Polyamine biosynthesis in rat prostate. Substrate and inhibitor properties of 7-deaza analogues of decarboxylated S-adenosylmethionine and 5'-methylthioadenosine. 1977

J K Coward, and N C Motola, and J D Moyer

The 7-deaza analogue of 5'-methylthioadenosine, a nucleoside end product in polyamine biosynthesis, has been synthesized. This analogue has been shown to competitively inhibit the hydrolytic cleavage of the purine-ribose bond in methylthioadenosine with Ki congruent to Km. In addition, the 7-deaza analogue of decarboxylated S-adenosylmethionine, a cofactor in the biosynthesis of both spermidine and spermine, has been synthesized. This analogue has been shown to act as a substrate in the reaction catalyzed by spermidine synthase, 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.

UI MeSH Term Description Entries
D007700 Kinetics The rate dynamics in chemical or physical systems.
D008297 Male Males
D010430 Pentosyltransferases Enzymes of the transferase class that catalyze the transfer of a pentose group from one compound to another.
D011073 Polyamines Amine compounds that consist of carbon chains or rings containing two or more primary amino groups. Polyamine
D011436 Spermidine Synthase An enzyme that catalyzes the transfer of the propylamine moiety from 5'-deoxy-5'-S-(3-methylthiopropylamine)sulfonium adenosine to putrescine in the biosynthesis of spermidine. The enzyme has a molecular weight of approximately 73,000 kDa and is composed of two subunits of equal size. Aminopropyltransferase,Propylamine Transferase,Spermidine Synthetase,Putrescine Aminopropyltransferase,Aminopropyltransferase, Putrescine,Synthase, Spermidine,Synthetase, Spermidine,Transferase, Propylamine
D011467 Prostate A gland in males that surrounds the neck of the URINARY BLADDER and the URETHRA. It secretes a substance that liquefies coagulated semen. It is situated in the pelvic cavity behind the lower part of the PUBIC SYMPHYSIS, above the deep layer of the triangular ligament, and rests upon the RECTUM. Prostates
D003864 Depression, Chemical The decrease in a measurable parameter of a PHYSIOLOGICAL PROCESS, including cellular, microbial, and plant; immunological, cardiovascular, respiratory, reproductive, urinary, digestive, neural, musculoskeletal, ocular, and skin physiological processes; or METABOLIC PROCESS, including enzymatic and other pharmacological processes, by a drug or other chemical. Chemical Depression,Chemical Depressions,Depressions, Chemical
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
D012436 S-Adenosylmethionine Physiologic methyl radical donor involved in enzymatic transmethylation reactions and present in all living organisms. It possesses anti-inflammatory activity and has been used in treatment of chronic liver disease. (From Merck, 11th ed) AdoMet,Ademetionine,FO-1561,Gumbaral,S Amet,S-Adenosyl-L-Methionine,S-Adenosylmethionine Sulfate Tosylate,SAM-e,Samyr,FO 1561,FO1561,S Adenosyl L Methionine,S Adenosylmethionine,S Adenosylmethionine Sulfate Tosylate

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