Macrocycles containing azo groups: recognition, assembly and application

Geng, Wen‐Chao; Sun, Hongwei; Guo, Dong‐Sheng

doi:10.1007/s10847-018-0819-8

Cited by 29 publications

(11 citation statements)

References 561 publications

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“…Such a noncovalent strategy is easily amenable to other azo‐containing macrocycles for not only hypoxia‐responsive imaging but also drug delivery. Noticeably, over 1200 azo‐containing macrocycles have been reported up to now; however, no hypoxia‐responsive application has ever been demonstrated. This work not only paves a new way to imaging hypoxia but also explores new biomedical applications of azo macrocycles.…”

Section: Methodsmentioning

confidence: 99%

A Noncovalent Fluorescence Turn‐on Strategy for Hypoxia Imaging

et al. 2019

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Hypoxia plays crucial roles in many diseases and is a central target for them. Present hypoxia imaging is restricted to the covalent approach, which needs tedious synthesis. In this work, a new supramolecular host–guest approach, based on the complexation of a hypoxia‐responsive macrocycle with a commercial dye, is proposed. To exemplify the strategy, a carboxyl‐modified azocalix[4]arene (CAC4A) was designed that binds to rhodamine 123 (Rho123) and quenches its fluorescence. The azo groups of CAC4A were selectively reduced under hypoxia, leading to the release of Rho123 and recovery of its fluorescence. The noncovalent strategy was validated through hypoxia imaging in living cells treated with the CAC4A–Rho123 reporter pair.

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Section: Methodsmentioning

confidence: 99%

A Noncovalent Fluorescence Turn‐on Strategy for Hypoxia Imaging

et al. 2019

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“…Such an oncovalent strategy is easily amenable to other azo-containing macrocycles for not only hypoxiaresponsive imaging but also drug delivery.N oticeably,o ver 1200 azo-containing macrocycles have been reported up to now; [32] however,n oh ypoxia-responsive application has ever been demonstrated. Such an oncovalent strategy is easily amenable to other azo-containing macrocycles for not only hypoxiaresponsive imaging but also drug delivery.N oticeably,o ver 1200 azo-containing macrocycles have been reported up to now; [32] however,n oh ypoxia-responsive application has ever been demonstrated.…”

Section: Angewandte Chemiementioning

confidence: 99%

“…In conclusion, we demonstrate anew noncovalent strategy for imaging hypoxia based on the concept of supramolecular chemistry,which was validated in living cells.Compared with widely used covalent strategies,t he present noncovalent strategy based on host-guest chemistry exhibits several intrinsic advantages:1)the use of commercial probes without time-and cost-consuming synthesis;2 )releasing probes with high fidelity under hypoxia;3 )easy adaptability to other probes (and even treating agents) for constructing auniversal platform. Such an oncovalent strategy is easily amenable to other azo-containing macrocycles for not only hypoxiaresponsive imaging but also drug delivery.N oticeably,o ver 1200 azo-containing macrocycles have been reported up to now; [32] however,n oh ypoxia-responsive application has ever been demonstrated. This work not only paves an ew way to imaging hypoxia but also explores new biomedical applications of azo macrocycles.…”

Section: Angewandte Chemiementioning

confidence: 99%

A Noncovalent Fluorescence Turn‐on Strategy for Hypoxia Imaging

et al. 2019

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Hypoxia playscrucial roles in many diseases and is acentral target for them. Present hypoxia imaging is restricted to the covalent approach, which needs tedious synthesis.Inthis work, anew supramolecular host-guest approach, based on the complexation of ahypoxia-responsive macrocycle with acommercial dye,isproposed. To exemplify the strategy,acarboxylmodified azocalix[4]arene (CAC4A) was designed that binds to rhodamine 123 (Rho123) and quenches its fluorescence.The azo groups of CAC4A were selectively reduced under hypoxia, leading to the release of Rho123 and recovery of its fluorescence.The noncovalent strategy was validated through hypoxia imaging in living cells treated with the CAC4A-Rho123 reporter pair.Supportinginformation and the ORCID identification number(s) for the author(s) of this article can be found under: https://doi.

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“…Macrocyclic hosts constitute a family of well-studied artificial receptors with a discrete cavity that is selective for complementary binding to certain guests [9]. Modulation of properties of organic fluorophores through supramolecular encapsulation using artificial macrocyclic hosts has always been an active research area [10–12].…”

Section: Introductionmentioning

confidence: 99%

“…Calixarenes are the third generation of macrocyclic compounds composed of phenolic units bridged with methylene groups at the o -positions of phenolic hydroxy groups [9]. We have focused on molecular recognition and self-assembly of water-soluble calixarene derivatives for a long time, directed by exploring biomedical applications of these compounds.…”

Section: Introductionmentioning

confidence: 99%

Complexation of a guanidinium-modified calixarene with diverse dyes and investigation of the corresponding photophysical response

Wang¹,

Kong²,

Zheng³

et al. 2019

Beilstein J. Org. Chem.

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We herein describe the comprehensive investigation of the complexation behavior of a guanidinium-modified calix[5]arene pentaisohexyl ether (GC5A) with a variety of typical luminescent dyes. Fluorescein, eosin Y, rose bengal, tetraphenylporphine sulfonate and sulfonated aluminum phthalocyanine were employed as classical aggregation-induced quenching dyes. 2-(p-Toluidinyl)naphthalene-6-sulfonic acid and 1-anilinonaphthalene-8-sulfonic acid were selected as representatives of intramolecular charge-transfer dyes. Phosphated tetraphenylethylene was involved as the classical aggregation-induced emission dye. Sulfonated acedan representing one example of two-photon fluorescent probes, was also investigated. A ruthenium(II) complex with carboxylated bipyridyl ligands was included as a representative candidate of luminescent transition-metal complexes. We determined the association constants of the GC5A–dye complexes by fluorescence titration and discuss the complexation-induced photophysical changes. In addition, a comparison of the complexation behavior of GC5A with that of other macrocycles and potential applications according to the diverse photophysical responses are provided.

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Macrocycles containing azo groups: recognition, assembly and application

Cited by 29 publications

References 561 publications

A Noncovalent Fluorescence Turn‐on Strategy for Hypoxia Imaging

A Noncovalent Fluorescence Turn‐on Strategy for Hypoxia Imaging

A Noncovalent Fluorescence Turn‐on Strategy for Hypoxia Imaging

Complexation of a guanidinium-modified calixarene with diverse dyes and investigation of the corresponding photophysical response

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