Vanilloid Derivatives as Tyrosinase Inhibitors Driven by Virtual Screening‐Based QSAR Models

BackgroundSynthetic dyes represent a broad and heterogeneous class of durable pollutants, that are released in large amounts by the textile industry. The ability of two immobilized metalloporphines (structurally emulating the ligninolytic peroxidases) to bleach six chosen dyes (alizarin red S, phenosafranine, xylenol orange, methylene blue, methyl green, and methyl orange) was compared to enzymatic catalysts. To achieve a green and sustainable process, very mild conditions were chosen.ResultsIPS/MnTSPP was the most promising biomimetic catalyst as it was able to effectively and quickly bleach all tested dyes. Biomimetic catalysis was fully characterized: maximum activity was centered at neutral pH, in the absence of any organic solvent, using hydrogen peroxide as the oxidant. The immobilized metalloporphine kept a large part of its activity during multi-cycle use; however, well-known redox mediators were not able to increase its catalytic activity. IPS/MnTSPP was also more promising for use in industrial applications than its enzymatic counterparts (lignin peroxidase, laccase, manganese peroxidase, and horseradish peroxidase).ConclusionsOn the whole, the conditions were very mild (standard pressure, room temperature and neutral pH, using no organic solvents, and the most environmental-friendly oxidant) and a significant bleaching and partial mineralization of the dyes was achieved in approximately 1 h. Therefore, the process was consistent with large-scale applications. The biomimetic catalyst also had more promising features than the enzymatic catalysts.

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“…Concentrations of the substrates were also measured by UV-HPLC and GC-MS, using previously described methods [30,31]. …”

Section: Methodsmentioning

confidence: 99%

Degradation of textile dyes using immobilized lignin peroxidase-like metalloporphines under mild experimental conditions

Zucca

Rescigno²,

Pintus³

et al. 2012

Chemistry Central Journal

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“…Experiments were performed to check for possible contaminant enzyme activities [Rescigno et al, 2007]. In particular, syringaldazine was used as the substrate [Zucca et al, 2011] to rule out laccase activity (<0.001 E.U./mL [Zucca et al, 2010b]) because contaminant laccases might share substrates, i.e., o-diphenols, with tyrosinase, leading to ambiguous results.…”

Section: Tyrosinase Inhibitionmentioning

confidence: 99%

“…Tyrosinase (or polyphenol oxidase, PPO) is a copper monooxygenase involved in melanogenesis and food browning [Marongiu et al, 2007;Rescigno et al, 2011]. This enzyme catalyzes the hydroxylation of monophenols to o-diphenols and the oxidation of o-diphenols to o-quinones in the presence of molecular oxygen.…”

Section: Anti-tyrosinase Activitymentioning

confidence: 99%

Biological Activities and Nutraceutical Potentials of Water Extracts from Different Parts of Cynomorium coccineum L. (Maltese Mushroom)

Zucca¹,

Argiolas²,

Nieddu³

et al. 2016

Pol. J. Food Nutr. Sci.

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Maltese Mushroom (Cynomorium coccineum L.) is a non-photosynthetic plant that has been used in traditional medicine for many centuries. In this paper, water extracts from the whole plant, external layer and peeled plant were studied to determine the main components responsible for its biological activities, i.e., its antimicrobial, antioxidant, and anti-tyrosinase activities; its cytotoxicity against mouse melanoma B16F10 cells; and its pro-erectile activity in adult male rats. The results of electron transfer and hydrogen transfer assays showed that the antioxidant activity was mainly due to anthocyanins in the external layer, whereas the external layer and peeled plant extracts both inhibited the microbial growth of several Gram-positive strains. In contrast, the whole plant extract had the highest anti-tyrosinase activity and exhibited pro-erectile activity when administered subcutaneously. Overall, this study elucidated which parts of Maltese Mushroom are responsible for its antimicrobial, antioxidant, and anti-tyrosinase activities and thus which extracts have potential for use in nutraceutical formulations.

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“…In recent times, Quantitative Structure-Activity Relationships (QSARs) are the most widely used approach in drug design and have been applied successfully in the discovery of novel tyrosinase inhibitors [18,[43][44][45][46][47][48][49]. Hence, this method could constitute the principal "switch" for sequential workflow aiding to new lead compounds identification.…”

Section: Multiclassifiers Guided By Qsar Modelsmentioning

confidence: 99%

A Rational Workflow for Sequential Virtual Screening of Chemical Libraries on Searching for New Tyrosinase Inhibitors

Le-Thi-Thu¹,

Casañola-Martín²,

Marrero-Ponce³

et al. 2014

CTMC

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The tyrosinase is a bifunctional, copper-containing enzyme widely distributed in the phylogenetic tree. This enzyme is involved in the production of melanin and some other pigments in humans, animals and plants, including skin pigmentations in mammals, and browning process in plants and vegetables. Therefore, enzyme inhibitors has been under the attention of the scientist community, due to its broad applications in food, cosmetic, agricultural and medicinal fields, to avoid the undesirable effects of abnormal melanin overproduction. However, the research of novel chemical with antityrosinase activity demands the use of more efficient tools to speed up the tyrosinase inhibitors discovery process. This chapter is focused in the different components of a predictive modeling workflow for the identification and prioritization of potential new compounds with activity against the tyrosinase enzyme. In this case, two structure chemical libraries Spectrum Collection and Drugbank are used in this attempt to combine different virtual screening data mining techniques, in a sequential manner helping to avoid the usually expensive and time consuming traditional methods. Some of the sequential steps summarize here comprise the use of drug-likeness filters, similarity searching, classification and potency QSAR multiclassifier systems, modeling molecular interactions systems, and similarity/diversity analysis. Finally, the methodologies showed here provide a rational workflow for virtual screening hit analysis and selection as a promissory drug discovery strategy for use in target identification phase.

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Vanilloid Derivatives as Tyrosinase Inhibitors Driven by Virtual Screening‐Based QSAR Models

Cited by 26 publications

References 51 publications

Degradation of textile dyes using immobilized lignin peroxidase-like metalloporphines under mild experimental conditions

Degradation of textile dyes using immobilized lignin peroxidase-like metalloporphines under mild experimental conditions

Biological Activities and Nutraceutical Potentials of Water Extracts from Different Parts of Cynomorium coccineum L. (Maltese Mushroom)

A Rational Workflow for Sequential Virtual Screening of Chemical Libraries on Searching for New Tyrosinase Inhibitors

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