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A4036

Sigma-Aldrich

Adenosine

BioReagent, suitable for cell culture

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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
Beilstein:
93029
EC Number:
200-389-9
MDL number:
MFCD00005752
UNSPSC Code:
12352207
eCl@ss:
32160413
PubChem Substance ID:
24890739
NACRES:
NA.75

biological source

synthetic (organic)

Quality Level

200

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

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

The nucleoside adenosine consists of the purine adenine and the sugar ribose. Thus, it is also referred as adenine-D-ribose. 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.

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
  • to maintain the CGR8 ES (germ-line competent cell line) cells
  • for plasmid transfection and cloning of embryonic stem cells

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

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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Mosby's Dictionary of Medicine, Nursing & Health Professions, 41-41 (2013)
Adenosine and kidney function
Vallon V, et al.
Physiological Reviews, 86(3), 901-940 (2006)
Generation and characterization of cardiomyocytes under serum-free conditions
Embryonic Stem Cell Protocols, 191-219 (2006)
Mast cell-mediated stimulation of angiogenesis: cooperative interaction between A2B and A3 adenosine receptors
Feoktistov I, et al.
Circulation Research, 92(5), 485-492 (2003)
Chimeric analysis with newly established EGFP/DsRed2-tagged ES cells identify HYDIN as essential for spermiogenesis in mice
Oura S, et al.
Experimental Animals, 18-0071 (2018)
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