Ribonucleoside reactivities with singlet (1Δg) molecular oxygen

Clagett, Donald C.; Galen, Theodore J.

doi:10.1016/s0003-9861(71)80056-5

Cited by 18 publications

(10 citation statements)

References 25 publications

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“…This trend in reactivity with 1 O 2 is opposite than what was observed in the direct photochemical reactions and is most likely due to the relative number of guanine bases in the oligomers (10 in oligomer B and 1 in oligomer A). Whereas uracil and cytosine are the most sensitive bases to direct photo-oxidation, guanine bases are the most-reactive with 1 O 2 and other oxidants …”

Section: Resultsmentioning

confidence: 99%

“…Whereas uracil and cytosine are the most sensitive bases to direct photo-oxidation, guanine bases are the most-reactive with 1 O 2 and other oxidants. 54 There was no statistical difference in reaction kinetics measured by quantitative MALDI-TOF-MS and RT-qPCR (Figure 4 and Table 2), suggesting that the same 1 O 2 -induced RNA damage is detected by both techniques. It should be noted that reactions between the oligomers and 1 O 2 resulted in products that interfered with the MALDI oligomer peaks.…”

Section: Environmental Science and Technologymentioning

confidence: 88%

“…Reported reaction rate constants for 1 O 2 with RNA monomer bases offer an opportunity to relate our results with established chemical kinetics. 54,56 By summing up the reported rate constants of the individual bases in our oligomers, we predicted second-order rate constants of 7.8 × 10 6 M −1 s −1 for oligomer A and 1.3 × 10 7 M −1 s −1 for oligomer B (Table S2). The predicted rate constants are 7 times and 2 times higher than the measured rate constants, respectively.…”

Section: Environmental Science and Technologymentioning

confidence: 99%

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Direct and Indirect Photochemical Reactions in Viral RNA Measured with RT-qPCR and Mass Spectrometry

Zhong

Wigginton

2016

Environ. Sci. Technol.

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RNA carries the genetic instructions for many viruses to replicate in their host cells. The photochemical reactions that take place in RNA and affect viral infectivity in natural and engineered environments, however, remain poorly understood. We exposed RNA oligomer segments from the genome of bacteriophage MS2 to UV, simulated sunlight, and singlet oxygen (O) and analyzed the oligomer reaction kinetics with reverse transcription quantitative PCR (RT-qPCR) and quantitative matrix-assisted laser desorption-ionization time-of-flight (MALDI-TOF) mass spectrometry (MS). Following UV exposure, quantitative MALDI-TOF-MS detected significantly more RNA modifications than did RT-qPCR, suggesting that certain chemical modifications in the RNA were not detected by the reverse transcriptase enzyme. In contrast, MALDI-TOF-MS tracked as much O-induced RNA damage as RT-qPCR. After 5 h of simulated sunlight exposure (5100 J/m UVB and 1.2 × 10 J/m UVA), neither MALDI-TOF-MS nor RT-qPCR detected significant decreases in the oligomer concentrations. High-resolution electrospray ionization (ESI)-Orbitrap MS analyses identified pyrimidine photohydrates as the major UV products, which likely contributed to the discrepancy between the MS- and RT-qPCR-based results. Reactions between RNA oligomers and O resulted in an unidentified major product with a mass change of +6 Da. These results shed light on the photochemical reactions that take place in RNA and suggest that the analytical techniques used to detect RNA reactivity could bias the observed reaction kinetics.

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Section: Resultsmentioning

confidence: 99%

Section: Environmental Science and Technologymentioning

confidence: 88%

Section: Environmental Science and Technologymentioning

confidence: 99%

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Direct and Indirect Photochemical Reactions in Viral RNA Measured with RT-qPCR and Mass Spectrometry

Zhong

Wigginton

2016

Environ. Sci. Technol.

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“…Singlet oxygen may also be involved in the ¢X174 form I DNA strand breakage because scavengers for singlet oxygen inhibit the ¢X174 form I DNA strand breaks and the breakage of nucleic acids by singlet oxygen was reported. 27 ) …”

Section: Discussionmentioning

confidence: 99%

Induction of Strand Break in DNA by Reducing Sugar Phosphates

Morita¹,

Komano²

1983

Agricultural and Biological Chemistry

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“…As example, rubrene (4) reacts rapidly with '0, to yield the endoperoxide 5 (Wilson, 1966) and has recently been proposed as a means of detection of '0, in enzyme systems (Khan, 1976). However, rubrene is bleached by ozone to unidentified products 4 5 (Murray and Kaplan, 1969;Clagett and Galen, 1971) and oxidized by NaOCl or by hydrogen peroxide to the endoperoxide 5 (Khan, 1976). and we have observed a colorless product with the chromatographic properties of 5 formed in air oxidations of 4 induced by 6oCo gamma radiation (Gibson and Smith.…”

Section: Introductionmentioning

confidence: 99%

Sterol Metabolism. Xlii. On the Interception of Singlet Molecular Oxygen by Sterols

Smith¹,

Stroud²

1978

Photochem & Photobiology

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Abstract— The use of cyclic 1,3‐dienes and polycyclic aromatic hydrocarbons as xenobiotic substrates for the interception of electronically excited (singlet) molecular oxygen (1O2) in biological systems is reviewed and criticized, and the possibility of utilization of reactive endogenous substrates for 1O2 interception is considered. The common sterols, cholesterol, 5α‐cholest‐7‐en‐3β‐ol, and 5α‐lanost‐8‐en‐3β‐ol each give oxidation products with 1O2 different from those with ground‐state molecular oxygen that can be distinguished from one another by simple chromatographic means.

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Ribonucleoside reactivities with singlet (1Δg) molecular oxygen

Cited by 18 publications

References 25 publications

Direct and Indirect Photochemical Reactions in Viral RNA Measured with RT-qPCR and Mass Spectrometry

Direct and Indirect Photochemical Reactions in Viral RNA Measured with RT-qPCR and Mass Spectrometry

Induction of Strand Break in DNA by Reducing Sugar Phosphates

Sterol Metabolism. Xlii. On the Interception of Singlet Molecular Oxygen by Sterols

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