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01890

Adenosine

Name: Adenosine
Brand: SIGMA

Synonym(s):

9-β-D-Ribofuranosyladenine, Adenine riboside, Adenine-9-β-D-ribofuranoside

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About This Item

Empirical Formula (Hill Notation):

C₁₀H₁₃N₅O₄

CAS Number:

58-61-7

Molecular Weight:

267.24

PubChem Substance ID:

329747369

eCl@ss:

32160413

UNSPSC Code:

12352200

NACRES:

NA.77

EC Number:

200-389-9

MDL number:

MFCD00005752

Beilstein/REAXYS Number:

93029

Form:

powder

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form

powder

Quality Level

200

optical activity

[α]20/D −70±3°, c = 2% in 5% NaOH

ign. residue

≤0.1% (as SO₄)

mp

234-236 °C (lit.)

cation traces

Ca: ≤10 mg/kg, Cd: ≤5 mg/kg, Co: ≤5 mg/kg, Cr: ≤5 mg/kg, Cu: ≤5 mg/kg, Fe: ≤5 mg/kg, Mg: ≤20 mg/kg, Mn: ≤5 mg/kg, Ni: ≤5 mg/kg, Pb: ≤5 mg/kg, Zn: ≤5 mg/kg

storage temp.

2-8°C

SMILES string

Nc1ncnc2n(cnc12)[C@@H]3O[C@H](CO)[C@@H](O)[C@H]3O

InChI

1S/C10H13N5O4/c11-8-5-9(13-2-12-8)15(3-14-5)10-7(18)6(17)4(1-16)19-10/h2-4,6-7,10,16-18H,1H2,(H2,11,12,13)/t4-,6-,7-,10-/m1/s1

InChI key

OIRDTQYFTABQOQ-KQYNXXCUSA-N

Gene Information

human ... ADORA1(134), ADORA2A(135), ADORA2B(136), ADORA3(140)

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Bioactive Small Molecules

General description

Adenosine is a purine nucleoside base. It consists of adenine bound to a ribose sugar molecule via a glycosidic bond. Adenosine is found intracellularly and extracellularly in living cells. It acts as a precursor and as a metabolite of adenine nucleotides. In all living organisms, adenosine acts as an essential structural factor for adenosinetriphosphate (ATP), adenosine diphosphate (ADP), and cyclic adenosine monophosphate (cAMP), thereby playing an important role in energy transfer. Adenosine plays a crucial role in the central nervous system, endocrine system, inflammatory and immune response, and cardiovascular system. It is an important endogenous modulator of kidney function, lung function, pain, and sleep via the activation of adenosine receptors.

Application

Adenosine has been used as a standard to determine the adenosine content in whole heart samples from mice.

Biochem/physiol Actions

Endogenous neurotransmitter at adenosine receptors. Cardioprotective effects may relate to activation of A₁ adenosine receptors. The antiplatelet and anti−inflammatory actions of adenosine appear to be mediated via the A₂ adenosine receptor. In contrast, adenosine appears to be a pro-inflammatory mediator in asthma and chronic obstructive pulmonary disease (COPD).

Endogenous neurotransmitter. Cardioprotective effects may relate to activation of A₁ adenosine receptors. The antiplatelet and anti−inflammatory actions of adenosine appear to be mediated via the A₂ adenosine receptor. In contrast, adenosine appears to be a pro-inflammatory mediator in asthma and chronic obstructive pulmonary disease (COPD).

Other Notes

Substrate for the assay of adenosine deaminase

Storage Class

11 - Combustible Solids

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

Eyeshields, Gloves, type N95 (US)

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P. Nygaard

Methods in Enzymology, 508-508 null

The adenosine A2B G protein-coupled receptor: Recent advances and therapeutic implications.

Elizabeth A Vecchio et al.

Pharmacology & therapeutics, 198, 20-33 (2019-01-25)

The adenosine A2B receptor (A2BAR) is one of four adenosine receptor subtypes belonging to the Class A family of G protein-coupled receptors (GPCRs). Until recently, the A2BAR remained poorly characterised, in part due to its relatively low affinity for the

Transgenic over expression of ectonucleotide triphosphate diphosphohydrolase-1 protects against murine myocardial ischemic injury.

Ming Cai et al.

Journal of molecular and cellular cardiology, 51(6), 927-935 (2011-09-24)

Modulation of purinergic signaling is critical to myocardial homeostasis. Ectonucleoside triphosphate diphosphohydrolase 1 (ENTPD-1; CD39) which converts the proinflammatory molecules ATP or ADP to AMP is a key regulator of purinergic modulation. However, the salutary effects of transgenic over expression

Adenosine deaminase from human erythrocytes.

R P Agarwal et al.

Methods in enzymology, 51, 502-507 (1978-01-01)

PI3Kγ Regulatory Protein p84 Determines Mast Cell Sensitivity to Ras Inhibition-Moving Towards Cell Specific PI3K Targeting?

Julie R Jin et al.

Frontiers in immunology, 11, 585070-585070 (2020-11-17)

Mast cells are the major effector cells in immunoglobulin E (IgE)-mediated allergy. The high affinity IgE receptor FcεRI, as well as G protein-coupled receptors (GPCRs) on the mast cell surface signals to phosphoinositide 3-kinase γ (PI3Kγ) to initiate degranulation, cytokine

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Global Trade Item Number

SKU	GTIN
228540-25G	04061836825843
01890-100G	04061833380314
01890-5G	04061838611338
01890-25G	04061838611321

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