558-63-4Relevant articles and documents
Studies toward the development of new silicon-containing building blocks for the direct 18F-labeling of peptides
Dialer, Lukas O.,Selivanova, Svetlana V.,Müller, Carmen J.,Müller, Adrienne,Stellfeld, Timo,Graham, Keith,Dinkelborg, Ludger M.,Kr?mer, Stefanie D.,Schibli, Roger,Reiher, Markus,Ametamey, Simon M.
, p. 7552 - 7563 (2013/11/06)
Silicon-containing prosthetic groups have been conjugated to peptides to allow for a single-step labeling with 18F radioisotope. The fairly lipophilic di-tert-butylphenylsilane building block contributes unfavorably to the pharmacokinetic profile of bombesin conjugates. In this article, theoretical and experimental studies toward the development of more hydrophilic silicon-based building blocks are presented. Density functional theory calculations were used to predict the hydrolytic stability of di-tert-butylfluorosilanes 2-23 with the aim to improve the in vivo properties of 18F-labeled silicon-containing biomolecules. As a further step toward improving the pharmacokinetic profile, hydrophilic linkers were introduced between the lipophilic di-tert-butylphenylsilane building block and the bombesin congeners. Increased tumor uptake was shown with two of these peptides in xenograft-bearing mice using positron emission tomography and biodistribution studies. The introduction of a hydrophilic linker is thus a viable approach to improve the tumor uptake of 18F-labeled silicon-bombesin conjugates.
18F-labeling of peptides by means of an organosilicon-based fluoride acceptor
Schirrmacher, Ralf,Bradtmoeller, Gerrit,Schirrmacher, Esther,Thews, Oliver,Tillmanns, Julia,Siessmeier, Thomas,Buchholz, Hans G.,Bartenstein, Peter,Waengler, Bjoern,Niemeyer, Christof M.,Jurkschat, Klaus
, p. 6047 - 6050 (2007/10/03)
(Chemical Equation Presented) F on: Fluorotriorganosilyl-derivatized Tyr3-octreotate was labeled with 18F- providing the first practical formulation in 18F-radiochemistry for the labeling of a peptide (see schem
(p-d) ? Bonding in Fluorosilanes? Gas-Phase Structures of (CH3)4-nSiFn with n = 1-3 and of t-Bu2SiF2
Rempfer, Beate,Oberhammer, Heinz,Auner, Norbert
, p. 3893 - 3897 (2007/10/02)
The gas-phase structures (rg values) of the methylfluorosilanes (CH3)4-nSiFn with n = 1-3 and of di-tert-butyl-difluorosilane, t-Bu2SiF2, have been determined by electron diffraction.In the case of CH3SiF3 the microwave rotational constant was included in the structure analysis.In the methylfluorosilane series a steady decrease of Si-F and Si-C bond lengths is observed with increasing fluorination: Si-F = 1.600(2), 1.586(2), and 1.570(2) Angstroem and Si-C = 1.848(2), 1.836(2), and 1.828(4) Angstroem for (CH3)3SiF, (CH3)2SiF2, and CH3SiF3, respectively.These trends are rationalized by increasing polar contributions and contraction of the silicon valence shell.Ab initio calculations for SiF4 indicate that (p-d) ? bonding is negligible.Substitution of the methyl groups in (CH3)2SiF2 by tert-butyl groups leads to lengthening of Si-F and Si-C bonds and strong variations in the silicon bond angles: Si-F = 1.586(2), 1.606(4) Angstroem; Si-C = 1.836(2), 1.869(3) Angstroem; CSiC = 116.7(6) deg, 125.5(11) deg; and FSiF = 104.6(4) deg, 97.7(8) deg in (CH3)2SiF2 and t-Bu2SiF2, respectively.
