Analyses on intracellular Fe<sup>3+</sup> with a rhodamine probe: “turn-on” response, specific recognition and bioimaging

Cheng, Zhao; Liu, Xiaojing; Zheng, Lei; Xu, Yue; He, Hao

doi:10.1039/d2ay00280a

Cited by 4 publications

(2 citation statements)

References 30 publications

(45 reference statements)

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“…Hence, these results demonstrate the feasibility of designing a universal molecular scaffold for various afterglow molecular probes. Considering the ease of modifying the carboxylic acid in the spirocyclization of rhodamine–indole molecules, numerous other probes that are responsive to HClO, NO, Fe 3+ , Zn 2+ , Hg 2+ , Pb 2+ , and Au + may be designed in the future by introducing the function group of formohydrazide, o-phenylenediamine, 2-aminopyrazine, syringaldehyde, thiosemicarbazide, hydrazine hydrate, and o-phenylenediamine bearing propargyl moiety into carboxylic acid of MAS, respectively. − …”

Section: Resultsmentioning

confidence: 99%

Noninvasive Imaging of Tumor Glycolysis and Chemotherapeutic Resistance via De Novo Design of Molecular Afterglow Scaffold

Lei,

Yang,

Meng

et al. 2023

J. Am. Chem. Soc.

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Chemotherapeutic resistance poses a significant challenge in cancer treatment, resulting in the reduced efficacy of standard chemotherapeutic agents. Abnormal metabolism, particularly increased anaerobic glycolysis, has been identified as a major contributing factor to chemotherapeutic resistance. To address this issue, noninvasive imaging techniques capable of visualizing tumor glycolysis are crucial. However, the currently available methods (such as PET, MRI, and fluorescence) possess limitations in terms of sensitivity, safety, dynamic imaging capability, and autofluorescence. Here, we present the de novo design of a unique afterglow molecular scaffold based on hemicyanine and rhodamine dyes, which holds promise for low-background optical imaging. In contrast to previous designs, this scaffold exhibits responsive "OFF-ON" afterglow signals through spirocyclization, thus enabling simultaneous control of photodynamic effects and luminescence efficacy. This leads to a larger dynamic range, broader detection range, higher signal enhancement ratio, and higher sensitivity. Furthermore, the integration of multiple functionalities simplifies probe design, eliminates the need for spectral overlap, and enhances reliability. Moreover, we have expanded the applications of this afterglow molecular scaffold by developing various probes for different molecular targets. Notably, we developed a water-soluble pH-responsive afterglow nanoprobe for visualizing glycolysis in living mice. This nanoprobe monitors the effects of glycolytic inhibitors or oxidative phosphorylation inhibitors on tumor glycolysis, providing a valuable tool for evaluating the tumor cell sensitivity to these inhibitors. Therefore, the new afterglow molecular scaffold presents a promising approach for understanding tumor metabolism, monitoring chemotherapeutic resistance, and guiding precision medicine in the future.

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Section: Resultsmentioning

confidence: 99%

Noninvasive Imaging of Tumor Glycolysis and Chemotherapeutic Resistance via De Novo Design of Molecular Afterglow Scaffold

Lei,

Yang,

Meng

et al. 2023

J. Am. Chem. Soc.

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“…Both probes were shown to respond to exogenously added Fe(III) ions in the perinuclear regions of the cytoplasm in mouse fibroblast cells (L929). Dyes 95 – 97 were similarly produced by linking rhodamine B with hetero-atom substituted aromatic amines as binding sites for Fe(III) ions and showed a strong emission peak corresponding to the complexation of the ring-opened form with Fe(III) as observed by their fluorescence imaging in L929 cells. − Kan’s laboratory modified rhodamine B hydrazide with a sulfonyl group to generate RBPH ( 98 ), which gave a strong emission response to Fe(III) ions and was used in HeLa cells and zebrafish to track exogenously added ferric ions …”

Section: Fluorescent Sensors For Ironmentioning

confidence: 99%

Small-Molecule Fluorescent Probes for Binding- and Activity-Based Sensing of Redox-Active Biological Metals

Grover,

Koblova,

Pezacki

et al. 2024

Chem. Rev.

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Although transition metals constitute less than 0.1% of the total mass within a human body, they have a substantial impact on fundamental biological processes across all kingdoms of life. Indeed, these nutrients play crucial roles in the physiological functions of enzymes, with the redox properties of many of these metals being essential to their activity. At the same time, imbalances in transition metal pools can be detrimental to health. Modern analytical techniques are helping to illuminate the workings of metal homeostasis at a molecular and atomic level, their spatial localization in real time, and the implications of metal dysregulation in disease pathogenesis. Fluorescence microscopy has proven to be one of the most promising non-invasive methods for studying metal pools in biological samples. The accuracy and sensitivity of bioimaging experiments are predominantly determined by the fluorescent metal-responsive sensor, highlighting the importance of rational probe design for such measurements. This review covers activity-and binding-based fluorescent metal sensors that have been applied to cellular studies. We focus on the essential redox-active metals: iron, copper, manganese, cobalt, chromium, and nickel. We aim to encourage further targeted efforts in developing innovative approaches to understanding the biological chemistry of redox-active metals. CONTENTS5908 8.2. Activity-Based Fluorescent Sensors for Ni(II) 5911 9. Outlook 5911 Author Information 5912 Corresponding Authors 5912

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A mitochondria-targeted fluorescent probe based on biocompatible RBH-U for the enhanced response of Fe3+ in living cells and quenching of Cu2+ in vitro

Ahmed

Xiong

2023

Analytica Chimica Acta

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Analyses on intracellular Fe³⁺ with a rhodamine probe: “turn-on” response, specific recognition and bioimaging

Abstract: To overcome the existing difficulty in distinguishing ferric from ferrous ions, a rhodamine-containing probe was designed to combine Fe3+ based on an opening-closing transformation of the spirolactam ring in rhodamine...

Cited by 4 publications

References 30 publications

Noninvasive Imaging of Tumor Glycolysis and Chemotherapeutic Resistance via De Novo Design of Molecular Afterglow Scaffold

Noninvasive Imaging of Tumor Glycolysis and Chemotherapeutic Resistance via De Novo Design of Molecular Afterglow Scaffold

Small-Molecule Fluorescent Probes for Binding- and Activity-Based Sensing of Redox-Active Biological Metals

A mitochondria-targeted fluorescent probe based on biocompatible RBH-U for the enhanced response of Fe3+ in living cells and quenching of Cu2+ in vitro

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Analyses on intracellular Fe3+ with a rhodamine probe: “turn-on” response, specific recognition and bioimaging

Abstract: To overcome the existing difficulty in distinguishing ferric from ferrous ions, a rhodamine-containing probe was designed to combine Fe3+ based on an opening-closing transformation of the spirolactam ring in rhodamine...

Cited by 4 publications

References 30 publications

Noninvasive Imaging of Tumor Glycolysis and Chemotherapeutic Resistance via De Novo Design of Molecular Afterglow Scaffold

Noninvasive Imaging of Tumor Glycolysis and Chemotherapeutic Resistance via De Novo Design of Molecular Afterglow Scaffold

Small-Molecule Fluorescent Probes for Binding- and Activity-Based Sensing of Redox-Active Biological Metals

A mitochondria-targeted fluorescent probe based on biocompatible RBH-U for the enhanced response of Fe3+ in living cells and quenching of Cu2+ in vitro

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Analyses on intracellular Fe³⁺ with a rhodamine probe: “turn-on” response, specific recognition and bioimaging