Allergic contact dermatitis caused by naturally occurring quinones

Lepoittevin, Jean‐Pierre; Benezra, Claude

doi:10.1007/bf01981527

Cited by 19 publications

(13 citation statements)

References 15 publications

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“…Moreover, anthraquinone derivatives from rhubarb further indicate that natural quinones with similar configuration may provide a huge resource of amyloid inhibitors. Although some quinones from plants have been thought to be allerg en s58, quinones are still important sources for deriving new anti-amyloid inhibitors. And more extensive conditions such as metal ions,crowding, pressure and shear force may be considered to validate the present results.…”

Section: Discussionmentioning

confidence: 99%

Effects of several quinones on insulin aggregation

Gong

Peng

et al. 2014

Sci Rep

132

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Protein misfolding and aggregation are associated with more than twenty diseases, such as neurodegenerative diseases and metabolic diseases. The amyloid oligomers and fibrils may induce cell membrane disruption and lead to cell apoptosis. A great number of studies have focused on discovery of amyloid inhibitors which may prevent or treat amyloidosis diseases. Polyphenols have been extensively studied as a class of amyloid inhibitors, with several polyphenols under clinical trials as anti-neurodegenerative drugs. As oxidative intermediates of natural polyphenols, quinones widely exist in medicinal plants or food. In this study, we used insulin as an amyloid model to test the anti-amyloid effects of four simple quinones and four natural anthraquinone derivatives from rhubarb, a traditional herbal medicine used for treating Alzheimer's disease. Our results demonstrated that all eight quinones show inhibitory effects to different extent on insulin oligomerization, especially for 1,4-benzoquinone and 1,4-naphthoquinone. Significantly attenuated oligomerization, reduced amount of amyloid fibrils and reduced hemolysis levels were found after quinones treatments, indicating quinones may inhibit insulin from forming toxic oligomeric species. The results suggest a potential action of native anthraquinone derivatives in preventing protein misfolding diseases, the quinone skeleton may thus be further explored for designing effective anti-amyloidosis compounds.

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Section: Discussionmentioning

confidence: 99%

Effects of several quinones on insulin aggregation

Gong

Peng

et al. 2014

Sci Rep

132

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“…The binding of quinones to proteins can also lead, through the recognition of quinonebound epitopes from degraded protein, to immunological damage. For instance, quinone-protein conjugation has been implicated in playing a causative role in the incidence of certain allergic or idiosyncratic drug reactions (Lepoittevin and Benezra 1991;Parrish et al 1997;Petersen 2002). Contact allergic reactions have been linked to 2-hydroxy-2,4-naphthoquinone (henna) (27), a principal ingredient in many types of body dyes (Bolhaar et al 2001;Calogiuri et al 2010).…”

Section: Nucleophilic Addition Of Quinonesmentioning

confidence: 99%

The chemical and biological activities of quinones: overview and implications in analytical detection

et al. 2011

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Quinones are a class of natural and synthetic compounds that have several beneficial effects. Quinones are electron carriers playing a role in photosynthesis. As vitamins, they represent a class of molecules preventing and treating several illnesses such as osteoporosis and cardiovascular diseases. Quinones, by their antioxidant activity, improve general health conditions. Many of the drugs clinically approved or still in clinical trials against cancer are quinone related compounds. Quinones have also toxicological effects through their presence as photoproducts from air pollutants. Quinones are fast redox cycling molecules and have the potential to bind to thiol, amine and hydroxyl groups. The aforementioned properties make the analytical detection of quinones problematic. However, recent advances of the available analytical techniques along with the possibility of using labeled compound facilitate their detection hence allowing a better understanding of their action. This review summarizes the current knowledge with respect to the oxido-reductive and electrophilic properties of quinones as well as to the analytical tools used for their analysis. It includes a general introduction about the physiological, and therapeutical functions of quinones. A number of studies are reported to cover the chemical reactivity in an attempt to understand quinones as biologically active compounds. Data ranging from normal analytical methods to study quinones derived from plant or biological matrices to the use of labeled compounds are presented. The examples illustrate how chemical, biological and analytical knowledge can be integrated to have a better understanding of the mode of action of the quinones.

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“…The reason for the very slow reactivity of 1,2-NQ is not known other than the fact that it is highly pH dependent. The kinetics of the investigated Q were compared with the kinetics of BQ reported by Olusegun and Martincigh [45] because BQ is an established and well-known skin sensitizer. In this comparison, we examined BQ as the parent structure from which the other Q were derived, therefore, their reaction rate constants were compared as presented in Table 3.…”

Section: Effect Of Phmentioning

confidence: 99%

Understanding the Role of pH in Protein‐Haptenation Reaction: Kinetics and Mechanisms of the Protein‐Haptenation Reactions of Selected Quinones Present in the Environment

Olusegun

Martincigh

2020

ChemistrySelect

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There are several xenobiotics (allergens) in the environment which may induce allergic contact dermatitis (ACD), an occupational and environmental health disease. This health disease is of global concern because it has no cure and can only be managed in affected individuals by preventing them from further exposure to these allergens. The following quinones (Q) are known to be air pollutants: 1,2‐naphthoquinone (1,2‐NQ), 1,4‐naphthoquinone (1,4‐NQ), 9,10‐phenanthraquinone (PQ), and 9,10‐anthraquinone (AQ). There have been studies on the cytotoxicity of these air pollutants, but no kinetic studies have been carried out on them to determine their chemical reactivity and, more especially, their interaction with model proteins so as to ascertain if they can react with skin proteins thereby causing allergic reactions. This article provides details on the kinetics studies carried out on the protein‐haptenation reactions of these quinones with 4‐nitrobenzenethiol (NBT), a model nucleophile, as well as the mechanisms of their reactions. The NBT−Q reactions were investigated under pseudo‐first‐order conditions at various concentration ratios at a temperature of 25 °C at three different pH values by either ultraviolet‐visible (UV‐Vis) or stopped‐flow spectrophotometry, as appropriate. The reaction rate constants obtained for the NBT−Q reactions were in the following order: at pH 7.42: 1,2‐NQ>1,4‐NQ>PQ>AQ while at pH 5.65, the order was observed to be 1,2‐NQ>1,4‐NQ>PQ>AQ and at pH 8.41, it was 1,4‐NQ>PQ>AQ>1,2‐NQ. These trends for the reaction rate constants of the Q at the three pH values can be attributed to inductive effects and the position of oxo‐groups on the phenyl rings. The NBT−Q reactions were further investigated by determining the effect of ionic strength on the reaction rate constants with potassium sulphate as the background electrolyte. Our findings showed that there are no charged species at the transition state of the NBT−Q reactions. The products of the NBT−Q reactions were isolated and characterized by means of UV‐Vis and FTIR spectrophotometry and NMR and TOF‐MS spectrometry. The deduced mechanisms for the NBT−Q reactions were validated by computer simulation with “Simkine3” software.

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Allergic contact dermatitis caused by naturally occurring quinones

Cited by 19 publications

References 15 publications

Effects of several quinones on insulin aggregation

Effects of several quinones on insulin aggregation

The chemical and biological activities of quinones: overview and implications in analytical detection

Understanding the Role of pH in Protein‐Haptenation Reaction: Kinetics and Mechanisms of the Protein‐Haptenation Reactions of Selected Quinones Present in the Environment

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