Biomaterial Database

A new photoaffinity analog of cGMP: potent inhibitor of cyclic nucleotide phosphodiesterase. 1994

J W Clack, and P J Stein

Department of Biology, Indiana University-Purdue University at Indianapolis, Columbus 47203.

A purine nucleotide analog, 2'-O-(4-benzoylbenzoyl)guanosine cyclic 3',5'-monophosphate (BBcGMP), was synthesized from 4-benzoylbenzoic acid and cGMP. BBcGMP was found to inhibit several types of cyclic nucleotide phosphodiesterases (PDEs) at low concentrations. Besides its activity as a PDE inhibitor, the benzophenone moiety of BBcGMP provides it with UV light-induced photoreactivity toward organic compounds. This photoreactivity of BBcGMP was exploited to radiolabel specifically the light-stimulated cGMP PDE of the rod outer segment with [alpha-32P]BBcGMP. These results suggest that benzoylbenzoic derivatives of cyclic nucleotides can be of general use in the inhibition of cyclic nucleotide PDEs. The results further suggest that radiolabeled cyclic nucleotide derivatives may be useful in the identification and active site determination of cyclic nucleotide-binding proteins and enzymes.

UI	MeSH Term	Description	Entries
D010777	Photochemistry	A branch of physical chemistry which studies chemical reactions, isomerization and physical behavior that may occur under the influence of visible and/or ultraviolet light.	Photochemistries
D002417	Cattle	Domesticated bovine animals of the genus Bos, usually kept on a farm or ranch and used for the production of meat or dairy products or for heavy labor.	Beef Cow,Bos grunniens,Bos indicus,Bos indicus Cattle,Bos taurus,Cow,Cow, Domestic,Dairy Cow,Holstein Cow,Indicine Cattle,Taurine Cattle,Taurus Cattle,Yak,Zebu,Beef Cows,Bos indicus Cattles,Cattle, Bos indicus,Cattle, Indicine,Cattle, Taurine,Cattle, Taurus,Cattles, Bos indicus,Cattles, Indicine,Cattles, Taurine,Cattles, Taurus,Cow, Beef,Cow, Dairy,Cow, Holstein,Cows,Dairy Cows,Domestic Cow,Domestic Cows,Indicine Cattles,Taurine Cattles,Taurus Cattles,Yaks,Zebus
D006152	Cyclic GMP	Guanosine cyclic 3',5'-(hydrogen phosphate). A guanine nucleotide containing one phosphate group which is esterified to the sugar moiety in both the 3'- and 5'-positions. It is a cellular regulatory agent and has been described as a second messenger. Its levels increase in response to a variety of hormones, including acetylcholine, insulin, and oxytocin and it has been found to activate specific protein kinases. (From Merck Index, 11th ed)	Guanosine Cyclic 3',5'-Monophosphate,Guanosine Cyclic 3,5 Monophosphate,Guanosine Cyclic Monophosphate,Guanosine Cyclic-3',5'-Monophosphate,3',5'-Monophosphate, Guanosine Cyclic,Cyclic 3',5'-Monophosphate, Guanosine,Cyclic Monophosphate, Guanosine,Cyclic-3',5'-Monophosphate, Guanosine,GMP, Cyclic,Guanosine Cyclic 3',5' Monophosphate,Monophosphate, Guanosine Cyclic
D000345	Affinity Labels	Analogs of those substrates or compounds which bind naturally at the active sites of proteins, enzymes, antibodies, steroids, or physiological receptors. These analogs form a stable covalent bond at the binding site, thereby acting as inhibitors of the proteins or steroids.	Affinity Labeling Reagents,Labeling Reagents, Affinity,Labels, Affinity,Reagents, Affinity Labeling
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
D012374	Rod Cell Outer Segment	The portion of a retinal rod cell situated between the ROD INNER SEGMENT and the RETINAL PIGMENT EPITHELIUM. It contains a stack of photosensitive disk membranes laden with RHODOPSIN.	Rod Outer Segment,Rod Outer Segments,Outer Segment, Rod,Outer Segments, Rod
D015106	3',5'-Cyclic-GMP Phosphodiesterases	Enzymes that catalyze the hydrolysis of cyclic GMP to yield guanosine-5'-phosphate.	3',5'-Cyclic GMP 5'-Nucleotidohydrolase,3',5'-Cyclic GMP Phosphodiesterase,3',5'-Cyclic-GMP Phosphodiesterase,3,5-Cyclic GMP 5-Nucleotidohydrolase,3,5-Cyclic GMP Phosphodiesterase,3',5' Cyclic GMP 5' Nucleotidohydrolase,3',5' Cyclic GMP Phosphodiesterase,3',5' Cyclic GMP Phosphodiesterases,3,5 Cyclic GMP 5 Nucleotidohydrolase,3,5 Cyclic GMP Phosphodiesterase,5'-Nucleotidohydrolase, 3',5'-Cyclic GMP,5-Nucleotidohydrolase, 3,5-Cyclic GMP,GMP 5'-Nucleotidohydrolase, 3',5'-Cyclic,GMP 5-Nucleotidohydrolase, 3,5-Cyclic,GMP Phosphodiesterase, 3',5'-Cyclic,GMP Phosphodiesterase, 3,5-Cyclic,Phosphodiesterase, 3',5'-Cyclic GMP,Phosphodiesterase, 3',5'-Cyclic-GMP,Phosphodiesterase, 3,5-Cyclic GMP,Phosphodiesterases, 3',5'-Cyclic-GMP