Singlet oxygen production from the reactions of ozone with biological molecules

Kanofsky, Jeffrey R.; Sima, Paul D.

doi:10.1016/s0021-9258(18)31548-5

Cited by 146 publications

(30 citation statements)

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“…This observation is consistent with the hypothesis that a considerable number of genes conform to the scenario of induction through the transient release of transcriptional repression as illustrated in Figure 9c. In another example, ozone treatment shows significant overlap with 1 O 2 ‐induced genes (Figure 2b) commensurate with its ability to react with many biomolecules and produce 1 O 2 (Kanofsky & Sima, 1991). Intriguingly, the triple JA, ethylene and salicylic acid mutants, coi1 ein2 sid2 , were shown to be ineffective in suppressing ozone‐induced genes (Xu, Vaahtera, & Brosche, 2015).…”

Section: Discussionmentioning

confidence: 96%

Attenuation of cytosolic translation by RNA oxidation is involved in singlet oxygen‐mediated transcriptomic responses

Koh

Cohen

Brandis

et al. 2021

Plant Cell & Environment

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Singlet oxygen ( 1 O 2 ) production is associated with stress signalling. Here, using Arabidopsis as a model system, we study the effects of the accumulation of 8-hydroxyguanosine (8-oxoG), a major product of 1 O 2 -mediated RNA oxidation. We show that 8-oxoG can accumulate in vivo when 1 O 2 is produced in the cytoplasm.Conditions for such production include the application of RB in the light, dark-to-light transitions in the flu mutant, or subjecting plants to combined dehydration/light exposure. Transcriptomes of these treatments displayed a significant overlap with transcripts stimulated by the cytosolic 80S ribosomal translation inhibitors, cycloheximide and homoharringtonine. We demonstrate that 8-oxoG accumulation correlates with a decrease in RNA translatability, resulting in the rapid decrease of the levels of labile gene repressor elements such as IAA1 and JAZ1 in a proteasome-dependent manner. Indeed, genes regulated by the labile repressors of the jasmonic acid signalling pathway were induced by cycloheximide, RB or dehydration/light treatment independently of the hormone. The results suggest that 1 O 2 , by oxidizing RNA, attenuated cellular translatability and caused specific genes to be released from the repression of their cognate short half-life repressors. The findings here describe a novel means of gene regulation via the direct interaction of 1 O 2 with RNA.

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Section: Discussionmentioning

confidence: 96%

Attenuation of cytosolic translation by RNA oxidation is involved in singlet oxygen‐mediated transcriptomic responses

Koh

Cohen

Brandis

et al. 2021

Plant Cell & Environment

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“…It is well-known that in O 3 reactions singlet dioxygen [O 2 ( 1 ∆ g )] may be formed in high yields. 1,2 This is always the case when O-transfer reactions dominate. Spin conservation rules then demand that the resulting dioxygen molecule must be in its (excited) singlet state, because educt and O 3 as well as the product are in their singlet (ground) states.…”

mentioning

confidence: 99%

Singlet dioxygen formation in ozone reactions in aqueous solution

Muñoz

Mvula

Braslavsky

et al. 2001

J. Chem. Soc., Perkin Trans. 2

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In ozone reactions, singlet dioxygen [O 2 ( 1 ∆ g )] is formed when ozone reacts by O-atom transfer. O 2 ( 1 ∆ g ) yields were determined for more than 50 compounds using as reference the reaction of hydrogen peroxide with hypochlorite. Close to 100% yields were found in the reaction of O 3 with sulfides, disulfides, methanesulfinic acid, and nitrite. In accordance with this, the only products are: methionine sulfoxide, methanesulfonic acid, and nitrate for the reaction of O 3 with methionine, methanesulfinic acid, and nitrite, respectively. In the case of aliphatic tertiary amines (trimethylamine, triethylamine, and DABCO), the O 2 ( 1 ∆ g ) yields range between 70 and 90%, the aminoxide being the other major product. With EDTA and nitrilotriacetic acid (NTA), the O 2 ( 1 ∆ g ) yield is around 20%. The interpretation of the data with DABCO required the determination of the quenching constant of O 2 ( 1 ∆ g ) by this amine, k q = 1.8 × 10 9 dm 3 mol Ϫ1 s Ϫ1 in H 2 O and D 2 O, two orders of magnitude lower than previously reported. Aromatic tertiary amines give even lower O 2 ( 1 ∆ g ) yields [N,N-dimethylaniline (7%), N,N,N Ј,N Ј-tetramethylphenylenediamine (9%)]. Substantial amounts of O 2 ( 1 ∆ g ) are also formed with the DNA model compounds, 2Ј-deoxyguanosine (40%) and 2Ј-deoxyadenosine (15%, in the presence of tert-butyl alcohol as ؒ OH scavenger). The pyrimidine nucleobases only yield O 2 ( 1 ∆ g ) when deprotonated at N(1). O 2 ( 1 ∆ g ) formation is also observed with hydrogen sulfide (15%), azide (17%), bromide (56%), iodide (12%), and cyanide ions (20%). The O 2 ( 1 ∆ g ) yield from the reaction of O 3 with phenols and phenolates is typically around 20%, but may rise closer to 50% in the case of pentachloro-and pentabromophenolate. Low O 2 ( 1 ∆ g ) yields are found with unsaturated acids such as dihydroxyfumarate (6%), muconate (2%), and acetylenedicarboxylate (15%). With saturated compounds, also, no O 2 ( 1 ∆ g ) (e.g. with propan-2-ol, acetaldehyde, acetaldehyde dimethylacetal and glyoxal) or very little O 2 ( 1 ∆ g ) (formic acid; 6%, at high formate concentrations) was detected. As shown with some examples, knowledge of the O 2 ( 1 ∆ g ) yield (in combination with that of other products) is a prerequisite for the elucidation of the mechanisms of O 3 reactions in aqueous solutions.

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“…The reaction products of fatty acids are aldehydes, carbonic acids, and H202 [349], as well as secondary ozonides [338], whose decomposition results in radicals [338]. The reaction products of the proteins are the various oxidation products of the amino acids [339,350]. The reaction of ozone with tertiary amines, sulfides, sulfoxides, phosphites, sterically hindered olefins, certain ethers, and aldehydes [351][352][353][354] may even liberate singlet oxygen [350].…”

Section: Ozone's Effect On Organismsmentioning

confidence: 99%

“…The reaction products of the proteins are the various oxidation products of the amino acids [339,350]. The reaction of ozone with tertiary amines, sulfides, sulfoxides, phosphites, sterically hindered olefins, certain ethers, and aldehydes [351][352][353][354] may even liberate singlet oxygen [350]. In aqueous solutions, ozone even produces hydroxyl radicals and superoxide anions via radical chain reactions [355][356][357].…”

Section: Ozone's Effect On Organismsmentioning

confidence: 99%

Evolutionary aspects of copper binding centers in copper proteins

Abolmaali

Taylor

Weser

Structure and Bonding

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A great number of active centers in proteins and enzymes contain transition metals. Each metal imposes specific catalytic properties on the protein which could not be achieved when employing a different metal. The special role and characteristic reactivity of coordinated copper is illustrated by looking at the evolutionary aspects of copper proteins. The evolution of copper-binding sites is closely linked to that of copper proteins. Copper centers have evolved according to various principles, similar to the evolutionary development of proteins and enzymes. Three basic principles may be observed: the copper-binding centers of metallothioneins and type 1 copper centers developed in non-metal proteins; the transformation of the metal-binding centers of iron or manganese proteins led to the development of the type 2 copper centers; and the trinuclear copper-binding centers of the blue oxidases were formed by alterations and recombinations of type 1 copper centers. Simple, although as yet unknown, mononuclear copper centers gave rise to the type 3 copper-binding sites of the hemocyanins and tyrosinases, as well as to the Cu A-and CUB-centers of the cytochrome oxidases and N20reductase. According to this assignment, copper proteins containing either type 1 copper, type 3 copper, CUA-centers, or CUB-centers share a common ancestor. They developed at least in part by divergent evolution. Type 2 copper proteins are the products of convergent evolution and, consequently, show little or no phylogenetic homology.

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Singlet oxygen production from the reactions of ozone with biological molecules

Cited by 146 publications

References 0 publications

Attenuation of cytosolic translation by RNA oxidation is involved in singlet oxygen‐mediated transcriptomic responses

Attenuation of cytosolic translation by RNA oxidation is involved in singlet oxygen‐mediated transcriptomic responses

Singlet dioxygen formation in ozone reactions in aqueous solution

Evolutionary aspects of copper binding centers in copper proteins

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