Selenium(II)‐Nitrogen Exchange (SeNEx) Chemistry: A Good Chemistry Suitable for Nanomole‐Scale Parallel Synthesis, DNA‐encoded Library Synthesis, and Bioconjugation DOI
Wei Hou,

Shaoneng Hou,

Yuang Gu

et al.

ChemBioChem, Journal Year: 2024, Volume and Issue: unknown

Published: Oct. 9, 2024

The continuous development of click reactions with new connecting linkage is crucial for advancing the frontiers chemistry. Selenium-nitrogen exchange (SeNEx) chemistry, a versatile chemistry in represents an all-encompassing term nucleophilic substitution events that replace nitrogen at electrophilic selenium(II) center, enabling flexible and efficient assembly linkages around Se(II) core. Several SeNEx chemistries have been developed inspired by biochemical reaction between Ebselen cysteine residue, demonstrated significant potential on-plate nanomole-scale parallel synthesis, selenium-containing DNA-encoded library (SeDEL) as well peptide protein bioconjugation. This concept aims to present origins, advancements, applications selenium(II)-nitrogen while also outlining directions future research this field.

Language: Английский

Advances in drug structure-activity-relationships for the development of selenium-based compounds against HIV DOI

Dazhou Shi,

Shujing Xu,

Dang Ding

et al.

Expert Opinion on Drug Discovery, Journal Year: 2023, Volume and Issue: 19(2), P. 139 - 146

Published: Nov. 20, 2023

Introduction Selenium possesses numerous advantageous properties in the field of medicine, and a variety selenium-containing compounds have been documented to exhibit anti-HIV activity. This paper aims categorize these conduct SAR analysis offer guidance for drug design optimization.

Language: Английский

Citations

2
Bioinspired Selenium‐Nitrogen Exchange (SeNEx) Click Chemistry Suitable for Nanomole‐Scale Medicinal Chemistry and Bioconjugation DOI
Wei Hou,

Yiyuan Zhang,

Fuchao Huang

et al.

Angewandte Chemie, Journal Year: 2024, Volume and Issue: 136(15)

Published: Feb. 12, 2024

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

Language: Английский

Citations

0
Selenium: The Emerging Element in the Medicinal Chemist’s Toolkit DOI

Lanmeng Cui,

Wei Hou, Hongtao Xu

et al.

Future Medicinal Chemistry, Journal Year: 2024, Volume and Issue: 16(6), P. 493 - 496

Published: Feb. 20, 2024

Future Medicinal ChemistryVol. 16, No. 6 EditorialSelenium: the emerging element in medicinal chemist's toolkitLanmeng Cui, Wei Hou & Hongtao XuLanmeng CuiCollege of Pharmaceutical Science Institute Drug Development Chemical Biology, Zhejiang University Technology, Hangzhou, 310014, China, *Author for correspondence: E-mail Address: [email protected]://orcid.org/0000-0002-9027-8991College China Xu **Author [email protected]://orcid.org/0000-0001-5174-9079Shanghai Advanced Immunochemical Studies, ShanghaiTech University, Shanghai, 201210, ChinaPublished Online:20 Feb 2024https://doi.org/10.4155/fmc-2024-0041AboutSectionsView ArticleView Full TextPDF/EPUB ToolsAdd to favoritesDownload CitationsTrack CitationsPermissionsReprints ShareShare onFacebookTwitterLinkedInRedditEmail View articleKeywords: biocompatibleDNA-encoded libraryparallel synthesisseleniumReferences1. Rayman MP. Selenium and human health. Lancet 379(9822), 1256–1268 (2012).Medline CASGoogle Scholar2. W, H. Incorporating selenium into heterocycles natural products-from chemical properties pharmacological activities. J. Med. Chem. 65(6), 4436–4456 (2022).Medline Scholar3. Wrobel JK, Power R, Toborek M. Biological activity selenium: revisited. IUBMB Life 68(2), 97–105 (2016).Medline Scholar4. Leszczynska G, Cypryk M, Gostynski B et al. C5-substituted 2-selenouridines ensure efficient base pairing with guanosine; consequences reading NNG-3′ synonymous mRNA codons. Int. Mol. Sci. 21(8), 2882 (2020).Medline Scholar5. Dong H, Zhang X, Wang Y, Su L, as an versatile player products modification. Discov. Today 27(8), 2268–2277 Scholar6. Alhasan Nasim MJ, Jacob C, Gaucher C. Selenoneine: a unique reactive species from blood tuna implications diseases. Curr. Pharmacol. Reports. 5(3), 163–173 (2019).CASGoogle Scholar7. Feng Pan Qian Z Discovery selenium-containing STING agonists orally available antitumor agents. 65(22), 15048–15065 Scholar8. Rech TDST, Ribeiro EH, Castro ET Antidepressant potential functionalized 3-selanyl benzo[b]furan compound mice: focus on serotonergic system. ACS Neurosci. 14(6), 1181–1192 (2023).Medline Scholar9. Deng Xie B, Li Q novel bicyclic phenylselenyl-containing hybrids: bioavailable, potential, multiacting class estrogen receptor modulators against endocrine-resistant breast cancer. 65(11), 7993–8010 Scholar10. Pyka P, Haberek Więcek M First-in-class potent serotonin 5-HT agents beneficial neuroprotective profile Alzheimer's disease. 67(2), 1580–1610 (2024).Medline Scholar11. Bijian K, Wernic D, Nivedha AK Novel aurora A protein kinase C (α, β1, β2 θ) multitarget inhibitors: impact atoms potency selectivity. 65(4), 3134–3150 Scholar12. Kayrouz CM, Huang J, Hauser N, Seyedsayamdost MR. Biosynthesis small molecules diverse microorganisms. Nature 610(7930), 199–204 Scholar13. Beletskaya IP, Ananikov VP. Transition-metal-catalyzed C–S, C–Se C–Te bond formations via cross-coupling atom-economic addition reactions. achievements challenges. Rev. 122(21), 16110–16293 Scholar14. Cheng F, Guo Zheng S, S. Enzymatic synthesis organoselenium compounds C-Se formation mediated by sulfur carrier proteins. Nat. Synth. doi: 10.1038/s44160-023-00477-2 (2024) (Online).Google Scholar15. Yao Y Clickable selenylation - paradigm seleno-medicinal chemistry. ChemMedChem. 17(17), e202200324 Scholar16. Amporndanai Meng Shang W Inhibition mechanism SARS-CoV-2 main protease ebselen its derivatives. Commun. 12(1), 3061 (2021).Medline Scholar17. Gu S chemistry incorporation DNA-encoded libraries. Angew. Ed. 59(32), 13273–13280 Scholar18. H Selenylation suitable on-plate parallel on-DNA library enabling high-throughput 61(35), e202206516 Scholar19. Zhou Z, Wu L Organo-Se BTSAs-enabled performance: racemic asymmetric click application. 9(11), 3335–3346 (2023).CASGoogle Scholar20. Brenner Lerner RA. Encoded combinatorial Proc. Natl Acad. USA 89(12), 5381–5383 (1992).Medline Scholar21. Ma Evolution selection technology library. Acta Pharm. Sin. B. 14(2), 492–516 ScholarFiguresReferencesRelatedDetails Vol. STAY CONNECTED Metrics Downloaded 57 times History Received 5 February 2024 Accepted Published online 20 print March Information© Expert Publishing Ltd trading Taylor FrancisKeywordsbiocompatibleDNA-encoded synthesisseleniumAuthor contributionsW Cui wrote draft manuscript. HT revised draft. behalf all authors, submitted this All authors have approved submission manuscript.Financial disclosureThis work was supported Natural Foundation (numbers 21977070, 21907085 U19A2011) Fundamental Research Funds Provincial Universities Zhejiang, (No. RFA2022008). The no other relevant affiliations or financial involvement any organization entity interest conflict subject matter materials discussed manuscript apart those disclosed.Competing interests disclosureThe competing This includes employment, consultancies, honoraria, stock ownership options, expert testimony, grants patents received pending royalties.Writing disclosureNo writing assistance utilized production manuscript.PDF download

Language: Английский

Citations

0
Selenium(II)‐Nitrogen Exchange (SeNEx) Chemistry: A Good Chemistry Suitable for Nanomole‐Scale Parallel Synthesis, DNA‐encoded Library Synthesis, and Bioconjugation DOI
Wei Hou,

Shaoneng Hou,

Yuang Gu

et al.

ChemBioChem, Journal Year: 2024, Volume and Issue: unknown

Published: Oct. 9, 2024

The continuous development of click reactions with new connecting linkage is crucial for advancing the frontiers chemistry. Selenium-nitrogen exchange (SeNEx) chemistry, a versatile chemistry in represents an all-encompassing term nucleophilic substitution events that replace nitrogen at electrophilic selenium(II) center, enabling flexible and efficient assembly linkages around Se(II) core. Several SeNEx chemistries have been developed inspired by biochemical reaction between Ebselen cysteine residue, demonstrated significant potential on-plate nanomole-scale parallel synthesis, selenium-containing DNA-encoded library (SeDEL) as well peptide protein bioconjugation. This concept aims to present origins, advancements, applications selenium(II)-nitrogen while also outlining directions future research this field.

Language: Английский

Citations

0