New estrogenic antagonists bearing dicarba-closo-dodecaborane as a hydrophobic pharmacophore.
We have designed and synthesized estrogen antagonists bearing dicarba-closo-dodecaborane (carborane) as a hydrophobic pharmacophore based on the structure of 1-(4-hydroxyphenyl)-1,12-dicarba-closo-dodecaborane, a potent estrogen agonist that we reported previously. Compounds with a long alkyl chain bearing an amide moiety on the carborane skeleton (6, 7) showed estrogen antagonistic activity in a luciferase reporter gene assay using COS-1 cells transfected with a rat ER alpha-expression plasmid and as an appropriate reporter plasmid.
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Graduate School of Pharmaceutical Sciences, University of Tokyo, Japan.
Yoshimi
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Yamakoshi
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D000818:Animals; D001896:Boron Compounds / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology; D019556:COS Cells / Q000187:drug effects; D002522:Chlorocebus aethiops; D004965:Estrogen Antagonists / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology; D004967:Estrogens / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology; D017930:Genes, Reporter / Q000187:drug effects; D008156:Luciferases / Q000737:chemistry / Q000235:genetics; D009682:Magnetic Resonance Spectroscopy; D013058:Mass Spectrometry; D051381:Rats; D011960:Receptors, Estrogen / Q000737:chemistry / Q000187:drug effects / Q000235:genetics; D013329:Structure-Activity Relationship
D001896:Boron Compounds; D004965:Estrogen Antagonists; D004967:Estrogens; D011960:Receptors, Estrogen; D008156:Luciferases