Formation of a nonaoxirane from A2E, a lipofuscin fluorophore related to macular degeneration, and evidence of singlet oxygen involvement

Shimon Ben-Shabat; Yasuhiro Itagaki; Steffen Jockusch; Janet R. Sparrow; Nicholas J. Turro; Koji Nakanishi

doi:10.1002/1521-3773(20020301)41:5<814::AID-ANIE814>3.0.CO;2-2

Formation of a nonaoxirane from A2E, a lipofuscin fluorophore related to macular degeneration, and evidence of singlet oxygen involvement

Shimon Ben-Shabat, Yasuhiro Itagaki, Steffen Jockusch, Janet R. Sparrow, Nicholas J. Turro, Koji Nakanishi

Research output: Contribution to journal › Article › peer-review

193 Scopus citations

Abstract

Nine epoxide rings are formed sequentially when A2E is irradiated with blue light in the presence of oxygen [Eq. (1)]. Mechanistically, A2E generates singlet oxygen and reacts with it to give the polyoxiranes. An understanding of the reaction of A2E with oxygen is important as blue light induces the apoptotic death of A2E-laden retinal pigment epithelium cells, which are typical of age-related macular degeneration.

Original language	English
Pages (from-to)	814-817
Number of pages	4
Journal	Angewandte Chemie - International Edition
Volume	41
Issue number	5
DOIs	https://doi.org/10.1002/1521-3773(20020301)41:5<814::AID-ANIE814>3.0.CO;2-2
State	Published - 1 Mar 2002
Externally published	Yes

Keywords

Heterocycles
Macular degeneration
Peroxides
Photochemistry
Singlet oxygen

ASJC Scopus subject areas

Catalysis
General Chemistry

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10.1002/1521-3773(20020301)41:5<814::AID-ANIE814>3.0.CO;2-2

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Ben-Shabat, S., Itagaki, Y., Jockusch, S., Sparrow, J. R., Turro, N. J., & Nakanishi, K. (2002). Formation of a nonaoxirane from A2E, a lipofuscin fluorophore related to macular degeneration, and evidence of singlet oxygen involvement. Angewandte Chemie - International Edition, 41(5), 814-817. https://doi.org/10.1002/1521-3773(20020301)41:5<814::AID-ANIE814>3.0.CO;2-2

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abstract = "Nine epoxide rings are formed sequentially when A2E is irradiated with blue light in the presence of oxygen [Eq. (1)]. Mechanistically, A2E generates singlet oxygen and reacts with it to give the polyoxiranes. An understanding of the reaction of A2E with oxygen is important as blue light induces the apoptotic death of A2E-laden retinal pigment epithelium cells, which are typical of age-related macular degeneration.",

keywords = "Heterocycles, Macular degeneration, Peroxides, Photochemistry, Singlet oxygen",

author = "Shimon Ben-Shabat and Yasuhiro Itagaki and Steffen Jockusch and Sparrow, {Janet R.} and Turro, {Nicholas J.} and Koji Nakanishi",

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doi = "10.1002/1521-3773(20020301)41:5<814::AID-ANIE814>3.0.CO;2-2",

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Ben-Shabat, S, Itagaki, Y, Jockusch, S, Sparrow, JR, Turro, NJ & Nakanishi, K 2002, 'Formation of a nonaoxirane from A2E, a lipofuscin fluorophore related to macular degeneration, and evidence of singlet oxygen involvement', Angewandte Chemie - International Edition, vol. 41, no. 5, pp. 814-817. https://doi.org/10.1002/1521-3773(20020301)41:5<814::AID-ANIE814>3.0.CO;2-2

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T1 - Formation of a nonaoxirane from A2E, a lipofuscin fluorophore related to macular degeneration, and evidence of singlet oxygen involvement

AU - Ben-Shabat, Shimon

AU - Itagaki, Yasuhiro

AU - Jockusch, Steffen

AU - Sparrow, Janet R.

AU - Turro, Nicholas J.

AU - Nakanishi, Koji

PY - 2002/3/1

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N2 - Nine epoxide rings are formed sequentially when A2E is irradiated with blue light in the presence of oxygen [Eq. (1)]. Mechanistically, A2E generates singlet oxygen and reacts with it to give the polyoxiranes. An understanding of the reaction of A2E with oxygen is important as blue light induces the apoptotic death of A2E-laden retinal pigment epithelium cells, which are typical of age-related macular degeneration.

AB - Nine epoxide rings are formed sequentially when A2E is irradiated with blue light in the presence of oxygen [Eq. (1)]. Mechanistically, A2E generates singlet oxygen and reacts with it to give the polyoxiranes. An understanding of the reaction of A2E with oxygen is important as blue light induces the apoptotic death of A2E-laden retinal pigment epithelium cells, which are typical of age-related macular degeneration.

KW - Heterocycles

KW - Macular degeneration

KW - Peroxides

KW - Photochemistry

KW - Singlet oxygen

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JO - Angewandte Chemie - International Edition

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Formation of a nonaoxirane from A2E, a lipofuscin fluorophore related to macular degeneration, and evidence of singlet oxygen involvement

Abstract

Keywords

ASJC Scopus subject areas

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