Description
Key facts
CAS number:37739-05-2,
Purity:>98%,
Form:SolidSee storage information,
Molecular weight:369.8 Da,
Molecular formula:C15H20ClN5O4,
PubChem:123807,
Nature:Synthetic,
Solubility:Soluble in water to 5 mMSoluble in DMSO to 100 mM,
Biochemical name:2-Chloro-N6-cyclopentyladenosine,
Biological description:Highly potent and selective A1 receptor agonist (Ki values are 0.8, 2300 and 42 nM for human A1, A2A and A3 receptors, respectively). Shows >2000-fold selectivity over A2A. Centrally active following systemic administration and anticonvulsive *in vivo*.,
Canonical smiles:C1CCC(C1)NC2=C3C(=NC(=N2)Cl)N(C=N3)C4C(C(C(O4)CO)O)O,
Isomeric smiles:C1CCC(C1)NC2=C3C(=NC(=N2)Cl)N(C=N3)[C@H]4[C@@H]([C@@H]([C@H](O4)CO)O)O,
InChi:InChI=1S/C15H20ClN5O4/c16-15-19-12(18-7-3-1-2-4-7)9-13(20-15)21(6-17-9)14-11(24)10(23)8(5-22)25-14/h6-8,10-11,14,22-24H,1-5H2,(H,18,19,20)/t8-,10-,11-,14-/m1/s1,
InChiKey:XSMYYYQVWPZWIZ-IDTAVKCVSA-N,
IUPAC Name:(2R,3R,4S,5R)-2-[2-chloro-6-(cyclopentylamino)purin-9-yl]-5-(hydroxymethyl)oxolane-3,4-diol
Properties and Storage Information:
Shipped at conditions-Ambient - Can Ship with Ice, Appropriate short-term storage conditions-Ambient, Appropriate long-term storage conditions-Ambient, 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 A1 Receptor Adenosine Receptor A2a and Adenosine A3 Receptor commonly referred to as A1 A2a and A3AR belong to the G protein-coupled receptor (GPCR) family. These receptors allow cells to respond to extracellular adenosine. The molecular mass of these receptors can vary: generally A1 is around 36-38 kDa A2a is about 45 kDa and A3AR ranges between 36-38 kDa. These receptors have widespread expression in various tissues. A1 receptors are prominently found in the brain heart and adipose tissues. A2a receptors are largely seen in the brain spleen and immune cells. A3AR is present in the testis brain and also a bit in the lung.
Biological function summary
These receptors mediate cellular responses to adenosine leading to changes in cellular activity. They are not part of a single complex but may interact with other proteins as part of signaling pathways. A1 receptors typically lead to an inhibitory effect by reducing cyclic AMP levels. A2a receptors however usually result in a stimulatory effect by increasing cyclic AMP levels. A3AR can have either effect depending on cellular context. These activities influence physiological processes like heart rate neurotransmitter release and immune response modulation.
Pathways
These receptors play significant roles in cardiovascular and neurological pathways. The A1 receptor participates importantly in the cardiac adenosine pathway influencing heart contractility and rhythm by working with proteins like Gi protein. The A2a receptor has a notable role in the dopaminergic signaling pathway within the central nervous system interacting with proteins such as dopamine receptors. A3AR is involved in inflammatory pathways sometimes linking with proteins like NF-kB to modulate immune cell activity.
The dysfunction or abnormal regulation of these adenosine receptors is linked to cardiovascular diseases and neurological disorders. For instance the A1 receptor's role in cardiac function connects it to conditions like myocardial ischemia. The A2a receptor's involvement in dopaminergic pathways relates to neurodegenerative diseases such as Parkinson's disease with interactions involving dopamine receptors. A3AR's role in inflammation associates it with disorders like asthma often involving proteins in inflammatory pathways.
