Translating the concept of peptidelabeling with 5-deoxy-5-[¹⁸F]fluororibose into preclinical practice: ¹⁸F-labeling of Siglec-9 peptide for PET imaging of inflammation

Abstract

Peptide glycosylation with 5-deoxy-5-[(18)F]fluororibose was translated into preclinical settings. The novel (18)F-labeled Siglec-9 peptide was produced using an automated synthesis procedure. The (18)F-labeled Siglec-9 peptide showed favorable binding in the animal model of inflammation in vivo.

Enzymatic Fluorination and Biotechnological Developments of the Fluorinase

“…Also peptide Siglec-9 adduct 56, which has been developed as an inflammation marker, was successfully tagged with [ 18 F]-42 to image inflammation in a mouse model PET imaging study. 80,81 …”

Comparison of Somatostatin Receptor 2-Targeting PET Tracers in the Detection of Mouse Atherosclerotic Plaques

“…In negative controls the primary antibody was omitted from the protocol. [24,25]. Briefly, 5-deoxy-5-[ 18 F]-fluororibose as a prosthetic group was conjugated to the somatostatin analogue NOC peptide (0.3 mM, ABX GmbH, Radeberg, Germany) in anilinium buffer (0.3 M, pH 4.6) for 10 min at room temperature.…”

Sweetening Pharmaceutical Radiochemistry by18F-Fluoroglycosylation: A Short Review

“…This is a drawback when using large peptides which can undergo degradation under such high temperatures and acidic conditions. The use of 5-[ 18 F]fluoro-5-deoxyribose ([ 18 F]FDR) (Scheme 4) could compensate for these limitations because the location of the fluorine at C-5 of the 5-membered ring might facilitate the formation of the acyclic form of [ 18 F]FDR making it possible to perform the oxime formation at room temperature at pH 6.0 with high yields [37]. …”

“…In the endeavor to improve the oxime conjugation step, 5-[ 18 F]fluoro-5-deoxyribose ([ 18 F]FDR) has been considered as an alternative prosthetic group (Scheme 4) [36, 37, 55, 56]. The idea is that, in comparison to [ 18 F]FDG, the 5-membered ring sugar [ 18 F]FDR with the fluorine at C-5 instead of C-6 favors the ring opening of the sugar to the aldehydic form and therefore promotes the oxime ligation with aminooxy-functionalized peptides even under mild reaction conditions, such as ambient temperature and less acidic pH of 4.6.…”