Selenium as an emerging versatile player in heterocycles and natural products modification

Hou, Wenhua; Dong, Hewei; Zhang, Xiang; Wang, Yan; Su, Lin; Xu, Hongtao

doi:10.1016/j.drudis.2022.03.020

Cited by 51 publications

(38 citation statements)

References 63 publications

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“…However, only rare methods have been reported for the construction of Org‐Se compound libraries up to now. Therefore, the development of selenylation chemistries that suitable for parallel synthesis of Org‐Se library and/or Se‐containing DNA‐encoded library ( Se DEL) are highly needed for the development of seleno‐medicinal chemistry [9,10] …”

Section: Hit Generation: From Traditional High‐throughput Screening T...mentioning

confidence: 99%

“…Notably, accumulated evidence in chemical biology and medicinal chemistry has indicated that the special chemical properties of Se play a key role in the pharmacological activity, toxicity and metabolic property of Org-Se compounds. [3,9,10] The incorporation of Se into small molecules or natural products have been reported to bring additional benefits, which are closely correlated with the specific Se species as well as their ability to modulate the oxidative stress status of cells, mainly including antioxidation and prooxidation (Figure 1). [9,10] All of these merits indicate the versatile ability of Se in medicinal chemistry.…”

Section: Background: Selenium Is An Emerging Player In Medicinal Chem...mentioning

confidence: 99%

“…[3,9,10] The incorporation of Se into small molecules or natural products have been reported to bring additional benefits, which are closely correlated with the specific Se species as well as their ability to modulate the oxidative stress status of cells, mainly including antioxidation and prooxidation (Figure 1). [9,10] All of these merits indicate the versatile ability of Se in medicinal chemistry. However, the research on Org-Se therapeutic agents is still in its infancy at present, the lack and lag of efficient synthetic toolbox to access a large chemical space of Org-Se compounds is one of the key bottle necks.…”

Section: Background: Selenium Is An Emerging Player In Medicinal Chem...mentioning

confidence: 99%

“…Therefore, the development of selenylation chemistries that suitable for parallel synthesis of Org-Se library and/or Se-containing DNA-encoded library (SeDEL) are highly needed for the development of seleno-medicinal chemistry. [9,10] In this concept, we analyzed the established click chemistries that can be used for parallel synthesis of compound libraries, which are suitable for in situ biological activity screening. We paid special attention on the clickable selenylation reaction, and the DNA compatible selenylation chemistries that have been developed for SeDEL synthesis.…”

Section: Background: Selenium Is An Emerging Player In Medicinal Chem...mentioning

confidence: 99%

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Clickable Selenylation – a Paradigm for Seleno‐Medicinal Chemistry

et al. 2022

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Selenium (Se) is an emerging versatile player in medicinal chemistry. The incorporation of Se into small molecules and natural products could have multiple benefits. However, the lack of efficient methods for the synthesis of Se-containing chemical library has greatly hindered the development of seleno-medicinal chemistry. With the aim to address this issue, we proposed the development of "clickable selenylation" reactions, which can be used in the synthesis of Se-containing in situ library and DNA-encoded library (SeDEL), thereby quickly producing ultra-large collections of Se-containing compounds and boosting the development of seleno-medicinal chemistry. This research paradigm can be concluded as "clickable selenylation chemistry development!in situ library construction/SeDEL synthesis!phenotype-or target-based screening! seleno-hit compound".

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Section: Hit Generation: From Traditional High‐throughput Screening T...mentioning

confidence: 99%

Section: Background: Selenium Is An Emerging Player In Medicinal Chem...mentioning

confidence: 99%

Section: Background: Selenium Is An Emerging Player In Medicinal Chem...mentioning

confidence: 99%

Section: Background: Selenium Is An Emerging Player In Medicinal Chem...mentioning

confidence: 99%

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Clickable Selenylation – a Paradigm for Seleno‐Medicinal Chemistry

et al. 2022

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“…Thus, the toxic effect of 4a and 5b is not determined by genotoxicity. Many organoselenium compounds exhibit antioxidant activity closely correlated to their ability to scavenge reactive oxygen species (ROS) [24]. It was recently shown that selenoureas of the similar structures possess moderate antioxidant activity [25].…”

Section: Tests On Living Cellsmentioning

confidence: 99%

Anti-Inflammatory Activity of Soluble Epoxide Hydrolase Inhibitors Based on Selenoureas Bearing an Adamantane Moiety

Burmistrov

Morisseau

Babkov

et al. 2022

IJMS

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Bioinspired Selenium‐Nitrogen Exchange (SeNEx) Click Chemistry Suitable for Nanomole‐Scale Medicinal Chemistry and Bioconjugation

Hou,

Zhang,

Huang

et al. 2024

Angewandte Chemie

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Click chemistry is a powerful molecular assembly strategy for rapid functional discovery. The development of click reaction with new connecting linkage is of great importance for expanding the click chemistry toolbox. We report the first Selenium‐Nitrogen Exchange (SeNEx) click chemistry between benzoselenazolones and terminal alkynes (Se‐N to Se‐C), which is inspired by the biochemical SeNEx between Ebselen and cysteine (Cys) residue (Se‐N to Se‐S). The formed selenoalkyne connection is readily elaborated, thus endowing this chemistry with multidimensional molecular diversity. Besides, this reaction is characterized by modular, predictable, high‐yielding, fast kinetics (k2 ≥ 14.43 M‐1s‐1), excellent functional group compatibility, and working well at miniaturization (nanomole‐scale), opening up many interesting opportunities for organo‐Se synthesis and bioconjugation, as exemplified by sequential click chemistry (coupled with ruthenium‐catalyzed azide–alkyne cycloaddition (RuAAC) and sulfur‐fluoride exchange (SuFEx), seleno‐macrocycle synthesis, nanomole‐scale synthesis of Se‐containing natural product library and DNA‐encoded library (DEL), late‐stage peptide modification and ligation, and multiple functionalization of proteins. These results indicated that SeNEx is a useful strategy for new click chemistry development, and the established SeNEx chemistry will serve as a transformative platform in multidisciplinary fields such as synthetic chemistry, material science, chemical biology, medical chemistry, and drug discovery.

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Selenium as an emerging versatile player in heterocycles and natural products modification

Cited by 51 publications

References 63 publications

Clickable Selenylation – a Paradigm for Seleno‐Medicinal Chemistry

Clickable Selenylation – a Paradigm for Seleno‐Medicinal Chemistry

Anti-Inflammatory Activity of Soluble Epoxide Hydrolase Inhibitors Based on Selenoureas Bearing an Adamantane Moiety

Bioinspired Selenium‐Nitrogen Exchange (SeNEx) Click Chemistry Suitable for Nanomole‐Scale Medicinal Chemistry and Bioconjugation

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