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
MDL number:
UNSPSC Code:
41106305
PubChem Substance ID:
NACRES:
NA.22
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Quality Level
Assay
95%
optical activity
[α]21/D −32°, c = 1 in H2O
mp
227-230 °C (lit.)
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
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
InChI key
VDCRFBBZFHHYGT-IOSLPCCCSA-N
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Application
Loxoribine is a selective toll-like receptor 7 (TLR7) agonist that activates immune cells and increases cytokine production.
Storage Class Code
11 - Combustible Solids
WGK
WGK 3
Flash Point(F)
Not applicable
Flash Point(C)
Not applicable
Personal Protective Equipment
dust mask type N95 (US), Eyeshields, Gloves
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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
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
Marjorie Robbins et al.
Molecular therapy : the journal of the American Society of Gene Therapy, 15(9), 1663-1669 (2007-06-21)
RNA molecules such as single-stranded RNA (ssRNA) and small interfering RNA (siRNA) duplexes induce Toll-like receptor (TLR)-mediated immune stimulation after intracellular delivery. We have previously shown that selective incorporation of 2'-O-methyl (2'OMe) residues into siRNA abrogates cytokine production without reduction
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