Multivalent Phthalocyanine-Based Cationic Polymers with Enhanced Photodynamic Activity for the Bacterial Capture and Bacteria-Infected Wound Healing

Abstract

The solubility and photosensitive activity of phthalocyanine are crucial to photodynamic antibacterial performance. However, highly conjugated phthalocyanine with high singlet oxygen generation efficiency tends to aggregate in aqueous environments, leading to poor solubility and photodynamic antibacterial activity. Herein, we propose a novel photodynamic antibacterial therapeutic platform by a phthalocyanine-based polymeric photosensitizer for the efficient healing of a bacteria-infected wound. A prepared phthalocyanine-based chain-transfer agent and a tertiary amino group-containing monomer are applied in the reversible addition–fragmentation chain-transfer polymerization for the preparation of the polymeric photosensitizer, which is subsequently quaternized to obtain a positively charged surface. This water-soluble phthalocyanine-based polymer can strongly concentrate on bacterial membranes via electrostatic interaction. The formed singlet oxygen by the phthalocyanine-based polymer after 680 nm light irradiation plays an essential role in killing the Gram-positive and Gram-negative bacteria. The study of antibacterial action indicates that this nanocomposite can cause irreversible damage to the bacterial membranes, which can cause cytoplasm leakage and bacterial death. Moreover, this therapeutic platform has excellent biocompatibility and the capacity to heal the wounds of bacterial infections. Experimental results indicate that the design strategy of this phthalocyanine-based polymer can extend the application of the hydrophobic photosensitizer in the biomedical field.

Unleashing the Power of PET-RAFT Polymerization: Journey from Porphyrin-Based Photocatalysts to Combinatorial Technologies and Advanced Bioapplications

“…27,28,137 Studies have shown promising results regarding the efficacy of these biomacromolecules in treating various diseases such as cancer, 138,139 cardiovascular disorders, 140 and wound healing. 141 The PET-RAFT process, which utilizes catalysts derived from aromatic macrocyclic compounds, has significantly advanced the field, enabling the development of novel designs and applications. Through ongoing research and refinement, PET-RAFT holds great promise in providing effective and targeted treatment options for patients facing diverse ailments.…”

Photodynamic and photothermal therapies for bacterial infection treatment

“…A phthalocyanine‐based cationic polymer Pc‐pDMAEMA‐C 4 with an improved water solubility, a stronger photodynamic antibacterial effect, and a negligible cytotoxicity was synthesized by the Mei group (Figure 5a). [20] Pc‐pDMAEMA‐C 4 was prepared by the reversible addition fragmentation chain transfer polymerization using the DMAEMA monomer, followed by quaternization with 1‐bromobutane onto the tertiary amino group of the DMAEMA chain to form a cationic amino group. The hydrophilic p‐DMAEMA‐C 4 chains and hydrophobic phthalocyanine self‐assemble to a polymeric nanomicelle in an aqueous environment and thus show enhanced water solubility and dispersibility.…”

“…(b) Bacterial growth inhibition using various concentrations of Pc-pDMAEMA-C4 with and without 680 nm light irradiation. Reproduced from Ref [20]…”

Films of substituted zinc phthalocyanines as active layers of chemiresistive sensors for ammonia detection

“…Metal phthalocyanines (MPcs) are highly conjugated cyclic molecules that consist of four isoindole units linked by nitrogen atoms to a central metal. Since the discovery of phthalocyanines as dyes in 1907, 1 their popularity has increased due to their semiconducting, optical and electrochemical properties, thermal stability and chemical inertness, as well as non-toxicity, which led to their use in medicine, [2][3][4] photocatalysis, [5][6][7] catalysis, 8,9 in solar cells, 10,11 and other fields. Another important area of application of phthalocyanines is chemical sensing.…”