pH-Responsive Fluorescent Switches through Intramolecular Conjugate Addition Reactions and Application in Fluorogenic Bioimaging

Xiangkun Si; Wanyi Yu; Naikun Song; Peng Zhang; Hongbei Wei; Jie Zhang; Eric V. Anslyn; Xiaolong Sun

doi:10.1021/acs.orglett.4c03197

pH-Responsive Fluorescent Switches through Intramolecular Conjugate Addition Reactions and Application in Fluorogenic Bioimaging

Xiangkun Si
, Wanyi Yu
, Naikun Song
, Peng Zhang
, Hongbei Wei
, Jie Zhang
, Eric V. Anslyn
, Xiaolong Sun

Research output: Contribution to journal › Article › peer-review

4 Scopus citations

Abstract

We report new photoluminescent switching systems achieved through pH-induced intramolecular oxa-Michael conjugate addition reactions. Ratiometric absorbance and fluorescence emission were observed across conjugate acceptors triggered by pH, resulting in specific pseudo pK_a values. The effect of substituents on the pseudo pK_a’s was investigated, showing increased values from electron-withdrawing to electron-donating groups. Inspired by the physiologically related pK_a, a fluorescent probe was designed, successfully distinguishing cancer cells from normal cells through live cellular imaging.

Original language	English
Pages (from-to)	8389-8393
Number of pages	5
Journal	Organic Letters
Volume	26
Issue number	39
DOIs	https://doi.org/10.1021/acs.orglett.4c03197
State	Published - 4 Oct 2024

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10.1021/acs.orglett.4c03197

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title = "pH-Responsive Fluorescent Switches through Intramolecular Conjugate Addition Reactions and Application in Fluorogenic Bioimaging",

abstract = "We report new photoluminescent switching systems achieved through pH-induced intramolecular oxa-Michael conjugate addition reactions. Ratiometric absorbance and fluorescence emission were observed across conjugate acceptors triggered by pH, resulting in specific pseudo pKa values. The effect of substituents on the pseudo pKa{\textquoteright}s was investigated, showing increased values from electron-withdrawing to electron-donating groups. Inspired by the physiologically related pKa, a fluorescent probe was designed, successfully distinguishing cancer cells from normal cells through live cellular imaging.",

author = "Xiangkun Si and Wanyi Yu and Naikun Song and Peng Zhang and Hongbei Wei and Jie Zhang and Anslyn, \{Eric V.\} and Xiaolong Sun",

note = "Publisher Copyright: {\textcopyright} 2024 American Chemical Society.",

year = "2024",

month = oct,

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doi = "10.1021/acs.orglett.4c03197",

language = "英语",

volume = "26",

pages = "8389--8393",

journal = "Organic Letters",

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TY - JOUR

T1 - pH-Responsive Fluorescent Switches through Intramolecular Conjugate Addition Reactions and Application in Fluorogenic Bioimaging

AU - Si, Xiangkun

AU - Yu, Wanyi

AU - Song, Naikun

AU - Zhang, Peng

AU - Wei, Hongbei

AU - Zhang, Jie

AU - Anslyn, Eric V.

AU - Sun, Xiaolong

PY - 2024/10/4

Y1 - 2024/10/4

N2 - We report new photoluminescent switching systems achieved through pH-induced intramolecular oxa-Michael conjugate addition reactions. Ratiometric absorbance and fluorescence emission were observed across conjugate acceptors triggered by pH, resulting in specific pseudo pKa values. The effect of substituents on the pseudo pKa’s was investigated, showing increased values from electron-withdrawing to electron-donating groups. Inspired by the physiologically related pKa, a fluorescent probe was designed, successfully distinguishing cancer cells from normal cells through live cellular imaging.

AB - We report new photoluminescent switching systems achieved through pH-induced intramolecular oxa-Michael conjugate addition reactions. Ratiometric absorbance and fluorescence emission were observed across conjugate acceptors triggered by pH, resulting in specific pseudo pKa values. The effect of substituents on the pseudo pKa’s was investigated, showing increased values from electron-withdrawing to electron-donating groups. Inspired by the physiologically related pKa, a fluorescent probe was designed, successfully distinguishing cancer cells from normal cells through live cellular imaging.

UR - https://www.scopus.com/pages/publications/85205741347

U2 - 10.1021/acs.orglett.4c03197

DO - 10.1021/acs.orglett.4c03197

M3 - 文章

C2 - 39321334

AN - SCOPUS:85205741347

SN - 1523-7060

VL - 26

SP - 8389

EP - 8393

JO - Organic Letters

JF - Organic Letters

IS - 39

ER -

pH-Responsive Fluorescent Switches through Intramolecular Conjugate Addition Reactions and Application in Fluorogenic Bioimaging

Abstract

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