DNA cleavage by di- and trihydroxyalkylbenzenes. Characterization of products and the roles of O2, Cu(II), and alkali

Singh, Udai S.; Scannell, Ralph T.; An, Hongyu; Carter, Barbara J.; Hecht, Sidney M.

doi:10.1021/ja00156a005

Cited by 88 publications

(77 citation statements)

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“…Many biologically active compounds belonging to this class of derivatives also include other functional groups in the aromatic ring as well as in the 526 D. Petrelli et al alkyl chain. Antimicrobial, antiparasitic, anticancer and genotoxic activities have been reported to date for this group of compounds (Lytollis et al 1995;Singh et al 1995;Kozubek et al 2001).…”

Section: Introductionmentioning

confidence: 97%

Antimicrobial activity of the protozoan toxin climacostol and its derivatives

et al. 2012

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Climacostol is a defense toxin produced by the ciliated protozoan Climacostomum virens and belongs to resorcinolic lipids, a group of compounds that shows antimicrobial, antiparasitic, and cytotoxic activities. In this study we investigate the antimicrobial activity of climacostol and its alkyl and alkynyl derivatives against a panel of bacterial and fungal pathogens. Our results show a good and comparable antimicrobial activity of the three compounds, which have resulted effective against Gram-positive bacteria and Candida with MIC and MBC ranging from 8 to 32 mg L −1 , whereas no significant effect against Gram-negative species has been observed. Taken as a whole, the experimental data reported in the current study suggest that differences in the saturation rate of the lateral chain of climacostol are not related to the activity of the molecule. Therefore, it is likely that the general structure of the two moieties, i.e., the di-hydroxy-phenyl group and the alkenyl chains, contributes to the overall antibiotic behaviour.

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Section: Introductionmentioning

confidence: 97%

Antimicrobial activity of the protozoan toxin climacostol and its derivatives

et al. 2012

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“…To date, several compounds that show antimicrobial, antiparasitic, antitumoral and genotoxic activities have been identified among the alkylresorcinols (Picardo et al 1987;Lytollis et al 1995;Singh et al 1995;Kozubek et al 2001). In addition, their potential use in the therapy and/or prevention of specific classes of diseases has attracted particular attention (Itokawa et al 1989;Suresh & Ray 1990;Gasiorowsky et al 1996;Kozubek et al 2001;Filip et al 2002;Barbini et al 2006).…”

Section: Introductionmentioning

confidence: 99%

The protozoan toxin climacostol and its derivatives: Cytotoxicity studies on 10 species of free-living ciliates

Buonanno

Ortenzi

2010

Biologia

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Climacostol (5-(Z)-non-2-enyl-benzene-1,3-diol) is a natural toxin isolated from the freshwater ciliated protozoan Climacostomum virens and belongs to resorcinolic lipids, a group of compounds that show antimicrobial, antiparasitic, and anticancer activities. We investigated the cytotoxic activity of the chemically synthesized toxin and its alkyl and alkynyl derivatives on C. virens and nine other common species of free-living freshwater ciliates. Our results show that the cytotoxic potency of climacostol can be modulated by the substitution of the double bond present in the aliphatic chain of the toxin with a single or a triple one that was previously obtained during the synthesis of the unsaturated and saturated derivatives of the parent molecule. We demonstrated that the cytotoxicity level of the molecules considered in this study appears to be inversely correlated to the unsaturation level of their aliphatic chains, and that the potency of their action is also related to the target organism.

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“…1 Anticarcinogenic properties of ARs were related to induced DNA strand scission caused by incorporation of the AR chain in the double helix of DNA. 23 This effect was related to the formation of reactive oxygen species (hydroxyl radicals) generated during the oxidation of ARs to hydroquinones and quinones in the presence of alkali, oxygen and divalent copper. 23 Based on this ®nding, Kozubek and Tyman hypothesised that antioxidant effects of ARs might be attributed to possible formation of intermediate 1,2,3-and/or 1,3,4-trihydroxy-5-n-ARs with strong antioxidant properties.…”

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confidence: 99%