A9251

Adenosine

≥99%

• Synonym(s): Adenine riboside, Adenine-9-β-D-ribofuranoside, 9-β-D-Ribofuranosyladenine
• Empirical Formula (Hill Notation): C₁₀H₁₃N₅O₄
• CAS Number: 58-61-7
• Molecular Weight: 267.24
• Beilstein: 93029
• EC Number: 200-389-9
• MDL number: MFCD00005752
• eCl@ss: 32160413
• PubChem Substance ID: 24277685
• NACRES: NA.77

Properties

• 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.

Packaging

1, 5, 25, 100 g in poly bottle

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 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.

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.

Safety Information

• Storage Class Code: 11 - Combustible Solids
• WGK: WGK 2
• Flash Point(F): Not applicable
• Flash Point(C): Not applicable
• Personal Protective Equipment: dust mask type N95 (US), Eyeshields, Gloves