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
相关论文
共 65 条
  • [1] ISOLATION AND STRUCTURE OF BOMBESIN AND ALYTESIN, 2 ANALOGOUS ACTIVE PEPTIDES FROM SKIN OF EUROPEAN AMPHIBIANS BOMBINA AND ALYTES
    ANASTASI, A
    ERSPAMER, V
    BUCCI, M
    [J]. EXPERIENTIA, 1971, 27 (02): : 166 - &
  • [2] Direct One-Step18F-Labeling of Peptides via Nucleophilic Aromatic Substitution
    Becaud, Jessica
    Mu, Linjing
    Karramkam, Mylene
    Schubiger, Pius A.
    Ametamey, Simon M.
    Graham, Keith
    Stellfeld, Timo
    Lehmann, Lutz
    Borkowski, Sandra
    Berndorff, Dietmar
    Dinkelborg, Ludger
    Srinivasan, Ananth
    Smits, Rene
    Koksch, Beate
    [J]. BIOCONJUGATE CHEMISTRY, 2009, 20 (12) : 2254 - 2261
  • [3] Molecular imaging of gastrin-releasing peptide receptor-positive tumors in mice using 64Cu- and 86Y-DOTA-(Pro1,Tyr4)-Bombesin(1-14)
    Biddlecombe, Grainne B.
    Rogers, Buck E.
    de Visser, Monique
    Parry, Jesse J.
    de Jong, Marion
    Erion, Jack L.
    Lewis, Jason S.
    [J]. BIOCONJUGATE CHEMISTRY, 2007, 18 (03) : 724 - 730
  • [4] USE OF 2-HYDROXYPROPYL-BETA-CYCLODEXTRIN AS A SOLUBILIZING AND STABILIZING EXCIPIENT FOR PROTEIN DRUGS
    BREWSTER, ME
    HORA, MS
    SIMPKINS, JW
    BODOR, N
    [J]. PHARMACEUTICAL RESEARCH, 1991, 8 (06) : 792 - 795
  • [5] Strain-Promoted Copper-Free "Click" Chemistry for 18F Radiolabeling of Bombesin
    Campbell-Verduyn, Lachlan S.
    Mirfeizi, Leila
    Schoonen, Anne K.
    Dierckx, Rudi A.
    Elsinga, Philip H.
    Feringa, Ben L.
    [J]. ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2011, 50 (47) : 11117 - 11120
  • [6] Chen XY, 2004, J NUCL MED, V45, P1390
  • [7] COY DH, 1989, J BIOL CHEM, V264, P14691
  • [8] 68Ga-Labeled bombesin studies in patients with gastrointestinal stromal tumors:: Comparison with 18F-FDG
    Dimitrakopoulou-Strauss, Antonia
    Hohenberger, Peter
    Haberkorn, Uwe
    Maecke, Helmut R.
    Eisenhut, Michael
    Strauss, Ludwig G.
    [J]. JOURNAL OF NUCLEAR MEDICINE, 2007, 48 (08) : 1245 - 1250
  • [9] Dolci L, 1999, J LABELLED COMPD RAD, V42, P975, DOI 10.1002/(SICI)1099-1344(199910)42:10<975::AID-JLCR256>3.0.CO
  • [10] 2-E
1234567