MedKoo Cat#: 562513 | Name: Adenosine N1-oxide
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Description:

WARNING: This product is for research use only, not for human or veterinary use.

Adenosine N1-oxide is an inhibitor of secretion of inflammatory mediators. It acts by suppressing pro-inflammatory cytokine secretion.

Chemical Structure

Adenosine N1-oxide
CAS#146-92-9

Theoretical Analysis

MedKoo Cat#: 562513

Name: Adenosine N1-oxide

CAS#: 146-92-9

Chemical Formula: C10H13N5O5

Exact Mass: 283.0917

Molecular Weight: 283.24

Elemental Analysis: C, 42.41; H, 4.63; N, 24.73; O, 28.24

Price and Availability

Size Price Availability Quantity
5mg USD 350.00 2 Weeks
10mg USD 650.00 2 Weeks
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Related CAS #
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Synonym
Adenosine N1-oxide; Adenosine N1 oxide; Adenosine N1oxide; ANO; Adenosine, 1-oxide;
IUPAC/Chemical Name
(2R,3R,4S,5R)-2-(1-Hydroxy-6-iminopurin-9-yl)-5-(hydroxymethyl)oxolane-3,4-diol
InChi Key
QHFLZHVITNUFMV-KQYNXXCUSA-N
InChi Code
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
SMILES Code
O[C@H]1[C@H](N2C=NC3=C2N=CN(O)C3=N)O[C@H](CO)[C@H]1O
Appearance
Solid powder
Purity
>98% (or refer to the Certificate of Analysis)
Shipping Condition
Shipped under ambient temperature as non-hazardous chemical. This product is stable enough for a few weeks during ordinary shipping and time spent in Customs.
Storage Condition
Dry, dark and at 0 - 4 C for short term (days to weeks) or -20 C for long term (months to years).
Solubility
Soluble in DMSO
Shelf Life
>2 years if stored properly
Drug Formulation
This drug may be formulated in DMSO
Stock Solution Storage
0 - 4 C for short term (days to weeks), or -20 C for long term (months).
HS Tariff Code
2934.99.9001
More Info

Preparing Stock Solutions

The following data is based on the product molecular weight 283.24 Batch specific molecular weights may vary from batch to batch due to the degree of hydration, which will affect the solvent volumes required to prepare stock solutions.

Recalculate based on batch purity %
Concentration / Solvent Volume / Mass 1 mg 5 mg 10 mg
1 mM 1.15 mL 5.76 mL 11.51 mL
5 mM 0.23 mL 1.15 mL 2.3 mL
10 mM 0.12 mL 0.58 mL 1.15 mL
50 mM 0.02 mL 0.12 mL 0.23 mL
1: Harvey R, McCaughan C, Wise LM, Mercer AA, Fleming SB. Orf virus inhibits interferon stimulated gene expression and modulates the JAK/STAT signalling pathway. Virus Res. 2015 Oct 2;208:180-8. doi: 10.1016/j.virusres.2015.06.014. Epub 2015 Jun 22. PubMed PMID: 26113305. 2: Kohno K, Ohashi E, Sano O, Kusano H, Kunikata T, Arai N, Hanaya T, Kawata T, Nishimoto T, Fukuda S. Anti-inflammatory effects of adenosine N1-oxide. J Inflamm (Lond). 2015 Jan 20;12(1):2. doi: 10.1186/s12950-014-0045-0. eCollection 2015. PubMed PMID: 25632271; PubMed Central PMCID: PMC4308844. 3: Deng L, Dai P, Ding W, Granstein RD, Shuman S. Vaccinia virus infection attenuates innate immune responses and antigen presentation by epidermal dendritic cells. J Virol. 2006 Oct;80(20):9977-87. PubMed PMID: 17005676; PubMed Central PMCID: PMC1617288. 4: Smee DF, Sidwell RW. A review of compounds exhibiting anti-orthopoxvirus activity in animal models. Antiviral Res. 2003 Jan;57(1-2):41-52. Review. PubMed PMID: 12615302. 5: Baker RO, Bray M, Huggins JW. Potential antiviral therapeutics for smallpox, monkeypox and other orthopoxvirus infections. Antiviral Res. 2003 Jan;57(1-2):13-23. PubMed PMID: 12615299. 6: Najarro P, Traktman P, Lewis JA. Vaccinia virus blocks gamma interferon signal transduction: viral VH1 phosphatase reverses Stat1 activation. J Virol. 2001 Apr;75(7):3185-96. PubMed PMID: 11238845; PubMed Central PMCID: PMC114112. 7: Hilton JC, Temple CA, Rajagopalan KV. Re-design of Rhodobacter sphaeroides dimethyl sulfoxide reductase. Enhancement of adenosine N1-oxide reductase activity. J Biol Chem. 1999 Mar 26;274(13):8428-36. PubMed PMID: 10085074. 8: Signorini N, Molko D, Cadet J. Polyclonal antibodies to adenine N1-oxide: characterization and use for the measurement of DNA damage. Chem Res Toxicol. 1998 Oct;11(10):1169-75. PubMed PMID: 9778313. 9: Kwong CD, Krauth CA, Shortnacy-Fowler AT, Arnett G, Hollingshead MG, Shannon WM, Montgomery JA, Secrist JA 3rd. Synthesis and antiviral evaluation of analogs of adenosine-N1-oxide and 1-(Benzyloxy)adenosine. Nucleosides Nucleotides. 1998 Aug;17(8):1409-43. PubMed PMID: 9672703. 10: Kane EM, Shuman S. Adenosine N1-oxide inhibits vaccinia virus replication by blocking translation of viral early mRNAs. J Virol. 1995 Oct;69(10):6352-8. PubMed PMID: 7666536; PubMed Central PMCID: PMC189534. 11: Szabados E, Hindmarsh EJ, Phillips L, Duggleby RG, Christopherson RI. 5-Aminoimidazole-4-carboxamide ribotide transformylase-IMP cyclohydrolase from human CCRF-CEM leukemia cells: purification, pH dependence, and inhibitors. Biochemistry. 1994 Nov 29;33(47):14237-45. PubMed PMID: 7947835. 12: Shimizu S, Shiozaki S, Ohshiro T, Yamada H. Occurrence of S-adenosylhomocysteine hydrolase in prokaryote cells. Characterization of the enzyme from Alcaligenes faecalis and role of the enzyme in the activated methyl cycle. Eur J Biochem. 1984 Jun 1;141(2):385-92. PubMed PMID: 6428887. 13: Guranowski A, Montgomery JA, Cantoni GL, Chiang PK. Adenosine analogues as substrates and inhibitors of S-adenosylhomocysteine hydrolase. Biochemistry. 1981 Jan 6;20(1):110-5. PubMed PMID: 7470463. 14: Guranowski A, Schneider Z. Purification and characterization of adenosine nucleosidase from barley leaves. Biochim Biophys Acta. 1977 May 12;482(1):145-58. PubMed PMID: 861230. 15: Jebeleanu G, Ty NG, Mantsch HH, Bârzu O, Niac G, Abrudan I. Participation of N1-oxide derivatives of adenine nucleotides in the phosphotransferase activity of liver mitochondria. Proc Natl Acad Sci U S A. 1974 Nov;71(11):4630-4. PubMed PMID: 4373722; PubMed Central PMCID: PMC433942. 16: Frederiksen S, Jorgensen AO, Rasmussen AH, Tonnesen T. The effect of adenosine N1-oxide on the incorporation of radioactive precursors into the nucleic acids. Mol Pharmacol. 1968 Jul;4(4):358-66. PubMed PMID: 5690986. 17: Sigel H, Brintzinger H. [Inosine-N(1)-oxide nucleotide in complex formation. I. Synthesis of inosine-N(1)-oxide and its 5'-monophosphate from adenosine-N(1)-oxide and its 5'monophosphate by deamination with nitrosyl chloride]. Helv Chim Acta. 1965 Apr 20;48(3):433-7. German. PubMed PMID: 5863920. 18: KOESSEL H, DOEHRING S. REACTION OF ADENOSINE-1-N-OXIDE WITH DIAZOTIZED SULFANILIC ACID. Biochim Biophys Acta. 1965 Apr 19;95:663-4. PubMed PMID: 14324817.