Acid‐resistant BODIPY amino acids for peptide‐based fluorescence imaging of GPR54 receptors in pancreatic islets
- Author
- Lorena Mendive-Tapia, Laia Miret Casals (UGent) , Nicole Barth, Jinling Wang, Anne de Bray, Massimiliano Beltramo, Vincent Robert, Christophe Ampe (UGent) , David Hodson, Annemieke Madder (UGent) and Marc Vendrell
- Organization
- Project
- Abstract
- The G protein-coupled kisspeptin receptor (GPR54 or KISS1R) is an important mediator in reproduction, metabolism and cancer biology; however, there are limited fluorescent probes or antibodies for direct imaging of these receptors in cells and intact tissues, which can help to interrogate their multiple biological roles. Herein, we describe the rational design and characterization of a new acid-resistant BODIPY-based amino acid (Trp-BODIPY PLUS), and its implementation for solid-phase synthesis of fluorescent bioactive peptides. Trp-BODIPY PLUS retains the binding capabilities of both short linear and cyclic peptides and displays notable turn-on fluorescence emission upon target binding for wash-free imaging. Finally, we employed Trp-BODIPY PLUS to prepare some of the first fluorogenic kisspeptin-based probes and visualized the expression and localization of GPR54 receptors in human cells and in whole mouse pancreatic islets by fluorescence imaging.
- Keywords
- General Chemistry, Catalysis, Solid-Phase Peptide Synthesis, Probes, GPCRs, Fluorescence, Diabetes
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Please use this url to cite or link to this publication: http://hdl.handle.net/1854/LU-01GVWP1M7EHV2JT62AG40K8ZDV
- MLA
- Mendive-Tapia, Lorena, et al. “Acid‐resistant BODIPY Amino Acids for Peptide‐based Fluorescence Imaging of GPR54 Receptors in Pancreatic Islets.” ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, vol. 62, no. 20, Wiley, 2023, doi:10.1002/anie.202302688.
- APA
- Mendive-Tapia, L., Miret Casals, L., Barth, N., Wang, J., de Bray, A., Beltramo, M., … Vendrell, M. (2023). Acid‐resistant BODIPY amino acids for peptide‐based fluorescence imaging of GPR54 receptors in pancreatic islets. ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 62(20). https://doi.org/10.1002/anie.202302688
- Chicago author-date
- Mendive-Tapia, Lorena, Laia Miret Casals, Nicole Barth, Jinling Wang, Anne de Bray, Massimiliano Beltramo, Vincent Robert, et al. 2023. “Acid‐resistant BODIPY Amino Acids for Peptide‐based Fluorescence Imaging of GPR54 Receptors in Pancreatic Islets.” ANGEWANDTE CHEMIE-INTERNATIONAL EDITION 62 (20). https://doi.org/10.1002/anie.202302688.
- Chicago author-date (all authors)
- Mendive-Tapia, Lorena, Laia Miret Casals, Nicole Barth, Jinling Wang, Anne de Bray, Massimiliano Beltramo, Vincent Robert, Christophe Ampe, David Hodson, Annemieke Madder, and Marc Vendrell. 2023. “Acid‐resistant BODIPY Amino Acids for Peptide‐based Fluorescence Imaging of GPR54 Receptors in Pancreatic Islets.” ANGEWANDTE CHEMIE-INTERNATIONAL EDITION 62 (20). doi:10.1002/anie.202302688.
- Vancouver
- 1.Mendive-Tapia L, Miret Casals L, Barth N, Wang J, de Bray A, Beltramo M, et al. Acid‐resistant BODIPY amino acids for peptide‐based fluorescence imaging of GPR54 receptors in pancreatic islets. ANGEWANDTE CHEMIE-INTERNATIONAL EDITION. 2023;62(20).
- IEEE
- [1]L. Mendive-Tapia et al., “Acid‐resistant BODIPY amino acids for peptide‐based fluorescence imaging of GPR54 receptors in pancreatic islets,” ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, vol. 62, no. 20, 2023.
@article{01GVWP1M7EHV2JT62AG40K8ZDV,
abstract = {{The G protein-coupled kisspeptin receptor (GPR54 or KISS1R) is an important mediator in reproduction, metabolism and cancer biology; however, there are limited fluorescent probes or antibodies for direct imaging of these receptors in cells and intact tissues, which can help to interrogate their multiple biological roles. Herein, we describe the rational design and characterization of a new acid-resistant BODIPY-based amino acid (Trp-BODIPY PLUS), and its implementation for solid-phase synthesis of fluorescent bioactive peptides. Trp-BODIPY PLUS retains the binding capabilities of both short linear and cyclic peptides and displays notable turn-on fluorescence emission upon target binding for wash-free imaging. Finally, we employed Trp-BODIPY PLUS to prepare some of the first fluorogenic kisspeptin-based probes and visualized the expression and localization of GPR54 receptors in human cells and in whole mouse pancreatic islets by fluorescence imaging.}},
articleno = {{e202302688}},
author = {{Mendive-Tapia, Lorena and Miret Casals, Laia and Barth, Nicole and Wang, Jinling and de Bray, Anne and Beltramo, Massimiliano and Robert, Vincent and Ampe, Christophe and Hodson, David and Madder, Annemieke and Vendrell, Marc}},
issn = {{1433-7851}},
journal = {{ANGEWANDTE CHEMIE-INTERNATIONAL EDITION}},
keywords = {{General Chemistry,Catalysis,Solid-Phase Peptide Synthesis,Probes,GPCRs,Fluorescence,Diabetes}},
language = {{eng}},
number = {{20}},
pages = {{9}},
publisher = {{Wiley}},
title = {{Acid‐resistant BODIPY amino acids for peptide‐based fluorescence imaging of GPR54 receptors in pancreatic islets}},
url = {{http://doi.org/10.1002/anie.202302688}},
volume = {{62}},
year = {{2023}},
}
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