Harnessing aggregation-induced emission property of indolizine derivative as a fluorogenic bioprobe for endoplasmic reticulum

Arun, V.; Choi, Soobong; Han, Ji Hye; Choi, Hongseo; Kim, Hyungmo; Kim, Wook; Choi, Jun Won; Kim, Jonghoon; Kim, Eunha

doi:10.1016/j.dyepig.2022.110118

Cited by 7 publications

(6 citation statements)

References 38 publications

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“…Pyrrolo[2,1,5cd]indolizine derivative 29 could be obtained through cycloaddition of 12a with ethyl propiolate (path i). Furthermore, the formal synthesis of Aru68, 47 an AIE active molecule, was achieved via benzoylation and desilylation reaction (Figure 5H). Finally, compound 32 48 that could function as an OLED material was prepared in one step (Figure 5I).…”

Section: ■ Results and Discussionmentioning

confidence: 99%

Catalytic Intermolecular Deoxygenative Coupling of Carbonyl Compounds with Alkynes by a Cp*Mo(II)-Catalyst

Wang,

Wu,

Luo

et al. 2024

J. Am. Chem. Soc.

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Carbonyl is highly accessible and acts as an essential functional group in chemical synthesis. However, the direct catalytic deoxygenative functionalization of carbonyl compounds via a putative metal carbene intermediate is a formidable challenge due to the requirement of a high activation energy for the cleavage of strong C�O double bonds. Here, we report a class of bench stable and readily available Cp*Mo(II)-complexes as efficient deoxygenation catalysts that could catalyze the direct intermolecular deoxygenative coupling of carbonyl compounds with alkynes. Enabled by this powerful Cp*Mo(II)-catalyst, various valuable heteroarenes (10 different classes) were obtained in generally good yields and remarkable chemo-and regioselectivities. Mechanistic studies suggested that this reaction might proceed via a sequence of C�O double bonds cleavage, carbene-alkyne metathesis, cyclization, and aromatization processes. This strategy not only provided a general catalytic platform for the rapid preparation of heteroarenes but also opened a new window for the applications of Cp*Mo(II)-catalysts in organic synthesis.

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Section: ■ Results and Discussionmentioning

confidence: 99%

Catalytic Intermolecular Deoxygenative Coupling of Carbonyl Compounds with Alkynes by a Cp*Mo(II)-Catalyst

Wang,

Wu,

Luo

et al. 2024

J. Am. Chem. Soc.

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“…In 2022, Kim et al 75 synthesized an AIE-type fluorescence probe for endoplasmic reticulum (ER) detection in the cell by the click reaction between azide-modified glibenclamide and an alkyne-containing indolizine core skeleton. Aru68 accumulated inside the ER and induced the AIE process through both intramolecular charge transfer (ICT) and restriction of molecular motion (RIM) mechanisms.…”

Section: Aie-based Fluorogenic Reactionsmentioning

confidence: 99%

Fluorogenic Reactions in Chemical Biology: Seeing Chemistry in Cells

Chen

Jiang

Hao

et al. 2023

Chemical & Biomedical Imaging

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“…In compound 12, cyclohexyl sulfonylurea moiety was used for the ER targeting which successfully bio-imaged ER in the live Chang liver cells in a wash-free procedure. [41]…”

Section: Imaging Ermentioning

confidence: 99%

“…developed a novel indolizine based AIEgen (12, Figure 2a) conjugated with glibenclamide. In compound 12, cyclohexyl sulfonylurea moiety was used for the ER targeting which successfully bio‐imaged ER in the live Chang liver cells in a wash‐free procedure [41] …”

Section: Aiegens For Organelle Imagingmentioning

confidence: 99%

Illuminating Sub‐Cellular Organelles by Small Molecule AIEgens

2022

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Sub‐cellular organelles play a critical role in a myriad biological phenomena. Consequently, organelle structures and functions are invariably highjacked in diverse diseases including metabolic disorders, aging, and cancer. Hence, illuminating organelle dynamics is crucial in understanding the diseased states as well as developing organelle‐targeted next generation therapeutics. In this review, we outline the novel small molecules which show remarkable aggregation‐induced emission (AIE) properties due to restriction in intramolecular motion (RIM). We outline the examples of small molecules developed to image organelles like mitochondria, endoplasmic reticulum (ER), Golgi, lysosomes, nucleus, cell membrane and lipid droplets. These AIEgens have tremendous potential for next‐generation phototherapy.

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Harnessing aggregation-induced emission property of indolizine derivative as a fluorogenic bioprobe for endoplasmic reticulum

Cited by 7 publications

References 38 publications

Catalytic Intermolecular Deoxygenative Coupling of Carbonyl Compounds with Alkynes by a Cp*Mo(II)-Catalyst

Catalytic Intermolecular Deoxygenative Coupling of Carbonyl Compounds with Alkynes by a Cp*Mo(II)-Catalyst

Fluorogenic Reactions in Chemical Biology: Seeing Chemistry in Cells

Illuminating Sub‐Cellular Organelles by Small Molecule AIEgens

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