What question did this study set out to answer?

The study aims to explore how modifications to BODIPY photosensitizers affect their imaging and therapeutic properties, focusing on their interactions within cells.

February 9, 2026

Quaternary ammonium‐modified water‐soluble boron‐dipyrromethene photosensitizers for fluorescence imaging and photodynamic therapy

Puntos clave

The study aims to explore how modifications to BODIPY photosensitizers affect their imaging and therapeutic properties, focusing on their interactions within cells.
Synthesis of cationic BODIPY derivatives with various para-substituents.
Evaluation of photophysical properties including absorption and emission characteristics.
Assessment of singlet oxygen quantum yields and fluorescence quantum yields.
Cellular studies to investigate cytotoxicity and mitochondrial targeting using confocal microscopy.
BODIPY derivatives exhibited varying degrees of fluorescence quantum yields, with BITP showing the highest.
Singlet oxygen quantum yields were influenced by electronic effects from meso-phenyl substituents.
Light-activated cytotoxicity was significant for BITP and BMTP, while dark cytotoxicity was negligible.
Confocal studies confirmed effective mitochondrial targeting of the compounds.

Resumen

Abstract Quaternary‐ammonium‐functionalized BODIPY photosensitizers were synthesized and systematically investigated to elucidate the influence of meso‐phenyl electronic substitution on photophysical properties, intracellular behavior, and photodynamic therapy (PDT) performance. Four water‐soluble, cationic BODIPY derivatives bearing para‐substituents (–H, –OMe, –NO 2 , and –I) were prepared via an azide–alkyne click reaction, enabling a controlled structure–property comparison using a fixed mitochondrial‐targeting scaffold. All compounds exhibited characteristic BODIPY absorption and emission profiles, with BHTP, BMTP, and BITP maintaining high fluorescence quantum yields, whereas BNTP showed pronounced fluorescence quenching due to photo‐induced electron transfer. Singlet oxygen quantum yields (ΦΔ = 0.01–0.06) were strongly dependent on meso‐phenyl electronic effects, with BITP displaying the highest ΦΔ as a result of the heavy‐atom effect. Cellular studies revealed negligible dark cytotoxicity for all derivatives and pronounced light‐induced cytotoxicity for BITP and BMTP. Confocal co‐localization experiments confirmed preferential mitochondrial accumulation, as evidenced by strong overlap with MitoTracker Red signals. Collectively, these results demonstrate that meso‐phenyl electronic tuning, combined with a fixed cationic and water‐soluble BODIPY scaffold, provides an effective strategy for balancing fluorescence imaging and PDT activity, offering design guidelines for mitochondria‐targeted theranostic photosensitizers.

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