A new approach for BODIPY derivatives: Increasing the singlet oxygen formation by sonophotochemical technique

Abstract

Research to explore the therapeutic capacities of sensitizers in Photodynamic Therapy (PDT) has been among the topics that have been frequently explored in recent years.In this context, studies that improve the ability of sensitizers to produce singlet oxygen with the help of ultrasound draw so much attention. In addition, the importance of BODIPYs used as sensitizers in photodynamic and/or sonodynamic therapy (SDT) is increasing. Although the positive effect of sonophotodynamic therapy (SPDT) on phthalocyanine derivatives has been shown in both photophysicochemical and in vivo studies, according to the best of our knowledge, the effect of sonophotochemical measurements for BODIPY derivatives has not been reported in the literature yet. Evaluation of the sonophotochemical potentials of BODIPY derivatives and meeting this need in the literature are the biggest impetus of this study. In this context, we have synthesized a new BODIPY compound (BDPY2) with methoxystyryl substituents to evaluate the capability of singlet oxygen production by sonophotochemical method. Synthesized compound was illuminated using different spectroscopic techniques encompassing 1H-NMR, 13C-NMR,19F-NMR, UV-Vis, MS, and elemental analysis. phi Delta value of BDPY2 was calculated by the photochemical method as 0.33, while phi Delta value reached 0.68 by applying the sonophotochemical method. The obtained data proved that the singlet oxygen production increased considerably by changing the method from light irradiation to ultrasound/light. This result will be a pioneer study to comprehend the sonophotochemical measurements of BODIPY derivatives for in vivo or in vitro studies in the future.