DMAP-BODIPY Alkynes: A Convenient Tool for Labeling Biomolecules for Bimodal PET-Optical Imaging

被引：28
作者：
Brizet, Bertrand [1 ,2 ]
Goncalves, Victor [1 ]
Bernhard, Claire [1 ]
Harvey, Pierre D. [2 ]
Denat, Franck [1 ]
Goze, Christine [1 ]
机构：
[1] Univ Bourgogne, Inst Chim Mol, UMR 6302, F-21078 Dijon, France
[2] Univ Sherbrooke, Dept Chim, Sherbrooke, PQ J1K 2R1, Canada
来源：
CHEMISTRY-A EUROPEAN JOURNAL | 2014年 / 20卷 / 40期
基金：
加拿大自然科学与工程研究理事会;
关键词：
alkynes; click chemistry; fluorine; imaging agents; luminescence; radiochemistry; EMISSION-TOMOGRAPHY; DYES; CHEMISTRY; AGENTS; PEPTIDES; BOMBESIN; YIELD;
D O I：
10.1002/chem.201402379
中图分类号：
O6 [化学];
学科分类号：
0703 ;
摘要：
Several new boron dipyrromethene/N,N-dimethylaminopyridine (BODIPY-DMAP) assemblies were synthesized as precursors for bimodal imaging probes (optical imaging, I/positron emission tomography, PET). The photophysical properties of the new compounds were also studied. The first proof-of-concept was obtained with the preparation of several new BODIPY-labeled bombesins and evaluation of the affinity for bombesin receptors by using a competition binding assay. Fluorination reactions were investigated on DMAP-BODIPY precursors as well as on DMAP-BODIPY-labeled bombesins. Chemical modifications on the BODIPY core were also performed to obtain luminescent dyes emitting in the therapeutic window (650-900 nm), suitable for in vivo imaging, making these compounds promising precursors for PET/optical dual-modality imaging agents.
引用
收藏
页码：12933 / 12944
页数：12
相关论文
共 55 条
  • [1] Dual-Labeling Strategies for Nuclear and Fluorescence Molecular Imaging: A Review and Analysis
    Azhdarinia, Ali
    Ghosh, Pradip
    Ghosh, Sukhen
    Wilganowski, Nathaniel
    Sevick-Muraca, Eva M.
    [J]. MOLECULAR IMAGING AND BIOLOGY, 2012, 14 (03) : 261 - 276
  • [2] FLUORESCENCE SPECTROSCOPIC ANALYSIS OF N AND P ISOMERS OF DODCI
    BAUMLER, W
    PENZKOFER, A
    [J]. CHEMICAL PHYSICS, 1990, 140 (01) : 75 - 97
  • [3] First bodipy-DOTA derivatives as probes for bimodal imaging
    Bernhard, Claire
    Goze, Christine
    Rousselin, Yoann
    Denat, Franck
    [J]. CHEMICAL COMMUNICATIONS, 2010, 46 (43) : 8267 - 8269
  • [4] Fluorescent indicators based on BODIPY
    Boens, Noel
    Leen, Volker
    Dehaen, Wim
    [J]. CHEMICAL SOCIETY REVIEWS, 2012, 41 (03) : 1130 - 1172
  • [5] Boron functionalization of BODIPY by various alcohols and phenols
    Brizet, Bertrand
    Bernhard, Claire
    Volkova, Yulia
    Rousselin, Yoann
    Harvey, Pierre D.
    Goze, Christine
    Denat, Franck
    [J]. ORGANIC & BIOMOLECULAR CHEMISTRY, 2013, 11 (44) : 7729 - 7737
  • [6] Standards for photoluminescence quantum yield measurements in solution (IUPAC Technical Report)
    Brouwer, Albert M.
    [J]. PURE AND APPLIED CHEMISTRY, 2011, 83 (12) : 2213 - 2228
  • [7] CHENG Y, 1973, BIOCHEM PHARMACOL, V22, P3099
  • [8] A novel heterotrifunctional peptide-based cross-linking reagent for facile access to bioconjugates.: Applications to peptide fluorescent labelling and immobilisation
    Clave, Guillaume
    Boutal, Herve
    Hoang, Antoine
    Perraut, Francois
    Volland, Herve
    Renard, Pierre-Yves
    Romieu, Anthony
    [J]. ORGANIC & BIOMOLECULAR CHEMISTRY, 2008, 6 (17) : 3065 - 3078
  • [9] Difluorobora-s-diazaindacene dyes as highly selective dosimetric reagents for fluoride anions
    Coskun, A
    Akkaya, EU
    [J]. TETRAHEDRON LETTERS, 2004, 45 (25) : 4947 - 4949
  • [10] Fluorine-18-labelled fluoropyridines:: Advances in radiopharmaceutical design
    Dollé, F
    [J]. CURRENT PHARMACEUTICAL DESIGN, 2005, 11 (25) : 3221 - 3235
123456