Acid‐Resistant BODIPY Amino Acids for Peptide‐Based Fluorescence Imaging of GPR54 Receptors in Pancreatic Islets
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.
- Location
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Deutsche Nationalbibliothek Frankfurt am Main
- Extent
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Online-Ressource
- Language
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Englisch
- Bibliographic citation
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Acid‐Resistant BODIPY Amino Acids for Peptide‐Based Fluorescence Imaging of GPR54 Receptors in Pancreatic Islets ; day:12 ; month:04 ; year:2023 ; extent:9
Angewandte Chemie / International edition. International edition ; (12.04.2023) (gesamt 9)
- Creator
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Mendive‐Tapia, Lorena
Miret‐Casals, Laia
Barth, Nicole D.
Wang, Jinling
de Bray, Anne
Beltramo, Massimiliano
Robert, Vincent
Ampe, Christophe
Hodson, David J.
Madder, Annemieke
Vendrell, Marc
- DOI
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10.1002/anie.202302688
- URN
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urn:nbn:de:101:1-2023041315120331225731
- Rights
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Open Access; Der Zugriff auf das Objekt ist unbeschränkt möglich.
- Last update
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14.08.2025, 10:55 AM CEST
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Associated
- Mendive‐Tapia, Lorena
- Miret‐Casals, Laia
- Barth, Nicole D.
- Wang, Jinling
- de Bray, Anne
- Beltramo, Massimiliano
- Robert, Vincent
- Ampe, Christophe
- Hodson, David J.
- Madder, Annemieke
- Vendrell, Marc
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Acid‐Resistant BODIPY Amino Acids for Peptide‐Based Fluorescence Imaging of GPR54 Receptors in Pancreatic Islets
Rational Design of Phe‐BODIPY Amino Acids as Fluorogenic Building Blocks for Peptide‐Based Detection of Urinary Tract Candida Infections
Acid‐Activatable Transmorphic Peptide‐Based Nanomaterials for Photodynamic Therapy
Efficient deprotection of F-BODIPY derivatives: removal of BF2 using Brønsted acids
Automated Amino Acid Analysis with Sensitive Fluorescence Detection
Nucleic acid-mediated fluorescence activation and chromophore assembly
The B & B approach: Ball-milling conjugation of dextran with phenylboronic acid (PBA)-functionalized BODIPY
Bioinspired Synthesis of Pulvinic Acids Including Xerocomic Acid and Fluorescence Properties of Bis‐lactone Intermediates
A fluorescence‐based yeast sensor for monitoring acetic acid
Peptide-based materials
Design of synthetic peptide-based fluorescence probes for turn-on detection of hyaluronan
Tatooche Islets,
Acid‐Resistant BODIPY Amino Acids for Peptide‐Based Fluorescence Imaging of GPR54 Receptors in Pancreatic Islets
Rational Design of Phe‐BODIPY Amino Acids as Fluorogenic Building Blocks for Peptide‐Based Detection of Urinary Tract Candida Infections
Acid‐Activatable Transmorphic Peptide‐Based Nanomaterials for Photodynamic Therapy
Efficient deprotection of F-BODIPY derivatives: removal of BF2 using Brønsted acids
Automated Amino Acid Analysis with Sensitive Fluorescence Detection
Nucleic acid-mediated fluorescence activation and chromophore assembly
The B & B approach: Ball-milling conjugation of dextran with phenylboronic acid (PBA)-functionalized BODIPY
Bioinspired Synthesis of Pulvinic Acids Including Xerocomic Acid and Fluorescence Properties of Bis‐lactone Intermediates
A fluorescence‐based yeast sensor for monitoring acetic acid
Peptide-based materials
Design of synthetic peptide-based fluorescence probes for turn-on detection of hyaluronan