Studies on the Mechanism of Antibacterial Action of 2-Methyl-1,4-Naphthoquinone

Colwell, Charlotte A.; McCall, Mary Sue

doi:10.1126/science.101.2632.592

Cited by 39 publications

(13 citation statements)

References 12 publications

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“…With all the three micro-organisms tested, the activity was reduced to less than 10% by either inhibitor; bacterial growth, however, was partially inhibited by glutathione and cysteine in a control experiment; as observed by Colwell & McCall (1946) and Holmes et al (1964) on other 2-or 2,3-substituted naphthoquinones. Under these experimental conditions sulphydryl compounds react with the naphthoquinones to give inactive compounds.…”

Section: Resultsmentioning

confidence: 83%

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Studies on the antibacterial and antifungal properties of 1, 4‐naphthoquinones

Ambrogi¹,

Artini²,

Carneri³

et al. 1970

British J Pharmacology

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Summary . New halogenated 1,4‐naphthoquinones were synthesized and together with other known 1,4‐naphthoquinones, were screened for antibacterial activity by a turbidimetric method, and for antifungal activity by the diffusion method on agar plates. . The half‐wave potentials and the influence on the oxidative phosphorylation of some of these compounds were determined. . 2‐chloro‐3,2′‐chloro‐ethyl‐1,4‐naphthoquinone (half‐wave potential = −187 mV) was the most active compound, completely inhibiting cell respiration. . While the natural active naphthoquinones, vitamin K and ubiquinones, possess, as substituent, the electron repelling methyl group, the microbiologically active 1,4‐naphthoquinones are substituted, in the quinone moiety, with electron attracting groups such as OH or Cl. . The half‐wave potentials can give only an initial indication of the activity of the compounds studied; a good correlation, on the contrary, can be found between the ultraviolet spectra of such compounds and their activity which seems to depend on the ability of active compounds to exist in an extensively conjugated structure and to form hydrogen bonds.

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Section: Resultsmentioning

confidence: 83%

“…Other derivatives are active against bacteria and fungi (Thalhimer & Palmer, 1911;Colwell & McCall, 1946;Oster & Golden, 1948;Akiya, 1956;Holmes, Currie, Maltman, Silver, Lough & Lesky, 1964), their activity being increased through halogenation in the nucleus (Jouin & Buu-Hoi, 1946).…”

Section: Introductionmentioning

confidence: 99%

Studies on the antibacterial and antifungal properties of 1, 4‐naphthoquinones

Ambrogi¹,

Artini²,

Carneri³

et al. 1970

British J Pharmacology

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“…The toxicity of 1,4-quinones is believed to be due to reactions with sulfhydryl groups, as indicated by work with several bacterial species in protective studies [Colwell and McCall, 1945;Geiger, 1946]. Lower activity of hydroquinones is due to their inability to participate in the same type of reaction [Geiger, 1946].…”

Section: Toxicity Of Stable Quinones and Precursorsmentioning

confidence: 99%

Comparative toxicity of allelochemicals and their enzymatic oxidation products to maize fungal pathogens, emphasizing Fusarium graminearum

1997

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A series of stable quinones and their precursors, and enzymatic oxidation products of plant allelochemicals were tested for their effect on maize fungal pathogens, primarily Fusarium graminearum. Benzoquinone was typically significantly more toxic than hydroquinone, while 1,2-naphthoquinone was typically significantly more toxic than 1,2-dihydroxynaphthalene. Aspergillus flavus was the most resistant fungus to these compounds, while Phoma medicaginis was the most susceptible. Applying tyrosinase in conjunction with several phenolic compounds only increased the toxicity of gallic acid to Fusarium graminearum. Applying peroxidase generally increased toxicity of all compounds tested to this fungus in a dose-dependent fashion. Ferulic acid was generally the most toxic compound, both alone and when combined with peroxidase and H 2 O 2 , followed by coumaric acid. These results suggest that enzymatic oxidation of plant allelochemicals may result in the generation of products that either are directly toxic to maize pathogens, or indirectly inhibitory due to their ability to tie up nutrients. Nat.

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“…Quinonic drugs are widely used in chemotherapy, including that of cancer [5], bacterial [6,7] and fungal [8] diseases. Quinones have also been reported to exhibit potent antimalarial capacity [9][10][11].…”

Section: Introductionmentioning

confidence: 99%

Novel naphthoquinonyl derivatives: Potential structural components for the synthesis of cytotoxic peptides

et al. 1996

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Syntheses and physicochemical properties are described of several novel naphthoquinonyl amino acid derivatives, which are potential components in cytotoxic peptide conjugates. These compounds include N E-and N~-naphthoquinonyl derivatives of lysine as well as N-naphthoquinonyl-carboxylic derivatives. The former class of compounds can be employed as building blocks in a stepwise peptide synthesis, whereas the latter two are adequate for postpeptide chain-assembly modifications. The ability of the naphthoquinonyl derivatives to produce semiquinone radicals and hydroxyl radicals ('OH), using chemical (i.e. NaBH4) and enzymatic (i.e. NADPH-cytochrome P-450 reductase) routes, respectively, was evaluated employing electron spin resonance spectroscopy.

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Studies on the Mechanism of Antibacterial Action of 2-Methyl-1,4-Naphthoquinone

Cited by 39 publications

References 12 publications

Studies on the antibacterial and antifungal properties of 1, 4‐naphthoquinones

Studies on the antibacterial and antifungal properties of 1, 4‐naphthoquinones

Comparative toxicity of allelochemicals and their enzymatic oxidation products to maize fungal pathogens, emphasizing Fusarium graminearum

Novel naphthoquinonyl derivatives: Potential structural components for the synthesis of cytotoxic peptides

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