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C101 Sigma-Aldrich

8-Cyclopentyl-1,3-dipropylxanthine

solid

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

  • CAS Number 102146-07-6

  • Empirical Formula (Hill Notation) C16H24N4O2

  • Molecular Weight 304.39

  •  MDL number MFCD00055117

  •  PubChem Substance ID 24277697

  •  NACRES NA.77

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Properties

Related Categories Adenosines/P2 Nucleotide Receptor - Antagonists, Adenosines/P2 Nucleotide Receptors (Purinergics), Antagonists, Bioactive Small Molecule Alphabetical Index, Bioactive Small Molecules,
Quality Level   100
form   solid
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)

Description

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.

Packaging

25, 100 mg in poly bottle

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 also offered as part of Sigma′s Library of Pharmacologically Active Compounds (LOPAC®1280), a biologically annotated collection of high-quality, ready-to-screen compounds. Click here to learn more.

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.

Legal Information

LOPAC is a registered trademark of Sigma-Aldrich Co. LLC

Safety & Documentation

Safety Information

Symbol 
GHS07  GHS07
Signal word 
Warning
Hazard statements 
Precautionary statements 
Personal Protective Equipment 
RIDADR 
NONH for all modes of transport
WGK Germany 
WGK 3
Flash Point(F) 
Not applicable
Flash Point(C) 
Not applicable

Documents

Certificate of Analysis (COA)

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Protocols & Articles

Articles

Fluorescent G protein-coupled receptors (GPCRs)

G protein-coupled receptors (GPCRs) are the largest class of transmembrane proteins and the targets for almost half of the clinical drugs in the market today. Advances in X-ray crystallography and ot...
Mike Earley, Market Segment Manager
Biofiles Vol. 8, No. 4
Keywords: Clinical, Confocal microscopy, Ligands, Microscopy

Peer-Reviewed Papers
15

References

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