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Synthesis and biological activity of some 8-substituted selenoguanosine cyclic 3',5'-phosphates and related compounds. 1975

S H Chu, and C Y Shiue, and M Y Chu

8-Bromoguanosine cyclic 3',5'-monophosphate, 8-bromoguanosine 5'-monophosphate, and 8-bromoguanosine served as intermediates for the chemical synthesis of a series of 8-substituted seleno cyclic nucleotides, nucleotides, and their nucleosides. Selenourea was found to be a useful reagent in synthesizing these seleno-substituted nucleoside, nucleotide, and cyclic nucleotide. A nucleic acid analyzer was used to study the hydrolysis of these cyclic nucleotides by phosphodiesterase. It was found that all of the 8-substituted selenoguanosine cyclic 3',5'-phosphates synthesized, except 8-MeSe-cGMP, were resistant to hydrolyze by phosphodiesterase. These 8-substituted seleno cyclic GMP derivatives showed some antitumor activities against murine leukemic cells (L5178Y) in vitro and in vivo.

UI MeSH Term Description Entries
D007942 Leukemia, Experimental Leukemia induced experimentally in animals by exposure to leukemogenic agents, such as VIRUSES; RADIATION; or by TRANSPLANTATION of leukemic tissues. Experimental Leukemia,Experimental Leukemias,Leukemia Model, Animal,Leukemias, Experimental,Animal Leukemia Model,Animal Leukemia Models,Leukemia Models, Animal
D009712 Nucleotides, Cyclic Cyclic Nucleotide,Cyclic Nucleotides,Nucleotide, Cyclic
D006150 Guanine Nucleotides Guanine Nucleotide,Guanosine Phosphates,Nucleotide, Guanine,Nucleotides, Guanine,Phosphates, Guanosine
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
D006868 Hydrolysis The process of cleaving a chemical compound by the addition of a molecule of water.
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
D012643 Selenium An element with the atomic symbol Se, atomic number 34, and atomic weight 78.97. It is an essential micronutrient for mammals and other animals but is toxic in large amounts. Selenium protects intracellular structures against oxidative damage. It is an essential component of GLUTATHIONE PEROXIDASE. Selenium-80,Selenium 80
D013056 Spectrophotometry, Ultraviolet Determination of the spectra of ultraviolet absorption by specific molecules in gases or liquids, for example Cl2, SO2, NO2, CS2, ozone, mercury vapor, and various unsaturated compounds. (McGraw-Hill Dictionary of Scientific and Technical Terms, 4th ed) Ultraviolet Spectrophotometry
D015105 3',5'-Cyclic-AMP Phosphodiesterases Enzymes that catalyze the hydrolysis of CYCLIC AMP to form adenosine 5'-phosphate. The enzymes are widely distributed in animal tissue and control the level of intracellular cyclic AMP. Many specific enzymes classified under this heading demonstrate additional spcificity for 3',5'-cyclic IMP and CYCLIC GMP. 3',5'-Cyclic AMP 5'-Nucleotidohydrolase,3',5'-Cyclic-Nucleotide Phosphodiesterase,CAMP Phosphodiesterase,3',5' Cyclic AMP Phosphodiesterase,3',5'-Cyclic AMP Phosphodiesterase,3',5'-Cyclic Nucleotide Phosphodiesterase,3',5'-Cyclic-AMP Phosphodiesterase,3',5'-Nucleotide Phosphodiesterase,3,5-Cyclic AMP 5-Nucleotidohydrolase,3,5-Cyclic AMP Phosphodiesterase,3',5' Cyclic AMP 5' Nucleotidohydrolase,3',5' Cyclic AMP Phosphodiesterases,3',5' Cyclic Nucleotide Phosphodiesterase,3',5' Nucleotide Phosphodiesterase,3,5 Cyclic AMP 5 Nucleotidohydrolase,3,5 Cyclic AMP Phosphodiesterase,5'-Nucleotidohydrolase, 3',5'-Cyclic AMP,5-Nucleotidohydrolase, 3,5-Cyclic AMP,AMP 5'-Nucleotidohydrolase, 3',5'-Cyclic,AMP 5-Nucleotidohydrolase, 3,5-Cyclic,AMP Phosphodiesterase, 3',5'-Cyclic,AMP Phosphodiesterase, 3,5-Cyclic,Nucleotide Phosphodiesterase, 3',5'-Cyclic,Phosphodiesterase, 3',5'-Cyclic AMP,Phosphodiesterase, 3',5'-Cyclic Nucleotide,Phosphodiesterase, 3',5'-Cyclic-AMP,Phosphodiesterase, 3',5'-Cyclic-Nucleotide,Phosphodiesterase, 3',5'-Nucleotide,Phosphodiesterase, 3,5-Cyclic AMP,Phosphodiesterase, CAMP,Phosphodiesterases, 3',5'-Cyclic-AMP
D051379 Mice The common name for the genus Mus. Mice, House,Mus,Mus musculus,Mice, Laboratory,Mouse,Mouse, House,Mouse, Laboratory,Mouse, Swiss,Mus domesticus,Mus musculus domesticus,Swiss Mice,House Mice,House Mouse,Laboratory Mice,Laboratory Mouse,Mice, Swiss,Swiss Mouse,domesticus, Mus musculus

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