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496812

Sigma-Aldrich

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
MDL number:
MFCD00867591
UNSPSC Code:
41106305
PubChem Substance ID:
24873084
NACRES:
NA.22

Quality Level

100

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

11 - Combustible Solids

wgk_germany

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
06915AC
08628ES

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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
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
Saradiya Chatterjee et al.
Cancer research, 74(18), 5008-5018 (2014-07-31)
Toll-like receptors (TLR) recognize pathogen molecules and danger-associated signals that stimulate inflammatory processes. TLRs have been studied mainly in antigen-presenting cells, where they exert important immune regulatory functions, but they are also expressed by epithelial tumor cells, where they have
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