Synthesis and characterization of novel BODIPYs and their antioxidant, antimicrobial, photodynamic antimicrobial, antibiofilm and DNA interaction activities

Abstract

In the current study, we synthesized and characterized new BODIPY derivatives (1–4) having pyridine or thienyl‐pyridine substituents at meso‐ position and 4‐dibenzothienyl or benzo[b]thien‐2‐yl moieties at 2‐,6‐ positions. We investigated fluorescence properties and the ability to form singlet oxygen. In addition, various biological activities of BODIPYs such as DPPH scavenging, DNA binding/cleavage ability, cell viability inhibition, antimicrobial activity, antimicrobial photodynamic therapy (aPDT) and biofilm inhibition properties were performed. BODIPY derivatives BDPY‐3 (3) and BDPY‐4 (4) have high fluorescence quantum yields as 0.50 and 0.61 and 1O2 quantum yields were calculated as 0.83 for BDPY‐1 (1), 0.12 for BDPY‐2 (2), 0.11 for BDPY‐3 and 0.23 for BDPY‐4. BODIPY derivatives BDPY‐2, BDPY‐3 and BDPY‐4 displayed 92.54 ± 5.41%, 94.20 ± 5.50%, and 95.03 ± 5.54% antioxidant ability, respectively. BODIPY compounds showed excellent DNA chemical nuclease activity. BDPY‐2, BDPY‐3 and BDPY‐4 also exhibited 100% APDT activity against E. coli at all tested concentrations. In addition to these, they demonstrated a highly effective biofilm inhibition activity against Staphyloccous aureus and Pseudomans aeruginosa. BDPY‐4 showed the most effective antioxidant and DNA cleavage activity, while BDPY‐3 exhibited the most effective antimicrobial and antibiofilm activity.

Effects on Colonization Factors and Mechanisms Involved in Antimicrobial Sonophotodynamic Inactivation Mediated by Curcumin

“…In this context, antimicrobial photodynamic inactivation (PDI) is a powerful treatment that has been studied and proposed worldwide, and its effectiveness against bacteria, fungi and viruses has been demonstrated in a series of in vitro, in vivo and clinical studies. The PDI is based on the combination of three compounds: a photosensitizer (PS), a light source at an appropriate wavelength to excite the PS and molecular oxygen in the target tissue [6]. The mechanisms involved in the PDI action are very well known and described.…”

“…Both type 1 and 2 reactions occur simultaneously, but depending on the PS chemical structure, one of the reactions will be preferential. The efficiency of the PDI is often related to the 1 O 2 quantum yield of the PS [6][7][8][9][10][11].…”