Small‐Molecule Quenchers for Förster Resonance Energy Transfer: Structure, Mechanism, and Applications

Fang, Bin; Shen, Yu; Peng, Bo; Bai, Hua; Wang, Limin; Zhang, Jiaxin; Fu, Li; Zhang, Wei; Li, Lin; Huang, Wei

doi:10.1002/ange.202207188

Cited by 6 publications

(2 citation statements)

References 269 publications

(260 reference statements)

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“…Currently, there are two major options for the development of dual-locked optical probes for simultaneous detection of two enzymes being dual-quenching and tandem-locked approaches, wherein Förster resonance energy transfer (FRET) and intramolecular charge transfer (ICT) inhibition are the respective mechanisms to induce low FL signal at the native state (Figure ). However, the former contains two chromophore quenchers and often possesses a large molecular size, which could impact its in vitro diffusion and in vivo biodistribution abilities . Although the latter has a relatively compact structure, it requires enzymes with a high peptide sequence selectivity to enable sequential cleavage of two tandem moieties.…”

Section: Introductionmentioning

confidence: 99%

Bienzyme-Locked Activatable Fluorescent Probes for Specific Imaging of Tumor-Associated Mast Cells

Hu,

Yu,

et al. 2024

J. Am. Chem. Soc.

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Tumor-associated mast cells (TAMCs) have been recently revealed to play a multifaceted role in the tumor microenvironment. Noninvasive optical imaging of TAMCs is thus highly desired to gain insights into their functions in cancer immunotherapy. However, due to the lack of a single enzyme that is specific to mast cells, a common probe design approach based on single-enzyme activation is not applicable. Herein, we reported a bienzyme-locked molecular probe (THC MC ) based on a photoinduced electron transfer-intramolecular charge-transfer hybrid strategy for in vivo imaging of TAMCs. The bienzyme-locked activation mechanism ensures that THC MC exclusively turns on near-infrared (NIR) fluorescence only in the presence of both tryptase and chymase specifically coexpressed by mast cells. Thus, THC MC effectively distinguishes mast cells from other leukocytes, including T cells, neutrophils, and macrophages, a capability lacking in single-locked probes. Such a high specificity of THC MC allows noninvasive tracking of the fluctuation of TAMCs in the tumor of living mice during cancer immunotherapy. The results reveal that the decreased intratumoral signal of THC MC after combination immunotherapy correlates well with the reduced population of TAMCs, accurately predicting the inhibition of tumor growth. Thus, this study not only presents the first NIR fluorescent probe specific for TAMCs but also proposes a generic bienzymelocked probe design approach for in vivo cell imaging.

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Section: Introductionmentioning

confidence: 99%

Bienzyme-Locked Activatable Fluorescent Probes for Specific Imaging of Tumor-Associated Mast Cells

Hu,

Yu,

et al. 2024

J. Am. Chem. Soc.

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“…7 In this process, the formation of a locally excited state on anthracene is followed by singlet-singlet energy transfer to the phenol-pyridine chromophore. Despite the lack of spectral overlap of the donor emission and acceptor absorption spectra required for the Förster resonance (dipole-dipole) mechanism, [8][9] the process was made possible by coupling proton transfer in the phenol-pyridine unit with energy transfer that lowered its excited-state energy. The question is whether such a mechanism would also be operational in the triplet electronic manifold, as most antenna systems absorbing visible/near-infrared light exhibit a relatively efficient intersystem crossing (ISC) to produce longer-lived triplet states.…”

Section: Introductionmentioning

confidence: 99%

Proton-Coupled Triplet-Triplet Energy Transfer: Carbon Monoxide Photorelease from Porphyrin-Flavonol Hybrids

Ramundo

Janos

Muchová

et al. 2022

Preprint

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A new photochemical mechanism, termed proton-coupled energy transfer (PCEnT), was recently discovered in anthracene-phenol-pyridine triads (Pettersson Rimgard et al., Science 2022, 377, 742). It couples an electronic transition to nuclear motions allowing Förster (dipole-dipole) energy transfer even though there is no overlap of the donor emission and acceptor absorption spectra. Here, we extend this concept to triplet-triplet energy transfer (TEnT) from light-harvesting porphyrin to a covalently bound flavonol group. While direct TEnT to the flavonol acceptor would be highly endergonic, it becomes feasible thanks to the flavonol energy stabilization upon intramolecular proton transfer in the triplet state. We describe the overall mechanism as proton-coupled TEnT (PCTEnT) – a one-photon process that enables the activation of a UV-absorbing chromophore by visible light. Several porphyrin-flavonol hybrids containing 4 flavonol units attached to the porphyrin meso positions were designed as photoactivatable carbon monoxide (CO)-releasing molecules (photoCORMs). The photoreaction mechanism was studied by steady-state and transient absorption spectroscopy techniques and complementary quantum-chemical calculations. While intrinsically toxic, CO is an endogenous signaling molecule with therapeutic potential that regulates various physiological processes, and photoCORMs offer precise spatial and temporal control of CO administration. We evaluated the viability of the human hepatoblastoma HepG2 cells in the presence of the studied hybrids and tested the effects associated with the intracellular release of CO and the production of singlet oxygen. We demonstrate that the PCTEnT process could be used to devise new photoactivatable molecular devices with potential biological applications.

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Full‐Color “Off–On” Thermochromic Fluorescent Fibers for Customizable Smart Wearable Displays in Personal Health Monitoring

Zhan,

Xu,

et al. 2024

Small

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Responsive thermochromic fiber materials capable of miniaturization and integrating comfortably and compliantly onto the soft and dynamically deforming human body are promising materials for visualized personal health monitoring. However, their development is hindered by monotonous colors, low‐contrast color changes, and poor reversibility. Herein, full‐color “off–on” thermochromic fluorescent fibers are prepared based on self‐crystallinity phase change and Förster resonance energy transfer for long‐term and passive body‐temperature monitoring, especially for various personalized customization purposes. The off–on switching luminescence characteristic is derived from the reversible conversion of the dispersion state and fluorescent emission by fluorophores and quencher molecules, which are embedded in the matrix of a phase‐change material, during the crystallizing/melting processes. The achievement of full‐color fluorescence is attributed to the large modulation range of fluorescence colors according to primary color additive theory. These thermochromic fluorescent fibers exhibit good mechanical properties, fluorescent emission contrast, and reversibility, showing their great potential in flexible smart display devices. Moreover, the response temperature of the thermochromic fibers is controllable by adjusting the phase‐change material, enabling body‐temperature‐triggered luminescence; this property highlights their potential for human body‐temperature monitoring and personalized customization. This work presents a new strategy for designing and exploring flexible sensors with higher comprehensive performances.

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Small‐Molecule Quenchers for Förster Resonance Energy Transfer: Structure, Mechanism, and Applications

Cited by 6 publications

References 269 publications

Bienzyme-Locked Activatable Fluorescent Probes for Specific Imaging of Tumor-Associated Mast Cells

Bienzyme-Locked Activatable Fluorescent Probes for Specific Imaging of Tumor-Associated Mast Cells

Proton-Coupled Triplet-Triplet Energy Transfer: Carbon Monoxide Photorelease from Porphyrin-Flavonol Hybrids

Full‐Color “Off–On” Thermochromic Fluorescent Fibers for Customizable Smart Wearable Displays in Personal Health Monitoring

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