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A9251

Adenosine

Name: Adenosine
Brand: SIGMA

≥99% (HPLC), powder, neurotransmitter

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

NACRES:

NA.77

PubChem Substance ID:

24277685

eCl@ss:

32160413

UNSPSC Code:

12352200

EC Number:

200-389-9

MDL number:

MFCD00005752

Beilstein/REAXYS Number:

93029

Assay:

≥99%

Form:

powder

Quality level:

200

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Properties

Product Name

Adenosine, ≥99%

Quality Level

200

assay

≥99%

form

powder

mp

234-236 °C (lit.)

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 ... ADA(100), ADORA1(134), ADORA2A(135), ADORA2B(136), ADORA3(140), ERBB2(2064), ERBB4(2066)
rat ... Adcy2(81636), Adora1(29290), Adora2a(25369), Adora3(25370)

Description

General description

In the extracellular space, ecto-5′-nucleotidase (CD73) dephosphorylates adenosine triphosphate (ATP) to produce adenosine. Adenosine has four receptors namely A1R, A2AR A2BR and A3R. Adenosine plays a key role in the osteogenic differentiation. A1R induces osteoclast differentiation and A2AR induces osteoblast differentiation.

Application

Adenosine has been used:

as a supplement in embryonic type culture medium for in vitro osteogenic differentiation
for evaluation of its effect on cell survival by 3-(4,5-dimethylthiazol-2-yl)-2,5-diphenyl tetrazolium bromide (MTT assay) and cell proliferation by ³H-thymidine incorporation assay in multi drug resistant glioblastoma stem-like cells (GSCs), and as a standard in high performance liquid chromatography (HPLC).
as a constituent in collagenase solution for the collagenase digestion of mice fat tissue.

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).

Features and Benefits

This compound is a featured product for Cyclic Nucleotide research. Click here to discover more featured Cyclic Nucleotide products. Learn more about bioactive small molecules for other areas of research at sigma.com/discover-bsm.

This compound is featured on the Adenylyl cyclases and Phosphoinositide Kinases pages of the Handbook of Receptor Classification and Signal Transduction. To browse other handbook pages, click here.

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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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