Nickel Phthalocyanines as Potential Aggregation‐Induced Antibacterial Agents: Fenton‐Like Pathways Driven by Near‐Infrared Light

Abstract

The present report uncovers the Fenton‐like and solar‐Fenton activity of nickel‐coordinated phthalocyanines and their potential as antibacterial agents. In particular, two NiPcs, one achiral and the other chiral, with both having similar molecular structures, are designed. Both compounds aggregate to form crystals with large diversity in molecular stacking. The crystal grown from the achiral NiPc demonstrates superior Fenton‐like activity especially under NIR‐light illumination, and also exhibits efficient antibacterial activity in vitro toward both E. coli and S. aureus. On the contrary, the crystal formed from stacked chiral molecules demonstrates weak Fenton‐like reactivity and is inefficient for bacterial disinfection. By examining the differences between the two crystals, we have disclosed the mechanism of the Fenton‐like reactivity of the NiPcs associated with molecular aggregation. Moreover, the chiral NiPc and its crystal provide a good platform to inspect the correlation between the functions, for instance the antibacterial activity between the chiral selections. This work indicates that controlling small differences in molecular structure can provide an effective way to achieve specific functions, such as Fenton‐like activity, of organic semiconductors.

Antibacterial Chemodynamic Therapy: Materials and Strategies

“…Besides the commonly used metal elements (e.g., Fe, Cu, and Mn), other metal elements that have multiple redox states can also convert H 2 O 2 into toxic •OH via Fenton-like reactions for antibacterial CDT. Recently, metal elements like cobalt (Co) [ 139 , 140 ], molybdenum (Mo) [ 141 – 145 ], platinum (Pt) [ 146 , 147 ], tungsten (W) [ 148 , 149 ], nickel (Ni) [ 150 , 151 ], silver (Ag) [ 152 , 153 ], ruthenium (Ru) [ 154 ], vanadium (V) [ 155 , 156 ], gold (Au) [ 157 ], and zinc (Zn) [ 158 ] have been applied to the design of antibacterial platforms.…”

Superior photo-induced antibacterial/antibiofilm activities of ZnPcs/TiO2 and computational simulation studies

“…Accordingly, the achiral NiPc showed excellent Fenton-like activity under light illumination and also exhibited superior antibacterial effects on E. coli and S. aureus. 11 The process of revealing the binding affinity of receptorligand complexes with in silico structures using different software is called molecular docking. 19 Molecular docking has been regarded as a chemical compound modelling method, which could minimize wet lab errors.…”

“…Phthalocyanines (Pcs) are colored macrocyclic compounds with a very robust structure formed by the bonding of four pyrrole derivatives and can be synthesized as metal or metal-free. 11 Pcs have been a beacon of hope in the fight against pathogenic microorganisms due to their wide light absorption range, being an aromatic macrocyclic, with steerable photophysical and photochemical activities. 12 Pcs as photosensitizers, after light illumination, can cause the formation of cytotoxic and genotoxic reactive oxygen species (ROS), which damage target tissues and cells and also create the photothermal effect.…”

“…Accordingly, the achiral NiPc showed excellent Fenton-like activity under light illumination and also exhibited superior antibacterial effects on E. coli and S. aureus . 11…”