Estradiol-mimetic probes. Preparation of 17 alpha-(6-aminohexynyl)estradiol biotin, fluorescein and acridinium conjugates.
3-O-tert-Butyldimethylsilyl-17 alpha-(6-mesyloxyhexynyl)estradiol was converted to the azide in 60-70% yield with NaN3/DMPU, then reduced to the corresponding amine (> 95% yield). Acylation with the N-hydroxysuccinimide esters of biotin, 5-carboxyfluorescein and 10-(3-sulfopropyl)-N-tosyl-N-(3- carboxypropyl)acridinium-9-carboxamide gave the title conjugates. The KDs of the tracers with an estradiol antibody ranged from 97-197 nM.
Adamczyk
M
M
Department of Chemistry, Abbott Laboratories, Abbott Park, IL 60064-3500, USA.
Chen
Y Y
YY
Moore
J A
JA
Mattingly
P G
PG
D000166:Acridines / Q000138:chemical synthesis* / Q000737:chemistry; D000911:Antibodies, Monoclonal; D001710:Biotin / Q000031:analogs & derivatives* / Q000138:chemical synthesis / Q000737:chemistry; D004958:Estradiol / Q000031:analogs & derivatives* / Q000138:chemical synthesis / Q000737:chemistry; D005452:Fluoresceins / Q000138:chemical synthesis* / Q000737:chemistry*; D005456:Fluorescent Dyes / Q000138:chemical synthesis* / Q000737:chemistry; D007118:Immunoassay; D018716:Molecular Mimicry
D000166:Acridines; D000911:Antibodies, Monoclonal; D005452:Fluoresceins; D005456:Fluorescent Dyes; D004958:Estradiol; D001710:Biotin; C045132:4-carboxyfluorescein