CCPA (biochemistry)
 | This article appears to have been generated by a large language model (such as ChatGPT) without having been rigorously scrutinized for verifiability, neutrality, original research, and copyright compliance. It may include misleading or inaccurate claims and fake references that sound plausible. (October 2025) (Learn how and when to remove this template message) |
| File:2-Chloro-N(6)cyclopentyladenosine.svg | |
| Names | |
|---|---|
| IUPAC name
2-Chloro-N6-cyclopentyladenosine
| |
| Systematic IUPAC name
(2R,3R,4S,5R)-2-[2-Chloro-6-(cyclopentylamino)-9H-purin-9-yl]-5-(hydroxymethyl)oxolane-3,4-diol | |
| Identifiers | |
3D model (JSmol)
|
|
| Abbreviations | CCPA |
| ChEMBL | |
| ChemSpider | |
| ECHA InfoCard | Lua error in Module:Wikidata at line 879: attempt to index field 'wikibase' (a nil value). Lua error in Module:Wikidata at line 879: attempt to index field 'wikibase' (a nil value). |
| E number | Lua error in Module:Wikidata at line 879: attempt to index field 'wikibase' (a nil value). |
| MeSH | 2-chloro-N(6)cyclopentyladenosine |
PubChem CID
|
|
CompTox Dashboard (EPA)
|
|
| |
| |
| Properties | |
| C15H20ClN5O4 | |
| Molar mass | 369.80 g/mol |
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). | |
 verify (what is   ?)
| |
| Infobox references | |
2-Chloro-N6-cyclopentyladenosine (CCPA) is a specific receptor agonist for the Adenosine A1 receptor.[1] It is similar to N6-cyclopentyladenosine. Initially developed to probe the physiological and pharmacological roles of adenosine receptors, CCPA has become a pivotal tool in cardiovascular and neurological research. Due to CCPA's high affinity for Adenosine A1 receptors, its tritiated derivative [3H]CCPA can be used as a diagnostic tool for detecting the receptors in tissue with low receptor density.
Chemical Structure and Properties
CCPA is chemically characterized by the addition of a chlorine atom at the 2-position and a cyclopentyl group at the N6 position of the adenosine molecule. These modifications enhance its receptor selectivity and binding affinity. The molecular formula of CCPA is C15H19ClN5O4, with a molecular weight of approximately 367.80 g/mol.
Pharmacological Profile
Affinity and Selectivity for Adenosine Receptors
CCPA exhibits a high binding affinity for A1 adenosine receptors. In rat brain membranes, it demonstrated a Ki value of 0.4 nM, indicating potent interaction. Its selectivity is underscored by a significantly lower affinity for A2A receptors, with a Ki value of 3,900 nM, reflecting nearly 10,000-fold selectivity for A1 over A2A.[2][3]
Functional Effects
As an A1 receptor agonist, CCPA effectively inhibits adenylate cyclase activity. In rat adipocyte membranes, it achieved an IC 50 of 33 nM, demonstrating its potency. Conversely, its influence on A2A receptors is minimal, requiring much higher concentrations to elicit comparable effects.
Interaction with A3 Adenosine Receptors
Interestingly, while CCPA acts as an agonist at A1 receptors, it functions as a moderate antagonist at human A3 adenosine receptors. Studies using Chinese hamster ovary cells expressing human A3 receptors revealed that CCPA binds with a Ki of 38 nM but does not activate the receptor. Instead, it competitively inhibits the effects of A3 receptor agonists, highlighting its dual role depending on the receptor subtype.[2][4]
Applications in Biomedical Research
CCPA's selectivity and efficacy make it an invaluable tool in exploring adenosine receptor functions. In cardiovascular studies, it has been employed to investigate A1 receptor-mediated cardioprotective mechanisms, including modulation of heart rate and ischemic responses (Ischemia). In neurological contexts, CCPA aids in elucidating the role of A1 receptors in neurotransmission and neuroprotection. Additionally, its antagonistic properties at A3 receptors provide insights into the complex interplay between different adenosine receptor subtypes.
2-Chloro-N6-cyclopentyladenosine (CCPA) stands out as a potent and selective adenosine A1 receptor agonist with unique antagonistic effects on A3 receptors.[5] Its distinct chemical structure underpins its receptor specificity, rendering it a crucial compound in cardiovascular and neurological research. Ongoing studies continue to uncover its potential therapeutic applications and deepen our understanding of adenosine receptor pharmacology.
References
- ↑ Karl-Norbert Klotz; Martin J. Lohse; Ulrich Schwabe; Gloria Cristalli; Sauro Vittori; Mario Grifantini (1989). "2-Chloro-N6-[3H]cyclopentyladenosine ([3HCCPA) — a high affinity agonist radioligand for A1 adenosine receptors". Naunyn-Schmiedeberg's Archives of Pharmacology. 340 (6): 679–683. doi:10.1007/BF00717744. PMID 2615857. Unknown parameter
|s2cid=ignored (help) - ↑ 2.0 2.1 Gao, Zhan-guo; Jacobson, Kenneth A. (May 2002). "2-Chloro-N6-cyclopentyladenosine, adenosine A1 receptor agonist, antagonizes the adenosine A3 receptor". European Journal of Pharmacology. 443 (1–3): 39–42. doi:10.1016/S0014-2999(02)01552-2. PMC 8358783 Check
|pmc=value (help). PMID 12044789. - ↑ Cristalli, Gloria; Volpini, Rosaria; Vittori, Sauro; Camaioni, Emidio; Monopoli, Angela; Conti, Annamaria; Dionisotti, Silvio; Zocchi, Cristina; Ongini, Ennio (May 1994). "2-Alkynyl Derivatives of Adenosine-5'-N-ethyluronamide: Selective A2 Adenosine Receptor Agonists with Potent Inhibitory Activity on Platelet Aggregation". Journal of Medicinal Chemistry. 37 (11): 1720–1726. doi:10.1021/jm00037a024. ISSN 0022-2623. PMID 8201607.
- ↑ Lohse, MartinJ.; Klotz, Karl-Norbert; Schwabe, Ulrich; Cristalli, Gloria; Vittori, Sauro; Grifantini, Mario (June 1988). "2-Chloro-N6-cyclopentyladenosine: a highly selective agonist at A1 adenosine receptors". Naunyn-Schmiedeberg's Archives of Pharmacology. 337 (6): 687–689. doi:10.1007/BF00175797. ISSN 0028-1298. PMID 3216901.
- ↑ Fabera, Petr; Parizkova, Martina; Uttl, Libor; Vondrakova, Katerina; Kubova, Hana; Tsenov, Grygoriy; Mares, Pavel (2019-06-14). "Adenosine A1 Receptor Agonist 2-chloro-N6-cyclopentyladenosine and Hippocampal Excitability During Brain Development in Rats". Frontiers in Pharmacology. 10. doi:10.3389/fphar.2019.00656. ISSN 1663-9812. PMC 6587156 Check
|pmc=value (help). PMID 31258477. Unknown parameter|article-number=ignored (help)
| Stub icon | This drug article relating to the nervous system is a stub. You can help EverybodyWiki by expanding it. |
This article "CCPA (biochemistry)" is from Wikipedia. The list of its authors can be seen in its historical and/or the page Edithistory:CCPA (biochemistry). Articles copied from Draft Namespace on Wikipedia could be seen on the Draft Namespace of Wikipedia and not main one.
cyclopentyladenosine.svg){kind=link}
