Novel textile dye obtained through transformation of 2-amino-3-methoxybenzoic acid by free and immobilised laccase from a Pleurotus ostreatus strain

Wlizło, Kamila; Polak, Jolanta; Jarosz-Wilkołazka, Anna; Pogni, Rebecca; Petricci, Elena

doi:10.1016/j.enzmictec.2019.109398

Cited by 15 publications

(12 citation statements)

References 40 publications

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“…Bactericidal effect of AB2 dye against Staphylococcus aureus may result from the phenazine structure of dye, as well as from the presence of electron-donating groups. Good dyeing properties of tested AB2 dye may be the result of ionic bonds formation between the free amino groups of wool fibre and carboxyl groups of the dye (Figure 8a), what is in agreement with good dyeing ability of other dyes obtained from laccase-mediated oxidation of carboxylic acid as well as natural dyes [21,27].…”

Section: Discussionsupporting

confidence: 77%

“…It was possible due to low values of redox potential and K M of substrate A, in contrary to the high values of both redox potential and K M of aminonaphthalenesulfonic acids (substrates B). Despite that these three different structural isomers tested as a potential substrate of laccase possess one amino group each (the well-known reactive substituent involving in the LAC-mediated coupling reaction), low intensity coloured product was formed only in the case of substrate B1 homomolecular transformation [27,28]. Different effects of ring activation are observed in different isomers, what in the case of para compounds is responsible for the substrates redox potential lowering and the easier LAC-mediated oxidation [15,28].…”

Section: Discussionmentioning

confidence: 99%

“…All of tested substrates possess at least one amino substituent, being a very reactive group for the LAC-mediated coupling reaction with other substrates to yield coloured products [26]. However, only substrate A, containing additional reactive methoxy group, was transformed into orange product about low toxicity during its homomolecular transformation and the dye obtained was able to colour natural fibres [24,25,27]. It was possible due to low values of redox potential and K M of substrate A, in contrary to the high values of both redox potential and K M of aminonaphthalenesulfonic acids (substrates B).…”

Section: Discussionmentioning

confidence: 99%

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Structure and Bioactive Properties of Novel Textile Dyes Synthesised by Fungal Laccase

Polak

Wlizło

Pogni

et al. 2020

IJMS

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Novel sustainable processes involving oxidative enzymatic catalysts are considered as an alternative for classical organic chemistry. The unique physicochemical and bioactive properties of novel bio-products can be obtained using fungal laccase as catalyst. Among them are textile biodyes synthesised during oxidation of substrates belonging to the amine and methoxy organic derivatives. The process of synthesis occurs in mild conditions of pH, temperature, and pressure, and without using harmful oxidants. The effect of fungal laccase activity on the substrates mixture transformation efficiency was analysed in terms of antimicrobial dye synthesis on a large scale. Three new phenazine dyes, obtained in the presence of laccase from Cerrena unicolor, were studied for their structure and properties. The phenazine core structure of the products was a result of tri-molecular transformation of aminomethoxybenzoic acid and aminonaphthalene sulfonic acid isomers. One of the compounds from the synthesised dye, namely 10-((2-carboxy-6-methoxyphenyl)amino)-11-methoxybenzo[a]phenazine-8-carboxylic acid, was able to inhibit the growth of Staphylococcus aureus. The high concentration of substrates (5 g/L) was efficiently transformed during 72 h in the mild conditions of pH 4 with the use of laccase with an activity of 200 U per g of the substrates mixture. The new bioactive dye exhibited excellent dyeing properties with concomitant antibacterial and antioxidative activity. The proposed enzyme-mediated synthesis represents an alternative eco-friendly route for the synthesis of novel antimicrobial compounds with high importance for the medical textile industry.

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Section: Discussionsupporting

confidence: 77%

Section: Discussionmentioning

confidence: 99%

Section: Discussionmentioning

confidence: 99%

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Structure and Bioactive Properties of Novel Textile Dyes Synthesised by Fungal Laccase

Polak

Wlizło

Pogni

et al. 2020

IJMS

Self Cite

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“…The formation of a phenazine based orange dye by the homomolecular transformation of the 2-amino-3-methoxybenzoic acid in the presence of free and immobilised laccase from the P. ostreatus strain was very recently reported ( Scheme 12 A) [ 89 ]. Interestingly, the enzyme, when immobilised on Purolite ® carriers, showed a remarkable storage stability (21 days) and thermostability at 40 °C and 60 °C as compared to its free form.…”

Section: Application Of Laccases In Bio-oxidative Synthesis Of Heterocyclic Compoundsmentioning

confidence: 99%

“… Synthesis of phenazines as a result of a laccase-mediated ( A ) homocoupling reaction and ( B ) heterocoupling reactions of 2-amino-3-methoxybenzoic acid [ 89 , 90 ]. …”

Section: Figures Schemes and Tablementioning

confidence: 99%

Laccases: Versatile Biocatalysts for the Synthesis of Heterocyclic Cores

2021

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Laccases are multicopper oxidases that have shown a great potential in various biotechnological and green chemistry processes mainly due to their high relative non-specific oxidation of phenols, arylamines and some inorganic metals, and their high redox potentials that can span from 500 to 800 mV vs. SHE. Other advantages of laccases include the use of readily available oxygen as a second substrate, the formation of water as a side-product and no requirement for cofactors. Importantly, addition of low-molecular-weight redox mediators that act as electron shuttles, promoting the oxidation of complex bulky substrates and/or of higher redox potential than the enzymes themselves, can further expand their substrate scope, in the so-called laccase-mediated systems (LMS). Laccase bioprocesses can be designed for efficiency at both acidic and basic conditions since it is known that fungal and bacterial laccases exhibit distinct optimal pH values for the similar phenolic and aromatic amines. This review covers studies on the synthesis of five- and six-membered ring heterocyclic cores, such as benzimidazoles, benzofurans, benzothiazoles, quinazoline and quinazolinone, phenazine, phenoxazine, phenoxazinone and phenothiazine derivatives. The enzymes used and the reaction protocols are briefly outlined, and the mechanistic pathways described.

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Immobilization as Sustainable Solutions to Textiles Chemical Processing

Madhu

2022

Sustainable Textiles: Production, Processing, Manufacturing &Amp; Chemistry

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Novel textile dye obtained through transformation of 2-amino-3-methoxybenzoic acid by free and immobilised laccase from a Pleurotus ostreatus strain

Cited by 15 publications

References 40 publications

Structure and Bioactive Properties of Novel Textile Dyes Synthesised by Fungal Laccase

Structure and Bioactive Properties of Novel Textile Dyes Synthesised by Fungal Laccase

Laccases: Versatile Biocatalysts for the Synthesis of Heterocyclic Cores

Immobilization as Sustainable Solutions to Textiles Chemical Processing

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