A4036

Adenosine

BioReagent, suitable for cell culture

• Synonym(s): 9-β-D-Ribofuranosyladenine, Adenine riboside, Adenine-9-β-D-ribofuranoside
• Empirical Formula (Hill Notation): C₁₀H₁₃N₅O₄
• CAS Number: 58-61-7
• Molecular Weight: 267.24
• NACRES: NA.75
• PubChem Substance ID: 24890739
• eCl@ss: 32160413
• UNSPSC Code: 12352207
• EC Number: 200-389-9
• MDL number: MFCD00005752
• Beilstein/REAXYS Number: 93029

Properties

• Product Name: Adenosine, BioReagent, suitable for cell culture
• Quality Level: 300
• InChI key: OIRDTQYFTABQOQ-KQYNXXCUSA-N
• 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
• SMILES string: Nc1ncnc2n(cnc12)[C@@H]3O[C@H](CO)[C@@H](O)[C@H]3O
• biological source: synthetic (organic)
• product line: BioReagent
• assay: ≥99% (HPLC)
• form: powder
• technique(s): cell culture | mammalian: suitable
• mp: 234-236 °C (lit.)
• solubility: 1 M NH4OH: 50 mg/mL, clear, colorless
• storage temp.: 2-8°C
• 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

Application

Adenosine has been used as a supplement in DMEM (Dulbecco′s modified Eagle medium):

• to evaluate the outgrowth of the interspecies somatic cell nucleus transfer (iSCNT)-derived blastocysts[1]
• to maintain the CGR8 ES (germ-line competent cell line) cells[2]
• for plasmid transfection and cloning of embryonic stem cells[3]

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).

Tissue injury, ischemia and abnormal cell proliferation stimulate the release of adenosine. Adenosine helps in countering the effects of reduced oxygen and energy[4] in organs such as heart, brain and skeletal muscles mediating vasodialation.[5] It delivers its action through G protein-coupled receptors. Adenosine also reduces the release of neurotransmitters and cellular metabolism.[5]

General description

The nucleoside adenosine consists of the purine adenine and the sugar ribose.[6] Thus, it is also referred as adenine-D-ribose.[7] Adenosine is an important molecule that forms nucleotides, which is a part of nucleic acids forming the DNA and RNA. The nucleotides include: adenosine monophosphate, adenosine diphosphate and adenosine triphosphate.[7]

Safety Information

• Storage Class: 11 - Combustible Solids
• wgk: WGK 2
• flash_point_f: Not applicable
• flash_point_c: Not applicable
• ppe: Eyeshields, Gloves, type N95 (US)