Synthesis of spermidine and norspermidine dimers as high affinity polyamine transport inhibitors

A series of novel spermidine and sym-norspermidine dimers was synthesized by crosslinking the polyamine backbones via alkylation of their secondary amino groups to butyl, trans-2-butenyl, 2-butenyl or p-xylyl bridges. The resulting hexamines behaved as high-affinity antagonists of polyamine uptake,...

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Bibliographic Details
Published in:Bioorganic & medicinal chemistry letters 1999-06, Vol.9 (12), p.1709-1714
Main Authors: Covassin, Laurence, Desjardins, Michel, Charest-Gaudreault, René, Audette, Marie, Bonneau, Marie-Josée, Poulin, Richard
Format: Article
Language:English
Subjects:
Antineoplastic agents
Biological and medical sciences
Biological Transport - drug effects
Cross-Linking Reagents - chemistry
Dimerization
General aspects
Humans
Medical sciences
Pharmacology. Drug treatments
Polyamines - metabolism
Spermidine - analogs & derivatives
Spermidine - chemical synthesis
Spermidine - chemistry
Spermidine - pharmacology
Structure-Activity Relationship
Tumor Cells, Cultured
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Summary:A series of novel spermidine and sym-norspermidine dimers was synthesized by crosslinking the polyamine backbones via alkylation of their secondary amino groups to butyl, trans-2-butenyl, 2-butenyl or p-xylyl bridges. The resulting hexamines behaved as high-affinity antagonists of polyamine uptake, with a relative potency that was dependent on the geometry of the linker structure. Novel polyamine dimers were obtained by crosslinking spermidine or norspermidine via alkylation of their central amino groups. The linker region is a major determinant of polyamine transport inhibition.
ISSN:0960-894X
1464-3405
DOI:10.1016/S0960-894X(99)00262-0