496812
7-Allyl-7,8-dihydro-8-oxoguanosine
95%
Synonym(s):
Loxoribine
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About This Item
Empirical Formula (Hill Notation):
C13H17N5O6
CAS Number:
Molecular Weight:
339.30
NACRES:
NA.22
PubChem Substance ID:
UNSPSC Code:
41106305
MDL number:
InChI
1S/C13H17N5O6/c1-2-3-17-6-9(15-12(14)16-10(6)22)18(13(17)23)11-8(21)7(20)5(4-19)24-11/h2,5,7-8,11,19-21H,1,3-4H2,(H3,14,15,16,22)/t5-,7-,8-,11-/m1/s1
SMILES string
NC1=NC2=C(N(CC=C)C(=O)N2[C@@H]3O[C@H](CO)[C@@H](O)[C@H]3O)C(=O)N1
InChI key
VDCRFBBZFHHYGT-IOSLPCCCSA-N
assay
95%
optical activity
[α]21/D −32°, c = 1 in H2O
mp
227-230 °C (lit.)
Quality Level
Related Categories
Application
Loxoribine is a selective toll-like receptor 7 (TLR7) agonist that activates immune cells and increases cytokine production.
Storage Class
11 - Combustible Solids
wgk
WGK 3
flash_point_f
Not applicable
flash_point_c
Not applicable
ppe
Eyeshields, Gloves, type N95 (US)
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Marion Jurk et al.
European journal of immunology, 36(7), 1815-1826 (2006-06-20)
Toll-like receptors (TLR) 7 and 8 are closely related members of the TLR family of pathogen-associated molecular pattern recognition receptors and have an important function in activation of innate immune responses upon viral infection. TLR7 can be activated selectively by
Kristie A Jenkins et al.
Developmental and comparative immunology, 33(5), 660-667 (2008-12-23)
Although Toll-like receptors (TLRs) have been well characterised in mammals, less work has been carried out in non-mammalian species, such as chickens. In this study the response of chicken cells to the TLR9 subfamily of ligands was characterised in vitro
Niranjan B Butchi et al.
Journal of immunology (Baltimore, Md. : 1950), 180(11), 7604-7612 (2008-05-21)
Activation of astrocytes and microglia and the production of proinflammatory cytokines and chemokines are often associated with virus infection in the CNS as well as a number of neurological diseases of unknown etiology. These inflammatory responses may be initiated by
Clett Erridge et al.
The Journal of biological chemistry, 283(36), 24748-24759 (2008-06-19)
The generation of reactive oxygen species is a central feature of inflammation that results in the oxidation of host phospholipids. Oxidized phospholipids, such as 1-palmitoyl-2-arachidonyl-sn-glycero-3-phosphorylcholine (OxPAPC), have been shown to inhibit signaling induced by bacterial lipopeptide or lipopolysaccharide (LPS), yet
Julien Cherfils-Vicini et al.
The Journal of clinical investigation, 120(4), 1285-1297 (2010-03-20)
Compelling evidence suggests that inflammation, cell survival, and cancer are linked, with a central role played by NF-kappaB. Recent studies implicate some TLRs in tumor development based on their ability to facilitate tumor growth; however, to our knowledge, involvement of
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