Selenophene-Modified Boron Dipyrromethene-Based Photosensitizers Exhibit Photodynamic Inhibition on a Broad Range of Bacteria

Abstract

Microorganisms are crucial for human survival in view of both mutualistic and pathogen interactions. The control of the balance could be achieved by use of the antibiotics. There is a continuous arms race that exists between the pathogen and the antibiotics. The emergence of multidrug-resistant (MDR) bacteria threatens health even for insignificant injuries. However, the discovery of new antibiotics is not a fast process, and the healthcare system will suffer if the evolution of MDR lingers in its current frequency. The cationic photosensitizers (PSs) provide a unique approach to develop novel, light-inducible antimicrobial drugs. Here, we examine the antimicrobial activity of innovative selenophene-modified boron dipyrromethene (BODIPY)-based PSs on a variety of Gram (+) and Gram (−) bacteria. The candidates demonstrate a level of confidence in both light-dependent and independent inhibition of bacterial growth. Among them, selenophene conjugated PS candidates (BOD-Se and BOD-Se-I) are promising agents to induce photodynamic inhibition (PDI) on all experimented bacteria: E. coli , S. aureus , B. cereus , and P. aeruginosa . Further characterizations revealed that photocleavage ability on DNA molecules could be potentially advantageous over extracellular DNA possessing biofilm-forming bacteria such as B. cereus and P. aeruginosa . Microscopy analysis with fluorescent BOD-H confirmed the colocalization on GFP expressing E. coli .

Synthesis and Spectroscopic Properties of Selenophene[3, 2-b]-Fused BODIPYs

“…17−20 In addition, selenophene-modified BODIPY showed good application prospects in photodynamic therapy (PDT) for cancer treatment in a hypoxic environment 19 and anti-bacterial aspects. 20 Heterocyclic fused ring BODIPY is an effective modification method, and many types of [a]/[b]/ zig-zag-position heterocyclic-fused ring-modified BODIPY are developed. 21−26 So far, there is no report on selenophene-fusion BODIPY, which may be related to the lack of a proper synthesis method.…”

“…Selenophene is a unique heterocycle moiety, mainly due to the larger radius, higher polarizability, and lower electronegativity of the selenium atom compared to the sulfur atom. , Functional materials containing selenophenes tend to have narrow optical bands and strong intermolecular forces, showing good charge transport capabilities. , At present, selenophene-modified BODIPY is mainly loaded with one or more selenophene units at the periphery of its parent nucleus, achieving a series of photosensitizers with near-infrared absorption (Scheme ). − In addition, selenophene-modified BODIPY showed good application prospects in photodynamic therapy (PDT) for cancer treatment in a hypoxic environment and anti-bacterial aspects . Heterocyclic fused ring BODIPY is an effective modification method, and many types of [a]/[b]/zig-zag-position heterocyclic-fused ring-modified BODIPY are developed. − So far, there is no report on selenophene-fusion BODIPY, which may be related to the lack of a proper synthesis method.…”

Small Molecular Fluorescent Probes: Application Progress of Specific Bacteria Detection and Antibacterial Phototherapy

“…examine selenophene‐modified boron dipyrromethene (BODIPY)‐based PSs to induce photodynamic inhibition for a variety of Gram (+) and Gram (−) bacteria: E. coli , S. aureus , B. cereus , and P. aeruginosa . The inherent limitation of PDT is the generation of ROS which is restricted by the hypoxic microenvironment in infection sites [80] . Zhang et al [81] .…”

“…Many researchers have devoted themselves to the development of BODIPY PS for its adjustable emission to the near-infrared region (NIR) through structural modification. [79] Gunbas et al [80] examine selenophene-modified boron dipyrromethene (BODIPY)-based PSs to induce photodynamic inhibition for a variety of Gram (+) and Gram (À ) bacteria: E. coli, S. aureus, B. cereus, and P. aeruginosa. The inherent limitation of PDT is the generation of ROS which is restricted by the hypoxic microenvironment in infection sites.…”

Nano‐Econazole Enhanced PD‐L1 Checkpoint Blockade for Synergistic Antitumor Immunotherapy against Pancreatic Ductal Adenocarcinoma

“…Photodynamic therapy (PDT) depends on the levels of light‐dependent reactive oxygen species (ROS) induced by photosensitizers. [ 8 ] It is a promising approach in oncotherapy with the advantages of a low incidence of adverse effects and high specificity. The combination of PDT and photothermal therapy (PTT), is another potential phototherapy strategy that utilizes laser light to activate photosensitizers and produces energy for tumor eradication, effectively overcoming the drawbacks of PDT and enhancing the therapeutic effects.…”