التفاصيل البيبلوغرافية
| العنوان: |
Rapid and Highly Selective Fluorescent Labeling of Peptides via a Thia-Diels–Alder Cycloaddition: Application to Apelin |
| المؤلفون: |
Timothé Maujean (14279551), Patrick Wagner (395007), Christel Valencia (1689829), Stéphanie Riché (1821982), Xavier Iturrioz (1821976), Pascal Villa (783039), Nicolas Girard (321735), Julie Karpenko (10323838), Mihaela Gulea (1402234), Dominique Bonnet (236351) |
| سنة النشر: |
2022 |
| مصطلحات موضوعية: |
Biophysics, Biochemistry, Medicine, Pharmacology, Biotechnology, Inorganic Chemistry, Space Science, Biological Sciences not elsewhere classified, Chemical Sciences not elsewhere classified, cell optical imaging, based competition assays, 37 ° c, three different fluorophores, lissamine rhodamine b, fully deprotected apelin, also successfully involved, resulting fluorescent ligand, 18 , 17 ± 0, 1 h ), 1 , 2 , successfully applied, fluorophores functionalized, apelin herein, wash conditions, throughput screening, straightforward labeling, resolved fret, peptides via |
| الوصف: |
Herein, we describe a catalyst-free thia-Diels–Alder cycloaddition for the chemoselective labeling of fully deprotected phosphonodithioester–peptides in solution with fluorophores functionalized with an exocyclic diene. The reaction was optimized on the model tripeptide 1 containing a lysine residue, which enabled its rapid and straightforward labeling with three different fluorophores (fluorescein, lissamine rhodamine B, and squaraine) in very mild conditions (H 2 O/ i PrOH, 37 °C, 1 h). The reaction was then successfully applied to the chemoselective labeling of fully deprotected apelin-13 with squaraine dye. The resulting fluorescent ligand 18 exhibited a high affinity (0.17 ± 0.03 nM) for apelinR. It enabled the development of time-resolved FRET-based competition assays for high-throughput screening and drug discovery. Thanks to its fluorogenic properties, ligand 18 was also successfully involved in the live-cell optical imaging of apelinR in no-wash conditions. |
| نوع الوثيقة: |
article in journal/newspaper |
| اللغة: |
unknown |
| Relation: |
https://figshare.com/articles/journal_contribution/Rapid_and_Highly_Selective_Fluorescent_Labeling_of_Peptides_via_a_Thia-Diels_Alder_Cycloaddition_Application_to_Apelin/21753412 |
| DOI: |
10.1021/acs.bioconjchem.2c00500.s001 |
| الاتاحة: |
https://doi.org/10.1021/acs.bioconjchem.2c00500.s001 |
| Rights: |
CC BY-NC 4.0 |
| رقم الانضمام: |
edsbas.303FC126 |
| قاعدة البيانات: |
BASE |