Merck

A9251

Sigma-Aldrich

Adenosine

≥99%

Sinónimos:
9-β-D-Ribofuranosyladenine, Adenine riboside, Adenine-9-β-D-ribofuranoside
Empirical Formula (Hill Notation):
C10H13N5O4
Número de CAS:
Peso molecular:
267.24
Beilstein:
93029
Número de EC:
Número MDL:
eCl@ss:
32160413
ID de la sustancia en PubChem:
NACRES:
NA.77

Nivel de calidad

Análisis

≥99%

formulario

powder

mp

234-236 °C (lit.)

temp. de almacenamiento

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

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Este artículo
PHR11381012123PHL80977
Adenosine ≥99%

Sigma-Aldrich

A9251

Adenosine

Adenosine Pharmaceutical Secondary Standard; Certified Reference Material

Supelco

PHR1138

Adenosine

Adenosine United States Pharmacopeia (USP) Reference Standard

USP

1012123

Adenosine

Adenosine phyproof® Reference Substance

PHL80977

Adenosine

form

powder

form

-

form

-

form

solid

storage temp.

2-8°C

storage temp.

2-8°C

storage temp.

-

storage temp.

2-8°C

Quality Level

200

Quality Level

300

Quality Level

-

Quality Level

-

mp

234-236 °C (lit.)

mp

234-236 °C (lit.)

mp

234-236 °C (lit.)

mp

234-236 °C (lit.)

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)

Gene Information

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

Gene Information

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

Gene Information

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

Descripción general

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.

Aplicación

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.

Acciones bioquímicas o fisiológicas

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).

Características y beneficios

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.

Código de clase de almacenamiento

11 - Combustible Solids

WGK

WGK 2

Punto de inflamabilidad F

Not applicable

Punto de inflamabilidad C

Not applicable

Equipo de protección personal

Eyeshields, Gloves, type N95 (US)


Certificates of Analysis (COA)

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Las referencias de los producto se combinan con los tamaños de envase y las cantidades cuando se muestran en la página web, por ejemplo: T1503-25G. Asegúrese de introducir el número de producto ÚNICAMENTE en el campo del Número de producto (Ejemplo T1503).

Ejemplo

T1503
Referencia del producto
-
25G
Tamaño del envase/cantidad

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MMYOMAG-74K-13

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Cordycepin from Cordyceps militaris

Sigma-Aldrich

C3394

Cordycepin

Uridine ≥99%

Sigma-Aldrich

U3750

Uridine

Adenine ≥99%

Sigma-Aldrich

A8626

Adenine

Guanosine BioReagent, suitable for cell culture

Sigma-Aldrich

G6264

Guanosine

EHNA hydrochloride ≥98% (HPLC)

Sigma-Aldrich

E114

EHNA hydrochloride

Cordycepin phyproof® Reference Substance

PHL82505

Cordycepin

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)
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)
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)
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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Cyclic nucleotides, including cyclic AMP (cAMP), cyclic GMP (cGMP) and cyclic ADP-ribose, have been extensively studied as second messengers of intracellular events initiated by activation of GPCRs. cAMP modifies cell function in all eukaryotic cells, principally through the activation of cAMP-dependent protein kinase (PKA), but also through cAMP-gated ion channels and guanine nucleotide exchange factors directly activated by cAMP.

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