Description
Key facts
CAS number:35920-39-9,
Purity:>98%,
Form:SolidSee storage information,
Molecular weight:308.29 Da,
Molecular formula:C12H16N6O4,
PubChem:448222,
Nature:Synthetic,
Solubility:Soluble in DMSO to 50 mM,
Biochemical name:5'-N-Ethylcarboxamidoadenosine,
Biological description:Potent agonist of adenosine receptors, non-selective analog of adenosine (Ki values are 14 (A1), 20 (A2A), 330 (A2B), and 6.2 nM (A3)). Offers cardio-protection by limiting infarction in situ.,
Canonical smiles:CCNC(=O)C1C(C(C(O1)N2C=NC3=C(N=CN=C32)N)O)O,
Isomeric smiles:CCNC(=O)[C@@H]1[C@H]([C@H]([C@@H](O1)N2C=NC3=C(N=CN=C32)N)O)O,
InChi:InChI=1S/C12H16N6O4/c1-2-14-11(21)8-6(19)7(20)12(22-8)18-4-17-5-9(13)15-3-16-10(5)18/h3-4,6-8,12,19-20H,2H2,1H3,(H,14,21)(H2,13,15,16)/t6-,7+,8-,12+/m0/s1,
InChiKey:JADDQZYHOWSFJD-FLNNQWSLSA-N,
IUPAC Name:(2S,3S,4R,5R)-5-(6-aminopurin-9-yl)-N-ethyl-3,4-dihydroxyoxolane-2-carboxamide
Properties and Storage Information:
Shipped at conditions-Ambient - Can Ship with Ice, Appropriate short-term storage conditions-+4°C, Appropriate long-term storage conditions-+4°C, Storage information-Store under desiccating conditions, The product can be stored for up to 12 months
Supplementary Information:
This supplementary information is collated from multiple sources and compiled automatically.
The adenosine receptor family includes four subtypes: Adenosine A1 Receptor Adenosine Receptor A2a Adenosine A3 Receptor (A3AR) and Adenosine A2b Receptor (ADORA2B). These receptors are G protein-coupled receptors (GPCRs) that each have distinct roles in cellular signaling. They bind adenosine a nucleoside and trigger various downstream effects. For example these receptors are integral to the regulation of myocardial oxygen consumption and cerebral blood flow. They are most commonly expressed in the central nervous system but also show presence in peripheral tissues. Each receptor subtype varies in molecular mass which can influence its interaction with ligands.
Biological function summary
These receptors modulate a wide array of physiological functions. As parts of receptor complexes they influence neurotransmission inflammation and immune responses. Specifically adenosine acts through these receptors to inhibit neurotransmitter release in the brain providing a neuroprotective effect under stress conditions. Adenosine A2a Receptor is known to play a role in vasodilation and immune cell regulation while A3AR has implications in both cardioprotection and cancer biology. These receptors function collectively and independently facilitating cellular communication and maintaining homeostasis.
Pathways
These receptors engage in important signaling cascades such as the cyclic AMP (cAMP) pathway where they either inhibit or stimulate cAMP production through different G proteins. They also participate in MAPK and PI3K/Akt pathways which are critical for cell survival and proliferation. Adenosine Receptor A2a is often studied in relation to dopamine D2 receptors highlighting its role in neuromodulation and potential therapeutic targets for neurological disorders.
Dysfunction of adenosine receptors links to several conditions including cardiovascular diseases and neurological disorders. Changes in adenosine A1 Receptor activity can influence ischemic brain injury recovery while irregularities in Adenosine Receptor A2a activity are associated with chronic inflammatory diseases like asthma. Adenosine receptor activity connects to these diseases through interaction with toll-like receptors and cytokines illustrating an interplay between adenosine signaling and immune response.
