Bioactive Properties of a Novel Antibacterial Dye Obtained from Laccase-Mediated Oxidation of 8-Anilino-1-naphthalenesulfonic Acid.

Jolanta Polak,Roman Paduch,Katarzyna Szałapata,Marcin Grąz,Justyna Kapral-Piotrowska,Kamila Wlizło,Anna Jarosz-Wilkołazka

doi:10.3390/molecules27020487

Jolanta Polak, Roman Paduch + Show 5 more

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https://doi.org/10.3390/molecules27020487

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Abstract

Fungal laccase obtained from a Cerrena unicolor strain was used as an effective biocatalyst for the transformation of 8-anilino-1-naphthalenesulfonic acid into a green-coloured antibacterial compound, which can be considered as both an antimicrobial agent and a textile dye, simultaneously. The process of biosynthesis was performed in buffered solutions containing methanol as a co-solvent, allowing better solubilisation of substrate. The transformation process was optimised in terms of the buffer pH value, laccase activity, and concentrations of the substrate and co-solvent. The crude product obtained exhibited low cytotoxicity, antibacterial properties against Staphylococcus aureus and Staphylococcus epidermidis, and antioxidant properties. Moreover, the synthesised green-coloured compound proved non-allergenic and demonstrated a high efficiency of dyeing wool fibres.

Highlights

Laccase (LAC) is a versatile oxidiser of a wide range of compounds from simple phenols to more complex aromatic amines with a benzene, naphthalene, or anthraquinone framework
There are numerous examples of fungal strains with the ability to synthesise laccase, but the most commonly mentioned in the context of biocatalysis are white-rot fungi such as Trametes sp., Pleurotus sp., or C. unicolor [10,28]
The results indicated the high commercial potential of the dye synthesised during the homomolecular transformation of 8-anilinonaphthalenesulfonic acid using fungal laccase as a natural biocatalyst into a non-irritating, antimicrobial green dye suitable for staining of wool

Summary

Introduction

Laccase (LAC) is a versatile oxidiser of a wide range of compounds from simple phenols to more complex aromatic amines with a benzene, naphthalene, or anthraquinone framework. It is an important biocatalyst with enormous potential for industrial and biotechnological applications in the food and textile industries, organic synthesis, bio-sensors, biodegradation, and bioremediation [1,2,3,4,5]. A large group of products obtained via laccase-mediated oxidation has been found to exhibit se-veral different activities or properties, for instance phenazine and phenoxazine dyes cha-racterised by both dyeing and bioactive properties, which enhance their application potential [15,16,17,18]. Other more structurally complex chemicals such as azo dyes, i.e., common wastewater pollutants from the textile and dyeing industry, can be considered dye precursors, as described by Enaud and co-workers, where laccase was an effective catalyst for the biotransformation of anthraquinonic dye Acid Blue 62 into a non-toxic red azo dye, namely LAR1 with novel dyeing properties [19]

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