title: 8-Oxo-7,8-dihydroadenine and 8-Oxo-7,8-dihydroadenosine-Chemistry, Structure, and Function in RNA and Their Presence in Natural Products and Potential Drug Derivatives.
abstract: A description and history of the role that 8-oxo-7,8-dihydroadenine (8-oxoAde) and 8-oxo-7,8-dihydroadenosine (8-oxoA) have in various fields has been compiled. This Review focusses on 1) the formation of this oxidatively generated modification in RNA, its interactions with other biopolymers, and its potential role in the development/progression of disease; 2) the independent synthesis and incorporation of this modified nucleoside into oligonucleotides of RNA to display the progress that has been made in establishing its behavior in biologically relevant systems; 3) reported synthetic routes, which date back to 1890, along with the progress that has been made in the total synthesis of the nucleobase, nucleoside, and their corresponding derivatives; and 4) the isolation, total synthesis, and biological activity of natural products containing these moieties as the backbone. The current state of research regarding this oxidatively generated lesion as well as its importance in the context of RNA, natural products, and potential as drug derivatives is illustrated using all available examples reported to date.
authors.affiliation: Department of Chemistry, University of Colorado Denver, Science Building, 1151 Arapahoe St., Denver, CO, 80204, USA.
authors.forename: Yu Jung
authors.initials: YJ
authors.lastname: Choi
authors.affiliation: Department of Chemistry, University of Colorado Denver, Science Building, 1151 Arapahoe St., Denver, CO, 80204, USA.
authors.forename: Stephanie J
authors.initials: SJ
authors.lastname: Chang
authors.affiliation: Department of Chemistry, University of Colorado Denver, Science Building, 1151 Arapahoe St., Denver, CO, 80204, USA.
authors.forename: Krzysztof S
authors.initials: KS
authors.lastname: Gibala
authors.affiliation: Department of Chemistry, University of Colorado Denver, Science Building, 1151 Arapahoe St., Denver, CO, 80204, USA.
authors.forename: Marino J E
authors.identifier: http://orcid.org/0000-0001-5631-2722
authors.initials: MJE
authors.lastname: Resendiz
mesh_terms: D000225:Adenine / Q000031:analogs & derivatives* / Q000138:chemical synthesis / Q000737:chemistry; D000241:Adenosine / Q000031:analogs & derivatives* / Q000138:chemical synthesis / Q000737:chemistry; D001688:Biological Products / Q000138:chemical synthesis / Q000737:chemistry*; D010084:Oxidation-Reduction; D011685:Purine Nucleotides / Q000737:chemistry; D012313:RNA / Q000737:chemistry*; D013053:Spectrophotometry
chemical_list: C000626543:8-oxo-7,8-dihydroadenine; C000626544:8-oxo-7,8-dihydroadenosine; D001688:Biological Products; D011685:Purine Nucleotides; C068885:phosmidosine; D012313:RNA; D000225:Adenine; D000241:Adenosine
keywords: 8-oxoA drug derivatives; RNA function; natural products; oxidatively damaged RNA