Convenient Access to Fluorescent Probes by Chemoselective Acylation of Hydrazinopeptides: Application to the Synthesis of the First Far-Red Ligand for Apelin Receptor Imaging

Margathe Jean-Francois; Iturrioz Xavier; Regenass Pierre; Karpenko Iuliia A.; Humbert Nicolas; de Rocquigny Hugues; Hibert Marcel; Llorens-Cortes Catherine; Bonnet Dominique

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Convenient Access to Fluorescent Probes by Chemoselective Acylation of Hydrazinopeptides: Application to the Synthesis of the First Far-Red Ligand for Apelin Receptor Imaging

机译：通过水合肽的化学选择性酰化作用方便地访问荧光探针：在合成第一个远红配体用于Apelin受体成像中的应用

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Herein, we develop a convenient method to facilitate the solution-phase fluorescent labelling of peptides based on the chemoselective acylation of alpha-hydrazinopeptides. This approach combines the advantages of using commercially available amine-reactive dyes and very mild conditions, which are fully compatible with the chemical sensitivity of the dyes. The usefulness of this approach was demonstrated by the labelling of apelin-13 peptide. Various fluorescent probes were readily synthesized, enabling the rapid optimization of their affinities for the apelin receptor. Thus, the first far-red fluorescent ligand with sub-nanomolar affinity for the apelin receptor was characterized and shown to track the receptor efficiently in living cells by fluorescence confocal microscopy.

机译：在本文中，我们基于α-肼基肽的化学选择性酰化，开发了一种方便的方法来促进肽的溶液相荧光标记。这种方法结合了使用可商购的胺反应性染料的优势和非常温和的条件，这些条件与染料的化学敏感性完全兼容。通过标记apelin-13肽证明了这种方法的有效性。各种荧光探针易于合成，可以快速优化其对apelin受体的亲和力。因此，通过荧光共聚焦显微镜表征并显示了对apelin受体具有亚纳摩尔亲和力的第一个远红外线荧光配体，并显示出该荧光配体可有效追踪活细胞中的受体。

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《Chemistry: A European journal》 |2016年第4期|共7页
作者
Margathe Jean-Francois; Iturrioz Xavier; Regenass Pierre; Karpenko Iuliia A.; Humbert Nicolas; de Rocquigny Hugues; Hibert Marcel; Llorens-Cortes Catherine; Bonnet Dominique;
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正文语种 eng
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chemical ligation; fluorescent probes; G-protein-coupled receptors; hydrazinopeptides; receptors;

机译：化学连接;荧光探针;G蛋白偶联受体;肼肽;受体;

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1. Convenient Access to Fluorescent Probes by Chemoselective Acylation of Hydrazinopeptides: Application to the Synthesis of the First Far-Red Ligand for Apelin Receptor Imaging [J] . Margathe Jean-Francois, Iturrioz Xavier, Regenass Pierre, Chemistry: A European journal . 2016,第4期

机译：通过水合肽的化学选择性酰化作用方便地访问荧光探针：在合成第一个远红配体用于Apelin受体成像中的应用
2. Far-red and near infrared BODIPY dyes: synthesis and applications for fluorescent pH probes and bio-imaging [J] . Yong Ni, Jishan Wu Organic & biomolecular chemistry . 2014,第23期

机译：远红和近红外BODIPY染料：荧光pH探针和生物成像的合成及应用
3. Convenient one-pot synthesis of 4-(dialkylaminobenzyl)triphenylphosphonium salts - Application to the synthesis of a fluorescent probe for multiphotonic imaging of biological membranes [J] . Porres L., Bhatthula BKG., Blanchard-Desce M. Synthesis: International Journal of Methods in Synthetic Organic Chemistry . 2003,第10期

机译：方便的一锅合成4-（二烷基氨基苄基）三苯基-盐-在生物膜多光子成像荧光探针的合成中的应用
4. A Turn-on Imaging Probe for GABA(A) Receptors Allows for Construction of Fluorescent Biosensor [C] . Seiji Sakamoto, Fumio Harada, Kei Yamaura 日本化学会春季年会講演予稿集 . 2018

机译：用于GABA（A）受体的导通成像探针允许荧光生物传感器的构建
5. I. The synthesis and coordination chemistry of novel 1,1,1-tris(aminomethyl)ethane (TAME) derived ligands and their use as size selective fluorescent zinc(II) sensors. II. The synthesis of strongly and weakly binding ligands with nitrogen, oxygen, and sulfur-donor groups to be used as receptors in fluorescent ratiometric indicators for transition metal ions. [D] . Kennedy, Daniel Patrick. 2007

机译：I.新型1,1,1-三（氨基甲基）乙烷（TAME）衍生的配体的合成和配位化学及其作为尺寸选择荧光锌（II）传感器的用途。二。具有氮，氧和硫供体基团的强结合和弱结合配体的合成，将用作过渡金属离子的荧光比率指示剂中的受体。
6. Push-pull dioxaborine as fluorescent molecular rotor: far-red fluorogenic probe for ligand-receptor interactions [O] . Iuliia A. Karpenko, Yosuke Niko, Viktor P. Yakubovskyi, -1

机译：推挽二氧杂萘灵作为荧光分子转子：配体-受体相互作用的远红荧光探针
7. Bioimaging: Biocompatible Nanoparticles with Aggregation-Induced Emission Characteristics as Far-Red/Near-Infrared Fluorescent Bioprobes for in Vitro and In Vivo Imaging Applications (Adv. Funct. Mater. 4/2012) [O] . Qin, Wei, Ding, Dan, Liu, Jianzhao, 2012

机译：生物成像：具有聚集诱导的发射特性的生物相容性纳米粒子，作为用于体外和体内成像应用的远红/近红外荧光生物探针（Adv。Funct。Mater。4/2012）

Convenient Access to Fluorescent Probes by Chemoselective Acylation of Hydrazinopeptides: Application to the Synthesis of the First Far-Red Ligand for Apelin Receptor Imaging

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