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Quantitative kinetics of intracellular singlet oxygen generation using a fluorescence probe.

ABSTRACT: Singlet oxygen (¹O₂) is a type of reactive oxygen species involved in numerous physiological activities. We previously reported that ¹O₂-specific oxidation products are increased in patients with prediabetes, suggesting that measurement of ¹O₂ may be an important indicator of physiological and pathological conditions. The turnover in the generation and quenching of ¹O₂ is extremely rapid during biological activities owing to it high reactivity and short lifetime in solution. However, the dynamic changes in ¹O₂ generation in living cells have not been fully explored. In this study, we investigated whether the kinetics of ¹O₂ generation can be quantified using a far-red fluorescent probe for mitochondrial ¹O₂, Si-DMA, following addition of the ¹O₂ generator, endoperoxide, to mammalian cells. The kinetics of Si-DMA fluorescence intensity dose-dependently increased following treatment of mammalian living cells with endoperoxide. Alternatively, treatment with ¹O₂ quenchers decreased the fluorescence intensities following endoperoxide treatment. Our results indicate that the kinetics of intracellular ¹O₂ can be readily obtained using Si-DMA and time-lapse imaging, which provides new insights into the mechanism of ¹O₂ generation in mammalian cells and the exploration of ¹O₂ generators and quenchers.

SUBMITTER: Murotomi K

PROVIDER: S-EPMC7327044 | biostudies-literature | 2020 Jun

REPOSITORIES: biostudies-literature

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Quantitative kinetics of intracellular singlet oxygen generation using a fluorescence probe.

Murotomi Kazutoshi K Umeno Aya A Sugino Sakiko S Yoshida Yasukazu Y

Scientific reports 20200630 1

Singlet oxygen (1O2) is a type of reactive oxygen species involved in numerous physiological activities. We previously reported that 1O2-specific oxidation products are increased in patients with prediabetes, suggesting that measurement of 1O2 may be an important indicator of physiological and pathological conditions. The turnover in the generation and quenching of 1O2 is extremely rapid during biological act ...[more]

PMID: 32606330

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Project description:Heavy-atom-free sensitizers forming long-living triplet excited states via the spin-orbit charge transfer intersystem crossing (SOCT-ISC) process have recently attracted attention due to their potential to replace costly transition metal complexes in photonic applications. The efficiency of SOCT-ISC in BODIPY donor-acceptor dyads, so far the most thoroughly investigated class of such sensitizers, can be finely tuned by structural modification. However, predicting the triplet state yields and reactive oxygen species (ROS) generation quantum yields for such compounds in a particular solvent is still very challenging due to a lack of established quantitative structure-property relationship (QSPR) models. In this work, the available data on singlet oxygen generation quantum yields (ΦΔ ) for a dataset containing >70 heavy-atom-free BODIPY in three different solvents (toluene, acetonitrile, and tetrahydrofuran) were analyzed. In order to build reliable QSPR model, a series of new BODIPYs were synthesized that bear different electron donating aryl groups in the meso position, their optical and structural properties were studied along with the solvent dependence of singlet oxygen generation, which confirmed the formation of triplet states via the SOCT-ISC mechanism. For the combined dataset of BODIPY structures, a total of more than 5000 quantum-chemical descriptors was calculated including quantum-chemical descriptors using density functional theory (DFT), namely M06-2X functional. QSPR models predicting ΦΔ values were developed using multiple linear regression (MLR), which perform significantly better than other machine learning methods and show sufficient statistical parameters (R=0.88-0.91 and q2 =0.62-0.69) for all three solvents. A small root mean squared error of 8.2 % was obtained for ΦΔ values predicted using MLR model in toluene. As a result, we proved that QSPR and machine learning techniques can be useful for predicting ΦΔ values in different media and virtual screening of new heavy-atom-free BODIPYs with improved photosensitizing ability.

Dataset Information

Quantitative kinetics of intracellular singlet oxygen generation using a fluorescence probe.

Publications

Quantitative kinetics of intracellular singlet oxygen generation using a fluorescence probe.

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