409; PMCID: PMC3719946.
