WazaGaY: An Innovative Aza-BODIPY-Derived Near-Infrared Fluorescent Probe for Enhanced Tumor Imaging
Aza-BODIPYs represent a class of fluorophores in which the π-conjugated system is rigidified and stabilized by a boron atom. A promising strategy to enhance their fluorescence properties involves replacing the boron atom with a metal ion. Here, we describe the synthesis and characterization of a water-soluble derivative where the metal is a gallium(III) ion, termed WazaGaY (water-soluble aza-GaDIPY). Water solubility is ensured by two ammonium substituents, inducing a bathochromic shift and a significant increase in quantum yield compared to that of the dimethylamino analog. The cellular behavior of <b>WazaGaY-1</b> was observed across different tumor cells. <i>In vivo</i>, the distribution and safety profiles were determined, and tumor uptake was assessed in various tumor types. Following intravenous injection, <b>WazaGaY-1</b> enabled clear discrimination of tumors engrafted subcutaneously in mice with high tumor-to-muscle ratios (ranging from 7 to 20), even in the absence of specific conjugation. Its potential as a contrast agent for fluorescence-guided surgery was confirmed.
Authors
- Ewen Bodio (ORCID: https://orcid.org/0000-0003-2896-113X)
- Pierre Le Gendre (ORCID: https://orcid.org/0000-0003-2635-5216)
- Charlotte Cave
- Lucie Sancey (ORCID: https://orcid.org/0000-0002-0084-3775)
- Fabien Dalonneau
- Mohamed Bendellaa
- Benoît Busser (ORCID: https://orcid.org/0000-0002-9425-1577)
- Annika Sickinger (ORCID: https://orcid.org/0000-0001-8394-985X)
- Amélie Godard (ORCID: https://orcid.org/0000-0003-4697-1286)
- Olivier Maury (ORCID: https://orcid.org/0000-0002-4639-643X)
- Christine Goze (ORCID: https://orcid.org/0000-0002-3484-3837)
Institutions
- École Normale Supérieure de Lyon (FR)
- Centre National de la Recherche Scientifique (FR)
- Inserm (FR)
- Université de Bourgogne (FR)
- Institut Universitaire de France (FR)
- Institut de Chimie (FR)
- Laboratoire de Chimie (FR)
- Chimie et Interdisciplinarité, Synthèse, Analyse, Modélisation (FR)
- Institut pour l'avancée des biosciences (FR)
- Institut de Chimie Moléculaire de l'Université de Bourgogne (FR)
- Université Grenoble Alpes (FR)
- Nantes Université (FR)
Publication Details
- Journal
- Journal of Medicinal Chemistry
- Published
- 2024-09-17
- DOI
- https://doi.org/10.1021/acs.jmedchem.4c01435
- Citations
- 9
- Primary Topic
- Nanoplatforms for cancer theranostics
- Type
- article
- Field-Weighted Citation Impact
- 1.66
Funders
- Infrastructures en Biologie Santé et Agronomie
- Agence Nationale de la Recherche
- Ministère de l'Enseignement Supérieur et de la Recherche Scientifique
- Ligue Contre le Cancer
- Ministère de l'Enseignement Supérieur et de la Recherche
- Centre National de la Recherche Scientifique
- Conseil régional de Bourgogne-Franche-Comté
- Groupement des Entreprises Françaises dans la lutte contre le Cancer
- Société d'Accélération du Transfert de Technologies