Strategies for the Design of Donors and Precursors of Reactive Sulfur Species

Xu, Shi; Hamsath, Akil; Neill, Deshka L.; Wang, Yingying; Liu, Jinbao; Xian, Ming

doi:10.1002/chem.201804895

Cited by 41 publications

(36 citation statements)

References 86 publications

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“…new insights into this process. As many of these molecular tools have been extensively reviewed elsewhere (153)(154)(155)(156)(157)(158)(159), here we provide only a summary of the available approaches, while pointing out specific challenges to their use. H 2 S and RSS donors H 2 S donors largely fall into three main classes.…”

Section: Chemical Tools For Generation Detection and Quantificationmentioning

confidence: 99%

“…Whereas H 2 S donors have been extensively developed over the last 10 years, RSS donors typically found in the form of persulfide donors are comparatively less so (153,158). For in vitro chemical reactivity studies, we and others have relied on in situ thiol persulfide generation from the reaction of excess H 2 S with a disulfide, resulting in a mixture containing the thiol persulfide that is not easily separated from the remaining reactants of H 2 S, disulfide, and thiol (45).…”

Section: Chemical Tools For Generation Detection and Quantificationmentioning

confidence: 99%

“…ROS-activated H 2 S and persulfide donors have also garnered recent attention (Fig. 6B) (154,158) because these types of probes are particularly useful for studying ROS/H 2 S cross-talk, which is likely relevant at sites of infection. These donors are specific for H 2 O 2 activation and react readily to generate H 2 S or a persulfide species.…”

Section: Chemical Tools For Generation Detection and Quantificationmentioning

confidence: 99%

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H2S and reactive sulfur signaling at the host-bacterial pathogen interface

Walsh

Giedroc

2020

Journal of Biological Chemistry

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Bacterial pathogens that cause invasive disease in the vertebrate host must adapt to host efforts to cripple their viability. Major host insults are reactive oxygen and reactive nitrogen species as well as cellular stress induced by antibiotics. Hydrogen sulfide (H2S) is emerging as an important player in cytoprotection against these stressors, which may well be attributed to downstream more oxidized sulfur species termed reactive sulfur species (RSS). In this review, we summarize recent work that suggests that H2S/RSS impacts bacterial survival in infected cells and animals. We discuss the mechanisms of biogenesis and clearance of RSS in the context of a bacterial H2S/RSS homeostasis model, and the bacterial transcriptional regulatory proteins that act as “sensors” of cellular RSS that maintain H2S/RSS homeostasis. In addition, we cover fluorescence imaging- and mass spectrometry-based approaches used to detect and quantify RSS in bacterial cells. Lastly, we discuss proteome persulfidation (S-sulfuration) as potential mediators of H2S/RSS signaling in bacteria in the context of the writer-reader-eraser paradigm, and progress toward ascribing regulatory significance to this widespread post-translational modification.

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Section: Chemical Tools For Generation Detection and Quantificationmentioning

confidence: 99%

Section: Chemical Tools For Generation Detection and Quantificationmentioning

confidence: 99%

Section: Chemical Tools For Generation Detection and Quantificationmentioning

confidence: 99%

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H2S and reactive sulfur signaling at the host-bacterial pathogen interface

Walsh

Giedroc

2020

Journal of Biological Chemistry

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“…RNS, nitrogen-containing oxidants, consist of nitric oxide (NO•) and nitrogen dioxide radical (NO 2 •), peroxynitrite (HNO 3 − ), as well as other oxides of nitrogen. Similarly, reactive sulfur species (RSS) are sulfur-containing molecules, which include hydrogen sulfide (H 2 S), thiols (RSH), persulfides (RSSH), polysulfides, S-nitrosothiols (RSNO), hydrogen polysulfides, and sulfenic acids (RSOH), that have essential roles in the regulation of cellular systems ( Xu et al, 2019 ).…”

Section: Reactive Species and Oxidative Stressmentioning

confidence: 99%

Medicinal Prospects of Antioxidants From Algal Sources in Cancer Therapy

Ferdous

Yusof

2021

Front. Pharmacol.

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Though cancer therapeutics can successfully eradicate cancerous cells, the effectiveness of these medications is mostly restricted to several deleterious side effects. Therefore, to alleviate these side effects, antioxidant supplementation is often warranted, reducing reactive species levels and mitigating persistent oxidative damage. Thus, it can impede the growth of cancer cells while protecting the normal cells simultaneously. Moreover, antioxidant supplementation alone or in combination with chemotherapeutics hinders further tumor development, prevents chemoresistance by improving the response to chemotherapy drugs, and enhances cancer patients’ quality of life by alleviating side effects. Preclinical and clinical studies have been revealed the efficacy of using phytochemical and dietary antioxidants from different sources in treating chemo and radiation therapy-induced toxicities and enhancing treatment effectiveness. In this context, algae, both micro and macro, can be considered as alternative natural sources of antioxidants. Algae possess antioxidants from diverse groups, which can be exploited in the pharmaceutical industry. Despite having nutritional benefits, investigation and utilization of algal antioxidants are still in their infancy. This review article summarizes the prospective anticancer effect of twenty-three antioxidants from microalgae and their potential mechanism of action in cancer cells, as well as usage in cancer therapy. In addition, antioxidants from seaweeds, especially from edible species, are outlined, as well.

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“…In response to this need, chemists have developed different types of H 2 S donors in the last decade, which can be activated by different triggers, such as hydrolysis, [13][14][15] cellular thiols, [16][17][18][19][20][21][22][23][24][25][26] light, [27][28][29][30][31] pH modulation, [32][33] and enzymes [34][35] (Figure 1). [36][37][38][39][40][41][42][43] Among these donors, aryl thioamides have attracted attention due to their synthetic simplicity and ease of incorporation into common pharmaceutical compounds. 24 For example, when compared to regular non-steroidal anti-inflammatory drugs (NSAID), thioamide-coupled NSAIDs, such as ATB-346, have retained promising anti-inflammatory activities while significantly reducing side GI damage, suggesting potential applications of these donors as H 2 S-related therapeutics.…”

Section: Introductionmentioning

confidence: 99%

Cyclic Sulfenyl Thiocarbamates Release Carbonyl Sulfide and Hydrogen Sulfide Independently in Thiol-Promoted Pathways

2019

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Hydrogen sulfide (H 2 S) is an important signaling molecule that provides protective activities in a variety of physiological and pathological processes. Among the different types of H 2 S donor compounds, thioamides have attracted attention due to prior conjugation to non-steroidal antiinflammatory drugs (NSAIDs) to access H 2 S-NSAID hybrids with significantly-reduced toxicity, but the mechanism of H 2 S release from thioamides remains unclear. Herein, we reported the synthesis and evaluation of a class of thioamide-derived sulfenyl thiocarbamates (SulfenylTCMs) that function as a new class of H 2 S donors. These compounds are efficiently activated by cellular thiols to release carbonyl sulfide (COS), which is quickly converted to H 2 S by carbonic anhydrase (CA). In addition, through mechanistic investigations we establish that COS-independent H 2 S release pathways are also operative. In contrast to the parent thioamide-based donors, the SulfenylTCMs exhibit excellent H 2 S releasing efficiencies of up to 90% and operate through mechanistically well-defined pathways. In addition, we demonstrate that the sulfenyl thiocarbamate group is readily attached to common NSAIDs, such as naproxen, to generate YZ-597 as an efficient H 2 S-NSAID hybrid, which we demonstrate releases H 2 S in cellular environments. Taken together, this new class of H 2 S donor motifs provide an important platform for new donor development.

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Strategies for the Design of Donors and Precursors of Reactive Sulfur Species

Cited by 41 publications

References 86 publications

H2S and reactive sulfur signaling at the host-bacterial pathogen interface

H2S and reactive sulfur signaling at the host-bacterial pathogen interface

Medicinal Prospects of Antioxidants From Algal Sources in Cancer Therapy

Cyclic Sulfenyl Thiocarbamates Release Carbonyl Sulfide and Hydrogen Sulfide Independently in Thiol-Promoted Pathways

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