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A9251

Sigma-Aldrich

Adenosine

≥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
Beilstein:
93029
EC Number:
200-389-9
MDL number:
MFCD00005752
UNSPSC Code:
12352200
eCl@ss:
32160413
PubChem Substance ID:
24277685
NACRES:
NA.77

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)

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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).

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.

WGK

WGK 2

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

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TGF beta-induced osteogenic potential of human amniotic fluid stem cells via CD73-generated adenosine production
Hau KL, et al.
Scientific Reports, 7(1), 6601-6601 (2017)
Feeder-dependent and feeder-independent iPS cell derivation from human and mouse adipose stem cells
Sugii S, et al.
Nature Protocols, 6(3), 346-346 (2011)
Adenosine A3 receptor elicits chemoresistance mediated by multiple resistance-associated protein-1 in human glioblastoma stem-like cells
Torres A, et al.
Oncotarget, 7(41), 67373-67373 (2016)
Jeffrey Buter et al.
Nature chemical biology, 15(9), 889-899 (2019-08-21)
Mycobacterium tuberculosis (Mtb) is the world's most deadly pathogen. Unlike less virulent mycobacteria, Mtb produces 1-tuberculosinyladenosine (1-TbAd), an unusual terpene nucleoside of unknown function. In the present study 1-TbAd has been shown to be a naturally evolved phagolysosome disruptor. 1-TbAd
Dominik Eichin et al.
PloS one, 10(8), e0134721-e0134721 (2015-08-11)
The ectoenzyme CD73 catalyzes the hydrolysis of AMP, and is one of the most important producers of extracellular adenosine. On regulatory T cells, CD73 is necessary for immunosuppressive functions, and on Th17 cells CD73-generated adenosine exerts anti-inflammatory effects. However, the
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