2-Fluoropyridine prosthetic compounds for the 18F labeling of bombesin analogues

被引：13
作者：
Inkster, James [1 ,2 ]
Lin, Kuo-Shyan [3 ]
Ait-Mohand, Samia [4 ]
Gosselin, Simon [4 ]
Benard, Francois [3 ]
Guerin, Brigitte [4 ]
Pourghiasian, Maral [3 ]
Ruth, Thomas [1 ,3 ]
Schaffer, Paul [1 ]
Storr, Tim [2 ]
机构：
[1] TRIUMF, Div Nucl Med, Vancouver, BC V6T 2A3, Canada
[2] Simon Fraser Univ, Dept Chem, Burnaby, BC V5A 1S6, Canada
[3] British Columbia Canc Agcy, Dept Mol Oncol, Vancouver, BC V5Z 1L3, Canada
[4] Univ Sherbrooke, Dept Nucl Med & Radiobiol, Sherbrooke, PQ J1H 5N4, Canada
来源：
BIOORGANIC & MEDICINAL CHEMISTRY LETTERS | 2013年 / 23卷 / 13期
基金：
加拿大自然科学与工程研究理事会; 加拿大健康研究院;
关键词：
Bombesin; Positron emission tomography; Fluorine-18; CuAAC chemistry; Neuropeptides; GASTRIN-RELEASING-PEPTIDE; IN-VIVO EVALUATION; NUCLEOPHILIC AROMATIC-SUBSTITUTION; CLICK CHEMISTRY; HUMAN PROSTATE; HIGH-AFFINITY; BREAST-CANCER; MOUSE MODEL; RECEPTOR; GRP;
D O I：
10.1016/j.bmcl.2013.04.060
中图分类号：
R914 [药物化学];
学科分类号：
100701 ;
摘要：
Acetylene-bearing 2-[F-18]fluoropyridines [F-18]FPy5yne and PEG-[F-18]FPyKYNE were prepared via efficient nucleophilic heteroaromatic [F-18]fluorination of their corresponding 2-trimethylammoniumpyrdinyl precursors. The prosthetic groups were conjugated to azide- and PEG(3)-modified bombesin(6-14) analogues via copper-catalyzed azide-alkyne cycloaddition couplings to yield mono- and di-mini-PEGylated ligands for PET imaging of the gastrin- releasing peptide receptor. The PEG(3)- and PEG(2)/PEG(3)-bearing F-18 peptides showed decreased lipophilicity relative to an analogous non-mini-PEGylated F-18 peptide. Assessment of water-soluble peptide pharmacokinetics and tumour-targeting capabilities in a mouse model of prostate cancer is currently underway. (c) 2013 Elsevier Ltd. All rights reserved.
引用
收藏
页码：3920 / 3926
页数：7
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