• Title/Summary/Keyword: singlet oxygen

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SINGLET OXYGEN-MEDIATED PHOTOOXIDATION OF METHYL 11-HYDRO-13-(METHYLOXY)CARBONYLARTEMISINATE

  • Lee, Jung-Kul;Han, Jae-Hong;Kim, Jeong-Han;Lim, Yoong-Ho;Kim, Soo-Un
    • Journal of Photoscience
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    • v.1 no.2
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    • pp.127-129
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    • 1994
  • Singlet oxygen-mediated photooxidation and subsequent triplet oxygen insertion of 11-hydro-13-(methyloxy)carbonylartemisinate (4) yielded a diketo compound 5 as the major product instead of the expected 11-hydro-13-(methyloxy)carbonylartemisinin (6). The formation of the unexpected product was in part consistent with the mechanism proposed by Acton and Roth and is the first isolation of the diketo compound from the photooxidation of artemisinate.

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Application of Chemical Probes to Detect Superoxide Anion and Singlet Oxygen in Biological Systems during Gamma Irradiation

  • Lee, Min Hee;Cho, Eun Ju;Kim, Ji Hong;Kim, Ji Eun;Chung, Byung Yeoup;Cho, Jae-Young;Lee, Kang-Soo;Kim, Jin-Hong
    • Journal of Radiation Industry
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    • v.5 no.3
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    • pp.221-225
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    • 2011
  • To detect superoxide anion ($O_2{\cdot}^-$) or singlet oxygen ($^1O_2$) in biological systems during gamma irradiation, specific chemical probes, 4,5-dihydroxy-1,3-benzene disulfonic acid (Tiron) or 2,2,6,6-tetramethyl-piperidine (TEMP), were evaluated. Tiron or TEMP spin adducts was structurally stable in aqueous solution during gamma irradiation up to 500 or 1,000 Gy, respectively. The signal of Tiron semiquinone radical, a spin adduct of Tiron upon reaction with $O_2{\cdot}^-$, was slightly increased by gamma irradiation. This trend was dose-dependently manifested in $O_2$-saturated aqueous solution using nitro blue tetrazolium (NBT), a common probe for both hydrated electron ($e{^-}_{aq}$) and $O_2{\cdot}^-$. In contrast, a spin adduct of TEMP, was never inducible by gamma irradiation, while its signal was substantially enhanced by photosensitization of riboflavin. These results suggest that Tiron and NBT or TEMP could be utilized to detect $O_2{\cdot}^-$ or $^1O_2$ in biological systems during gamma irradiation, although $O_2{\cdot}^-$ or $^1O_2$ are not the main reactive oxygen species produced by water radiolysis.

Photophysical and Photochemical Property of ATX-S10

  • Ito, Toshiaki;Okazaki, Shigetoshi;Kageyama, Kazumi;Hirohata, Toru;Kohno, Eiji;Hirano, Toru
    • Journal of Photoscience
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    • v.9 no.2
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    • pp.527-529
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    • 2002
  • Photodynamic therapy (PDT) is a medical treatment using laser and photosensitizing drug taken up to destroy cancer cells. Singlet oxygen ($^1$0$_2$) generation is strongly related to this treatment. We have built a direct detection system monitoring feeble luminescence, in the near IR region, from $^1$0$_2$, We have comparatively studied the photophysical and photochemical properties in solution of a newly developed drug ATX-S10 and Photofrin already investigated clinically. We demonstrdted that ATX-S10 was capable of efficiently yielding $^1$0$_2$, which may lead to highly efficient PDT treatment. Successive laser excitation photobleached ATX -S10 readily in a dose-dependent manner. This result shows that ATX -S10 is useful in setting up suitable medical treatment conditions to minimize side effects.

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A Study on Generative Characteristics of Radicals in Aqueous Solutions of Humic Acids using Electron Spin Resonance (전자기공명기법을 이용한 Humic Acid 용액에서의 라디칼 발생 특성에 관한 연구)

  • Han, Sang-Kuk
    • Journal of Environmental Science International
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    • v.17 no.6
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    • pp.671-677
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    • 2008
  • We studied to determine quantitatively the radical species generated from humic acid (HA) solutions by irradiation(>400 mn). The formation of radical species from HA solutions was investigated with ESR spectroscopy. We gave ESR spectrum with g-value 2.0048 and line width 0.559mT, coincided with those of the semiquinone radical. 0.1 mg/L HA solution generated the radicals of $1.2{\times}10^{-6}M$, increased with increasing HA concentration. Also, pH and ionic strength effect of the amount of the semiquinone radical generate from HA solution. In this study, we have found that the singlet oxygen affects the semiquinone radicals generation in HA solution.

Self-Sensitized Photooxygenation of Oxodipyrromethene (자체증감작용으로 인한 옥소디피로메텐의 광산소화반응)

  • Yong-Tae Park
    • Journal of the Korean Chemical Society
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    • v.24 no.2
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    • pp.146-149
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    • 1980
  • Oxodipyrromethene was degraded by a self-photosensitized reaction, similar to the degradation of bilirubin by other investigators. Photodegradation of oxodipyrromethene was faster in methanol-d4, in which the life time of singlet oxygen is longer, than in methanol. It was slower in a solvent which contained a singlet oxygen quencher. Moreover, the products from sensitized and unsensitized reactions are same.

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Decreased Stability of Bisphenol A by Photosensitization (감광제 광산화에 의한 Bisphenol A 안정성 감소)

  • Park, Chan-Uk;Lee, Jae-Hwan
    • Korean Journal of Food Science and Technology
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    • v.42 no.3
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    • pp.277-280
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    • 2010
  • Bisphenol A (BPA) is an endocrine disruptor frequently used in food containers, including epoxy resin and polycarbonates. BPA concentrations were monitored by high performance liquid chromatography (HPLC) under photosensitization of riboflavin (RF), methylene blue (MB), rose bengal (RB), or titanium dioxide ($TiO_2$) and the involvement of singlet oxygen was determined using sodium azide ($NaN_3$). The stability of BPA decreased significantly in the order of RF, RB, and MB photosensitization (p<0.05), while the concentration of BPA in samples with $TiO_2$ was not significantly different from that of control samples without photosensitizers under light (p>0.05). The stability of BPA decreased in an MB concentration-dependent manner and increased as the concentration of added $NaN_3$ increased, implying that singlet oxygen was involved in the photodegradation of BPA during MB photosensitization. The results of this study may help control the BPA content in foods or the environments using photosensitized oxidation and visible light irradiation.

Relaxation Process of the Photoexcited State and Singlet Oxygen Generating Activity of Water-soluble meso-Phenanthrylporphyrin in a DNA Microenvironment

  • Hirakawa, Kazutaka;Ito, Yusuke;Yamada, Takashi;Okazaki, Shigetoshi
    • Rapid Communication in Photoscience
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    • v.3 no.4
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    • pp.81-84
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    • 2014
  • To examine the microenvironmental effect of DNA on the photosensitized reaction, the electron-donor-connecting porphyrin, meso-(9-phenanthryl)-tris(N-methyl-p-pyridinio) porphyrin (Phen-TMPyP), was synthesized. Phen-TMPyP can bind to oligonucleotides with two binding modes, depending on the DNA concentration. The fluorescence lifetime measurement of Phen-TMPyP shows a shorter component than that of the reference porphyrin without the phenanthryl moiety. However, the observed value is much longer than those of previously reported similar types of electron-donor-connecting porphyrins, suggesting that electron-transfer quenching by the phenanthryl moiety is not sufficient. The fluorescence quantum yield of Phen-TMPyP ($5{\mu}M$) decreased with an increase in DNA concentration of up to $5{\mu}M$ base pair (bp), possibly due to self-quenching through an aggregation along the DNA strand, increased with an increase in DNA concentration of more than $5{\mu}M$ bp and reached a plateau. The fluorescence quantum yield of Phen-TMPyP with a sufficient concentration of DNA was larger than that of the reference porphyrin. The singlet oxygen ($^1O_2$) generating activity of Phen-TMPyP was confirmed by the near-infrared emission spectrum measurement. The quantum yield of $^1O_2$ generation was decreased by a relatively small concentration of DNA, possibly due to the aggregation of Phen-TMPyP, and recovered with a sufficient concentration of DNA. The recovered quantum yield was rather smaller than that without DNA, indicating the quenching of $^1O_2$ by DNA. These results show that a DNA strand can stabilize the photoexcited state of a photosensitizer and, in a certain case, suppresses the $^1O_2$ generation.