Synthesis and evaluation of antimigratory and antiproliferative activities of lipid-linked [13]-macro-dilactones.
The biological activities of a family of novel, lipid-linked 13-membered-ring macro-dilactones are reported. These [13]-macro-dilactones were synthesized by diacylation of functionalized diols, followed by ring-closing metathesis under conditions we had previously reported. Antimigratory, cytostatic and cytotoxic activities of the compounds against cancer cells were evaluated. Compound 13 was the most potent in the series, while compound 10 had the broadest concentration range of subtoxic antiproliferative activity. These compounds share common structural components, namely the [13]-macro-dilactone templated by an octyl alpha-glucoside 4,6-diol.
Magpusao
Anniefer N
AN
Department of Chemistry, University of Connecticut, Storrs, CT 06269, USA.
Desmond
Richard T
RT
Billings
Katelyn J
KJ
Fenteany
Gabriel
G
Peczuh
Mark W
MW
D000970:Antineoplastic Agents / Q000138:chemical synthesis / Q000737:chemistry* / Q000494:pharmacology*; D045744:Cell Line, Tumor; D002465:Cell Movement / Q000187:drug effects; D049109:Cell Proliferation / Q000187:drug effects; D005960:Glucosides / Q000138:chemical synthesis / Q000737:chemistry* / Q000494:pharmacology*; D006801:Humans; D007783:Lactones / Q000138:chemical synthesis / Q000737:chemistry* / Q000494:pharmacology*; D008055:Lipids / Q000737:chemistry; D009369:Neoplasms / Q000188:drug therapy; D013329:Structure-Activity Relationship
D000970:Antineoplastic Agents; D005960:Glucosides; D007783:Lactones; D008055:Lipids; C018619:octyl-beta-D-glucoside