Developing a NIR emitting benzothiazolium-thioxanthene dye and its application for the design of lysosomes-targeting palladium(II) probe

Liu, Qiuchen; Ji, Li; Liu, Chang; He, Song; Zhao, Liwei; Zeng, Xianshun; Wang, Tianhui

doi:10.1016/j.dyepig.2021.109796

Cited by 12 publications

(6 citation statements)

References 70 publications

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“…The Mander’s overlap coefficient for CBT-SiPc with LysoTracker was 0.99. The CBT-SiPc targeting of lysosomes could be explained by the interaction of the S atoms of the CBT groups with the protein residues containing S atoms through S–S intermolecular interactions ( Gleiter et al, 2018 ; Brilkina et al, 2019 ; Liu et al, 2021 ; Liu et al, 2022 ).…”

Section: Resultsmentioning

confidence: 99%

Chlorophenyl thiophene silicon phthalocyanine: Synthesis, two-photon bioimaging-guided lysosome target, and in vitro photodynamic efficacy

Zhang

Huang

et al. 2023

Front. Pharmacol.

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The development of efficient photosensitizers with high singlet oxygen quantum yield, strong fluorescent emission, excellent photostability, and specific organelle targeting is in great demand for the enhancement of PDT treatment efficiency. This study designed and synthesized a new two-photon photosensitizer chlorophenyl thiophene axially substituted silicon (IV) phthalocyanine (CBT-SiPc). CBT-SiPc showed specific targeting of lysosomes in living cells and good biocompatibility. Furthermore, high 1O2 generation efficiency and high PDT efficiency in MCF-7 breast cancers under irradiation were also demonstrated. The novel CBT-SiPc showed great potential in the application of lysosome-targeted and two-photon bioimaging-guided photodynamic cancer therapy.

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Section: Resultsmentioning

confidence: 99%

Chlorophenyl thiophene silicon phthalocyanine: Synthesis, two-photon bioimaging-guided lysosome target, and in vitro photodynamic efficacy

Zhang

Huang

et al. 2023

Front. Pharmacol.

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“…Consequently, a substantial quantity of palladium is introduced into both living and nonliving systems, potentially leading to various health risks. Researchers investigated that the hydrolytic enzymes located within lysosomal compartments undergo deactivation when they interact with Pd 2+ , which binds to thiol groups or other negatively charged constituents of the enzyme . The utilization of suitably customized fluorescent probes assists in detecting, monitoring, and comprehending the harmful impact of the Pd 2+ ion on living systems.…”

Section: Lysosomal Metal Ion Detectionmentioning

confidence: 99%

“…(j) Fluorescence images of HeLa cells incubated with only probe 23 for 30 min (upper panel) and probe and PdCl 2 (1 μM) (lower panel λ ex = 635 nm, λ em = 700–800 nm). (h–j) is reprinted with permission from ref ( 30 ). Copyright 2021, Elsevier.…”

Section: Lysosomal Metal Ion Detectionmentioning

confidence: 99%

Review on Lysosomal Metal Ion Detection Using Fluorescent Probes

Silswal,

P.,

Koner

2024

ACS Omega

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Metal ions are indispensable and play an important role in living systems. Metal ions coordinated to metalloenzymes pocket activate the bound substrate and labile metal ions maintaining the ionic balance. The amount of metal ions present in various subcellular compartments of the cells is highly regulated for maintaining cellular homeostasis. An imbalance in the metal ion concentration is related to several diseases and results in serious pathological conditions. Mostly the internalized metal ions are processed in the lysosomal compartment of the cell. A delicate regulation of metal ions in the lysosomal compartment can modulate the lysosomal pH and inhibit hydrolytic enzymes, which ultimately causes lysosomal storage disorders. In the past decade, the understanding and regulation of lysosomal metal ions based on fluorometric methods have gained significant attention. In this review, we have comprehensively summarized the development of various fluorescent reporters over the past five years for a selective and sensitive estimation of lysosomal metal ion concentration. We believe this consolidated and timely review will help researchers working in the areas associated with lysosomal metal ions.

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“…As an example of its biological and pharmacological properties, anticancer, − antitumor, − antiviral, antimicrobial, − antibacterial, − and anti-inflammatory activities can be cited. Moreover, some types are also used as materials in dye technology, , sensor, , and organic light-emitting diodes (OLEDs) − due to the conjugation and heteroring in their structures, ensuring optical and electrochemical properties. In addition to these activities, the most noticeable biological activities of thioxanthenes are their use as drugs in many neurological diseases. − …”

Section: Introductionmentioning

confidence: 99%

Intramolecular Friedel–Crafts Reaction with Trifluoroacetic Acid: Synthesizing Some New Functionalized 9-Aryl/Alkyl Thioxanthenes

Deniz,

Yıldız,

Başpınar Küçük

2024

ACS Omega

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In this study, a series of halogen-substituted thioxanthenes were synthesized because the most important and biologically active derivatives of xanthenes are thioxanthenes. In order to obtain new thioxanthene derivatives, first, the starting molecules were synthesized by the appropriate reaction methods in two steps. The intramolecular Friedel−Crafts alkylation (FCA) method was used to convert the prepared three aromatic substituted starting alcohol compounds to their corresponding thioxanthenes by cyclization. For the intramolecular FCA reaction of secondary alcohols, which are the starting compounds (1a−1t), organic Bro̷ nsted acids, which require more innovative, easier, and suitable reaction conditions, were used instead of halide reagents with corrosive effects as classical FCA catalysts. Trifluoroacetic acid was determined to be the organocatalyst with the best yield. Therefore, some original 9-aryl/alkyl thioxanthene derivatives (2a−2t) were synthesized using the optimized FCA method. In addition, a new sulfone derivative of thioxanthene 3i was prepared by performing the oxidation reaction with one of the obtained new thioxanthene 2i. Thioxanthenes and their derivatives are important heterocyclic structures that contain pharmacologically valuable sulfur and are used in the treatment of psychotic diseases such as Alzheimer's or schizophrenia, as well as a number of potent biological activities.

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Developing a NIR emitting benzothiazolium-thioxanthene dye and its application for the design of lysosomes-targeting palladium(II) probe

Cited by 12 publications

References 70 publications

Chlorophenyl thiophene silicon phthalocyanine: Synthesis, two-photon bioimaging-guided lysosome target, and in vitro photodynamic efficacy

Chlorophenyl thiophene silicon phthalocyanine: Synthesis, two-photon bioimaging-guided lysosome target, and in vitro photodynamic efficacy

Review on Lysosomal Metal Ion Detection Using Fluorescent Probes

Intramolecular Friedel–Crafts Reaction with Trifluoroacetic Acid: Synthesizing Some New Functionalized 9-Aryl/Alkyl Thioxanthenes

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