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Title: Photo-excitation of carotenoids causes cytotoxicity via singlet oxygen production

Abstract

Highlights: Black-Right-Pointing-Pointer Some photo-excited carotenoids have photosensitizing ability. Black-Right-Pointing-Pointer They are able to produce ROS. Black-Right-Pointing-Pointer Photo-excited fucoxanthin can produce singlet oxygen through energy transfer. -- Abstract: Carotenoids, natural pigments widely distributed in algae and plants, have a conjugated double bond system. Their excitation energies are correlated with conjugation length. We hypothesized that carotenoids whose energy states are above the singlet excited state of oxygen (singlet oxygen) would possess photosensitizing properties. Here, we demonstrated that human skin melanoma (A375) cells are damaged through the photo-excitation of several carotenoids (neoxanthin, fucoxanthin and siphonaxanthin). In contrast, photo-excitation of carotenoids that possess energy states below that of singlet oxygen, such as {beta}-carotene, lutein, loroxanthin and violaxanthin, did not enhance cell death. Production of reactive oxygen species (ROS) by photo-excited fucoxanthin or neoxanthin was confirmed using a reporter assay for ROS production with HeLa Hyper cells, which express a fluorescent indicator protein for intracellular ROS. Fucoxanthin and neoxanthin also showed high cellular penetration and retention. Electron spin resonance spectra using 2,2,6,6-tetramethil-4-piperidone as a singlet oxygen trapping agent demonstrated that singlet oxygen was produced via energy transfer from photo-excited fucoxanthin to oxygen molecules. These results suggest that carotenoids such as fucoxanthin, which are capable ofmore » singlet oxygen production through photo-excitation and show good penetration and retention in target cells, are useful as photosensitizers in photodynamic therapy for skin disease.« less

Authors:
 [1];  [2];  [3];  [2];  [4];  [2];  [3];  [2];  [5];  [3];  [2]
  1. Research Center for Radiation Emergency Medicine, National Institute of Radiological Science, Chiba 263-8555 (Japan)
  2. (Japan)
  3. Molecular Imaging Center, National Institute of Radiological Science, Chiba 263-8555 (Japan)
  4. Biomedical Imaging Research Center, University of Fukui, Eiheiji, Fukui 910-1193 (Japan)
  5. Department of Biology, Nippon Medical School, Kawasaki, Kanagawa 211-0063 (Japan)
Publication Date:
OSTI Identifier:
22207647
Resource Type:
Journal Article
Resource Relation:
Journal Name: Biochemical and Biophysical Research Communications; Journal Volume: 417; Journal Issue: 1; Other Information: Copyright (c) 2011 Elsevier Science B.V., Amsterdam, The Netherlands, All rights reserved.; Country of input: International Atomic Energy Agency (IAEA)
Country of Publication:
United States
Language:
English
Subject:
60 APPLIED LIFE SCIENCES; ALGAE; APOPTOSIS; CAROTENOIDS; ELECTRON SPIN RESONANCE; ENERGY TRANSFER; EXCITATION; EXCITED STATES; FLUORESCENCE; MELANOMAS; OXYGEN; PROTEINS; RETENTION; SKIN; SKIN DISEASES; TOXICITY

Citation Formats

Yoshii, Hiroshi, E-mail: yoshii@nirs.go.jp, Faculty of Medical Sciences, University of Fukui, Eiheiji, Fukui 910-1193, Yoshii, Yukie, E-mail: yukiey@nirs.go.jp, Biomedical Imaging Research Center, University of Fukui, Eiheiji, Fukui 910-1193, Asai, Tatsuya, Faculty of Engineering, University of Fukui, Fukui 910-8507, Furukawa, Takako, Biomedical Imaging Research Center, University of Fukui, Eiheiji, Fukui 910-1193, Takaichi, Shinichi, Fujibayashi, Yasuhisa, and Biomedical Imaging Research Center, University of Fukui, Eiheiji, Fukui 910-1193. Photo-excitation of carotenoids causes cytotoxicity via singlet oxygen production. United States: N. p., 2012. Web. doi:10.1016/J.BBRC.2011.12.024.
Yoshii, Hiroshi, E-mail: yoshii@nirs.go.jp, Faculty of Medical Sciences, University of Fukui, Eiheiji, Fukui 910-1193, Yoshii, Yukie, E-mail: yukiey@nirs.go.jp, Biomedical Imaging Research Center, University of Fukui, Eiheiji, Fukui 910-1193, Asai, Tatsuya, Faculty of Engineering, University of Fukui, Fukui 910-8507, Furukawa, Takako, Biomedical Imaging Research Center, University of Fukui, Eiheiji, Fukui 910-1193, Takaichi, Shinichi, Fujibayashi, Yasuhisa, & Biomedical Imaging Research Center, University of Fukui, Eiheiji, Fukui 910-1193. Photo-excitation of carotenoids causes cytotoxicity via singlet oxygen production. United States. doi:10.1016/J.BBRC.2011.12.024.
Yoshii, Hiroshi, E-mail: yoshii@nirs.go.jp, Faculty of Medical Sciences, University of Fukui, Eiheiji, Fukui 910-1193, Yoshii, Yukie, E-mail: yukiey@nirs.go.jp, Biomedical Imaging Research Center, University of Fukui, Eiheiji, Fukui 910-1193, Asai, Tatsuya, Faculty of Engineering, University of Fukui, Fukui 910-8507, Furukawa, Takako, Biomedical Imaging Research Center, University of Fukui, Eiheiji, Fukui 910-1193, Takaichi, Shinichi, Fujibayashi, Yasuhisa, and Biomedical Imaging Research Center, University of Fukui, Eiheiji, Fukui 910-1193. Fri . "Photo-excitation of carotenoids causes cytotoxicity via singlet oxygen production". United States. doi:10.1016/J.BBRC.2011.12.024.
@article{osti_22207647,
title = {Photo-excitation of carotenoids causes cytotoxicity via singlet oxygen production},
author = {Yoshii, Hiroshi, E-mail: yoshii@nirs.go.jp and Faculty of Medical Sciences, University of Fukui, Eiheiji, Fukui 910-1193 and Yoshii, Yukie, E-mail: yukiey@nirs.go.jp and Biomedical Imaging Research Center, University of Fukui, Eiheiji, Fukui 910-1193 and Asai, Tatsuya and Faculty of Engineering, University of Fukui, Fukui 910-8507 and Furukawa, Takako and Biomedical Imaging Research Center, University of Fukui, Eiheiji, Fukui 910-1193 and Takaichi, Shinichi and Fujibayashi, Yasuhisa and Biomedical Imaging Research Center, University of Fukui, Eiheiji, Fukui 910-1193},
abstractNote = {Highlights: Black-Right-Pointing-Pointer Some photo-excited carotenoids have photosensitizing ability. Black-Right-Pointing-Pointer They are able to produce ROS. Black-Right-Pointing-Pointer Photo-excited fucoxanthin can produce singlet oxygen through energy transfer. -- Abstract: Carotenoids, natural pigments widely distributed in algae and plants, have a conjugated double bond system. Their excitation energies are correlated with conjugation length. We hypothesized that carotenoids whose energy states are above the singlet excited state of oxygen (singlet oxygen) would possess photosensitizing properties. Here, we demonstrated that human skin melanoma (A375) cells are damaged through the photo-excitation of several carotenoids (neoxanthin, fucoxanthin and siphonaxanthin). In contrast, photo-excitation of carotenoids that possess energy states below that of singlet oxygen, such as {beta}-carotene, lutein, loroxanthin and violaxanthin, did not enhance cell death. Production of reactive oxygen species (ROS) by photo-excited fucoxanthin or neoxanthin was confirmed using a reporter assay for ROS production with HeLa Hyper cells, which express a fluorescent indicator protein for intracellular ROS. Fucoxanthin and neoxanthin also showed high cellular penetration and retention. Electron spin resonance spectra using 2,2,6,6-tetramethil-4-piperidone as a singlet oxygen trapping agent demonstrated that singlet oxygen was produced via energy transfer from photo-excited fucoxanthin to oxygen molecules. These results suggest that carotenoids such as fucoxanthin, which are capable of singlet oxygen production through photo-excitation and show good penetration and retention in target cells, are useful as photosensitizers in photodynamic therapy for skin disease.},
doi = {10.1016/J.BBRC.2011.12.024},
journal = {Biochemical and Biophysical Research Communications},
number = 1,
volume = 417,
place = {United States},
year = {Fri Jan 06 00:00:00 EST 2012},
month = {Fri Jan 06 00:00:00 EST 2012}
}
  • The quantum yield of sensitized photoperoxidation of 2,5-dimethylfuran in oxygen-saturated n-hexane solution has been measured. The sensitizers used were 9-methylanthracene, 9-phenylanthracene, 9,10-dimethylanthracene, 9,10-diphenylanthracene, perylene, pyrene, 1,6-diphenylhexatriene, and rubrene, and the sensitized oxidation quantum yields were found to be 0.97, 1.09, 1.14, 1.20, 1.27, 0.79, 1.02, and 1.20, respectively. The experimental results indicate that singlet molecular oxygen can be produced directly from the oxygen quenching of the lowest excited singlet state of many aromatic molecules, i.e., the process S/sub 1/ + /sup 3/O/sub 2/ ..-->.. T/sub 1/ + /sup 1/O/sub 2/ is not negligible when compared to S/sub 1/ + /supmore » 3/O/sub 2/ ..-->.. T/sub 1/ + /sup 3/O/sub 2/. This shows that the former process must also be taken into consideration in the general treatment of oxygen quenching of the fluorescence from aromatic molecules.« less
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