Reversible Binding of Oxygen to Aromatic Compounds

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

doi:10.1002/chin.200348236

Cited by 33 publications

(50 citation statements)

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“…Typically, 9,10-dialkylanthracene endoperoxides undergo skeletal rearrangements rather than cycloreversion reactions 14. In notable contrast, endoperoxide 1EP cycloreverts at room temperature to completely regenerate the starting squaraine rotaxane and release molecular oxygen (see Supplementary Figs.…”

Section: Resultsmentioning

confidence: 99%

Storable, thermally activated, near-infrared chemiluminescent dyes and dye-stained microparticles for optical imaging

et al. 2010

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Optical molecular imaging employs relatively harmless, low-energy light and technically straightforward instrumentation. Self-illuminating, chemiluminescent systems are especially attractive since they have inherently high signal contrast due to the lack of background emission. Currently, chemiluminescence imaging involves short-lived molecular species that are not stored but instead generated in situ, and they typically emit visible light, which does not penetrate far through heterogeneous biological media. Here, we describe a new paradigm for optical molecular imaging using squaraine rotaxane endoperoxides (SREPs), interlocked fluorescent and chemiluminescent dye molecules that have a squaraine chromophore encapsulated inside a macrocycle endoperoxide. SREPs can be stored indefinitely at temperatures below −20 °C, but upon warming to body temperature they undergo a unimolecular chemical reaction and emit near infrared light that can pass through a living mouse. Dye-stained microparticles are easily prepared for in vivo near-infrared optical imaging using commercial imaging stations.

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Section: Resultsmentioning

confidence: 99%

Storable, thermally activated, near-infrared chemiluminescent dyes and dye-stained microparticles for optical imaging

et al. 2010

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“…A chemical probe is usually used to trap the singlet oxygen and then detection and quantification can be based on absorbance. A very characteristic reaction of singlet oxygen is the [4 + 2] cycloaddition to conjugated cyclic dienes and polycyclic aromatic hydrocarbons such as anthracene (Aubry, Pierlot, Rigaudy, & Schmidt, ). Anthracene traps reversibly singlet oxygen.…”

Section: Resultsmentioning

confidence: 99%

Scavenging effect of pasipay (passiflora incarnate L.) on singlet oxygen generation and fatty acid photooxygenation

Hajimohammadi

Nosrati

2018

Food Science & Nutrition

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Anthracene as a chemical probe is usually used to trap the singlet oxygen and then detection and quantification can be based on absorbance. In this study, oxidation of anthracene declared that rate of singlet oxygen quenching in the presence of pasipay (passiflora incarnate L.) as a natural antioxidant, 1,4 Diazabicyclo [2.2.2] octane (DABCO) as a well‐known singlet oxygen scavenger and highly effective synthetic antioxidants in food industry such as Butylated hydroxytoluene (BHT), Butylated hydroxyanisole (BHA), tert‐Butylhydroquinone (TBHQ) decreased in the order of DABCO >pasipay > TBHQ > BHT > BHA. On the other hand, lipid photooxidation is the undesirable chemical process in which singlet oxygen result in the peroxidation of fatty acids. The results of this study also showed that oleic acid oxidation with singlet oxygen in the presence of pasipay (contains 0.4576 mg flavonoid compounds) diminished about 11% which shows pasipay has an effective role to inhibit lipid peroxidation.

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“…The clean production of endoperoxides has been achieved, and many have been isolated in pure form and in high yields. Although endoperoxides have been created in organic and aqueous media, some are unstable above 0 C, and their decomposition may lead to the dissociation of oxygen [46][47][48]. Endoperoxide decomposition may also occur by OÀO bond cleavage, which results in the formation of bisepoxides (e.g., spiro [2.4]hepta-4,6-diene endoperoxide) [39] or ketones (an example is the conversion of the natural product kalasinamide via its endoperoxide to the corresponding quinone, marcanine A) [87].…”

Section: Discussionmentioning

confidence: 99%