title: Guanosine in a single stranded region of anticodon stem-loop tRNA models is prone to oxidatively generated damage resulting in dehydroguanidinohydantoin and spiroiminodihydantoin lesions.
abstract: Oxidation of RNA hairpin models corresponding to anticodon stem-loop (ASL) of transfer RNA led to RNA damage consisting solely of a unique loop guanine oxidation. Manganese porphyrin/oxone treatment of RNA resulted in dehydroguanidinohydantoin (DGh; major) and/or spiroiminodihydantoin (Sp) lesions. Ribose damage was not observed. This two-electron transfer oxidation reaction allowed the identification of guanine oxidation products for further study of RNA species carrying a unique lesion at a single G to investigate their biological impact.
authors.affiliation: Department of Bioorganic Chemistry, Centre of Molecular and Macromolecular Studies, Polish Academy of Sciences, Sienkiewicza 112, 90-363 Lodz (Poland).
authors.forename: Agnieszka
authors.initials: A
authors.lastname: Tomaszewska-Antczak
authors.forename: Piotr
authors.initials: P
authors.lastname: Guga
authors.forename: Barbara
authors.initials: B
authors.lastname: Nawrot
authors.forename: Geneviève
authors.initials: G
authors.lastname: Pratviel
mesh_terms: D000926:Anticodon; D006146:Guanidines / Q000737:chemistry* / Q000633:toxicity; D006151:Guanosine / Q000031:analogs & derivatives* / Q000737:chemistry* / Q000633:toxicity; D006827:Hydantoins / Q000737:chemistry* / Q000633:toxicity; D008956:Models, Chemical; D010084:Oxidation-Reduction; D012343:RNA, Transfer / Q000737:chemistry* / Q000378:metabolism; D012266:Ribose / Q000633:toxicity; D013141:Spiro Compounds / Q000737:chemistry* / Q000633:toxicity
chemical_list: D000926:Anticodon; D006146:Guanidines; D006827:Hydantoins; D013141:Spiro Compounds; C475501:dehydroguanidinohydantoin; C408822:spiroiminodihydantoin; D006151:Guanosine; D012266:Ribose; D012343:RNA, Transfer
keywords: RNA; nucleobases; oxidative stress; oxone; porphyrin