Acid-Resistant BODIPY Amino Acids for Peptide-Based Fluorescence Imaging of GPR54 Receptors in Pancreatic Islets.
Lorena Mendive-TapiaLaia Miret-CasalsNicole D BarthJinling WangAnne de BrayMassimiliano BeltramoVincent RobertChristophe AmpeDavid J HodsonAnnemieke MadderMarc VendrellPublished in: Angewandte Chemie (Weinheim an der Bergstrasse, Germany) (2023)
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.
Keyphrases
- living cells
- fluorescence imaging
- fluorescent probe
- amino acid
- single molecule
- photodynamic therapy
- binding protein
- fatty acid
- induced apoptosis
- high resolution
- primary care
- gene expression
- healthcare
- poor prognosis
- papillary thyroid
- cell cycle arrest
- cell death
- mass spectrometry
- dna binding
- cell proliferation
- signaling pathway
- quality improvement
- solid state
- tissue engineering