High Singlet Oxygen Generating Benzothienyl‐[b]‐fused BODIPY Nanoaggregates and Photoinduced Apoptosis in Human Carcinoma

Abstract

Heavy atom free organic materials absorbing in red to near infrared (NIR) region are potential candidates as photosensitizers (PS) in photodynamic therapy (PDT). PDT relies on many factors and one of them is singlet oxygen generation ability of PS in aqueous medium. In this contribution, we report the synthesis of a new PS i. e., 8‐thienyl bisbenzothieno‐[b]‐fused‐boron‐dipyrromethene (BT‐[b]‐fused BODIPY). This PS shows absorption (λabs) at ~650 nm in toluene while in its water‐dispersible nanoaggregates it is found at ~764 nm. Nanoaggregates of BT‐[b]‐fused BODIPY demonstrated dual advantages, (i) facilitating PS release in the cellular system and (ii) sharply enhanced singlet oxygen efficiency ( ~48 %) in aqueous medium. Intracellular reactive oxygen species (ROS) generation was confirmed by 2′,7′‐dichlorodihydrofluorescein diacetate (DCFDA) assay in A549 cells. In vitro photocytotoxic studies of BT‐[b]‐fused BODIPY are carried out in different carcinomas i. e., MCF‐7 and A549 cells. It has zero dark cell toxicity while half maximal inhibitory concentration (IC50) in MCF‐7 is found to be low (6.08±1.1) μM and 7.41±1.9 μM in A549 on 15 min light exposure. These nanoaggregates induce apoptosis in cancer cells on light irradiation thereby proving it to be a potential PS for PDT.