Reversible Binding of Oxygen to Aromatic Compounds

Aubry, Jean‐Marie; Pierlot, Christel; Rigaudy, J.; Schmidt, Reinhard H.

doi:10.1021/ar010086g

Cited by 371 publications

(301 citation statements)

References 61 publications

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“…The rhodium(I) complex 4 a can be recovered in 94 % yield; 75 % of 6 a (with respect to the amount 1 a) can be isolated. [23] Irradiation of a solution of 2,3-dimethylbut-2-ene and 1 a in benzene afforded neither the allylic hydroperoxide 3-hydroperoxy-2,3-dimethylbut-1-ene derived by a singlet-oxygen ene reaction nor acetone by [2+2] cycloaddition. [24] Therefore, we exclude release of singlet dioxygen from 1 a under the reaction conditions, which could also react with 3 to give 6 a.…”

mentioning

confidence: 99%

A Rhodium Peroxido Complex in Mono‐, Di‐, and Peroxygenation Reactions

Meier

Braun

2011

Angew Chem Int Ed

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confidence: 99%

A Rhodium Peroxido Complex in Mono‐, Di‐, and Peroxygenation Reactions

Meier

Braun

2011

Angew Chem Int Ed

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“…1 O 2 could reversibly react with some specific polycyclic aromatic hydrocarbons (e.g. naphthalene, anthracene or pyridine derivatives),90 and form endoperoxide which can subsequent release 1 O 2 via warming and revert to the original state. However, tumor hypoxia91 and PDT‐induced hypoxia92 hinder the development of PDT.…”

Section: Factitious Captivity and Releasementioning

confidence: 99%

Controllable Photodynamic Therapy Implemented by Regulating Singlet Oxygen Efficiency

et al. 2017

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With singlet oxygen (1O2) as the active agent, photodynamic therapy (PDT) is a promising technique for the treatment of various tumors and cancers. But it is hampered by the poor selectivity of most traditional photosensitizers (PS). In this review, we present a summary of controllable PDT implemented by regulating singlet oxygen efficiency. Herein, various controllable PDT strategies based on different initiating conditions (such as pH, light, H2O2 and so on) have been summarized and introduced. More importantly, the action mechanisms of controllable PDT strategies, such as photoinduced electron transfer (PET), fluorescence resonance energy transfer (FRET), intramolecular charge transfer (ICT) and some physical/chemical means (e.g. captivity and release), are described as a key point in the article. This review provide a general overview of designing novel PS or strategies for effective and controllable PDT.

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“…1,2 The corresponding light-mediated O 2 -adducts of such systems have been utilized for the targeted release of reactive oxygen species such as singlet oxygen. 3,4 Furthermore, the photochemical generation of oxygen-based biradical species from aromatic endoperoxide species has also been investigated in some detail. 5,6 Important biomedical and chemotherapeutic applications of such systems include the delayed triggering of singlet oxygen release, which can induce cellular damage in malignant tissue, 1 and the potential utilization of biomimetic endoperoxide-bond cleavage processes for the controlled deactivation of bacteria, viruses 7 and parasites such as Plasmodium falciparum, which is known to be responsible for the majority of fatal malaria infections.…”

Section: Introductionmentioning

confidence: 99%

Functionalized derivatives of 1,4-dimethylnaphthalene as precursors for biomedical applications: synthesis, structures, spectroscopy and photochemical activation in the presence of dioxygen

et al. 2012

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Decomposition of endoperoxide containing molecules is an attractive approach for the delayed release of singlet oxygen under mild reaction conditions. Here we describe a new method for the adaptation of the corresponding decay times by controlling the supramolecular functional structure of the surrounding matrix in the immediate vicinity of embedded singlet oxygen precursors. Thus, a significant prolongation of the lifetime of the endoperoxide species is possible by raising the energy barrier of the thermal 1 O 2 -releasing step via a restriction of the free volume of the applied carrier material. Enabling such a prolonged decomposition period is crucial for potential biomedical applications of endoperoxide containing molecules, since sufficient time for appropriate cell uptake and transport to the desired target region must be available under physiological conditions before the tissue damaging-power of the reactive oxygen species formed is completely exhausted. Two novel polyaromatic systems for the intermediate storage and transport of endoperoxides and the controlled release of singlet oxygen in the context of anticancer and antibiotic activity have been prepared and characterized. These compounds are based on functionalized derivatives of the 1,4-dimethylnaphthalene family which are readily forming metastable endoperoxide species in the presence of dioxygen, a photosensitizer molecule such as methylene blue and visible light. In contrast to previously known systems of similar photoreactivity, the endoperoxide carrying molecules have been designed with optimized molecular properties in terms of potential chemotherapeutic applications. These include modifications of polarity to improve their incorporation into various biocompatible carrier materials, the introduction of hydrogen bonding motifs to additionally influence the endoperoxide decay kinetics, and the synthesis of bifunctional derivatives to enable synergistic effects of multiple singlet oxygen binding sites with an enhanced local concentration of reactive species. With these compounds, a promising degree of endoperoxide stability adjustment within the carrier matrix has been achieved ( polymer films or nanoparticles), which now opens the stage for appropriate targeting of the corresponding pro-drugs into live cells. First results on cytocidal and cytostatic properties of these compounds embedded in ethylcellulose nanoparticles are presented. Furthermore, an efficient low-cost method for the photochemical production of reactive endoperoxides based on high-power 660 nm LED excitation at room temperature and ambient conditions in ethanol solution is reported.

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Reversible Binding of Oxygen to Aromatic Compounds

Cited by 371 publications

References 61 publications

A Rhodium Peroxido Complex in Mono‐, Di‐, and Peroxygenation Reactions

A Rhodium Peroxido Complex in Mono‐, Di‐, and Peroxygenation Reactions

Controllable Photodynamic Therapy Implemented by Regulating Singlet Oxygen Efficiency

Functionalized derivatives of 1,4-dimethylnaphthalene as precursors for biomedical applications: synthesis, structures, spectroscopy and photochemical activation in the presence of dioxygen

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