Deactivation of Singlet Molecular Oxygen by Thiols and Related Compounds, Possible Protectors Against Skin Photosensitivity

Rougée, Michel; Bensasson, René V.; Land, Edward J.; Parienté, R

doi:10.1111/j.1751-1097.1988.tb08835.x

Cited by 151 publications

(90 citation statements)

References 28 publications

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“…Therefore, glutathione at cellular concentrations does not appear sufficiently reactive with singlet oxygen to afford the cells protection, regardless of its location. This observation is consistent with the bimolecular rate constants observed for the reaction of glutathione with singlet oxygen (25). Further Figure 4 illustrates a model of the effect of the cell wall structure on singlet oxygen toxicity.…”

Section: Discussionsupporting

confidence: 76%

“…These authors also report that small peptides react at essentially the same rate as do their constituent amino acids, which implies that glutathione should react with singlet oxygen. Rougee and co-workers (25) have demonstrated that the bimolecular rate constants for glutathione and cysteine reactions with singlet oxygen are in fact similar. Glutathione must therefore be considered a potential protective agent against killing of bacteria by singlet oxygen.…”

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confidence: 99%

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Comparison of killing of gram-negative and gram-positive bacteria by pure singlet oxygen

1989

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Gram-negative and gram-positive bacteria were found to display different sensitivities to pure singlet oxygen generated outside of cells. Killing curves for Salmonella typhimurium and Escherichia coli strains were indicative of multihit killing, whereas curves for Sarcina lutea, Staphylococcus aureus, Streptococcus lactis, and Streptococcus faecalis exhibited single-hit kinetics. The S. typhimurium deep rough strain TA1975, which lacks nearly all of the cell wall lipopolysaccharide coat and manifests concomitant enhancement of penetration by some exogenous substances, responded to singlet oxygen with initially faster inactivation than did the S. typhimurium wild-type strain, although the maximum rates of killing appeared to be quite similar. The structure of the cell wall thus plays an important role in susceptibility to singlet oxygen. The outer membrane-lipopolysaccharide portion of the gram-negative cell wall initially protects the bacteria from extracellular singlet oxygen, although it may also serve as a source for secondary reaction products which accentuate the rates of cell killing. S. typhimurium and E. coli strains lacking the cellular antioxidant, glutathione, showed no difference from strains containing glutathione in response to the toxic effects of singlet oxygen. Strains of Sarcina lutea and Staphylococcus aureus that contained carotenoids, however, were far more resistant to singlet oxygen lethality than were both carotenoidless mutants of the same species and other gram-positive species lacking high levels of protective carotenoids.

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Section: Discussionsupporting

confidence: 76%

mentioning

confidence: 99%

Comparison of killing of gram-negative and gram-positive bacteria by pure singlet oxygen

1989

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“…In contrast, no cleavage was observed when DNA was incubated with AGE protein in the absence of irradiation or when irradiation was performed in the absence of sensitizer protein. Importantly, AGE sensitization of DNA damage was shown to proceed equally well under aerobic and nonaerobic conditions, and thus antioxidants such as catalase and superoxide dismutase had little effect on DNA cleavage by AGE sensitization, whereas excited state quenchers such as NaN 3 , KI, and organic thiol compounds were strongly protective when present during irradiation, either in the absence or presence of oxygen (Rougee et al, 1988;Beutner et al, 2000). Based on these earlier findings, DNA protection from AGE photosensitization by test compounds present during irradiation was used as a broad initial screen for the identification of agents capable of interfering with sensitized photodamage by mechanisms different from antioxidant or UV screening activity.…”

Section: Qpes Screen 1: Suppression Of Age-photosensitized Dna Damagementioning

confidence: 99%

Identification of Quenchers of Photoexcited States as Novel Agents for Skin Photoprotection

Wondrak

Jacobson

2004

J Pharmacol Exp Ther

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Photooxidative stress is a key mechanism in UVA-induced skin photodamage. Photoexcited states of endogenous UVA chromophores such as porphyrins, melanin precursors, and crosslink-fluorophores of skin collagen exert skin photodamage by direct reaction with substrate molecules (type I photosensitization) or molecular oxygen (type II), leading to formation of reactive oxygen species. Based on our previous research on the role of photoexcited states of endogenous skin chromophores as sensitizers of photooxidative stress, we describe here the identification of a novel class of chemopreventive agents for topical skin photoprotection: quenchers of photoexcited states (QPES). QPES compounds antagonize the harmful excited state chemistry of endogenous sensitizers by physical quenching, facilitating the harmless return of the sensitizer excited state to the electronic ground state by energy dissipation. To identify QPES compounds suitable for development, we designed a primary screening assay based on QPES suppression of photosensitized plasmid cleavage using conditions that exclude antioxidants. This screen is followed with a screen to test for nonsacrificial quenching of dye-sensitized singlet oxygen ( 1 O 2 ) formation by electron paramagnetic resonance detection of 2,2,6,6-tetramethyl-piperidine-1-oxyl, a stable free radical indicative of 1 O 2 formation. These initial screens identified a pyrrolidine pharmacophore with pronounced QPES activity, and L-proline and other noncytotoxic proline derivatives containing this pharmacophore were then screened for efficacy in cellular models of sensitized photodamage. These compounds showed QPES protection against dye-sensitized and psoralen-UVA-induced apoptosis and suppression of proliferation in cultured human skin keratinocytes and fibroblasts. Furthermore, QPES photoprotection of reconstructed full thickness human skin exposed to solar simulated light has been demonstrated.

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“…Ergothioneine also interacts with ROS, most probably through the quenching of singlet oxygen (Hartman et al, 1988). In addition, the compound reacts with hydroxyl radicals (Rougee et al, 1988;Akanmu et al, 1991), and scavenges hypochlorous acid (Akanmu et al, 1991), peroxyl radical (Asmus et al, 1996), and peroxynitrite (Aruoma et al, 1997). The effects of ergothioneine on oxidative and/or antioxidant enzymes are largely unexplored.…”

Section: Ergothioneine Protects Endothelial Cellsmentioning

confidence: 99%

Uptake and Protective Effects of Ergothioneine in Human Endothelial Cells

Yang²,

Sit

et al. 2014

J Pharmacol Exp Ther

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Ergothioneine is a thiourea derivative of histidine found in food, especially mushrooms. Experiments in cell-free systems and chemical assays identified this compound as a powerful antioxidant. Experiments were designed to test the ability of endothelial cells to take up ergothioneine and hence benefit from protection against oxidative stress. Reverse-transcription polymerase chain reaction and Western blotting demonstrated transcription and translation of an ergothioneine transporter in human brain microvascular endothelial cells (HBMECs). Uptake of [3 H]ergothioneine occurred by the organic cation transporter novel type-1 (OCTN-1), was sodium-dependent, and was reduced when expression of OCTN-1 was silenced by small interfering RNA (siRNA). The effect of ergothioneine on the production of reactive oxygen species (ROS) in HBMECs was measured using dichlorodihydrofluorescein and lucigenin, and the effect on cell viability was studied using the MTT [3-(4,5-dimethylthiazol-2-yl)-2,5-diphenyltetrazolium bromide] assay. ROS production and cell death induced by pyrogallol, xanthine oxidase plus xanthine, and high glucose were suppressed by ergothioneine. The antioxidant and cytoprotective effects of ergothioneine were abolished when OCTN-1 was silenced using siRNA. The expression of NADPH oxidase 1 was decreased, and those of glutathione reductase, catalase, and superoxide dismutase enhanced by the compound. In isolated rat basilar arteries, ergothioneine attenuated the reduction in acetylcholine-induced relaxation caused by pyrogallol, xanthine oxidase plus xanthine, or incubation in high glucose. Chronic treatment with the compound improved the response to acetylcholine in arteries of rats with streptozotocin-induced diabetes. In summary, ergothioneine is taken up by endothelial cells via OCTN-1, where the compound then protects against oxidative stress, curtailing endothelial dysfunction.

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Deactivation of Singlet Molecular Oxygen by Thiols and Related Compounds, Possible Protectors Against Skin Photosensitivity

Cited by 151 publications

References 28 publications

Comparison of killing of gram-negative and gram-positive bacteria by pure singlet oxygen

Comparison of killing of gram-negative and gram-positive bacteria by pure singlet oxygen

Identification of Quenchers of Photoexcited States as Novel Agents for Skin Photoprotection

Uptake and Protective Effects of Ergothioneine in Human Endothelial Cells

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