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doi-10.1016/j.dyepig.2004.06.023
2005-4-7-T23:29:40Z
0143-7208
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SRV : ID : article[1]/artid[1] type=pii
10.1016/j.dyepig.2004.06.023
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doi-10.1016/j.dyepig.2004.06.023
OXM02230
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SCISERVER
eng
ISO639-2
New long-wavelength ethanolamino-substituted hypocrellin: photodynamic activity and toxicity to MGC803 cancer cell
Elsevier Science
January, 2006
1-10
68
1
1-10
<p>To improve hydrophilicity and photoactivity of the new type of therapeutic agent, hypocrellin, a novel long-wavelength ethanolamino-substituted hypocrellin B (EAHB) was synthesized and its molecular structure was characterized by IR, NMR, MS, and UV–vis spectrometers, and EAHB had strong absorption at the phototherapeutic window (600–900nm). Illumination of deoxygenated DMSO solution containing EAHB generated a strong electron paramagnetic resonance (EPR) signal, which was assigned to the semiquinone anion radical of EAHB (EAHB<sup>−</sup>). Absorption measurements displayed that the absorptive bands at 632 and 565nm (shoulder) arose from the semiquinone anion radical (EAHB<sup>−</sup>) and the absorptive bands at 519 and 450nm (shoulder) belonged to hydroquinone (EAHBH<sub>2</sub>), which were formed via the decay of EAHB<sup>−</sup> in water-contained solution. Superoxide anion radical (O<sub>2</sub>
<sup>−</sup>) was produced via electron transfer from EAHB<sup>−</sup> (the precursor) to ground state oxygen. The presence of NADH, a bio-electron donor, significantly enhanced production of EAHB<sup>−</sup> and O<sub>2</sub>
<sup>−</sup>. Singlet oxygen O<sub>2</sub> (<sup>1</sup>Δ<sub>g</sub>) could be produced via energy transfer from triplet EAHB to ground state oxygen molecules. The quantum yield of O<sub>2</sub> (<sup>1</sup>Δ<sub>g</sub>) and the relative quantum yield of O<sub>2</sub>
<sup>−</sup> of EAHB were 0.15 and 0.76, respectively, with the parent compound hypocrellin B (HB) as the standard. It was inferred that Type I pathway was possibly a major photodynamic mechanism of EAHB. The study on photobiological action of EAHB on MGC803 cancer cells revealed that EAHB kept the same good phototoxic ability as HB but reduced 4 times cytotoxicity than HB, and also its photopotentiation factor increased 4-folds.</p>
en
en
Ethanolamino-substituted hypocrellin B
SRV : KEYWORD : article[1]/keyword-group[1]/keyword[1]
EPR spectra
SRV : KEYWORD : article[1]/keyword-group[1]/keyword[2]
Phototoxicity
SRV : KEYWORD : article[1]/keyword-group[1]/keyword[3]
Singlet oxygen
SRV : KEYWORD : article[1]/keyword-group[1]/keyword[4]
Superoxide anion radical
SRV : KEYWORD : article[1]/keyword-group[1]/keyword[5]
fla
SRV : DOCUMENTTYPE : article[1]/@artty
journals
SRV : LOAD : load[1]/data-info[1]/@data-type
Lee, Hua-Yang
Key Laboratory of Photochemistry, Center for Molecular Science, Institute of Chemistry, Chinese Academy of Sciences, Beijing 100080, PR China
author
Zhou, Zhi-Xiang
Institute of Biophysics, Chinese Academy of Sciences, Beijing 100101, PR China
author
Chen, Shen
Key Laboratory of Photochemistry, Center for Molecular Science, Institute of Chemistry, Chinese Academy of Sciences, Beijing 100080, PR China
author
Zhang, Man-Hua
Key Laboratory of Photochemistry, Center for Molecular Science, Institute of Chemistry, Chinese Academy of Sciences, Beijing 100080, PR China
tshen@infoc3.icas.ac.cn
author
Shen, Tao
Key Laboratory of Photochemistry, Center for Molecular Science, Institute of Chemistry, Chinese Academy of Sciences, Beijing 100080, PR China
author
vol. 68, no. 1
January, 2006
Journal
68:1<1
Dyes and Pigments
0143-7208
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EFFECT Loader
OXM02230
Elsevier Science
Dyes and Pigments
0143-7208
January, 2006
New long-wavelength ethanolamino-substituted hypocrellin: photodynamic activity and toxicity to MGC803 cancer cell
Hua-Yang
Lee
a
Key Laboratory of Photochemistry, Center for Molecular Science, Institute of Chemistry, Chinese Academy of Sciences, Beijing 100080, PR China
Zhi-Xiang
Zhou
b
Institute of Biophysics, Chinese Academy of Sciences, Beijing 100101, PR China
Shen
Chen
a
Key Laboratory of Photochemistry, Center for Molecular Science, Institute of Chemistry, Chinese Academy of Sciences, Beijing 100080, PR China
Man-Hua
Zhang
a
Key Laboratory of Photochemistry, Center for Molecular Science, Institute of Chemistry, Chinese Academy of Sciences, Beijing 100080, PR China
tshen@infoc3.icas.ac.cn
Tao
Shen
a
Key Laboratory of Photochemistry, Center for Molecular Science, Institute of Chemistry, Chinese Academy of Sciences, Beijing 100080, PR China
1-10
To improve hydrophilicity and photoactivity of the new type of therapeutic agent, hypocrellin, a novel long-wavelength ethanolamino-substituted hypocrellin B (EAHB) was synthesized and its molecular structure was characterized by IR, NMR, MS, and UV–vis spectrometers, and EAHB had strong absorption at the phototherapeutic window (600–900nm). Illumination of deoxygenated DMSO solution containing EAHB generated a strong electron paramagnetic resonance (EPR) signal, which was assigned to the semiquinone anion radical of EAHB (EAHB−). Absorption measurements displayed that the absorptive bands at 632 and 565nm (shoulder) arose from the semiquinone anion radical (EAHB−) and the absorptive bands at 519 and 450nm (shoulder) belonged to hydroquinone (EAHBH2), which were formed via the decay of EAHB− in water-contained solution. Superoxide anion radical (O2−) was produced via electron transfer from EAHB− (the precursor) to ground state oxygen. The presence of NADH, a bio-electron donor, significantly enhanced production of EAHB− and O2−. Singlet oxygen O2 (1Δg) could be produced via energy transfer from triplet EAHB to ground state oxygen molecules. The quantum yield of O2 (1Δg) and the relative quantum yield of O2− of EAHB were 0.15 and 0.76, respectively, with the parent compound hypocrellin B (HB) as the standard. It was inferred that Type I pathway was possibly a major photodynamic mechanism of EAHB. The study on photobiological action of EAHB on MGC803 cancer cells revealed that EAHB kept the same good phototoxic ability as HB but reduced 4 times cytotoxicity than HB, and also its photopotentiation factor increased 4-folds.
]]>
Ethanolamino-substituted hypocrellin B
EPR spectra
Phototoxicity
Singlet oxygen
Superoxide anion radical
Elsevier Ltd
Article Full-text (PDF)
Article Full-text (RAW)
Article Full-text (XML)
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