Coenzyme Q10 and related quinones oxidize H2S to polysulfides and thiosulfate

Olson, Kenneth R.; Clear, Kasey J.; Derry, Paul J.; Gao, Yan; Ma, Zhilin; Wu, Gang; Kent, Thomas A.; Straub, K. D.

doi:10.1016/j.freeradbiomed.2022.02.018

Cited by 15 publications

(21 citation statements)

References 55 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

“…Overall polysulfide concentration at 110 min was greater with 10 µM than with 30 µM 1,4-NQ which is consistent with Figure 2 and the SOD-enhancement of SSP4 fluorescence is consistent with our previous observations on quinones [17,18]. However, the rate of increase in SSP4 fluorescence was considerably greater with SOD in <1% O 2 than with SOD in 21% O 2 with either 10 µM or 30 µM.…”

Section: Effects Of Oxygen and Sod On Polysulfide Production Detected...supporting

confidence: 92%

“…We have previously shown that low oxygen decreases SSP4-detected polysulfide production when H 2 S is incubated with CoQ 0 , whereas in normoxic solutions SOD increases polysulfides when H 2 S is incubated with CoQ 0 [ 18 ]. This suggested that an examination of oxygen tension and SOD on 1,4-NQ reactions with H 2 S was also warranted.…”

Section: Resultsmentioning

confidence: 99%

“…Mass Spectrometry 4.7.1. LC-ESI-HRMS Protocol Inorganic polysulfides were identified using liquid chromatography electrospray ionization high resolution mass spectrometry (LC-ESI-HRMS) using a micrOTOF-Q II Mass Spectrometer (Bruker Daltronics, Billerica, MA, USA) coupled to an UltiMate 3000 (Thermo Fisher) UHPLC system, as described previously [18]. A Waters Acquity UPLC HSS T3 column (1.8 µm, 150 mm × 2.1 mm inner diameter) was used with mobile phases A (water containing 0.1% formic acid) and B (acetonitrile containing 0.1% formic acid).…”

Section: Absorbance Spectramentioning

confidence: 99%

“…Comparison of the relative rates of oxygen consumption (O 2 ) during autoxidation of NQs under various conditions from Munday a and this study. Right column shows polysulfide production (SSP4 fluorescence) by SOD with NQ and H 2 S. a,[40]; b, addition of corresponding oxidized NQ; c,[18]. Up arrows indicate degree of increase, horizontal arrow indicates no change and down arrows indicate degree of decrease.…”

mentioning

confidence: 99%

See 3 more Smart Citations

Naphthoquinones Oxidize H2S to Polysulfides and Thiosulfate, Implications for Therapeutic Applications

Olson

Clear

Derry

et al. 2022

IJMS

Self Cite

View full text Add to dashboard Cite

1,4-Napththoquinones (NQs) are clinically relevant therapeutics that affect cell function through production of reactive oxygen species (ROS) and formation of adducts with regulatory protein thiols. Reactive sulfur species (RSS) are chemically and biologically similar to ROS and here we examine RSS production by NQ oxidation of hydrogen sulfide (H2S) using RSS-specific fluorophores, liquid chromatography-mass spectrometry, UV-Vis absorption spectrometry, oxygen-sensitive optodes, thiosulfate-specific nanoparticles, HPLC-monobromobimane derivatization, and ion chromatographic assays. We show that NQs, catalytically oxidize H2S to per- and polysulfides (H2Sn, n = 2–6), thiosulfate, sulfite and sulfate in reactions that consume oxygen and are accelerated by superoxide dismutase (SOD) and inhibited by catalase. The approximate efficacy of NQs (in decreasing order) is, 1,4-NQ ≈ juglone ≈ plumbagin > 2-methoxy-1,4-NQ ≈ menadione >> phylloquinone ≈ anthraquinone ≈ menaquinone ≈ lawsone. We propose that the most probable reactions are an initial two-electron oxidation of H2S to S0 and reduction of NQ to NQH2. S0 may react with H2S or elongate H2Sn in variety of reactions. Reoxidation of NQH2 likely involves a semiquinone radical (NQ·−) intermediate via several mechanisms involving oxygen and comproportionation to produce NQ and superoxide. Dismutation of the latter forms hydrogen peroxide which then further oxidizes RSS to sulfoxides. These findings provide the chemical background for novel sulfur-based approaches to naphthoquinone-directed therapies.

show abstract

Section: Effects Of Oxygen and Sod On Polysulfide Production Detected...supporting

confidence: 92%

Section: Resultsmentioning

confidence: 99%

Section: Absorbance Spectramentioning

confidence: 99%

mentioning

confidence: 99%

See 2 more Smart Citations

Naphthoquinones Oxidize H2S to Polysulfides and Thiosulfate, Implications for Therapeutic Applications

Olson

Clear

Derry

et al. 2022

IJMS

Self Cite

View full text Add to dashboard Cite

show abstract

“…The generation or degradation of polysulfides by metalloproteins is an active area of investigation and additional enzymes involved in polysulfide metabolism are likely to be discovered. Finally, Olson and coworkers [ 83 ] have shown that ubiquinone (CoQ) and related quinones are capable of oxidizing H 2 S to polysulfides and thiosulfate in O 2 -dependent processes. The ubiquitous nature of CoQ in biological membranes indicates that the generation of polysulfides via H 2 S oxidation can occur in numerous locations and can be a common event.…”

Section: Introductionmentioning

confidence: 99%

The antioxidant and oxidant properties of hydropersulfides (RSSH) and polysulfide species

Switzer

Fukuto²

2022

Redox Biology

View full text Add to dashboard Cite

Oxidation of Hydrogen Sulfide to Polysulfide and Thiosulfate by a Carbon Nanozyme: Therapeutic Implications with an Emphasis on Down Syndrome

et al. 2023

View full text Add to dashboard Cite

Hydrogen sulfide (H2S) is a noxious, potentially poisonous, but necessary gas produced from sulfur metabolism in humans. In Down Syndrome (DS), the production of H2S is elevated and associated with degraded mitochondrial function. Therefore, removing H2S from the body as a stable oxide could be an approach to reducing the deleterious effects of H2S in DS. In this report we describe the catalytic oxidation of hydrogen sulfide (H2S) to polysulfides (HS2+n−) and thiosulfate (S2O32−) by poly(ethylene glycol) hydrophilic carbon clusters (PEG‐HCCs) and poly(ethylene glycol) oxidized activated charcoal (PEG‐OACs), examples of oxidized carbon nanozymes (OCNs). We show that OCNs oxidize H2S to polysulfides and S2O32− in a dose‐dependent manner. The reaction is dependent on O2 and the presence of quinone groups on the OCNs. In DS donor lymphocytes we found that OCNs increased polysulfide production, proliferation, and afforded protection against additional toxic levels of H2S compared to untreated DS lymphocytes. Finally, in Dp16 and Ts65DN murine models of DS, we found that OCNs restored osteoclast differentiation. This new action suggests potential facile translation into the clinic for conditions involving excess H2S exemplified by DS.

show abstract

Coenzyme Q10 and related quinones oxidize H2S to polysulfides and thiosulfate

Cited by 15 publications

References 55 publications

Naphthoquinones Oxidize H2S to Polysulfides and Thiosulfate, Implications for Therapeutic Applications

Naphthoquinones Oxidize H2S to Polysulfides and Thiosulfate, Implications for Therapeutic Applications

The antioxidant and oxidant properties of hydropersulfides (RSSH) and polysulfide species

Oxidation of Hydrogen Sulfide to Polysulfide and Thiosulfate by a Carbon Nanozyme: Therapeutic Implications with an Emphasis on Down Syndrome

Contact Info

Product

Resources

About