Tyrosinase inhibitors as potential antibacterial agents

Yuan, Ye; Jin, Wanli; Nazir, Yasir; Fercher, Christian; Blaskovich, Mark A. T.; Cooper, Matthew A.; Barnard, Ross; Ziora, Zyta M.

doi:10.1016/j.ejmech.2019.111892

Cited by 75 publications

(46 citation statements)

References 74 publications

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“…[8] The inhibition of tyrosinase activity is a widely used strategy for blocking melanogenesis thus reducing melanin synthesis. [9,10] Tyrosinase inhibitors such as kojic acid and arbutin are employed by pharmaceutical and cosmetic industries as active ingredients for the preparation of skin-whitening formulations, but they have shown low efficacy, low stability and cytotoxicity. [11][12][13] Particularly, it has been clearly demonstrated that kojic acid is poor human tyrosinase inhibitor.…”

Section: Introductionmentioning

confidence: 99%

“…Moreover, it has been reported that several tyrosinase inhibitors, both from synthetic [14] and natural sources, possess antibacterial activity. [9] In bacteria, melanin exerts a protective role against UV radiation, chelates metals in stress conditions and neutralize the effects of antibiotics, thus increasing cell viability. Therefore, the inhibition of tyrosinase activity and the subsequent reduction of melanin synthesis could be exploited as strategy for the development of new antibiotics.…”

Section: Introductionmentioning

confidence: 99%

“…However, more efforts are needed in order to clarify the mechanism that correlates the antimicrobial effect with the inhibition of melanin synthesis. [9] For these reasons there is a growing interest in the search of more effective and potent tyrosinase inhibitors. [11,12] In our previous studies we have identified a new class of tyrosinase inhibitors bearing the 4-fluorobenzyl substituent as a key structural motif, which establishes favorable contacts within catalytic site in proximity of the two copper ions.…”

Section: Introductionmentioning

confidence: 99%

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4‐Fluorobenzylpiperazine‐Containing Derivatives as Efficient Inhibitors of Mushroom Tyrosinase

et al. 2020

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Tyrosinase is a type‐3 copper protein involved in the biosynthesis of melanin pigments; therefore, the inhibition of its enzymatic activity represents a promising strategy for the treatment of hyperpigmentation‐related disorders. To address this point, we previously designed a class of 4‐(4‐fluorobenzyl)piperazin‐1‐yl‐based compounds, which proved to be more active inhibitors against tyrosinase from mushroom Agaricus bisporus than the positive control kojic acid. Herein, we report the synthesis of further series of 4‐(4‐fluorobenzyl)piperazin‐1‐yl analogues bearing a (hetero)aromatic fragment as key feature to improve protein affinity. The newly synthesized compounds were assayed in vitro and proved to be potent inhibitors in the low‐micromolar range. The active 2‐thienyl and 2‐furyl derivatives were selected for further modification to allow their binding mode to be analyzed by docking studies and to give satisfactory safety profiles.

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Section: Introductionmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

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4‐Fluorobenzylpiperazine‐Containing Derivatives as Efficient Inhibitors of Mushroom Tyrosinase

et al. 2020

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“…Tyrosinase is a key enzyme in the synthesis of melanin, which is main pigment in skin and eyes. At this point, tyrosinase inhibition is useful to manage hyperpigmentation problems [ 45 ]. As can be seen from Table 4 , tyrosinase inhibition effects were close in the tested mushroom extracts and the best ability was provided by H. depilatum with the value of 54.18 mg KAE/g.…”

Section: Resultsmentioning

confidence: 99%

Chemical Characterization, Antioxidant, Enzyme Inhibition and Antimutagenic Properties of Eight Mushroom Species: A Comparative Study

Alkan

Uysal

Kaşik

et al. 2020

JoF

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This study aimed to determine the chemical composition and biologic activities of eight mushroom species (Amanita crocea, Hemileccinum depilatum, Cyclocybe cylindracea, Lactarius deliciosus, Hygrocybe acutoconica, Neoboletus erythropus, Russula aurea and Russula sanguinea). The antioxidant, enzyme inhibitory and mutagenic/antimutagenic activities were evaluated to provide data on the biologic activities. With respect to the chemical composition, LC–MS/MS technique was used to determine individual phenolic compounds present in the extracts. Antioxidant properties were investigated by different chemical methods including radical quenching (DPPH and ABTS), reducing power (CUPRAC and FRAP), phosphomolybdenum and metal chelating. In the enzyme inhibitory assays, cholinesterases, tyrosinase, amylase and glucosidase were used. Mutagenic and antimutagenic properties were evaluated by the Ames assay. In general, the best antioxidant abilities were observed from H. depilatum and N. erythropus, which also showed highest level of phenolics. The best cholinesterase inhibition ability was found from C. cylindracea (1.02 mg GALAE/g for AChE; 0.99 mg GALAE/g for BChE). Tyrosinase inhibition ability varied from 48.83 to 54.18 mg KAE/g. The extracts exhibited no mutagenic effects and showed significant antimutagenic potential. H. acutoconica, in particular depicted excellent antimutagenicity with a ratio of 97% for TA100 and with a rate of 96% for TA98 strain against mutagens in the presence of metabolic activation system. Results presented in this study tend to show that the mushroom species could be exploited as potential sources of therapeutic bioactive agents, geared towards the management of oxidative stress, global health problems and cancer.

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“…Pyrrole/furan/thiophene derivatives, the nitrogen/oxygen/sulfur‐containing heterocycles, are potential inhibitors of tyrosinase, [ 112 ] DNA gyrase, topoisomerase IV, [ 113,114 ] tyrosyl‐tRNA synthetase, [ 115 ] efflux pump, [ 116 ] and metallo‐β‐lactamases. [ 117 ] Thus, the pyrrole/furan/thiophene derivatives possess an excellent activity against both drug‐sensitive and ‐resistant, even multidrug‐resistant, pathogens.…”

Section: Indole/isatin–pyrrole/furan/thiophene Hybridsmentioning

confidence: 99%

Indole/isatin‐containing hybrids as potential antibacterial agents

Song

Bian

et al. 2020

Archiv der Pharmazie

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The emergence and worldwide spread of drug-resistant bacteria have already posed a serious threat to human life, creating the urgent need to develop potent and novel antibacterial drug candidates with high efficacy. Indole and isatin (indole-2,3-dione) present a wide structural and mechanistic diversity, so their derivatives possess various pharmacological properties and occupy a salient place in the development of new drugs. Indole/isatin-containing hybrids, which demonstrate a promising activity against a panel of clinically important Gram-positive and Gram-negative bacteria, are privileged scaffolds for the discovery of novel antibacterial candidates. This review, covering articles published between January 2015 and May 2020, focuses on the development and structure-activity relationship (SAR) of indole/isatincontaining hybrids with potential application for fighting bacterial infections, to facilitate further rational design of novel drug candidates.

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Tyrosinase inhibitors as potential antibacterial agents

Cited by 75 publications

References 74 publications

4‐Fluorobenzylpiperazine‐Containing Derivatives as Efficient Inhibitors of Mushroom Tyrosinase

4‐Fluorobenzylpiperazine‐Containing Derivatives as Efficient Inhibitors of Mushroom Tyrosinase

Chemical Characterization, Antioxidant, Enzyme Inhibition and Antimutagenic Properties of Eight Mushroom Species: A Comparative Study

Indole/isatin‐containing hybrids as potential antibacterial agents

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