Laccase-mediated synthesis of a phenoxazine compound with antioxidative and dyeing properties – the optimisation process

Polak, Jolanta; Jarosz-Wilkołazka, Anna; Szałapata, Katarzyna; Grąz, Marcin; Osińska-Jaroszuk, Monika

doi:10.1016/j.nbt.2015.09.004

Cited by 26 publications

(13 citation statements)

References 31 publications

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“…The antimicrobial and antioxidative properties of organic compounds very often are associated with the presence of hydroxy substituents acting as electron donors. Tested biodyes possess substituents rich in free electrons, such as methoxy and amine, which can be involved in their antioxidative potential, what is in agreement with our previous observation [11]. 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.…”

Section: Discussionsupporting

confidence: 90%

“…In nature, phenazines with broad bioactivity are products of the idiophase of different bacteria, especially from Pseudomonas and Streptomyces strains [4,5]. Both natural and synthetic phenoxazines and phenazines known from the literature exhibit biological activities such as antibacterial [6][7][8], antitumoral [9], antiproliferative [10], and antioxidant [11] properties. The chemical route of phenazine synthesis requires the use of coupling agents and additives such as benzene, BBr 3 , DMF, and various other harsh, toxic, and mutagenic compounds [12].…”

Section: Introductionmentioning

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: 90%

Section: Introductionmentioning

confidence: 99%

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

Polak

Wlizło

Pogni

et al. 2020

IJMS

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“…The syntheses of APXOs most generally occur via oxidative radical homo‐dimerization of 1 s [15] . For this transformation, many oxidative catalysts were investigated, ranging from laccases, [13a,16] metal complexes, [17] and organocatalyst, [18] to heterogeneous nanomaterials [19] and electro‐oxidation, [15b] etc. It was noteworthy that, although there have been many investigations of the homo‐dimerization of 1 s, little hetero‐dimerization of different 1 s has been reported in the literature [20] …”

Section: Entry Metal Salts Hplc Yield(%)[b]mentioning

confidence: 99%

“…As expected, GA/Mn(OAc) 2 displayed remarkable catalytic performances for the homo‐dimerizations of various 2‐aminophenols. It should be pointed out that the homo‐dimerization of 4‐ or 5‐substituted 1 s, whose substituents included fluoro, chloro and bromo, gave rise to mono‐substituted products 2 d – g , as a result of the elimination of one substituent that reported in the oxidative homo‐dimerization by laccase [13a] and H 2 O 2. [17d] However, the substituent elimination did not occur in the homo‐dimerizations of methyl‐2‐aminophenols, which gave 2 b – c in 99 % and 94 % isolated yield, respectively.…”

Section: Entry Metal Salts Hplc Yield(%)[b]mentioning

confidence: 99%

Laccase‐Mimicking Syntheses of Phenoxazinones by Aerobic Oxidative Homo‐ and Hetero‐Dimerizations of Aminophenols

Duan

Tang

et al. 2021

ChemistrySelect

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“…These research efforts have been most recently reviewed by Polak and Jarosz-Wilkolazka [165]. Since then, numerous studies were published, reporting the synthesis of hair dyes [63], phenoxazine derivatives [166], benzene-and naphthalene-derived non-toxic dyes [167], 2,5-diaminobenzenesulfonic acid (2,5-DABSA) and catechol [67] or resorcinol [168] coupling derivatives, several aminoindamine and indoaniline dyes for hair dyeing and cosmetics applications [169], and even a dye for protein gel staining [170]. Moreover, the dyeing of fabrics by the in situ polymerization of phenol and amine compounds has been reported [115,171].…”

Section: Paints and Coatingsmentioning

confidence: 99%

Applications of Microbial Laccases: Patent Review of the Past Decade (2009–2019)

et al. 2019

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There is a high number of well characterized, commercially available laccases with different redox potentials and low substrate specificity, which in turn makes them attractive for a vast array of biotechnological applications. Laccases operate as batteries, storing electrons from individual substrate oxidation reactions to reduce molecular oxygen, releasing water as the only by-product. Due to society’s increasing environmental awareness and the global intensification of bio-based economies, the biotechnological industry is also expanding. Enzymes such as laccases are seen as a better alternative for use in the wood, paper, textile, and food industries, and they are being applied as biocatalysts, biosensors, and biofuel cells. Almost 140 years from the first description of laccase, industrial implementations of these enzymes still remain scarce in comparison to their potential, which is mostly due to high production costs and the limited control of the enzymatic reaction side product(s). This review summarizes the laccase applications in the last decade, focusing on the published patents during this period.

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Laccase-mediated synthesis of a phenoxazine compound with antioxidative and dyeing properties – the optimisation process

Cited by 26 publications

References 31 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

Laccase‐Mimicking Syntheses of Phenoxazinones by Aerobic Oxidative Homo‐ and Hetero‐Dimerizations of Aminophenols

Applications of Microbial Laccases: Patent Review of the Past Decade (2009–2019)

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