| Title | Isoindolium-Based Allenes: Reactivity Studies and Applications in Fluorescence Temperature Sensing and Cysteine Bioconjugation |
| Author | |
| Corresponding Author | Cui, Jian-Fang; Leung, Yun-Chung; Wong, Man-Kin |
| Publication Years | 2023-02-01
|
| DOI | |
| Source Title | |
| ISSN | 1433-7851
|
| EISSN | 1521-3773
|
| Volume | 62Issue:12 |
| Abstract | The reaction of a series of electron-deficient isoindolium-based allenes with sulfhydryl compounds has been studied, leading to the formation of isoindolium-based vinyl sulfides. The vinyl sulfides generated could be readily converted into the corresponding indanones and amines upon heating at 30-70 degrees C with good yields up to 61 %. The thermal cleavage reaction of vinyl sulfides was further studied for developing temperature-sensitive systems. Notably, a novel FRET-based fluorescent temperature sensor was designed and synthesized for temperature sensing at 50 degrees C, giving a 6.5-fold blue fluorescence enhancement. Moreover, chemoselective bioconjugation of cysteine-containing peptides with the isoindolium-based allenes for the construction of multifunctional peptide bioconjugates was investigated. Thermal cleavage of isoindoliums on the modified peptides at 35-70 degrees C gave indanone bioconjugates with up to >99 % conversion. These results indicated the biocompatibility of this novel temperature-sensitive reaction. |
| Keywords | |
| URL | [Source Record] |
| Indexed By | |
| Language | English
|
| Important Publications | NI Journal Papers
|
| SUSTech Authorship | Corresponding
|
| Funding Project | Hong Kong Research Grants Council[PolyU 153001/17P]
; Shenzhen Science and Technology Innovation Commission[JCYJ20170818104257975]
; State Key Laboratory of Chemical Biology and Drug Discovery, Dean's Reserve[P0034752]
; Hong Kong Polytechnic University[P0043816: WZ0Y]
|
| WOS Research Area | Chemistry
|
| WOS Subject | Chemistry, Multidisciplinary
|
| WOS Accession No | WOS:000929037900001
|
| Publisher | |
| ESI Research Field | CHEMISTRY
|
| Scopus EID | 2-s2.0-85147496022
|
| Data Source | Web of Science
|
| Citation statistics |
Cited Times [WOS]:0
|
| Document Type | Journal Article |
| Identifier | http://kc.sustech.edu.cn/handle/2SGJ60CL/479594 |
| Department | Department of Chemistry |
| Affiliation | 1.Hong Kong Polytech Univ, Res Inst Future Food, Dept Food Sci & Nutr, State Key Lab Chem Biol & Drug Discovery, Hong Kong, Peoples R China 2.Hong Kong Polytech Univ, Shenzhen Res Inst, Shenzhen 518057, Peoples R China 3.Southern Univ Sci & Technol, Dept Chem, 1088 Xueyuan Blvd, Shenzhen 518055, Peoples R China 4.Hong Kong Polytech Univ, Henry Cheng Res Lab Drug Dev, Hung Hom, Hong Kong, Peoples R China 5.Hong Kong Polytech Univ, Lo Ka Chung Ctr Nat Anticanc Drug Dev, Hung Hom, Hong Kong, Peoples R China |
| Corresponding Author Affilication | Department of Chemistry |
| Recommended Citation GB/T 7714 |
O, Wa-Yi,Cui, Jian-Fang,Yu, Qiong,et al. Isoindolium-Based Allenes: Reactivity Studies and Applications in Fluorescence Temperature Sensing and Cysteine Bioconjugation[J]. ANGEWANDTE CHEMIE-INTERNATIONAL EDITION,2023,62(12).
|
| APA |
O, Wa-Yi.,Cui, Jian-Fang.,Yu, Qiong.,Kung, Karen Ka-Yan.,Chung, Sai-Fung.,...&Wong, Man-Kin.(2023).Isoindolium-Based Allenes: Reactivity Studies and Applications in Fluorescence Temperature Sensing and Cysteine Bioconjugation.ANGEWANDTE CHEMIE-INTERNATIONAL EDITION,62(12).
|
| MLA |
O, Wa-Yi,et al."Isoindolium-Based Allenes: Reactivity Studies and Applications in Fluorescence Temperature Sensing and Cysteine Bioconjugation".ANGEWANDTE CHEMIE-INTERNATIONAL EDITION 62.12(2023).
|
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