Organic Fluorophores with Large Stokes Shift for Bioimaging and Biosensing

Liu, Hong; Jiang, Gangwei; Ke, Guoliang; Ren, Tian‐Bing; Yuan, Lin

doi:10.1002/cptc.202300277

Cited by 4 publications

(3 citation statements)

References 98 publications

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“…Due to the charge separation between the donor and the acceptor groups, the ICT state is highly polar and the excited state becomes significantly stabilized in polar solvents, causing the red shift of the emission . In addition, it seems that an asymmetric fluorophore exhibits larger degrees of asymmetric electron distribution of the HOMO and LUMO, thus exacerbating vibrational relaxation and resulting in a large Stokes shift. ,, Taken together, the asymmetric electronic structure and ICT features resulted in a large Stokes shift of TBy.…”

Section: Resultsmentioning

confidence: 99%

“…47 In addition, it seems that an asymmetric fluorophore exhibits larger degrees of asymmetric electron distribution of the HOMO and LUMO, thus exacerbating vibrational relaxation and resulting in a large Stokes shift. 30,44,48 Taken together, the asymmetric electronic structure and ICT features resulted in a large Stokes shift of TBy.…”

Section: Photophysical Properties Of Tbymentioning

confidence: 92%

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An Asymmetric NIR-II Organic Fluorophore with an Ultra-Large Stokes Shift for Imaging-Guided and Targeted Phototherapy

Li,

Zhou,

Zhou

et al. 2024

ACS Biomater. Sci. Eng.

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NIR-II imaging-guided phototherapy is an attractive, yet challenging, tumor treatment strategy. By monitoring the accumulation of phototherapy reagents at the tumor site through imaging and determining the appropriate therapy window, the therapeutic effect could be significantly improved. Probes with NIR-II (1000−1700 nm) fluorescence emission and a large Stokes shift hold great promise for fluorescence imaging with deep penetration, minimized self-quenching, and high spatiotemporal resolution. However, due to the lack of a suitable molecular framework, the design of a simple small-molecule dye with a large Stokes shift and NIR-II fluorescence emission has rarely been reported. Herein, we prepare an asymmetric D−π−A type NIR-II fluorescence probe (TBy). The probe is incapsulated in an amphiphilic polymer and modified with a fibronectin targeting peptide CREKA, which could recognize the fibrin−fibronectin complex overexpressed in multiple malignant tumors. The nanoparticles thus constructed (TByC-NPs) have maximum fluorescence emission at 1037 nm with a large Stokes shift of 426 nm, which is the largest Stokes shift among organic NIR-II fluorescent dyes reported in the literature. The TByC-NPs exhibit a good NIR-II imaging performance, active tumor targeting, and good photothermal and photodynamic capabilities. In vitro and in vivo studies verify that the TByC nanoplatform shows outstanding biocompatibility for NIR-II imaging-guided phototherapy and provides an excellent antitumor effect.

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Section: Resultsmentioning

confidence: 99%

Section: Photophysical Properties Of Tbymentioning

confidence: 92%

An Asymmetric NIR-II Organic Fluorophore with an Ultra-Large Stokes Shift for Imaging-Guided and Targeted Phototherapy

Li,

Zhou,

Zhou

et al. 2024

ACS Biomater. Sci. Eng.

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“…20 nm blue shifted, which makes excitation possible using the blue channel light sources of microscopes instead of the green needed for previous sensors. Combined with the 70 nm Stokes shift, this feature enables the filtration of scattered excitation light without significant losses in the collection of fluorescence photons [ 34 ]. Any light source under 420 nm, including the very popular 405 nm laser, enables the complete detection of emitted light, as the emission spectrum does not overlap with this region.…”

Section: Resultsmentioning

confidence: 99%

A Molecular Hybrid of the GFP Chromophore and 2,2′-Bipyridine: An Accessible Sensor for Zn2+ Detection with Fluorescence Microscopy

Csomos,

Madarász,

Turczel

et al. 2024

IJMS

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The few commercially available chemosensors and published probes for in vitro Zn2+ detection in two-photon microscopy are compromised by their flawed spectroscopic properties, causing issues in selectivity or challenging multistep syntheses. Herein, we present the development of an effective small molecular GFP chromophore-based fluorescent chemosensor with a 2,2′-bipyridine chelator moiety (GFZnP BIPY) for Zn2+ detection that has straightforward synthesis and uncompromised properties. Detailed experimental characterizations of the free and the zinc-bound compounds within the physiologically relevant pH range are presented. Excellent photophysical characteristics are reported, including a 53-fold fluorescence enhancement with excitation and emission maxima at 422 nm and 492 nm, respectively. A high two-photon cross section of 3.0 GM at 840 nm as well as excellent metal ion selectivity are reported. In vitro experiments on HEK 293 cell culture were carried out using two-photon microscopy to demonstrate the applicability of the novel sensor for zinc bioimaging.

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BOPHY Derivatives as Phototherapeutic Agents for the Photodynamic Inactivation of Microorganisms

Chávez Hernández,

Palacios,

Gonzalez Lopez

et al. 2024

ChemPhotoChem

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Photodynamic inactivation (PDI) of microorganisms is a promising antimicrobial therapy to fight against multiple‐resistant microbial pathogens. The optimization of this therapy depends on developing novel photosensitizers (PS). In this sense, three BOPHY derivatives (BP, BP‐Br and BP‐I) were synthetized, studied, and compared to assess their antimicrobial photodynamic properties. BP is a promising fluorescent probe for cell imaging, while the halogenated analogs (BP‐Br and BP‐I) are excellent oxygen photosensitizing agents. BP‐Br presented an adequate balance between ROS production and emission properties. The photokilling action and the binding to bacterial cells of BOPHYs were evaluated in vitro against methicillin‐resistant Staphylococcus aureus(MRSA) and Escherichia coli (resistant to β‐lactam antibiotics) bacteria. Our results demonstrated that the halogenated BOPHY derivatives were effective PS in inactivating MRSA. The antimicrobial action sensitized by these PS was potentiated by adding KI. The combination of halogenated BOPHY and KI led to a complete elimination of both Gram‐positive and Gram‐negative bacteria. To the best of our knowledge, this is the first time that BOPHY derivatives have been applied to photokill pathogenic microorganisms. This work establishes the groundwork for the development of new BOPHY‐based PS with potential applications in the field of PDI.

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Organic Fluorophores with Large Stokes Shift for Bioimaging and Biosensing

Cited by 4 publications

References 98 publications

An Asymmetric NIR-II Organic Fluorophore with an Ultra-Large Stokes Shift for Imaging-Guided and Targeted Phototherapy

An Asymmetric NIR-II Organic Fluorophore with an Ultra-Large Stokes Shift for Imaging-Guided and Targeted Phototherapy

A Molecular Hybrid of the GFP Chromophore and 2,2′-Bipyridine: An Accessible Sensor for Zn2+ Detection with Fluorescence Microscopy

BOPHY Derivatives as Phototherapeutic Agents for the Photodynamic Inactivation of Microorganisms

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