Page last updated: 2024-12-08

1-deaza-2-chloro-n(6)-cyclopentyladenosine

Description Research Excerpts Clinical Trials Roles Classes Pathways Study Profile Bioassays Related Drugs Related Conditions Protein Interactions Research Growth Market Indicators

Description

**1-Deaza-2-chloro-N(6)-cyclopentyladenosine** (also known as **Cl-CPA**) is a synthetic nucleoside analog.

**Structure and Properties:**

* **Structure:** Cl-CPA is an adenosine analog with a chlorine atom at the 2' position, a cyclopentyl group attached to the N6 position, and a deaza modification at the 1' position.
* **Properties:**
* **High affinity for adenosine receptors:** Cl-CPA is a potent and selective agonist of adenosine A1 receptors (A1ARs), meaning it binds strongly and activates these receptors.
* **Long duration of action:** It has a longer half-life compared to adenosine, making it a useful tool for studying the effects of A1AR activation over time.

**Importance for Research:**

Cl-CPA is a valuable tool in research for several reasons:

* **Studying the role of A1ARs:** By selectively activating A1ARs, Cl-CPA allows researchers to investigate the roles of these receptors in various physiological processes.
* **Neuroprotection:** A1ARs are involved in neuroprotection, and Cl-CPA has shown promise in protecting neurons from damage in models of stroke, Alzheimer's disease, and other neurological conditions.
* **Cardiovascular function:** A1ARs play a role in regulating heart rate, blood pressure, and blood flow. Cl-CPA helps researchers understand how these receptors contribute to cardiovascular health.
* **Inflammation and immune response:** A1ARs are also involved in regulating inflammation and immune responses. Cl-CPA is used to study the effects of A1AR activation on immune cell function.
* **Developing new therapeutics:** Cl-CPA's potent and selective activity at A1ARs makes it a potential lead compound for the development of new drugs targeting these receptors.
* **Neurological disorders:** Cl-CPA could be a promising candidate for treating neurodegenerative diseases and reducing neuronal damage.
* **Cardiovascular disease:** Cl-CPA's effects on heart rate and blood pressure could be beneficial in treating cardiovascular conditions.

**Overall:**

1-Deaza-2-chloro-N(6)-cyclopentyladenosine (Cl-CPA) is a powerful research tool that has helped advance our understanding of adenosine A1 receptors and their role in various physiological processes. Its potential therapeutic applications in areas like neuroprotection and cardiovascular disease make it a promising candidate for future drug development.

1-deaza-2-chloro-N(6)-cyclopentyladenosine: adenosine A(1) receptor agonist [Medical Subject Headings (MeSH), National Library of Medicine, extracted Dec-2023]

Cross-References

ID SourceID
PubMed CID464380
CHEMBL ID2113390
SCHEMBL ID19366712
MeSH IDM0174476

Synonyms (15)

Synonym
BIDD:GT0283
1-deaza-2-chloro-n(6)-cyclopentyladenosine
113646-62-1
PDSP2_001057
2cl-n(6)-cpen-1-deaza-a
(2r,3r,4s,5r)-2-[5-chloro-7-(cyclopentylamino)imidazo[4,5-b]pyridin-3-yl]-5-(hydroxymethyl)tetrahydrofuran-3,4-diol
2-chloro-n(6)-cyclopentyl-1-deazaadenosine
(2r,3r,4s,5r)-2-[5-chloro-7-(cyclopentylamino)imidazo[4,5-b]pyridin-3-yl]-5-(hydroxymethyl)oxolane-3,4-diol
bdbm50407524
chembl2113390 ,
1-dcca
3h-imidazol(4,5-b)pyridin-7-amine, 5-chloro-n-cyclopentyl-3-beta-d-ribofuranosyl-
DTXSID60150510
SCHEMBL19366712
2-chloro-n6-cyclopentyl-1-*deazaadenosin e
[information is derived through text-mining from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Protein Targets (6)

Inhibition Measurements

ProteinTaxonomyMeasurementAverageMin (ref.)Avg (ref.)Max (ref.)Bioassay(s)
Adenosine receptor A1Rattus norvegicus (Norway rat)IC50 (µMol)0.36000.00020.552110.0000AID31414
Adenosine receptor A1Rattus norvegicus (Norway rat)Ki0.02530.00011.20929.9700AID32012; AID32182
Adenosine receptor A2bRattus norvegicus (Norway rat)Ki13.20000.00061.353610.0000AID30656
Adenosine receptor A2aRattus norvegicus (Norway rat)Ki8.02000.00021.494010.0000AID30656; AID32863
Adenosine deaminase Bos taurus (cattle)Ki100.00000.00000.48937.0000AID33665
[prepared from compound, protein, and bioassay information from National Library of Medicine (NLM), extracted Dec-2023]

Activation Measurements

ProteinTaxonomyMeasurementAverageMin (ref.)Avg (ref.)Max (ref.)Bioassay(s)
Adenosine receptor A1Rattus norvegicus (Norway rat)EC50 (µMol)0.40800.00161.04608.2000AID224979
Adenosine receptor A2aHomo sapiens (human)EC50 (µMol)28.00000.00030.708110.0000AID30634
Adenosine receptor A2bHomo sapiens (human)EC50 (µMol)28.00000.00030.946110.0000AID30634
[prepared from compound, protein, and bioassay information from National Library of Medicine (NLM), extracted Dec-2023]

Biological Processes (66)

Processvia Protein(s)Taxonomy
synaptic transmission, dopaminergicAdenosine receptor A2aHomo sapiens (human)
response to amphetamineAdenosine receptor A2aHomo sapiens (human)
regulation of DNA-templated transcriptionAdenosine receptor A2aHomo sapiens (human)
phagocytosisAdenosine receptor A2aHomo sapiens (human)
apoptotic processAdenosine receptor A2aHomo sapiens (human)
inflammatory responseAdenosine receptor A2aHomo sapiens (human)
cellular defense responseAdenosine receptor A2aHomo sapiens (human)
adenylate cyclase-modulating G protein-coupled receptor signaling pathwayAdenosine receptor A2aHomo sapiens (human)
adenylate cyclase-activating G protein-coupled receptor signaling pathwayAdenosine receptor A2aHomo sapiens (human)
protein kinase C-activating G protein-coupled receptor signaling pathwayAdenosine receptor A2aHomo sapiens (human)
cell-cell signalingAdenosine receptor A2aHomo sapiens (human)
synaptic transmission, cholinergicAdenosine receptor A2aHomo sapiens (human)
central nervous system developmentAdenosine receptor A2aHomo sapiens (human)
blood coagulationAdenosine receptor A2aHomo sapiens (human)
sensory perceptionAdenosine receptor A2aHomo sapiens (human)
locomotory behaviorAdenosine receptor A2aHomo sapiens (human)
blood circulationAdenosine receptor A2aHomo sapiens (human)
negative regulation of cell population proliferationAdenosine receptor A2aHomo sapiens (human)
response to xenobiotic stimulusAdenosine receptor A2aHomo sapiens (human)
response to inorganic substanceAdenosine receptor A2aHomo sapiens (human)
positive regulation of glutamate secretionAdenosine receptor A2aHomo sapiens (human)
positive regulation of acetylcholine secretion, neurotransmissionAdenosine receptor A2aHomo sapiens (human)
regulation of norepinephrine secretionAdenosine receptor A2aHomo sapiens (human)
response to purine-containing compoundAdenosine receptor A2aHomo sapiens (human)
response to caffeineAdenosine receptor A2aHomo sapiens (human)
positive regulation of synaptic transmission, GABAergicAdenosine receptor A2aHomo sapiens (human)
synaptic transmission, glutamatergicAdenosine receptor A2aHomo sapiens (human)
positive regulation of urine volumeAdenosine receptor A2aHomo sapiens (human)
vasodilationAdenosine receptor A2aHomo sapiens (human)
eating behaviorAdenosine receptor A2aHomo sapiens (human)
negative regulation of vascular permeabilityAdenosine receptor A2aHomo sapiens (human)
negative regulation of neuron apoptotic processAdenosine receptor A2aHomo sapiens (human)
positive regulation of circadian sleep/wake cycle, sleepAdenosine receptor A2aHomo sapiens (human)
negative regulation of alpha-beta T cell activationAdenosine receptor A2aHomo sapiens (human)
astrocyte activationAdenosine receptor A2aHomo sapiens (human)
neuron projection morphogenesisAdenosine receptor A2aHomo sapiens (human)
positive regulation of protein secretionAdenosine receptor A2aHomo sapiens (human)
negative regulation of inflammatory responseAdenosine receptor A2aHomo sapiens (human)
regulation of mitochondrial membrane potentialAdenosine receptor A2aHomo sapiens (human)
membrane depolarizationAdenosine receptor A2aHomo sapiens (human)
regulation of calcium ion transportAdenosine receptor A2aHomo sapiens (human)
positive regulation of synaptic transmission, glutamatergicAdenosine receptor A2aHomo sapiens (human)
excitatory postsynaptic potentialAdenosine receptor A2aHomo sapiens (human)
inhibitory postsynaptic potentialAdenosine receptor A2aHomo sapiens (human)
prepulse inhibitionAdenosine receptor A2aHomo sapiens (human)
apoptotic signaling pathwayAdenosine receptor A2aHomo sapiens (human)
presynaptic modulation of chemical synaptic transmissionAdenosine receptor A2aHomo sapiens (human)
positive regulation of long-term synaptic potentiationAdenosine receptor A2aHomo sapiens (human)
positive regulation of apoptotic signaling pathwayAdenosine receptor A2aHomo sapiens (human)
G protein-coupled adenosine receptor signaling pathwayAdenosine receptor A2aHomo sapiens (human)
G protein-coupled adenosine receptor signaling pathwayAdenosine receptor A2bHomo sapiens (human)
positive regulation of chronic inflammatory response to non-antigenic stimulusAdenosine receptor A2bHomo sapiens (human)
G protein-coupled receptor signaling pathwayAdenosine receptor A2bHomo sapiens (human)
activation of adenylate cyclase activityAdenosine receptor A2bHomo sapiens (human)
positive regulation of vascular endothelial growth factor productionAdenosine receptor A2bHomo sapiens (human)
positive regulation of cGMP-mediated signalingAdenosine receptor A2bHomo sapiens (human)
cGMP-mediated signalingAdenosine receptor A2bHomo sapiens (human)
positive regulation of chemokine productionAdenosine receptor A2bHomo sapiens (human)
positive regulation of interleukin-6 productionAdenosine receptor A2bHomo sapiens (human)
mast cell degranulationAdenosine receptor A2bHomo sapiens (human)
positive regulation of mast cell degranulationAdenosine receptor A2bHomo sapiens (human)
relaxation of vascular associated smooth muscleAdenosine receptor A2bHomo sapiens (human)
presynaptic modulation of chemical synaptic transmissionAdenosine receptor A2bHomo sapiens (human)
adenylate cyclase-activating G protein-coupled receptor signaling pathwayAdenosine receptor A2bHomo sapiens (human)
vasodilationAdenosine receptor A2bHomo sapiens (human)
adenosine catabolic processAdenosine deaminase Bos taurus (cattle)
cell adhesionAdenosine deaminase Bos taurus (cattle)
nucleotide metabolic processAdenosine deaminase Bos taurus (cattle)
purine ribonucleoside monophosphate biosynthetic processAdenosine deaminase Bos taurus (cattle)
inosine biosynthetic processAdenosine deaminase Bos taurus (cattle)
[Information is prepared from geneontology information from the June-17-2024 release]

Molecular Functions (13)

Processvia Protein(s)Taxonomy
G protein-coupled adenosine receptor activityAdenosine receptor A2aHomo sapiens (human)
protein bindingAdenosine receptor A2aHomo sapiens (human)
calmodulin bindingAdenosine receptor A2aHomo sapiens (human)
lipid bindingAdenosine receptor A2aHomo sapiens (human)
enzyme bindingAdenosine receptor A2aHomo sapiens (human)
type 5 metabotropic glutamate receptor bindingAdenosine receptor A2aHomo sapiens (human)
identical protein bindingAdenosine receptor A2aHomo sapiens (human)
protein-containing complex bindingAdenosine receptor A2aHomo sapiens (human)
alpha-actinin bindingAdenosine receptor A2aHomo sapiens (human)
G protein-coupled adenosine receptor activityAdenosine receptor A2bHomo sapiens (human)
protein bindingAdenosine receptor A2bHomo sapiens (human)
G protein-coupled receptor activityAdenosine receptor A2bHomo sapiens (human)
G protein-coupled adenosine receptor activityAdenosine receptor A2aRattus norvegicus (Norway rat)
adenosine deaminase activityAdenosine deaminase Bos taurus (cattle)
protein bindingAdenosine deaminase Bos taurus (cattle)
zinc ion bindingAdenosine deaminase Bos taurus (cattle)
2'-deoxyadenosine deaminase activityAdenosine deaminase Bos taurus (cattle)
[Information is prepared from geneontology information from the June-17-2024 release]

Ceullar Components (17)

Processvia Protein(s)Taxonomy
plasma membraneAdenosine receptor A2aHomo sapiens (human)
intermediate filamentAdenosine receptor A2aHomo sapiens (human)
plasma membraneAdenosine receptor A2aHomo sapiens (human)
membraneAdenosine receptor A2aHomo sapiens (human)
dendriteAdenosine receptor A2aHomo sapiens (human)
axolemmaAdenosine receptor A2aHomo sapiens (human)
asymmetric synapseAdenosine receptor A2aHomo sapiens (human)
presynaptic membraneAdenosine receptor A2aHomo sapiens (human)
neuronal cell bodyAdenosine receptor A2aHomo sapiens (human)
postsynaptic membraneAdenosine receptor A2aHomo sapiens (human)
presynaptic active zoneAdenosine receptor A2aHomo sapiens (human)
glutamatergic synapseAdenosine receptor A2aHomo sapiens (human)
plasma membraneAdenosine receptor A2bHomo sapiens (human)
Schaffer collateral - CA1 synapseAdenosine receptor A2bHomo sapiens (human)
presynapseAdenosine receptor A2bHomo sapiens (human)
glutamatergic synapseAdenosine receptor A2bHomo sapiens (human)
plasma membraneAdenosine receptor A2bHomo sapiens (human)
Golgi membraneAdenosine receptor A2aRattus norvegicus (Norway rat)
lysosomeAdenosine deaminase Bos taurus (cattle)
cytoplasmic vesicle lumenAdenosine deaminase Bos taurus (cattle)
anchoring junctionAdenosine deaminase Bos taurus (cattle)
[Information is prepared from geneontology information from the June-17-2024 release]

Bioassays (16)

Assay IDTitleYearJournalArticle
AID32012Binding affinity for adenosine A1 receptor was assayed by displacement of [3H]DPCPX from rat cortical membranes.2000Journal of medicinal chemistry, Jan-27, Volume: 43, Issue:2
N-cycloalkyl derivatives of adenosine and 1-deazaadenosine as agonists and partial agonists of the A(1) adenosine receptor.
AID233030A1 selectivity as ratio of Ki for A2 receptor to Ki for A1 receptor1988Journal of medicinal chemistry, Jun, Volume: 31, Issue:6
Adenosine receptor agonists: synthesis and biological evaluation of 1-deaza analogues of adenosine derivatives.
AID224979Stimulation of [35S]GTP-gamma-S, binding to rat brain membranes by adenosine A1 receptor activation2000Journal of medicinal chemistry, Jan-27, Volume: 43, Issue:2
N-cycloalkyl derivatives of adenosine and 1-deazaadenosine as agonists and partial agonists of the A(1) adenosine receptor.
AID30634Stimulation of adenylate cyclase activity in human platelet membrane at A2 receptor1988Journal of medicinal chemistry, Jun, Volume: 31, Issue:6
Adenosine receptor agonists: synthesis and biological evaluation of 1-deaza analogues of adenosine derivatives.
AID31414Inhibition of Adenylate cyclase activity in rat fat cell membrane at adenosine A1 receptor1988Journal of medicinal chemistry, Jun, Volume: 31, Issue:6
Adenosine receptor agonists: synthesis and biological evaluation of 1-deaza analogues of adenosine derivatives.
AID33948Selectivity ratio of Ki of the adenosine A2a receptor and Ki of adenosine A1 receptor2000Journal of medicinal chemistry, Jan-27, Volume: 43, Issue:2
N-cycloalkyl derivatives of adenosine and 1-deazaadenosine as agonists and partial agonists of the A(1) adenosine receptor.
AID44812In vitro evaluation of cytotoxicity in C8166 cells infected with HIV-1 IIIB.1995Journal of medicinal chemistry, Sep-29, Volume: 38, Issue:20
Synthesis and biological evaluation of N6-cycloalkyl derivatives of 1-deazaadenine nucleosides: a new class of anti-human immunodeficiency virus agents.
AID189321Percent relative intrinsic activity compared to CCPA2000Journal of medicinal chemistry, Jan-27, Volume: 43, Issue:2
N-cycloalkyl derivatives of adenosine and 1-deazaadenosine as agonists and partial agonists of the A(1) adenosine receptor.
AID30791Maximal stimulation of adenylate cyclase activity relative to NECA for A2-receptor. (Stimulation by NECA=250+/-30%)1988Journal of medicinal chemistry, Jun, Volume: 31, Issue:6
Adenosine receptor agonists: synthesis and biological evaluation of 1-deaza analogues of adenosine derivatives.
AID233029A1 selectivity as ratio of EC50 at A2 receptor to IC50 at A1 receptor1988Journal of medicinal chemistry, Jun, Volume: 31, Issue:6
Adenosine receptor agonists: synthesis and biological evaluation of 1-deaza analogues of adenosine derivatives.
AID32182Displacement of [3H]PIA from adenosine A1 receptor of rat brain membranes1988Journal of medicinal chemistry, Jun, Volume: 31, Issue:6
Adenosine receptor agonists: synthesis and biological evaluation of 1-deaza analogues of adenosine derivatives.
AID30656Displacement of [3H]NECA from A2-receptor of rat striatal membranes1988Journal of medicinal chemistry, Jun, Volume: 31, Issue:6
Adenosine receptor agonists: synthesis and biological evaluation of 1-deaza analogues of adenosine derivatives.
AID32863Binding affinity for adenosine A2A receptor was determined by displacement of [3H]-DPCPX from rat striatal membranes.2000Journal of medicinal chemistry, Jan-27, Volume: 43, Issue:2
N-cycloalkyl derivatives of adenosine and 1-deazaadenosine as agonists and partial agonists of the A(1) adenosine receptor.
AID44801In vitro evaluation of anti-HIV-1 activity in C8166 cells infected with HIV-1 IIIB.1995Journal of medicinal chemistry, Sep-29, Volume: 38, Issue:20
Synthesis and biological evaluation of N6-cycloalkyl derivatives of 1-deazaadenine nucleosides: a new class of anti-human immunodeficiency virus agents.
AID30328Maximal inhibition of adenylate cyclase activity relative to R-PIA for Adenosine A1 receptor (Inhibition by R-PIA=53+/-10%)1988Journal of medicinal chemistry, Jun, Volume: 31, Issue:6
Adenosine receptor agonists: synthesis and biological evaluation of 1-deaza analogues of adenosine derivatives.
AID33665Inhibition calf intestine adenosine deaminase1995Journal of medicinal chemistry, Sep-29, Volume: 38, Issue:20
Synthesis and biological evaluation of N6-cycloalkyl derivatives of 1-deazaadenine nucleosides: a new class of anti-human immunodeficiency virus agents.
[information is prepared from bioassay data collected from National Library of Medicine (NLM), extracted Dec-2023]

Research

Studies (8)

TimeframeStudies, This Drug (%)All Drugs %
pre-19901 (12.50)18.7374
1990's5 (62.50)18.2507
2000's1 (12.50)29.6817
2010's1 (12.50)24.3611
2020's0 (0.00)2.80
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Market Indicators

Research Demand Index: 12.83

According to the monthly volume, diversity, and competition of internet searches for this compound, as well the volume and growth of publications, there is estimated to be weak demand-to-supply ratio for research on this compound.

MetricThis Compound (vs All)
Research Demand Index12.83 (24.57)
Research Supply Index2.20 (2.92)
Research Growth Index5.03 (4.65)
Search Engine Demand Index0.00 (26.88)
Search Engine Supply Index0.00 (0.95)

This Compound (12.83)

All Compounds (24.57)

Study Types

Publication TypeThis drug (%)All Drugs (%)
Trials0 (0.00%)5.53%
Reviews0 (0.00%)6.00%
Case Studies0 (0.00%)4.05%
Observational0 (0.00%)0.25%
Other8 (100.00%)84.16%
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]