Photobactericidal Porphyrin-Cellulose Nanocrystals: Synthesis, Characterization, and Antimicrobial Properties

• Published in: Biomacromolecules Vol. 12; no. 10; pp. 3528 - 3539
• Main Authors: Feese, Elke, Sadeghifar, Hasan, Gracz, Hanna S, Argyropoulos, Dimitris S, Ghiladi, Reza A
• Format: Journal Article
• Language: English
• Published: Washington, DC American Chemical Society 10.10.2011
• Subjects: Anti-Bacterial Agents - chemical synthesis; Anti-Bacterial Agents - pharmacology; Antibacterial agents; Antibiotics. Antiinfectious agents. Antiparasitic agents; Applied sciences; Azides - chemistry; Biological and medical sciences; Cellulose - chemistry; Cellulose and derivatives; Click Chemistry - methods; Disinfectants - chemical synthesis; Disinfectants - pharmacology; Escherichia coli; Escherichia coli - drug effects; Escherichia coli - growth & development; Escherichia coli - radiation effects; Exact sciences and technology; Humans; Light; Magnetic Resonance Spectroscopy; Medical sciences; Microbial Sensitivity Tests; Microbial Viability - drug effects; Microbial Viability - radiation effects; Molecular Structure; Mycobacterium smegmatis; Mycobacterium smegmatis - drug effects; Mycobacterium smegmatis - growth & development; Mycobacterium smegmatis - radiation effects; Nanoparticles - chemistry; Nanotechnology - methods; Natural polymers; Pharmacology. Drug treatments; Photosensitizing Agents - chemical synthesis; Photosensitizing Agents - pharmacology; Physicochemistry of polymers; Porphyrins - chemistry; Species Specificity; Staphylococcus aureus; Staphylococcus aureus - drug effects; Staphylococcus aureus - growth & development; Staphylococcus aureus - radiation effects; Thermogravimetry; 1,3-Dipolar cycloaddition; Pyridine derivative polymer; Surface reaction; Cellulose; Zinc complex; Photoinduced effect; Experimental study; Inactivation; Biological activity; Lateral group; Thermal stability; Azides; Chemical modification; Light sensitive polymer; Triazole derivative polymer; Preparation; Cellulose derivatives; Metalloporphyrin; Liquid solid reaction; Antibacterial agent; Nucleophilic substitution; Photosensitizer; Tosylation; Nanocrystal
• ISSN: 1525-7797; 1526-4602
• DOI: 10.1021/bm200718s

Adherence and survival of pathogenic bacteria on surfaces leading to concomitant transmission to new hosts significantly contributes to the proliferation of pathogens, which in turn considerably increases the threat to human health, particularly by antibiotic-resistant bacteria. Consequently, more research into effective surface disinfection and alternative materials (fabrics, plastics, or coatings) with antimicrobial and other bioactive characteristics is desirable. This report describes the synthesis and characterization of cellulose nanocrystals that were surface-modified with a cationic porphyrin. The porphyrin was appended onto the cellulose surface via the Cu(I)-catalyzed Huisgen–Meldal–Sharpless 1,3-dipolar cycloaddition having occurred between azide groups on the cellulosic surface and porphyrinic alkynes. The resulting, generally insoluble, crystalline material, CNC-Por (5), was characterized by infrared and diffusion 1H NMR spectroscopies, gel permeation chromatography, and thermogravimetric analysis. Although only suspended, and not dissolved, in an aqueous system, CNC-Por (5) showed excellent efficacy toward the photodynamic inactivation of Mycobacterium smegmatis and Staphylococcus aureus, albeit only slight activity against Escherichia coli. The synthesis, properties, and activity of CNC-Por (5) described herein serve as a benchmark toward our overall objectives of developing novel, potent, bioactive, photobactericidal materials that are effective against a range of bacteria, with potential utilization in the health care and food preparation industries.