A laccase-catalysed one-pot synthesis of aminonaphthoquinones and their anticancer activity

Wellington, Kevin W.; Kolesnikova, Natasha I.

doi:10.1016/j.bmc.2012.05.028

Cited by 75 publications

(34 citation statements)

References 62 publications

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“…On the other hand, modification of antibiotics using laccase coupling reactions produced compounds with lower activities 19 , however, using nitrogen compounds to modify the antibiotics, the synthesized products showed higher antibacterial activities 20,21 . The anticancer activity of naphtohydroquinones has been improved by nuclear monoamination with anilines using laccase 22 . These results indicate that the laccase-mediated amination of a phenolic compound could increase the biological activity.…”

Section: Introductionmentioning

confidence: 99%

Improvement of the Antifungal Activity Against Botrytis Cinerea of Syringic Acid, a Phenolic Acid From Grape Pomace

Mendoza

Castro

Melo

et al. 2016

J. Chil. Chem. Soc.

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The aim of this study was to improve the antifungal activity against Botrytis cinerea of syringic acid by using the enzyme laccase to synthesize a heterodimeric compound by a coupling reaction with aniline. The synthesized heterodimer is a quinone-imine like compound (2,6-dimethoxy-4-(phenylimino)benzenone), which was characterized by using 1 H and 13 C NMR, IR, and mass spectrometry. The antifungal activity of the heterodimeric compound against B. cinerea was determined in vitro and showed a higher antifungal effect than the substrates (syringic acid and aniline), inhibiting the mycelial growth with an IC 50 value of 0.14mM and delayed 2 hours the conidial germination. Also, using the fluorochrome calcofluor white, cell wall damage was observed when B. cinerea was incubated with the compound. This is the first report on antifungal activity of this type of compound against B. cinerea.

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Section: Introductionmentioning

confidence: 99%

Improvement of the Antifungal Activity Against Botrytis Cinerea of Syringic Acid, a Phenolic Acid From Grape Pomace

Mendoza

Castro

Melo

et al. 2016

J. Chil. Chem. Soc.

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“…The 1,4‐naphthohydroquinone 1 and the synthesized aminonaphthoquinones 2–12 (Wellington & Kolesnikova, )…”

Section: Resultsmentioning

confidence: 99%

“…The synthesis of the aminonaphthoquinones 2-12 has been previously reported (Wellington & Kolesnikova, 2012).…”

Section: Synthesismentioning

confidence: 99%

Investigation of the antimicrobial and anticancer activity of aminonaphthoquinones

Wellington

Kolesnikova

Nyoka

et al. 2018

Drug Development Research

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In this study, we report on the inhibitory activity of synthesized aminonaphthoquinones against two bacterial and one fungal species to determine their antimicrobial properties. A minimum inhibitory concentration (MIC) of 7.8 μg/mL was obtained against the fungus, Candida albicans, which was better than that of Amphotericin B (MIC = 31.25 μg/mL). Escherichia coli (Gram ‐), was inhibited at a MIC of 23.4 μg/mL and Staphylococcus aureus (Gram +) at a MIC of 31.3 μg/mL. The aminonaphthoquinones were also screened against HCT116 colon, PC3 prostate and HepG2 liver cancer cell lines to evaluate their cytostatic effects. They had potent activity (GI50 = 5.87–9.90 μM) which was about three‐6‐fold better than that of parthenolide (GI50 = 25.97 μM) against the prostate cancer cell line. These compounds were generally more selective for cancer cells than for normal human lung fetal fibroblasts (WI‐38).

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“…Antibiotic modifications using laccase coupling reactions have shown products with lower activities 9 ; however, using nitrogen compounds to modify the antibiotics, the synthesized products showed higher antibacterial activities 10,11 . The anticancer activity of naphtohydroquinones has been improved by nuclear monoamination with anilines using laccase 12 . These results indicate that the laccase-mediated amination of a phenolic compound could increase their biological activity.…”

Section: Introductionmentioning

confidence: 99%

Laçasse Catalyzed-Synthesis of 4,4'-Biphenyldiamine From P-Chloroaniline. Evaluation of Antifungal and Antioxidant Activities

Campos

Mendoza

Vásquez

et al. 2016

J. Chil. Chem. Soc.

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Laccase is a copper-containing oxidase that catalyzes reduction of molecular oxygen to water and the oxidation of a phenolic compound. In this paper, laccase was utilized to synthesize 4,4'-Biphenyldiamine using p-chloroaniline as substrate by means of a coupling reaction. The synthesized compound, 4,4'-Biphenyldiamine, presented low antifungal activity against the phytopathogenic fungus Botrytis cinerea, however the antioxidant ability, measurement by ORAC-PGR method, was higher than substrate.This work corresponds to the first report of synthesis 4,4'-Biphenyldiamine, from p-chloroaniline in a lacasse-catalyzed reaction.

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A laccase-catalysed one-pot synthesis of aminonaphthoquinones and their anticancer activity

Cited by 75 publications

References 62 publications

Improvement of the Antifungal Activity Against Botrytis Cinerea of Syringic Acid, a Phenolic Acid From Grape Pomace

Improvement of the Antifungal Activity Against Botrytis Cinerea of Syringic Acid, a Phenolic Acid From Grape Pomace

Investigation of the antimicrobial and anticancer activity of aminonaphthoquinones

Laçasse Catalyzed-Synthesis of 4,4'-Biphenyldiamine From P-Chloroaniline. Evaluation of Antifungal and Antioxidant Activities

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