GSK1795091   Click here for help

GtoPdb Ligand ID: 11150

Synonyms: compound 4 [PMID: 18835160] | CRX-601 | CRX601 | GSK'091 | GSK-1795091
Compound class: Synthetic organic
Comment: GSK1795091 is a dendritic glycolipid TLR4 agonist with potential immunoadjuvant activity [2-3]. Structurally it is a mimetic of bacterial lipid A [1]. TLR4 plays a key role in the activation of the innate immune response. Activating TLR4 stimulates dendritic cells (DCs), monocytes and macrophages to increase production of pro-inflammatory cytokines (IFNγ, TNFα, interleukins (IL), IL-1 beta, -6 and -12). This mechanism produces a Th1 immune response that offers adjuvant potential in combination with tumour antigen vaccines, and a subsequent cytotoxic T-lymphocyte response against the targeted tumour cells. It also enhances the immune response to checkpoint inhibitor cancer therapies.
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2D Structure
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Physico-chemical Properties
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Hydrogen bond acceptors 18
Hydrogen bond donors 6
Rotatable bonds 79
Topological polar surface area 264.75
Molecular weight 1445.13
XLogP 26.84
No. Lipinski's rules broken 4
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InChI InChI=1S/C81H157N2O16P/c1-7-13-19-25-31-37-40-46-52-58-69(93-61-55-49-43-34-28-22-16-10-4)64-74(85)82-72(80(88)89)68-96-81-77(83-75(86)65-70(59-53-47-41-38-32-26-20-14-8-2)94-62-56-50-44-35-29-23-17-11-5)79(78(73(67-84)97-81)99-100(90,91)92)98-76(87)66-71(60-54-48-42-39-33-27-21-15-9-3)95-63-57-51-45-36-30-24-18-12-6/h69-73,77-79,81,84H,7-68H2,1-6H3,(H,82,85)(H,83,86)(H,88,89)(H2,90,91,92)/t69-,70-,71-,72+,73-,77-,78-,79-,81-/m1/s1
1. Bazin HG, Murray TJ, Bowen WS, Mozaffarian A, Fling SP, Bess LS, Livesay MT, Arnold JS, Johnson CL, Ryter KT et al.. (2008)
The 'Ethereal' nature of TLR4 agonism and antagonism in the AGP class of lipid A mimetics.
Bioorg Med Chem Lett, 18 (20): 5350-4. [PMID:18835160]
2. Oberoi HS, Yorgensen YM, Morasse A, Evans JT, Burkhart DJ. (2016)
PEG modified liposomes containing CRX-601 adjuvant in combination with methylglycol chitosan enhance the murine sublingual immune response to influenza vaccination.
J Control Release, 223: 64-74. [PMID:26551346]
3. Spinner JL, Oberoi HS, Yorgensen YM, Poirier DS, Burkhart DJ, Plante M, Evans JT. (2015)
Methylglycol chitosan and a synthetic TLR4 agonist enhance immune responses to influenza vaccine administered sublingually.
Vaccine, 33 (43): 5845-5853. [PMID:26392012]