title: para-Functionalized aryl-di-tert-butylfluorosilanes as potential labeling synthons for (18)F radiopharmaceuticals.
abstract: Broad spectrum: Novel para-functionalized aryl-di-tert-butylfluorosilanes, p-(tBu(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 tBu(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 muPET and displayed an expedient in vivo stability over 180 min.
authors.affiliation: Lehrstuhl für Anorganische Chemie II, Technische Universität Dortmund, 44221 Dortmund, Germany.
authors.forename: Ljuba
authors.initials: L
authors.lastname: Iovkova
authors.forename: Björn
authors.initials: B
authors.lastname: Wängler
authors.forename: Esther
authors.initials: E
authors.lastname: Schirrmacher
authors.forename: Ralf
authors.initials: R
authors.lastname: Schirrmacher
authors.forename: Gabriele
authors.initials: G
authors.lastname: Quandt
authors.forename: Guido
authors.initials: G
authors.lastname: Boening
authors.forename: Markus
authors.initials: M
authors.lastname: Schürmann
authors.forename: Klaus
authors.initials: K
authors.lastname: Jurkschat
mesh_terms: D000818:Animals; D018360:Crystallography, X-Ray; D005462:Fluorine Radioisotopes; D006845:Hydrocarbons, Fluorinated / Q000097:blood / Q000138:chemical synthesis* / Q000737:chemistry; D008297:Male; D008968:Molecular Conformation; D015394:Molecular Structure; D049268:Positron-Emission Tomography; D019275:Radiopharmaceuticals / Q000097:blood / Q000138:chemical synthesis* / Q000737:chemistry; D051381:Rats; D012821:Silanes / Q000138:chemical synthesis* / Q000737:chemistry; D013237:Stereoisomerism
chemical_list: D005462:Fluorine Radioisotopes; D006845:Hydrocarbons, Fluorinated; D019275:Radiopharmaceuticals; D012821:Silanes