Exploring the relationship between structure and activity in BODIPYs designed for antimicrobial phototherapy

Abstract

A series of BODIPYs were evaluated for their phototoxic activity against Gram-positive S. aureus and Gram-negative P. aeruginosa. Specifically, carbohydrate/dibromosubstituted BODIPYs showed a highly effective inactivation of S. aureus.

Dipyrrinato‐Iridium(III) Complexes for Application in Photodynamic Therapy and Antimicrobial Photodynamic Inactivation

“…In this work, meso ‐substituted dipyrrins based on the 5‐pentafluorophenyl and the 5‐(4‐fluoro‐3‐nitrophenyl) moiety were tested for the preparation of dipyrrinato iridium(III) complexes. The pentafluorophenyl group, as well as the 4‐fluoro‐3‐nitrophenyl group, enable subsequent nucleophilic aromatic substitution reactions (S N Ar), introducing, e.g., sugar moieties [27a, 28e, 31] or alkynyl groups, giving access to subsequent 1,3‐dipolar cycloaddition reactions for the connection with biomolecules or polyethylene glycols (“click” chemistry) [32]…”

“…In preparation for the following experiments, the meso ‐substituted dipyrromethanes 1 – 15 were synthesized according to known procedures published by us and others [28a,b,d,e, 33] . Dipyrromethanes can then be transformed into the dipyrrins via oxidation with a suitable oxidation agent [22b, 27a, 28d, 33, 34] .…”

“… Synthesis of meso ‐substituted dipyrrins via oxidation of dipyrromethanes (dipyrromethanes were synthesized according to the literature) [28a,b,d,e, 33] …”

Hydrolytic Degradability, Cell Tolerance and On-Demand Antibacterial Effect of Electrospun Photodynamically Active Fibres

“…Variation of PS dosage and light intensity can be exploited to control the extent of photodynamic effect; however, accomplishing selective antimicrobial activity is still a challenge due to the concentration-dependent aggregation of PS molecules [ 9 ], which can lead to limited ROS generation [ 10 ], water solubility [ 6 , 11 ] and visible light absorption [ 12 ]. These limitations restrict the applicability of PDT in the clinical management of infectious diseases [ 13 ], at a time when the need for new antimicrobial strategies has never been more critical.…”

“…These limitations restrict the applicability of PDT in the clinical management of infectious diseases [ 13 ], at a time when the need for new antimicrobial strategies has never been more critical. Although the synthesis and testing of new PSs to address the above-mentioned challenges has been reported [ 10 , 11 , 14 ], encapsulation of PSs already in use in the clinic in polymer carriers represents a promising route to minimise PS aggregation, ensure a prolonged therapeutic window and comply with current regulatory framework [ 15 , 16 , 17 , 18 ]. With this strategy, control of the (i) release profile of PS from the carrier, (ii) PS uptake in both cells and bacteria and (iii) selectivity between the bactericidal effect and sparing effect upon host cells are key to successful performance.…”