title: Nitration and chlorination of folic acid by peroxynitrite and hypochlorous acid, and the selective binding of 10-nitro-folate to folate receptor beta.
abstract: The aim of this work was to characterize folates modified by ONOO(-) and HOCl and to evaluate the binding capacity of folates modified by ONOO(-) to folate receptor alpha and beta. For the modification of folate by ONOO(-), folic acid was reacted with the combination of PMA activated PMN and PAPA NONOate or chemically synthesized ONOO(-). For the modification of folate by HOCl, folic acid was reacted with the combination of MPO and H(2)O(2) or NaOCl. The structures of products were determined by 1H-NMR and MALDI-TOF mass. Nitrated folate species were identified as 10-nitro-folate and 12-nitro-folate, and chlorinated folate was identified as 12-chloro-folate. The 10-nitro-folate showed the selective binding to FR-beta, compared to folic acid.
authors.affiliation: Department of Immunology and Medical Zoology, School of Medicine, Kagoshima University, 8-35-1 Sakuragaoka, 890-8520, Kagoshima, Japan.
authors.forename: Motoyuki
authors.initials: M
authors.lastname: Nakamura
authors.forename: Ryusaku
authors.initials: R
authors.lastname: Nagayoshi
authors.forename: Kosei
authors.initials: K
authors.lastname: Ijiri
authors.forename: Noriko
authors.initials: N
authors.lastname: Nakashima-Matsushita
authors.forename: Toru
authors.initials: T
authors.lastname: Takeuchi
authors.forename: Takami
authors.initials: T
authors.lastname: Matsuyama
mesh_terms: D002352:Carrier Proteins / Q000378:metabolism*; D002460:Cell Line; D002713:Chlorine / Q000378:metabolism*; D002851:Chromatography, High Pressure Liquid; D018076:DNA, Complementary / Q000378:metabolism; D005434:Flow Cytometry; D058973:Folate Receptors, GPI-Anchored; D005492:Folic Acid / Q000031:analogs & derivatives / Q000737:chemistry* / Q000378:metabolism* / Q000494:pharmacology; D006801:Humans; D006997:Hypochlorous Acid / Q000494:pharmacology*; D009682:Magnetic Resonance Spectroscopy; D008956:Models, Chemical; D009504:Neutrophils / Q000378:metabolism; D009584:Nitrogen / Q000378:metabolism*; D016877:Oxidants / Q000737:chemistry; D030421:Peroxynitrous Acid / Q000494:pharmacology*; D011485:Protein Binding; D011956:Receptors, Cell Surface; D019032:Spectrometry, Mass, Matrix-Assisted Laser Desorption-Ionization; D013755:Tetradecanoylphorbol Acetate / Q000494:pharmacology; D013997:Time Factors; D014162:Transfection; D014466:Ultraviolet Rays
chemical_list: C468779:10-nitrofolic acid; C468780:12-nitrofolic acid; D002352:Carrier Proteins; D018076:DNA, Complementary; D058973:Folate Receptors, GPI-Anchored; D016877:Oxidants; D011956:Receptors, Cell Surface; D030421:Peroxynitrous Acid; D002713:Chlorine; D006997:Hypochlorous Acid; D005492:Folic Acid; D009584:Nitrogen; D013755:Tetradecanoylphorbol Acetate