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C8031

Sigma-Aldrich

N6-Cyclopentyladenosine

solid

Synonym(e):

CPA

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About This Item

Empirische Formel (Hill-System):
C15H21N5O4
CAS-Nummer:
41552-82-3
Molekulargewicht:
335.36
MDL-Nummer:
MFCD00036845
UNSPSC-Code:
12352200
PubChem Substanz-ID:
24277686
NACRES:
NA.77

Form

solid

Qualitätsniveau

200

Farbe

white to off-white

Löslichkeit

H2O: 1.7 mg/mL
0.1 M HCl: 12 mg/mL
DMSO: 23 mg/mL

Lagertemp.

2-8°C

SMILES String

OC[C@H]1O[C@H]([C@H](O)[C@@H]1O)n2cnc3c(NC4CCCC4)ncnc23

InChI

1S/C15H21N5O4/c21-5-9-11(22)12(23)15(24-9)20-7-18-10-13(16-6-17-14(10)20)19-8-3-1-2-4-8/h6-9,11-12,15,21-23H,1-5H2,(H,16,17,19)/t9-,11-,12-,15-/m1/s1

InChIKey

SQMWSBKSHWARHU-SDBHATRESA-N

Angaben zum Gen

human ... ADORA1(134) , ADORA2A(135) , ADORA3(140)
mouse ... Adora1(11539)
rat ... Adora1(29290) , Adora2a(25369) , Adora3(25370)

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Anwendung

N6-Cyclopentyladenosine has also been used to study its effect on p53 and caspase 3, 8, and 9 expression and apoptosis rate in MCF-7 breast cancer cell line.
N6-Cyclopentyladenosine has been used to study its effect on the cavernosal smooth muscle cells from lean and db/db (obesity and type II diabetes caused by a leptin receptor mutation) mice.

Biochem./physiol. Wirkung

N6-Cyclopentyladenosine (CPA) is an adenosine derivative and a potent A1 adenosine receptor agonist. It acts as an anticonvulsant and might exhibit protective actions against aminophylline (AMPH)-induced seizures.
N6-Cyclopentyladenosine also exhibits analgesic effect against acute, arthritis-induced and neuropathic pain.

Leistungsmerkmale und Vorteile

This compound is featured on the Adenosine Receptors page of the Handbook of Receptor Classification and Signal Transduction. To browse other handbook pages, click here.

Physikalische Form

hygroscopic solid

Lagerklassenschlüssel

11 - Combustible Solids

WGK

WGK 3

Flammpunkt (°F)

Not applicable

Flammpunkt (°C)

Not applicable

Persönliche Schutzausrüstung

Eyeshields, Gloves, type N95 (US)

Analysenzertifikate (COA)

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Individual and combined effects of N6-cyclopentyladenosine, flunarizine and diazepam on aminophylline-induced recurrent generalized seizures in mice
Jaishree J, et al.
Polish Journal of Pharmacology, 55(4), 559-564 (2003)
Cheng-Hui Hsiao et al.
Biomedical chromatography : BMC, 33(9), e4518-e4518 (2019-02-26)
The prominent stromal compartment surrounds pancreatic ductal adenocarcinoma and protects the tumor cells from chemo- or radiotherapy. We hypothesized that our nano formulation carrying cyclopamine (CPA, stroma modulator) and paclitaxel (PTX, antitumor agent) could increase the permeation of PTX through
Claudia Iasillo et al.
Nucleic acids research, 45(17), 10229-10241 (2017-10-04)
Termination of transcription is important for establishing gene punctuation marks. It is also critical for suppressing many of the pervasive transcription events occurring throughout eukaryotic genomes and coupling their RNA products to efficient decay. In human cells, the ARS2 protein
Yahaira Naaldijk et al.
BMC biotechnology, 16(1), 85-85 (2016-12-03)
Preservation of human skin fibroblasts and keratinocytes is essential for the creation of skin tissue banks. For successful cryopreservation of cells, selection of an appropriate cryoprotectant agent (CPA) is imperative. The aim of this study was to identify CPAs that
Ainhoa Bilbao et al.
Addiction biology, 24(5), 1008-1018 (2019-06-27)
The co-occurrence of chronic pain and alcohol use disorders (AUDs) involves complex interactions between genetic and neurophysiological aspects, and the research has reported mixed findings when they both co-occur. There is also an indication of a gender-dependent effect; males are
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