Coumarin-Quinazolinone conjugate with large two photon action cross-section assisted by intramolecular hydrogen bond for bioimaging

Yang, Jihuan; Zhang, Yaya; Bai, Xue-Jiao; Li, Guorui; Xing, Zhiming; Zhong, Cheng; Zhou, J.; Liu, Song; Song, Zhibin; Huang, Jing

doi:10.1016/j.snb.2019.126720

Cited by 18 publications

(17 citation statements)

References 74 publications

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“…In our previous study, CQ exhibited bright two-photon fluorescence in living cells (λ ex 820 nm) . Distinguished from CQ , MeCQ did not exhibit obvious fluorescence in living cells (Figure S17B).…”

Section: Resultsmentioning

confidence: 99%

“…Among G4 fluorescent probes, the probes utilizing the DIE effect provide a promising strategy for G4 visualization. − Recently, Erik Chorell and co-workers have shown that coumarin–quinazoline derivatives can be used as G4-specific probes via the DIE effect. , We developed a two-photon fluorophore based on the conjugate structure of coumarin and quinazolinone ( CQ ) . Interestingly, although CQ shows an obvious ACQ effect in aqueous solution, it exhibits bright fluorescence in living cells.…”

mentioning

confidence: 97%

“…32,33 We developed a two-photon fluorophore based on the conjugate structure of coumarin and quinazolinone (CQ). 34 Interestingly, although CQ shows an obvious ACQ effect in aqueous solution, it exhibits bright fluorescence in living cells. CQ with the intramolecular hydrogen bond possesses a large planar core structure, which might be prone to stack on the G-quartet.…”

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confidence: 99%

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Subtle Structural Changes of Dyes Lead to Distinctly Different Fluorescent Behaviors in Cellular Context: The Role of G-Quadruplex DNA Interaction Using Coumarin–Quinazolinone Conjugates as a Case Study

Liu

Zhang

et al. 2021

Anal. Chem.

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Fluorogenic organic materials have gained tremendous attention due to their unique properties. However, only a few of them are suitable for bioimaging. Their different behaviors in organic and cellular environments hinder their application in bioimaging. Thus understanding the photoluminescent behaviors of organic materials in a cellular context is particularly important for their rational design. Herein, we describe two coumarin-quinazolinone conjugates: CQ and MeCQ. The high structure similarity makes them possess similar physical and photophysical properties, including bright fluorescence ascribed to the monomer forms in organic solvents and aggregation-caused quenching (ACQ) effect due to self-assembly aggregation in aqueous solution. However, they behave quite differently in cellular context: that is, CQ exhibits bright fluorescence in living cells, while the fluorescence of MeCQ is almost undetectable. The different performance between CQ and MeCQ in living cells is attributed to their different scenario in G-quadruplex (G4) DNA interaction. CQ selectively binds with G4 DNA to recover its fluorescence via aggregation–disaggregation switching in living cells, while MeCQ remained in the aggregate form due to its poor interplay with G4 DNA. Furthermore, CQ is applied as a two-photon fluorescent dye, and its photoswitchable fluorescence capability is exploited for super-resolution imaging of the specific mitochondrial structure in living cells via the STORM technique.

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Section: Resultsmentioning

confidence: 99%

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confidence: 97%

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confidence: 99%

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Subtle Structural Changes of Dyes Lead to Distinctly Different Fluorescent Behaviors in Cellular Context: The Role of G-Quadruplex DNA Interaction Using Coumarin–Quinazolinone Conjugates as a Case Study

Liu

Zhang

et al. 2021

Anal. Chem.

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“…Recently we discovered a coumarin-quinazolinone (CQ) conjugate as a fluorophore with brilliant two photon fluorescence properties, and CQ derivatives preferentially aggregated in mitochondria. 27 Thus, CQ was used as moiety A. For moiety B, Page 14 of 39 CCS Chemistry This article presented here has been accepted for publication in CCS Chemistry and is posted at the © 2021 Chinese Chemical Society.…”

Section: Design and Synthesis Of Cqbmentioning

confidence: 99%

“…As our previous study, CQ motif exhibited potent fluorescence, which preferentially localized in mitochondria. 27 We then ask whether CQB has the similar property to CQ. The subcellular distribution of CQB was investigated.…”

Section: Page 25 Of 39mentioning

confidence: 99%

A Reactive Oxygen Species-Tyrosinase Cascade-Activated Prodrug for Selectively Suppressing Melanoma

Yang

Zhang

et al. 2022

CCS Chem

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Off-target effect" is one of the obstacles for targeted prodrugs in chemotherapy. To circumvent this issue, herein we proposed a dual biomarker cascade-activated prodrug strategy based on high levels of reactive oxygen species (ROS) and tyrosinase (TYR) in melanoma cells. A representative prodrug, Coumarin-Quinazolinone-phenylBoronic acid pinacol ester (CQB) was prepared. The prodrug contained coumarinquinazolinone (CQ) as mitochondria targeting and monitoring moiety, and phenylboronic acid pinacol ester as a cascade-activated pro-warhead. After activated by the endogenous ROS and subsequent TYR in melanoma cells, CQB can be converted to the final active reagent Coumarin-Quinazolinone-o-Quinone (CQQ) which

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Recent progress in the design principles, sensing mechanisms, and applications of small-molecule probes for nitroreductases

Guo

Chen

et al. 2020

Coordination Chemistry Reviews

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Coumarin-Quinazolinone conjugate with large two photon action cross-section assisted by intramolecular hydrogen bond for bioimaging

Cited by 18 publications

References 74 publications

Subtle Structural Changes of Dyes Lead to Distinctly Different Fluorescent Behaviors in Cellular Context: The Role of G-Quadruplex DNA Interaction Using Coumarin–Quinazolinone Conjugates as a Case Study

Subtle Structural Changes of Dyes Lead to Distinctly Different Fluorescent Behaviors in Cellular Context: The Role of G-Quadruplex DNA Interaction Using Coumarin–Quinazolinone Conjugates as a Case Study

A Reactive Oxygen Species-Tyrosinase Cascade-Activated Prodrug for Selectively Suppressing Melanoma

Recent progress in the design principles, sensing mechanisms, and applications of small-molecule probes for nitroreductases

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