title: A novel quinone derived from 5-hydroxyindoleacetic acid reacts with protein: Possible participation of oxidation of serotonin and its metabolite in the development of atherosclerosis.
abstract: The modification of 5-hydroxyindoleacetic acid (5HIAA) by myeloperoxidase with a xanthine oxidase system was investigated by chromatographic analyses. Two major products were identified as a dimer and quinone (indoleacetate dione) of 5HIAA. The formation of a quinone moiety was also confirmed by chemical trapping with o-phenylenediamine. In the presence of N-acetyl-cysteine (NAC), a quinone-NAC adduct was formed. When glyceraldehyde 3-phosphate dehydrogenase was exposed to the myeloperoxidase system with 5HIAA, quinone adducts were formed on the protein molecule. A monoclonal antibody was prepared using a quinone-modified protein as an immunogen to immunochemically detect the quinone on a protein. The established antibody recognized the quinone-NAC adduct, quinone-modified poly-L-lysine, and quinone-modified low-density lipoprotein. Quinone-modified proteins in human atherosclerotic lesions were immunohistochemically observed using the established antibody to the quinone and also a monoclonal antibody to tryptamine dione-modified protein, suggesting an occurrence of in vivo oxidation of serotonin and 5HIAA, accompanied by covalent adduction to biomolecules.
authors.affiliation: Graduate School of Human Science and Environment, University of Hyogo, Himeji, Hyogo, Japan. Electronic address: yojikato@shse.u-hyogo.ac.jp.
authors.forename: Yoji
authors.initials: Y
authors.lastname: Kato
authors.affiliation: Graduate School of Human Science and Environment, University of Hyogo, Himeji, Hyogo, Japan.
authors.forename: Kota
authors.initials: K
authors.lastname: Oki
authors.affiliation: Graduate School of Human Science and Environment, University of Hyogo, Himeji, Hyogo, Japan.
authors.forename: Naoko
authors.initials: N
authors.lastname: Suga
authors.affiliation: Graduate School of Human Science and Environment, University of Hyogo, Himeji, Hyogo, Japan.
authors.forename: Shigeki
authors.initials: S
authors.lastname: Ono
authors.affiliation: Graduate School of Human Science and Environment, University of Hyogo, Himeji, Hyogo, Japan.
authors.forename: Akari
authors.initials: A
authors.lastname: Ishisaka
authors.affiliation: Department of Molecular and Cellular Biology, Nagoya City University Graduate School of Medical Sciences, Nagoya, Aichi, Japan.
authors.forename: Yoko
authors.initials: Y
authors.lastname: Miura
authors.affiliation: Department of Molecular and Cellular Biology, Nagoya City University Graduate School of Medical Sciences, Nagoya, Aichi, Japan.
authors.forename: Satoshi
authors.initials: S
authors.lastname: Kanazawa
authors.affiliation: Division of Nutrition & Health, School and Graduate School of Life Studies, Sugiyama Jogakuen University, Nagoya, Aichi, Japan.
authors.forename: Michitaka
authors.initials: M
authors.lastname: Naito
authors.affiliation: Graduate School of Human Science and Environment, University of Hyogo, Himeji, Hyogo, Japan.
authors.forename: Noritoshi
authors.initials: N
authors.lastname: Kitamoto
authors.affiliation: Centre for Free Radical Research, Department of Pathology, University of Otago, Christchurch, New Zealand.
authors.forename: Anthony J
authors.initials: AJ
authors.lastname: Kettle
mesh_terms: D000111:Acetylcysteine / Q000737:chemistry; D000368:Aged; D000911:Antibodies, Monoclonal / Q000096:biosynthesis / Q000737:chemistry / Q000302:isolation & purification; D001011:Aorta / Q000737:chemistry / Q000378:metabolism / Q000473:pathology; D050197:Atherosclerosis / Q000097:blood* / Q000473:pathology; D005987:Glyceraldehyde-3-Phosphate Dehydrogenases / Q000737:chemistry / Q000378:metabolism; D006801:Humans; D006897:Hydroxyindoleacetic Acid / Q000737:chemistry* / Q000378:metabolism; D007150:Immunohistochemistry; D008297:Male; D008867:Microtomy; D009195:Peroxidase / Q000737:chemistry / Q000378:metabolism; D010655:Phenylenediamines; D011809:Quinones / Q000138:chemical synthesis* / Q000378:metabolism; D012701:Serotonin / Q000737:chemistry* / Q000378:metabolism; D014969:Xanthine Oxidase / Q000737:chemistry / Q000378:metabolism
chemical_list: D000911:Antibodies, Monoclonal; D010655:Phenylenediamines; D011809:Quinones; D012701:Serotonin; D006897:Hydroxyindoleacetic Acid; C034193:1,2-diaminobenzene; D009195:Peroxidase; D014969:Xanthine Oxidase; D005987:Glyceraldehyde-3-Phosphate Dehydrogenases; D000111:Acetylcysteine
keywords: 5-Hydroxyindoleacetic acid; Antibody; Atherosclerosis; Quinone; Serotonin