Selenoneine: a Unique Reactive Selenium Species From the Blood of Tuna With Implications for Human Diseases

Alhasan, Rama; Nasim, Muhammad Jawad; Jacob, Claus; Gaucher, Caroline

doi:10.1007/s40495-019-00175-8

Cited by 23 publications

(13 citation statements)

References 61 publications

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“…Owing to its strong nucleophilic power, Se readily coordinates with metal ions, such as Fe 2+ , Zn 2+ , Cd 2+ , Pt 2+ , and Hg 2+ , thus forming various Se–metal complexes to exert physiological or pharmacological effects. As depicted in Figure a, selenoneine 8a2 , a Se analog of ergothioneine 8a1 , has been identified as the predominant chemical form of organic Se in the blood of bluefin tuna (Thunnus thynnus). Importantly, the presence of selenol allows 8a2 to strongly bind to the heme moieties of myoglobin and hemoglobin, thereby protecting these central Fe-containing proteins from autoxidation, for instance, under hypoxic conditions when excessive amounts of ROS may be generated inside red blood cells.…”

Section: Case Studies Of Selenium In Medicinal Chemistrymentioning

confidence: 99%

Incorporating Selenium into Heterocycles and Natural Products─From Chemical Properties to Pharmacological Activities

Hou

2022

J. Med. Chem.

154

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Selenium (Se)-containing compounds have emerged as potential therapeutic agents for the treatment of a range of diseases. Through tremendous effort, considerable knowledge has been acquired to understand the complex chemical properties and biological activities of selenium, especially after its incorporation into bioactive molecules. From this perspective, we compiled extensive literature evidence to summarize and critically discuss the relationship between the pharmacological activities and chemical properties of selenium compounds and the strategic incorporation of selenium into organic molecules, especially bioactive heterocycles and natural products. We also provide perspectives regarding the challenges in selenium-based medicinal chemistry and future research directions.

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Section: Case Studies Of Selenium In Medicinal Chemistrymentioning

confidence: 99%

Incorporating Selenium into Heterocycles and Natural Products─From Chemical Properties to Pharmacological Activities

Hou

2022

J. Med. Chem.

154

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“…This rather familiar, still often overlooked sequence of chemical transforms provides new avenues leading to inorganic polysulfides and mixed selenosulfides and de facto opens up an entirely new field of bioinorganic chemistry, in microorganisms, plants, mammals and humans. Indeed, the field of biologically relevant selenium molecules is limited to a handful of molecules, such as the ergothioneine analogue selenoneine found in blue tuna, and such inorganic selenosulfides may spice up this field of biological chalcogen research considerably [34].…”

Section: Sources Of Polysulfidesmentioning

confidence: 99%

Inorganic Polysulfides and Related Reactive Sulfur–Selenium Species from the Perspective of Chemistry

et al. 2019

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Polysulfides (H2Sx) represent a class of reactive sulfur species (RSS) which includes molecules such as H2S2, H2S3, H2S4, and H2S5, and whose presence and impact in biological systems, when compared to other sulfur compounds, has only recently attracted the wider attention of researchers. Studies in this field have revealed a facet-rich chemistry and biological activity associated with such chemically simple, still unusual inorganic molecules. Despite their chemical simplicity, these inorganic species, as reductants and oxidants, metal binders, surfactant-like “cork screws” for membranes, components of perthiol signalling and reservoirs for inorganic hydrogen sulfide (H2S), are at the centre of complicated formation and transformation pathways which affect numerous cellular processes. Starting from their chemistry, the hidden presence and various roles of polysulfides in biology may become more apparent, despite their lack of clear analytical fingerprints and often murky biochemical footprints. Indeed, the biological chemistry of H2Sx follows many unexplored paths and today, the relationship between H2S and its oxidized H2Sx species needs to be clarified as a matter of “unmistaken identity”. Simultaneously, emerging species, such as HSSeSH and SenS8−n, also need to be considered in earnest.

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“…Surprisingly, there are very few examples of natural secondary metabolites that depend on selenium‐specific chemistry for function. From such molecules one could learn how and where organoselenides—optimized by evolution—would interfere with cellular processes . One of these rare examples is selenoneine (Figure a) .…”

Section: Figurementioning

confidence: 99%

“…From such molecules one could learn how and where organoselenides -optimized by evolution -would interfere with cellular processes. [14] One of these rare examples is selenoneine (Figure 1a). [15] This selenium isolog of ergothioneine ( Figure 1a) was first isolated from the muscle tissue of marine fish.…”

mentioning

confidence: 99%

Total Synthesis and Functional Characterization of Selenoneine

2019

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The N-a-trimethyl 2-selenohistidine selenoneine is the selenium isolog of the natural antioxidant ergothioneine. Sulfur-toselenium substitutions are known to endow proteins and nucleic acids with special activities. In contrast, secondary metabolites that exploit selenium-specific chemistry are rare. Selenoneine therefore provides a unique opportunity to study how natural organoselenides interact with cellular processes. In this report we describe the chemical synthesis of selenoneine and other 2-selenoimidazoles. With synthetic selenoneine at hand we discovered a set of reactivities that distinguish selenoneine from ergothioneine, showing that the two compounds can fill distinct functional niches. Synthetic access to 2selenoimidazoles should pave the way to explore the pharmaceutical potential and physiological function of this heretofore inaccessible class of compounds.

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Selenoneine: a Unique Reactive Selenium Species From the Blood of Tuna With Implications for Human Diseases

Cited by 23 publications

References 61 publications

Incorporating Selenium into Heterocycles and Natural Products─From Chemical Properties to Pharmacological Activities

Incorporating Selenium into Heterocycles and Natural Products─From Chemical Properties to Pharmacological Activities

Inorganic Polysulfides and Related Reactive Sulfur–Selenium Species from the Perspective of Chemistry

Total Synthesis and Functional Characterization of Selenoneine

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