Polyamine biosynthesis in rat prostate. Substrate and inhibitor properties of 7-deaza analogs of decarboxylated S-adenosylmethionine and 5'-methylthioadenosine
- 1 April 1977
- journal article
- research article
- Published by American Chemical Society (ACS) in Journal of Medicinal Chemistry
- Vol. 20 (4), 500-505
- https://doi.org/10.1021/jm00214a008
Abstract
The 7-deaza analogue of 5''-methylthioadenosine, a nucleoside end product in polyamine biosynthesis, was synthesized. This analogue competitively inhibits the hydrolytic cleavage of the purine-ribose bond in methylthioadenosine with Ki .simeq. Km. The 7-deaza analogue of decarboxylated S-adenosylmethionine, a cofactor in the biosynthesis of both spermidine and spermine, was synthesized. This analogue acts as a substrate in the reaction catalyzed by spermidine synthease, in which severe substrate inhibition by both the normal nucleoside substrate and the 7-deaza analogue is observed. These results are discussed in terms of possible end product regulation of polyamine biosynthesis and the possible substitution of the nucleoside antibiotic, tubercidin, for adenosine in reactions involving S-adenosylmethionine and its metabolites.This publication has 9 references indexed in Scilit:
- Potential inhibitors of S-adenosylmethionine-dependent methyltransferases. 4. Further modifications of the amino acid and base portions of S-adenosyl-L-homocysteineJournal of Medicinal Chemistry, 1976
- Potential inhibitors of S-adenosylmethionine-dependent methyltransferases. 6. Structural modifications of S-adenosylmethionineJournal of Medicinal Chemistry, 1976
- Potential inhibitors of S-adenosylmethionine-dependent methyltransferases. 5. Role of the asymmetric sulfonium pole in the enzymic binding of S-adenosyl-L-methionineJournal of Medicinal Chemistry, 1976
- Analogues of S-adenosylhomocysteine as potential inhibitors of biological transmethylation. Synthesis of analogues with modifications at the 5'-thioether linkageJournal of Medicinal Chemistry, 1976
- Irreversible inhibition of mammalian and yeast S-adenosylmethionine decarboxylase by 1,1′-(methylethanediylidenedinitrilo)-bis(3-aminoguanidine)Biochemical and Biophysical Research Communications, 1976
- EFFECT OF S-ADENOSYLHOMOCYSTEINE AND S-TUBERCIDINYLHOMOCYSTEINE ON TRANSFER RIBONUCLEIC-ACID METHYLATION IN PHYTOHEMAGGLUTININ-STIMULATED LYMPHOCYTES1975
- Purification and properties of N5, N10-methylenetetrahydrofolate dehydrogenase of calf thymusBiochimica et Biophysica Acta (BBA) - Enzymology and Biological Oxidation, 1965
- Observations on the metabolism of 5′-methylthioadenosineArchives of Biochemistry and Biophysics, 1964
- THE STABILITY AND HYDROLYSIS OF S-ADENOSYL-METHIONINE; ISOLATION OF S-RIBOSYLMETHIONINEJournal of Biological Chemistry, 1958