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C101

Sigma-Aldrich

8-Cyclopentyl-1,3-dipropylxanthine

solid

Synonym(s):

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

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About This Item

Empirical Formula (Hill Notation):
C16H24N4O2
CAS Number:
102146-07-6
Molecular Weight:
304.39
MDL number:
MFCD00055117
UNSPSC Code:
12352202
PubChem Substance ID:
24277697
NACRES:
NA.77

form

solid

Quality Level

100

color

white

solubility

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

SMILES string

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)

InChI key

FFBDFADSZUINTG-UHFFFAOYSA-N

Gene Information

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.

Biochem/physiol Actions

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.

Features and Benefits

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.

pictograms

Exclamation mark
GHS07

signalword

Warning

Hazard Classifications

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

target_organs

Respiratory system

Storage Class

11 - Combustible Solids

wgk_germany

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

dust mask type N95 (US), Eyeshields, Gloves

Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

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Lindsay Silva et al.
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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
Mariachiara Zuccarini et al.
Purinergic signalling, 13(4), 429-442 (2017-06-16)
Epithelial to mesenchymal transition (EMT) occurs during embryogenesis or under pathological conditions such as hypoxia, injury, chronic inflammation, or tissue fibrosis. In renal tubular epithelial cells (MDCK), TGF-β1 induces EMT by reducing or increasing epithelial or mesenchymal marker expression, respectively.
Flavia Varano et al.
Journal of medicinal chemistry, 59(23), 10564-10576 (2016-12-10)
In this study, we describe the design and synthesis of new N5-substituted-2-(2-furanyl) thiazolo[5,4-d]pyrimidine-5,7-diamines (2-18) and their pharmacological characterization as A2A adenosine receptor (AR) antagonists by using in vitro and in vivo assays. In competition binding experiments two derivatives (13 and
Daniela Patinha et al.
American journal of physiology. Renal physiology, 304(5), F614-F622 (2013-01-04)
Increased angiotensin II (ANG II) or adenosine can potentiate each other in the regulation of renal hemodynamics and tubular function. Diabetes is characterized by hyperfiltration, yet the roles of ANG II and adenosine receptors for controlling baseline renal blood flow
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