BIOMAT Database Logo BIOMAT Database Logo

Assessment of the enantiomeric purity of R- and S-N6-phenylisopropyladenosine (PIA): implications for adenosine receptor subclassification. 1994

R A Mathôt, and B C Van den Aarsen, and J K von Frijtag Drabble Künzel, and M Danhof, and A P Ijzerman
Division of Pharmacology, Leiden/Amsterdam Center for Drug Research, University of Leiden, The Netherlands.

A chiral column high-performance liquid chromatographic method was developed for the assessment of the enantiomeric purity of the stereoisomers of N6-phenylisopropyladenosine (PIA). The observed chiral purity of R-PIA was greater than 99.9%, whereas S-PIA was found to contain 4.4% of the R-enantiomer. In radioligand binding studies, the observed affinity of S-PIA for the adenosine A1 receptor (IC50 240 nM) could entirely be attributed to its content of R-PIA (IC50 7.8 nM). Calculation of a theoretical IC50 of pure S-PIA for the A2 receptor yielded a value of 6700 nM, which was 35-fold higher than for R-PIA (190 nM). Concludingly, the utilization of enantiomeric impure S-PIA in the definition of adenosine receptor subclasses is questionable.

UI MeSH Term Description Entries
D010627 Phenethylamines A group of compounds that are derivatives of beta- aminoethylbenzene which is structurally and pharmacologically related to amphetamine. (From Merck Index, 11th ed) Phenylethylamines
D010660 Phenylisopropyladenosine N-Isopropyl-N-phenyl-adenosine. Antilipemic agent. Synonym: TH 162. Isopropylphenyladenosine,L-Phenylisopropyladenosine,N(6)-Phenylisopropyl-Adenosine,L Phenylisopropyladenosine
D001921 Brain The part of CENTRAL NERVOUS SYSTEM that is contained within the skull (CRANIUM). Arising from the NEURAL TUBE, the embryonic brain is comprised of three major parts including PROSENCEPHALON (the forebrain); MESENCEPHALON (the midbrain); and RHOMBENCEPHALON (the hindbrain). The developed brain consists of CEREBRUM; CEREBELLUM; and other structures in the BRAIN STEM. Encephalon
D002462 Cell Membrane The lipid- and protein-containing, selectively permeable membrane that surrounds the cytoplasm in prokaryotic and eukaryotic cells. Plasma Membrane,Cytoplasmic Membrane,Cell Membranes,Cytoplasmic Membranes,Membrane, Cell,Membrane, Cytoplasmic,Membrane, Plasma,Membranes, Cell,Membranes, Cytoplasmic,Membranes, Plasma,Plasma Membranes
D002851 Chromatography, High Pressure Liquid Liquid chromatographic techniques which feature high inlet pressures, high sensitivity, and high speed. Chromatography, High Performance Liquid,Chromatography, High Speed Liquid,Chromatography, Liquid, High Pressure,HPLC,High Performance Liquid Chromatography,High-Performance Liquid Chromatography,UPLC,Ultra Performance Liquid Chromatography,Chromatography, High-Performance Liquid,High-Performance Liquid Chromatographies,Liquid Chromatography, High-Performance
D000241 Adenosine A nucleoside that is composed of ADENINE and D-RIBOSE. Adenosine or adenosine derivatives play many important biological roles in addition to being components of DNA and RNA. Adenosine itself is a neurotransmitter. Adenocard,Adenoscan
D000818 Animals Unicellular or multicellular, heterotrophic organisms, that have sensation and the power of voluntary movement. Under the older five kingdom paradigm, Animalia was one of the kingdoms. Under the modern three domain model, Animalia represents one of the many groups in the domain EUKARYOTA. Animal,Metazoa,Animalia
D013237 Stereoisomerism The phenomenon whereby compounds whose molecules have the same number and kind of atoms and the same atomic arrangement, but differ in their spatial relationships. (From McGraw-Hill Dictionary of Scientific and Technical Terms, 5th ed) Molecular Stereochemistry,Stereoisomers,Stereochemistry, Molecular,Stereoisomer
D014970 Xanthines Purine bases found in body tissues and fluids and in some plants.
D051381 Rats The common name for the genus Rattus. Rattus,Rats, Laboratory,Rats, Norway,Rattus norvegicus,Laboratory Rat,Laboratory Rats,Norway Rat,Norway Rats,Rat,Rat, Laboratory,Rat, Norway,norvegicus, Rattus

Related Publications

R A Mathôt, and B C Van den Aarsen, and J K von Frijtag Drabble Künzel, and M Danhof, and A P Ijzerman
The adenosine agonist N6-R-phenylisopropyladenosine (R-PIA) stimulates feeding in rats.
January 1989, Brain research,
R A Mathôt, and B C Van den Aarsen, and J K von Frijtag Drabble Künzel, and M Danhof, and A P Ijzerman
Activation of adenosine A1 receptor by N6-(R)-phenylisopropyladenosine (R-PIA) inhibits forskolin-stimulated tyrosine hydroxylase activity in rat striatal synaptosomes.
January 1990, Life sciences,
R A Mathôt, and B C Van den Aarsen, and J K von Frijtag Drabble Künzel, and M Danhof, and A P Ijzerman
Effect of phospholipases and proteases on the [3H]N6-(R)-phenylisopropyladenosine ([3H]R-PIA) binding to A1 adenosine receptors from pig cerebral cortex.
November 1991, Journal of cellular biochemistry,
R A Mathôt, and B C Van den Aarsen, and J K von Frijtag Drabble Künzel, and M Danhof, and A P Ijzerman
Age-related effects in rabbit hearts of N6-R-phenylisopropyladenosine, an adenosine A1 receptor agonist.
November 1995, The journals of gerontology. Series A, Biological sciences and medical sciences,
R A Mathôt, and B C Van den Aarsen, and J K von Frijtag Drabble Künzel, and M Danhof, and A P Ijzerman
[3H]-(R)-N6-Phenylisopropyladenosine agonist binding to the solubilized A1 adenosine receptor from bovine epididymal spermatozoa.
January 1997, Archives of biochemistry and biophysics,
R A Mathôt, and B C Van den Aarsen, and J K von Frijtag Drabble Künzel, and M Danhof, and A P Ijzerman
The effect of L-N6-phenylisopropyladenosine (L-PIA) on the isolated hemidiaphragm of the rat.
January 1986, Journal de pharmacologie,
R A Mathôt, and B C Van den Aarsen, and J K von Frijtag Drabble Künzel, and M Danhof, and A P Ijzerman
Antinociceptive effects in the rat of an adenosine analogue, N6-phenylisopropyladenosine.
October 1983, The Journal of pharmacy and pharmacology,
R A Mathôt, and B C Van den Aarsen, and J K von Frijtag Drabble Künzel, and M Danhof, and A P Ijzerman
Inhibition by the adenosine analogue, (R-)-N6-phenylisopropyladenosine, of kainic acid neurotoxicity in rat hippocampus after systemic administration.
June 1993, British journal of pharmacology,
R A Mathôt, and B C Van den Aarsen, and J K von Frijtag Drabble Künzel, and M Danhof, and A P Ijzerman
Antiepileptic effects of N6-L-phenylisopropyladenosine (L-PIA) on penicillin-induced epileptogenic focus in rabbits.
July 1988, Pharmacological research communications,
R A Mathôt, and B C Van den Aarsen, and J K von Frijtag Drabble Künzel, and M Danhof, and A P Ijzerman
Characterization of adenosine receptors in rat brain by (-)[3H]N6-phenylisopropyladenosine.
September 1980, Naunyn-Schmiedeberg's archives of pharmacology,
Copied contents to your clipboard!