Synthesis and structural characterization of a cardioactive biotinylated digoxin analogue.
We have biotinylated the terminal glycose of digoxin by reaction of the periodate-oxidized steroid with biotin hydrazide. A biotinylated product (BD-1) was formed which retained significant digoxin receptor (Na+/K+ ATPase) binding activity. Sustained reaction resulted in a second biotinylated product (BD-2) which showed reduced receptor binding activity. The products were characterized by FAB mass spectroscopy and shown to be the mono- and di-biotinylated digoxin conjugates of the oxidized glycose moiety. These analogues may prove useful in determining the subcellular site of digoxin binding.
Nutikka
A
A
Research Institute, Hospital for Sick Children, Toronto, Ontario, Canada.
Pang
H
H
Soldin
S
S
Lingwood
C
C
D001710:Biotin / Q000031:analogs & derivatives*; D002240:Carbohydrate Sequence; D002316:Cardiotonic Agents / Q000737:chemistry* / Q000378:metabolism; D004077:Digoxin / Q000031:analogs & derivatives* / Q000737:chemistry / Q000378:metabolism / Q000494:pharmacology; D006801:Humans; D008969:Molecular Sequence Data; D015394:Molecular Structure; D011955:Receptors, Drug / Q000378:metabolism
D002316:Cardiotonic Agents; D011955:Receptors, Drug; C053311:biotin hydrazide; D001710:Biotin; D004077:Digoxin