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-butynyl 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.
Faculty of Pharmacy, Laval University, Que., Canada.
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Covassin
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Desjardins
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Charest-Gaudreault
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Audette
M J
MJ
Bonneau
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Poulin
D001692:Biological Transport / Q000187:drug effects; D003432:Cross-Linking Reagents / Q000737:chemistry; D019281:Dimerization; D006801:Humans; D011073:Polyamines / Q000378:metabolism*; D013095:Spermidine / Q000031:analogs & derivatives* / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology; D013329:Structure-Activity Relationship; D014407:Tumor Cells, Cultured
D003432:Cross-Linking Reagents; D011073:Polyamines; C006760:norspermidine; D013095:Spermidine