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para ‐Functionalized Aryl‐di‐ tert ‐butylfluorosilanes as Potential Labeling Synthons for 18 F Radiopharmaceuticals
Author(s) -
Iovkova Ljuba,
Wängler Björn,
Schirrmacher Esther,
Schirrmacher Ralf,
Quandt Gabriele,
Boening Guido,
Schürmann Markus,
Jurkschat Klaus
Publication year - 2009
Publication title -
chemistry – a european journal
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.687
H-Index - 242
eISSN - 1521-3765
pISSN - 0947-6539
DOI - 10.1002/chem.200802266
Subject(s) - synthon , chemistry , aryl , yield (engineering) , derivative (finance) , stereochemistry , medicinal chemistry , organic chemistry , materials science , alkyl , economics , financial economics , metallurgy
Broad spectrum : Novel para ‐functionalized aryl‐di‐ tert ‐butylfluorosilanes, p ‐( t Bu 2 FSi)C 6 H 4 X (X=functional group), have been made available and broaden the spectrum of silicon‐based 18 F acceptors (SiFAs) for potential PET applications. For example, the [ 18 F]maleimido derivative 1 has been employed for the synthesis of [ 18 F] 1 ‐ labeled rat serum albumin (RSA), the applicability of which for PET has been verified by in vivo experiments.The syntheses of the functionalized triorganofluorosilanes t Bu 2 ( p ‐XC 6 H 4 )SiF ( 3 a , X=SH; 4 a , X=NCS; 4 b , X=NCO; 5 , X=NC 4 H 2 O 2 ; 7 , X=COOH; 8 a , X=COONC 4 H 4 O 2 ; 8 b , X=COOC 6 F 5 ) are reported. These compounds display potential as silicon‐based fluoride acceptors (SiFAs). The molecular structures of compounds 5 , 7 , and 8 a have been determined by single‐crystal X‐ray diffraction studies. With the exception of compounds 8 a and 8 b , all of the compounds could be 18 F‐labeled by isotopic exchange in good to high radiochemical yields (RCY) with good to excellent specific activities. As proof of applicability, the maleimido‐functionalized SiFA derivative 5 , which is specific for thiol groups, has been used for the labeling of rat serum albumin (RSA) that had been derivatized with 2‐iminothiolane. The incorporation of [ 18 F] 5 into the derivatized RSA reached a maximum yield after 30 min at ambient temperature. After purification, the [ 18 F]RSA was evaluated in a healthy rat by means of μPET and displayed an expedient in vivo stability over 180 min.