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C101

Sigma-Aldrich

8-Cyclopentyl-1,3-dipropylxanthine

solid

Synonyme(s) :

1,3-Dipropyl-8-cyclopentylxanthine, DPCPX, PD 116,948

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About This Item

Formule empirique (notation de Hill):
C16H24N4O2
Numéro CAS:
102146-07-6
Poids moléculaire :
304.39
Numéro MDL:
MFCD00055117
Code UNSPSC :
12352202
ID de substance PubChem :
24277697
Nomenclature NACRES :
NA.77

Forme

solid

Niveau de qualité

100

Couleur

white

Solubilité

DMSO: >10 mg/mL
0.1 M NaOH: 2 mg/mL
ethanol: 4 mg/mL
H2O: insoluble

εmax

14,800 at 276 nm in ethanol

Chaîne SMILES 

CCCN1C(=O)N(CCC)c2nc([nH]c2C1=O)C3CCCC3

InChI

1S/C16H24N4O2/c1-3-9-19-14-12(15(21)20(10-4-2)16(19)22)17-13(18-14)11-7-5-6-8-11/h11H,3-10H2,1-2H3,(H,17,18)

Clé InChI

FFBDFADSZUINTG-UHFFFAOYSA-N

Informations sur le gène

human ... ADORA1(134) , ADORA2A(135) , ADORA2B(136) , ADORA3(140)
rat ... Adora1(29290) , Adora2a(25369) , Adora2b(29316) , Adora3(25370)

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Application

8-Cyclopentyl-1,3-dipropylxanthine has been used as an adenosine receptor (A1AR) antagonist in macrophages and human umbilical vein endothelial cells (HUVECs). It has also been used as A1AR antagonist in MCF-7 breast cancer cell line to test its anti-cancer effect.

Actions biochimiques/physiologiques

8-Cyclopentyl-1,3-dipropylxanthine (DPCPX) is a selective A1 adenosine receptor antagonist. DPCPX possesses anti-cancer functionality. It induces apoptosis in breast cancer cells and favors mRNA expression of caspases.

Caractéristiques et avantages

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.

Pictogrammes

Exclamation mark
GHS07

Mention d'avertissement

Warning

Mentions de danger

H315,H319,H335

Classification des risques

Eye Irrit. 2 - Skin Irrit. 2 - STOT SE 3

Organes cibles

Respiratory system

Code de la classe de stockage

11 - Combustible Solids

Classe de danger pour l'eau (WGK)

WGK 3

Point d'éclair (°F)

Not applicable

Point d'éclair (°C)

Not applicable

Équipement de protection individuelle

dust mask type N95 (US), Eyeshields, Gloves

Certificats d'analyse (COA)

Recherchez un Certificats d'analyse (COA) en saisissant le numéro de lot du produit. Les numéros de lot figurent sur l'étiquette du produit après les mots "Lot" ou "Batch".

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Consulter la Bibliothèque de documents

Lindsay Silva et al.
Neurotoxicology and teratology, 58, 88-100 (2016-02-24)
Adolescents who use marijuana are more likely to exhibit anxiety, depression, and other mood disorders, including psychotic-like symptoms. Additionally, the age at onset of use and the stress history of the individual can affect responses to cannabis. To examine the
Hongjie Chen et al.
Experimental hematology, 37(5), 533-538 (2009-04-21)
The control of expression of tumor necrosis factor-alpha (TNF-alpha) impacts a variety of processes during a stress response. Macrophages are a major source of TNF-alpha, the level of which is known to be regulated by adenosine. Previous studies highlighted the
Vanessa R Haynes et al.
Molecular metabolism, 34, 54-71 (2020-03-18)
Nutrient sensing by hypothalamic neurons is critical for the regulation of food intake and energy expenditure. We aimed to identify long- and medium-chain fatty acid species transported into the brain, their effects on energy balance, and the mechanisms by which
Mehdi Nikbakht Dastjerdi et al.
Research in pharmaceutical sciences, 11(4), 303-310 (2016-09-22)
Adenosine receptor family especially A1 type is expressed in breast cancer cells in which P53 and caspase genes are wild-type. The aim of this study was to investigate the correlation between A1 receptor and either cell apoptosis or proliferation and
João M N Duarte et al.
Frontiers in neuroscience, 12, 1015-1015 (2019-01-29)
Diabetes affects the morphology and plasticity of the hippocampus, and leads to learning and memory deficits. Caffeine has been proposed to prevent memory impairment upon multiple chronic disorders with neurological involvement. We tested whether long-term caffeine consumption prevents type 2
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