1-Oxoadenosine

Name: 1-Oxoadenosine
SKU: ACM146929
Rating: 5 (1 reviews)

CAS

146-92-9

Catalog Number

ACM146929

Category

Main Products

Molecular Weight

283.24

Molecular Formula

C10H13N5O5

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Specification

Synonyms

Adenosine N1-oxide

Anti-Inflammatory Activity of Adenosine N1-Oxide (ANO) Study

Kohno, Keizo, et al.Journal of Inflammation, 2015, 12, 1-16.

Adenosine N1-oxide (ANO) is the result of adenosine oxidation at the N1 position of the adenine base moiety. This work studied ANO's anti-inflammatory effects both in vitro and in vivo. The results showed that ANO is better at combating inflammation than adenosine, which opens up a potential treatment option for inflammatory disorders.
· ANO blocked inflammatory mediator release at much lower concentration levels than adenosine and GK2 in peritoneal macrophages and THP-1 cells treated with LPS and IFN-. Its strong anti-inflammatory effect could not be entirely explained by its resistance to adenosine deaminase.
· ANO was also better than the synthetic A1 AR-selective agonist 2-chloro-N6-cyclopentyladenosine (CCPA), the A2A AR-selective agonist 2-[p-(2-carboxyethyl)phenethylamino]-5'-N-ethylcarboxamideadenosine hydrochloride (CGS21680), and the A3 AR-selective agonist N6-(3-iodobenzyl)adenosine-5'-N-methyluronamide (IB-MECA) in reducing multiple pro-inflammatory cytokines from peritoneal macrophages. The ability of ANO to inhibit pro-inflammatory cytokine production in THP-1 cells was similar to that of CCPA and IB-MECA.
· In line with its robust anti-inflammatory activity in vitro, intravenous ANO treatment dramatically reduced mortality in LPS-induced endotoxin shock, and oral administration also resulted in a higher survival rate. Mechanistic analyses showed that upregulation of the anti-inflammatory transcription factor c-Fos was at least partially to blame for ANO-induced inhibition of pro-inflammatory cytokine production.

The Regulatory Mechanism of Adenosine N1-Oxide on the Release of Proinflammatory Cytokines

Ohashi, Emiko, et al. Biological and Pharmaceutical Bulletin, 2019, 42(6), 968-976.

The regulatory mechanism of ANO on the release of proinflammatory cytokines was studied, focusing on the signaling pathway activated by Toll-like receptor (TLR)4 under LPS stimulation. In addition, ANO can promote osteoblast and adipocyte differentiation, further indicating its application in regenerative medicine. The specific research results are as follows:
· ANO inhibited the secretion of tumor necrosis factor (TNF)-α and interleukin (IL)-6 from LPS-stimulated RAW264.7 cells while not impacting cell proliferation. Additionally, ANO treatment did not alter the phosphorylation of mitogen-activated protein kinases (MAPK) members (ERK1/2, p38, and JNK) or nuclear factor-κB (NF-κB) p65. In contrast, ANO upregulated the phosphorylation of Akt (Ser473) and its downstream target glycogen synthase kinase-3β (GSK-3β) (Ser9), indicating that ANO enhanced GSK-3β phosphorylation via the phosphatidylinositol 3-kinase (PI3K)/Akt signaling pathway. The phosphorylation of GSK-3β at Ser9 is known to negatively regulate the inflammatory response induced by LPS.
· The activation of the PI3K/Akt pathway is also associated with the differentiation of mesenchymal stem cells into osteoblasts and adipocytes. Consistent with this, ANO increased alkaline phosphatase activity and stimulated calcium deposition in the mouse pre-osteoblastic MC3T3-E1 cell line. The ability of ANO to induce osteoblast differentiation was inhibited by coincubation with Wortmannin. Moreover, ANO facilitated the differentiation of mouse 3T3-L1 preadipocytes into adipocytes in response to insulin and dexamethasone at significantly lower concentrations than adenosine.

What is the molecular formula of 1-Oxoadenosine?

The molecular formula of 1-Oxoadenosine is C10H13N5O5.

What are the synonyms for 1-Oxoadenosine?

The synonyms for 1-Oxoadenosine are Adenosine N1-oxide and Adenosine, 1-oxide.

What is the molecular weight of 1-Oxoadenosine?

The molecular weight of 1-Oxoadenosine is 283.24 g/mol.

When was 1-Oxoadenosine created and modified?

1-Oxoadenosine was created on August 1, 2005, and last modified on October 21, 2023.

What is the IUPAC name of 1-Oxoadenosine?

The IUPAC name of 1-Oxoadenosine is (2R,3R,4S,5R)-2-(1-hydroxy-6-iminopurin-9-yl)-5-(hydroxymethyl)oxolane-3,4-diol.

What is the InChI of 1-Oxoadenosine?

The InChI of 1-Oxoadenosine is InChI=1S/C10H13N5O5/c11-8-5-9(13-3-15(8)19)14(2-12-5)10-7(18)6(17)4(1-16)20-10/h2-4,6-7,10-11,16-19H,1H2/t4-,6-,7-,10-/m1/s1.

What is the InChIKey of 1-Oxoadenosine?

The InChIKey of 1-Oxoadenosine is QHFLZHVITNUFMV-KQYNXXCUSA-N.

What is the Canonical SMILES of 1-Oxoadenosine?

The Canonical SMILES of 1-Oxoadenosine is C1=NC2=C(N1C3C(C(C(O3)CO)O)O)N=CN(C2=N)O.

What is the CAS number of 1-Oxoadenosine?

The CAS number of 1-Oxoadenosine is 146-92-9.

What is the XLogP3 value of 1-Oxoadenosine?

The XLogP3 value of 1-Oxoadenosine is -1.5.