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

Evolution of chemistry and selection technology for DNA-encoded library DOI Creative Commons
Peixiang Ma, Shuning Zhang, Qianping Huang

et al.

Acta Pharmaceutica Sinica B, Journal Year: 2023, Volume and Issue: 14(2), P. 492 - 516

Published: Oct. 11, 2023

DNA-encoded chemical library (DEL) links the power of amplifiable genetics and non-self-replicating phenotypes, generating a diverse world. In analogy with biological world, DEL world can evolve by using central dogma, wherein DNA replicates PCR reactions to amplify genetic codes, sequencing transcripts information, DNA-compatible synthesis translates into phenotypes. Importantly, is key expanding space. Besides, evolution-driven selection system pushes chemicals under selective pressure, i.e., desired strategies. this perspective, we summarized recent advances in synthetic toolbox panning strategies, which will shed light on drug discovery harnessing vitro evolution via DEL.

Language: Английский

Citations

24
Organoselenium compounds in medicinal chemistry DOI
Carola Gallo‐Rodriguez, Juan B. Rodríguez

ChemMedChem, Journal Year: 2024, Volume and Issue: 19(17)

Published: May 23, 2024

Abstract The chemical and biological interest in this element the molecules bearing selenium has been exponentially growing over years. Selenium, formerly designated as a toxin, becomes vital trace for life that appears selenocysteine its dimeric form, selenocystine, active sites of selenoproteins, which catalyze wide variety reactions, including detoxification reactive oxygen species modulation redox activities. From point view drug developments, organoselenium drugs are isosteres sulfur‐containing oxygen‐containing with advantage presence atom confers antioxidant properties high lipophilicity, would increase cell membrane permeation leading to better oral bioavailability. This statement is paramount relevance considering big number clinically employed compounds sulfur or atoms their structures nucleosides carbohydrates. Thus, article we have focused on relevant features application medicinal chemistry. With increasing chemistry, attempted highlight most significant published data subject, mainly concentrating analysis last In consequence, recent advances pharmacological discussed.

Language: Английский

Citations

11
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 International Edition, Journal Year: 2024, Volume and Issue: 63(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

10
Design, synthesis, and bioactivity evaluation of novel indole-selenide derivatives as P-glycoprotein inhibitors against multi-drug resistance in MCF-7/ADR cell DOI
Zhikun Yang,

Disheng Luo,

Chen Shao

et al.

European Journal of Medicinal Chemistry, Journal Year: 2024, Volume and Issue: 268, P. 116207 - 116207

Published: Feb. 10, 2024

Language: Английский

Citations

9
Electrochemical Selenylation of Sulfoxonium Ylides for the Synthesis of gem-Diselenides as Antimicrobials against Fungi DOI
Zhongnan Xu,

Jiwen Yao,

Kaihui Zhong

et al.

The Journal of Organic Chemistry, Journal Year: 2023, Volume and Issue: 88(9), P. 5572 - 5585

Published: April 21, 2023

Organoselenium compounds are important scaffolds in pharmaceutical molecules. Herein, we report metal-free, electrochemical, highly chemo- and regioselective synthesis of gem-diselenides through the coupling α-keto sulfoxonium ylides with diselenides. The versatility electrochemical manifold enabled selenylation ample scope broad functional group tolerance, as well setting stage for modification complex bioactive Detailed mechanistic studies revealed that key C-Se bond was constructed using n-Bu4NI an electrolyte catalyst electrosynthetic protocol. Finally, desired showed excellent antimicrobial activity against Candida albicans, which can be identified lead further exploration.

Language: Английский

Citations

19
Strategic application of CuAAC click chemistry in the modification of natural products for anticancer activity DOI Creative Commons

Zaozao Xiao,

Yuang Gu,

Hewei Dong

et al.

European Journal of Medicinal Chemistry Reports, Journal Year: 2023, Volume and Issue: 9, P. 100113 - 100113

Published: Sept. 7, 2023

Natural products play a key role in the history of human drug discovery, and especially for anticancer agents. Copper(I)-catalyzed alkyne-azide [3+2] cycloaddition (CuAAC) reaction is perhaps most powerful method efficient modification complex natural products, enabling direct incorporation various functional groups accompanied by formation multifunctional 1,2,3-triazole motif, which could not only serve as an basic hydrophilic connecting group but also bioisosteres 5- or 6-membered heterocycles amide group, thus facilitating improvement activities and/or drug-like properties. This contribution extensively summarizes state-of-the-art application activity. The aim to gain deep understanding fruitful achievements well limitations CuAAC click chemistry product activity, provide perspectives directions regarding future studies medicinal chemistry.

Language: Английский

Citations

10
Mask and Release Strategy‐Enabled Diversity‐Oriented Synthesis for DNA‐Encoded Library DOI Creative Commons
Silin Zhang,

Haiman Zhang,

Xiawen Liu

et al.

Advanced Science, Journal Year: 2023, Volume and Issue: 11(6)

Published: Dec. 3, 2023

Abstract An ideal DNA‐encoded library (DEL) selection requires the to consist of diverse core skeletons and cover chemical space as much possible. However, lack efficient on‐DNA synthetic approaches toward has greatly restricted diversity DEL. To mitigate this issue, work disclosed a “Mask & Release” strategy streamline challenging skeleton synthesis. N ‐phenoxyacetamide is used masked phenol versatile directing group mediate diversified DNA‐compatible C‐H functionalization, introducing 1st‐dimensional at defined site, simultaneously releasing functionality, which can facilitate introduction 2nd diversity. This not only provides set syntheses DNA‐conjugated drug‐like such ortho ‐alkenyl/sulfiliminyl/cyclopropyl phenol, benzofuran, dihydrobenzofuran but also paradigm for method development.

Language: Английский

Citations

9
Enolate–Azide [3 + 2]-Cycloaddition Reaction Suitable for DNA-Encoded Library Synthesis DOI

Kangyin Pan,

Ying Yao, Yiyuan Zhang

et al.

Bioconjugate Chemistry, Journal Year: 2023, Volume and Issue: 34(8), P. 1459 - 1466

Published: July 14, 2023

The DNA-encoded chemical library (DEL) is a powerful hit selection technique in either basic science or innovative drug discovery. With the aim to circumvent issue concerning DNA barcode damage conventional on-DNA copper-catalyzed azide–alkyne cycloaddition reaction (CuAAC), we have successfully developed first DNA-compatible enolate–azide [3 + 2] reaction. merits of this DEL chemistry include metal-free and high fidelity, conversions easy operation, broad substrate scope, ready access highly substituted 1,4,5-trisubstituted triazoles. Thus, it will not only further enrich toolbox but also great potential practical synthesis.

Language: Английский

Citations

6
FSO2N3-Mediated On-DNA Diazo-Transfer Chemistry DOI
Qianping Huang,

Yuang Gu,

An Qin

et al.

ACS Medicinal Chemistry Letters, Journal Year: 2024, Volume and Issue: 15(9), P. 1591 - 1597

Published: Aug. 23, 2024

DNA-encoded library (DEL) is a powerful hit selection technique in both basic science and innovative drug discovery. In this study, we report robust straightforward DNA-compatible diazo-transfer reaction utilizing FSO

Language: Английский

Citations

1
Selenium-containing heterocycles DOI
Hongtao Xu, Wei Hou

Elsevier eBooks, Journal Year: 2023, Volume and Issue: unknown, P. 915 - 930

Published: Jan. 1, 2023

Language: Английский

Citations

2