Document Detail


Inhibition of ornithine decarboxylase by the isomers of 1,4-dimethylputrescine.
MedLine Citation:
PMID:  2362277     Owner:  NLM     Status:  MEDLINE    
Abstract/OtherAbstract:
1,4-Dimethylputrescine (2,5-hexanediamine) was separated into its racemic and meso isomers by fractional crystallization of its dibenzoyl derivative. The racemic form was resolved into its (+)- and (-)-isomers with (+)- and (-)-dibenzoyltartaric acids. None of the three isomers (meso, +, and -) inhibited ornithine decarboxylase (ODC) activity in vitro, while all the three were strongly inhibitory of ODC when assayed in vivo in rats or in H-35 hepatoma cells. In rat liver the three isomers also decreased the putrescine pool while only the (+)-isomer decreased spermidine content. In the H-35 cells the (-)- and (+)-isomers decreased the spermidine and spermine content. When ODC was induced in the latter by insulin it was found that the (-)-isomer strongly inhibited protein and ODC synthesis, while the (+)-isomer and the meso isomer were less inhibitory. The meso isomer was a good inducer of ODC antizyme in rat liver, while the (+)- and (-)-isomers were poor inducers of the former.
Authors:
N Moyano; J Frydman; G Buldain; O Ruiz; R B Frydman
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Publication Detail:
Type:  Journal Article; Research Support, Non-U.S. Gov't; Research Support, U.S. Gov't, P.H.S.    
Journal Detail:
Title:  Journal of medicinal chemistry     Volume:  33     ISSN:  0022-2623     ISO Abbreviation:  J. Med. Chem.     Publication Date:  1990 Jul 
Date Detail:
Created Date:  1990-08-06     Completed Date:  1990-08-06     Revised Date:  2007-11-14    
Medline Journal Info:
Nlm Unique ID:  9716531     Medline TA:  J Med Chem     Country:  UNITED STATES    
Other Details:
Languages:  eng     Pagination:  1969-74     Citation Subset:  IM    
Affiliation:
Facultad de Farmacia y Bioquímica, Universidad de Buenos Aires, Argentina.
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MeSH Terms
Descriptor/Qualifier:
Animals
Cell Line
Female
Isomerism
Liver / drug effects,  enzymology
Liver Neoplasms, Experimental
Neoplasm Proteins / biosynthesis
Optical Rotation
Ornithine Decarboxylase / antagonists & inhibitors*
Polyamines / metabolism
Putrescine / analogs & derivatives*,  chemical synthesis,  isolation & purification,  pharmacology*
Rats
Rats, Inbred Strains
Structure-Activity Relationship
Thioacetamide / pharmacology
Tumor Cells, Cultured / drug effects,  metabolism
Grant Support
ID/Acronym/Agency:
GM-11973/GM/NIGMS NIH HHS
Chemical
Reg. No./Substance:
0/Neoplasm Proteins; 0/Polyamines; 110-60-1/Putrescine; 37143-63-8/1,4-dimethylputrescine; 62-55-5/Thioacetamide; EC 4.1.1.17/Ornithine Decarboxylase

From MEDLINE®/PubMed®, a database of the U.S. National Library of Medicine


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