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Merck
CN

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:
121288-39-9
Molecular Weight:
339.30
NACRES:
NA.22
PubChem Substance ID:
24873084
UNSPSC Code:
41106305
MDL number:
MFCD00867591

Key Documents

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Product Name

7-Allyl-7,8-dihydro-8-oxoguanosine, 95%

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

100

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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

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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Certificates of Analysis (COA)

Lot/Batch Number
MKBP0595V
MKBN8530V
05902JH
08628ES
06915AC

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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
Yusuke Murakami et al.
Scientific reports, 7, 44042-44042 (2017-03-08)
Toll-like Receptor 9 (TLR9) is an innate immune receptor recognizing microbial DNA. TLR9 is also activated by self-derived DNA, such as mitochondrial DNA, in a variety of inflammatory diseases. We show here that TLR9 activation in vivo is controlled by
C L Swaggerty et al.
Poultry science, 91(4), 1038-1042 (2012-03-09)
Young poultry exhibit a transient colonization by some food-borne pathogens, including Salmonella, during the first week of life that stems from immature innate and acquired defense mechanisms. Consequently, modulation of the hosts' natural immune response is emerging as an important
Mouldy Sioud et al.
European journal of immunology, 37(10), 2834-2846 (2007-09-14)
We recently reported that human bone marrow hematopoietic CD34(+) progenitors express functional Toll-like receptors (TLR) and can differentiate into myeloid cells just by stimulation with resiquimod (R848), a specific agonist for TLR7/8. However, the mechanisms by which R848 induces cell
Haiqi He et al.
Veterinary immunology and immunopathology, 123(3-4), 177-185 (2008-02-29)
The toll-like receptors (TLRs) recognize microbial pathogens and pathogen-associated molecular patterns and trigger inflammatory immune responses to control the infection. Here, we examined functional innate immune responses to Salmonella enteritidis (SE, live or formalin-killed) and various TLR agonists including lipoteichoic
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