A Noncovalent Fluorescence Turn‐on Strategy for Hypoxia Imaging

Geng, Wen‐Chao; Jia, Shaorui; Zheng, Zhe; Li, Zhihao; Ding, Dan; Guo, Dong‐Sheng

doi:10.1002/ange.201813397

Cited by 26 publications

(3 citation statements)

References 68 publications

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“…[ 62 ] Recently, calixarene and its derivatives have been found to be an ideal skeleton for biomedical applications in biological imaging, drug delivery, and theranostic agents. [ 63–65 ] For example, Ding and Guo developed several calixarene‐based antitumor PDT systems by using traditional PSs as guests. [ 66,67 ]…”

Section: Introductionmentioning

confidence: 99%

Supramolecular Assembly Based on Calix(4)arene and Aggregation‐Induced Emission Photosensitizer for Phototherapy of Drug‐Resistant Bacteria and Skin Flap Transplantation

Wang,

Liu,

Wang

et al. 2024

Adv Healthcare Materials

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Photodynamic therapy as a burgeoning and non‐invasive theranostic technique has drawn great attention in the field of antibacterial treatment, but often encounters undesired phototoxicity of photosensitizers during systemic circulation. Herein, a supramolecular substitution strategy is proposed for phototherapy of drug‐resistant bacteria and skin flap repair by using macrocyclic p‐sulfonatocalix[4]arene (SC4A) as a host, and two cationic AIEgens, namely TPE‐QAS and TPE‐2QAS, bearing quaternary ammonium group(s) as guests. Through host‐guest assembly, the obtained complex exhibits obvious blue fluorescence in the solution due to restriction of free motion of AIEgens and drastically inhibits efficient type I ROS generation. Then, upon addition of another guest 4,4′‐benzidine dihydrochloride, TPE‐QAS can be competitively replaced from the cavity of SC4A to restore its pristine ROS efficiency and photoactivity in aqueous solution. The dissociative TPE‐QAS shows a high bacterial binding ability with an efficient treatment for methicillin‐resistant Staphylococcus aureus (MRSA) in the dark and light irradiation. Meanwhile, it also exhibits an improved survival rate for MRSA‐infected skin flap transplantation and largely accelerates the healing process. Thus, such cascaded host‐guest assembly is an ideal platform for phototheranostics research.This article is protected by copyright. All rights reserved

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Section: Introductionmentioning

confidence: 99%

Supramolecular Assembly Based on Calix(4)arene and Aggregation‐Induced Emission Photosensitizer for Phototherapy of Drug‐Resistant Bacteria and Skin Flap Transplantation

Wang,

Liu,

Wang

et al. 2024

Adv Healthcare Materials

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“…[58][59][60][61] For example, Guo reported several calixarene-based supramolecular fluorescence probes for hypoxia imaging but without deeply exploring their antitumor capability. 62,63 Herein, we develop a supramolecular assembly strategy based on sulfonate-functionalized azocalix [4]arene (SAC4A) and red-emitting AIEgen for hypoxia-responsive bioimaging and photodynamic therapy. In this system, cationic AIEgen composed of triphenylamine and quaternary ammonium salt (namely TPA-H) can be encapsulated in the cavity of azocalix [4]arene through electrostatic interaction (Scheme 1A).…”

Section: Introductionmentioning

confidence: 99%

Self-Reporting Hypoxia-Responsive Supramolecular Phototheranostic Nanomaterials Based on AIEgen and Azocalixarene

Han,

Zhang,

Chen

et al. 2024

Preprint

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Hypoxia is a significant feature in most of solid tumors and developing hypoxia-responsive phototheranostic system is still a challenge. In this contribution, a supramolecular assembly strategy based on sulfonate-functionalized azocalix[4]arene (SAC4A) and cationic aggregation-induced emission photosensitizer (namely TPA-H) was proposed for hypoxia-responsive bioimaging and photodynamic therapy (PDT). Upon supramolecular complexation of TPA-H and SAC4A through electrostatic interaction, the fluorescence and reactive oxygen species (ROS) generation of TPA-H were largely inhibited. In hypoxic tumors, the azo group of SAC4A can be reduced to aniline derivative and release the included TPA-H to recover its pristine fluorescence and ROS. Interestingly, the free TPA-H undergoes cell membrane-to-mitochondria translocation during cell imaging, achieving a real-time self-reporting PDT system. In vivo tumor imaging and therapy reveal that this as-prepared supramolecular complexes have good biosafety and efficient antitumor activity under hypoxia. Such hypoxia-responsive supramolecular photosensitizer system will enrich image-guided PDT.

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“…Unfortunately, these PSs are often prepared via sophisticated molecular synthesis, require tedious organic purification, and show an inert response to external stimuli, which largely limit their high-throughput testing. Another strategy is the use of the supramolecular assembly to achieve improved PDT efficacy. − Compared with the single PS system, host–guest interactions have been recognized as an effective method to address dark cytotoxicity in vivo because the ROS generation and photophysical properties of PSs could be reversibly tuned by noncovalent molecular interactions, such as hydrophobic interactions, hydrogen bonding, coordinative bonds, and electrostatic interactions. , As an important component of host–guest architectures, regular-shaped organic macrocycles, such as calixarene, cyclodextrin, and cucurbituril, have been widely explored for their intrinsic cavities that can selectively bind guest molecules completely or partially. − Among them, calixarene is a well-known host motif and has emerged as an ideal skeleton for applications in drug delivery, biological imaging, and theranostic agents by virtue of its low toxicity and multiple response to stimuli. − For example, Guo and co-workers present a novel calixarene-based PDT system via biomarker-induced host–guest interactions …”

Section: Introductionmentioning

confidence: 99%

Substitution Activated Precise Phototheranostics through Supramolecular Assembly of AIEgen and Calixarene

et al. 2020

Self Cite

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Photodynamic therapy (PDT) is a promising noninvasive therapeutic technique and has attracted increasing interests in preclinical trials. However, the translation from laboratory to clinic often encounters the problem of undesired dark cytotoxicity of photosensitizers (PSs). Now, this challenge can be addressed by cascaded substitution activated phototheranostics using the host–guest strategy. Through electrostatical complexation of pyridinium-functionalized tetraphenylethylene, namely, TPE-PHO, and water-soluble calixarene, the dark cytotoxicity of TPE-PHO is dramatically inhibited. The nanoassemblies of the complex show enhanced biocompatibility and selectively locate at the cytoplasm in vitro. When TPE-PHO is competitively displaced from the cavity of calixarene by 4,4′-benzidine dihydrochloride at the tumor site, its dark cytotoxicity and photoactivity in tumor tissue are restored to give efficient PDT efficacy under light irradiation. The result from cell imaging reveals that TPE-PHO undergoes translocation from cytoplasm to mitochondria to kill the cancer cells during the cascaded supramolecular substitution process. In vivo tumor imaging and therapy are successfully implemented to evaluate the curative effect. Such a supramolecular strategy avoids tedious molecular synthesis and opens a new venue to readily tune the PS behaviors.

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A Noncovalent Fluorescence Turn‐on Strategy for Hypoxia Imaging

Cited by 26 publications

References 68 publications

Supramolecular Assembly Based on Calix(4)arene and Aggregation‐Induced Emission Photosensitizer for Phototherapy of Drug‐Resistant Bacteria and Skin Flap Transplantation

Supramolecular Assembly Based on Calix(4)arene and Aggregation‐Induced Emission Photosensitizer for Phototherapy of Drug‐Resistant Bacteria and Skin Flap Transplantation

Self-Reporting Hypoxia-Responsive Supramolecular Phototheranostic Nanomaterials Based on AIEgen and Azocalixarene

Substitution Activated Precise Phototheranostics through Supramolecular Assembly of AIEgen and Calixarene

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