{"@context":{"@vocab":"https://cir.nii.ac.jp/schema/1.0/","rdfs":"http://www.w3.org/2000/01/rdf-schema#","dc":"http://purl.org/dc/elements/1.1/","dcterms":"http://purl.org/dc/terms/","foaf":"http://xmlns.com/foaf/0.1/","prism":"http://prismstandard.org/namespaces/basic/2.0/","cinii":"http://ci.nii.ac.jp/ns/1.0/","datacite":"https://schema.datacite.org/meta/kernel-4/","ndl":"http://ndl.go.jp/dcndl/terms/","jpcoar":"https://github.com/JPCOAR/schema/blob/master/2.0/"},"@id":"https://cir.nii.ac.jp/crid/1363388843280855680.json","@type":"Article","productIdentifier":[{"identifier":{"@type":"DOI","@value":"10.1021/bi9620161"}},{"identifier":{"@type":"URI","@value":"https://pubs.acs.org/doi/pdf/10.1021/bi9620161"}},{"identifier":{"@type":"PMID","@value":"9048561"}},{"identifier":{"@type":"NAID","@value":"30010852646"}}],"dc:title":[{"@value":"Photoinduced Hydroxylation of Deoxyguanosine in DNA by Pterins:  Sequence Specificity and Mechanism"}],"description":[{"notation":[{"@value":"Pterin-sensitized DNA photodamage has been characterized by a DNA sequencing technique. Exposure of double-stranded DNA to 365-nm light in the presence of pterin, 6-carboxypterin, biopterin, neopterin, and folic acid produced sequence-specific DNA lesions, whereas photoinduced DNA lesions were not observed in the presence of xanthopterin or isoxanthopterin. The DNA photodamage induced by these pterin derivatives occurred specifically at the guanine located 5' to guanine. High-pressure liquid chromatography (HPLC) analysis revealed that the pterin-sensitized DNA photodamage was predominantly due to the formation of 7,8-dihydro-8-oxo-2'-deoxyguanosine (8-oxo-dG). The DNA photodamage with pterin was not enhanced in D2O, suggesting that lO2 is not the main active species. Electron spin resonance (ESR) spin destruction experiments demonstrated that the photoexcited pterins reacted specifically with dGMP to produce pterin anion radicals. In addition, the reactivities of the photoexcited pterin derivatives with dGMP were found to correlate well with their efficiencies of DNA photodamage induction. These results indicate that the photoexcited pterins specifically oxidize deoxyguanosine in DNA to produce 8-oxo-dG through an electron transfer reaction. With denatured single-stranded DNA, the extent of pterin-sensitized photodamage was decreased and the damage occurred at most guanine residues without specificity for those located 5' to guanine. The mechanism of pterin-induced sequence-specific guanine photodamage could be explained on the basis of a recent theoretical study [Sugiyama. H.,Saito, I. (1996) J. Am. Chem. Soc. 118, 7063-7068] concerning the ionization potentials of stacked dinucleotide base pairs. Sepiapterin, a model compound for the dihydropterins, induced similar sequence-specific photolesions in double-stranded DNA. However, DNA photodamage by sepiapterin was more extensive in the presence of Cu(II), and the sites of the photolesions were different from those induced in the absence of Cu(II). These data may provide a basis for the elucidation of the molecular mechanism of solar UV carcinogenesis."}]}],"creator":[{"@id":"https://cir.nii.ac.jp/crid/1383388843280855681","@type":"Researcher","foaf:name":[{"@value":"Kimiko Ito"}],"jpcoar:affiliationName":[{"@value":"Department of Public Health, Graduate School of Medicine, Kyoto University, Kyoto 606, Japan, and Department of Hygiene, Mie University School of Medicine, Tsu, Mie 514, Japan"}]},{"@id":"https://cir.nii.ac.jp/crid/1383388843280855680","@type":"Researcher","foaf:name":[{"@value":"Shosuke Kawanishi"}],"jpcoar:affiliationName":[{"@value":"Department of Public Health, Graduate School of Medicine, Kyoto University, Kyoto 606, Japan, and Department of Hygiene, Mie University School of Medicine, Tsu, Mie 514, Japan"}]}],"publication":{"publicationIdentifier":[{"@type":"PISSN","@value":"00062960"},{"@type":"EISSN","@value":"15204995"}],"prism:publicationName":[{"@value":"Biochemistry"}],"dc:publisher":[{"@value":"American Chemical Society (ACS)"}],"prism:publicationDate":"1997-02-01","prism:volume":"36","prism:number":"7","prism:startingPage":"1774","prism:endingPage":"1781"},"reviewed":"false","url":[{"@id":"https://pubs.acs.org/doi/pdf/10.1021/bi9620161"}],"createdAt":"2002-07-26","modifiedAt":"2021-10-12","foaf:topic":[{"@id":"https://cir.nii.ac.jp/all?q=Base%20Sequence","dc:title":"Base Sequence"},{"@id":"https://cir.nii.ac.jp/all?q=Photochemistry","dc:title":"Photochemistry"},{"@id":"https://cir.nii.ac.jp/all?q=Ultraviolet%20Rays","dc:title":"Ultraviolet Rays"},{"@id":"https://cir.nii.ac.jp/all?q=Pteridines","dc:title":"Pteridines"},{"@id":"https://cir.nii.ac.jp/all?q=Distamycins","dc:title":"Distamycins"},{"@id":"https://cir.nii.ac.jp/all?q=Magnesium%20Chloride","dc:title":"Magnesium Chloride"},{"@id":"https://cir.nii.ac.jp/all?q=Deoxyguanine%20Nucleotides","dc:title":"Deoxyguanine Nucleotides"},{"@id":"https://cir.nii.ac.jp/all?q=Deoxyguanosine","dc:title":"Deoxyguanosine"},{"@id":"https://cir.nii.ac.jp/all?q=Hydroxylation","dc:title":"Hydroxylation"},{"@id":"https://cir.nii.ac.jp/all?q=Pterins","dc:title":"Pterins"},{"@id":"https://cir.nii.ac.jp/all?q=Spectrometry,%20Fluorescence","dc:title":"Spectrometry, Fluorescence"},{"@id":"https://cir.nii.ac.jp/all?q=Spermine","dc:title":"Spermine"},{"@id":"https://cir.nii.ac.jp/all?q=DNA%20Damage","dc:title":"DNA Damage"}],"relatedProduct":[{"@id":"https://cir.nii.ac.jp/crid/1050282677915828992","@type":"Article","resourceType":"学術雑誌論文(journal article)","relationType":["isCitedBy"],"jpcoar:relatedTitle":[{"@language":"ja","@value":"DNA損傷における塩基配列特異性とその意義"},{"@language":"ja-Kana","@value":"DNA ソンショウ ニ オケル エンキ ハイレツ トクイセイ ト ソノ イギ"},{"@language":"en","@value":"Role of sequence-specificity of DNA damage"}]},{"@id":"https://cir.nii.ac.jp/crid/1360004232017008896","@type":"Article","resourceType":"学術雑誌論文(journal article)","relationType":["isReferencedBy"],"jpcoar:relatedTitle":[{"@value":"Calculation of the HOMO localization of Tetrahymena and Oxytricha telomeric quadruplex DNA"}]},{"@id":"https://cir.nii.ac.jp/crid/1360285708556938880","@type":"Article","resourceType":"学術雑誌論文(journal article)","relationType":["isReferencedBy"],"jpcoar:relatedTitle":[{"@value":"Product analysis of photooxidation in isolated quadruplex DNA; 8-oxo-7,8-dihydroguanine and its oxidation product at 3′-G are formed instead of 2,5-diamino-4H-imidazol-4-one"}]},{"@id":"https://cir.nii.ac.jp/crid/1360567189429489280","@type":"Article","resourceType":"学術雑誌論文(journal article)","relationType":["isReferencedBy"],"jpcoar:relatedTitle":[{"@value":"Analysis of Guanine Oxidation Products in Double-Stranded DNA and Proposed Guanine Oxidation Pathways in  Single-Stranded, Double-Stranded or Quadruplex DNA"}]},{"@id":"https://cir.nii.ac.jp/crid/1390001204671661568","@type":"Article","relationType":["isReferencedBy"],"jpcoar:relatedTitle":[{"@language":"en","@value":"8-Oxo-7,8-dihydro-2'-deoxyguanosine Forms a Relatively Unstable Tetrameric Structure Compared with 2'-Deoxyguanosine"}]},{"@id":"https://cir.nii.ac.jp/crid/1573387449941374720","@type":"Article","relationType":["isCitedBy"],"jpcoar:relatedTitle":[{"@language":"ja","@value":"環境因子による遺伝子損傷および発癌性予知に関する研究"},{"@language":"en","@value":"Analysis of Damage to Human Genes by Environmental Factors for Evaluation of Their Carcinogenic Potential"}]},{"@id":"https://cir.nii.ac.jp/crid/2051714791980362880","@type":"Article","resourceType":"学術雑誌論文(journal article)","relationType":["isReferencedBy"],"jpcoar:relatedTitle":[{"@value":"Generation, repair and replication of guanine oxidation products"}]}],"dataSourceIdentifier":[{"@type":"CROSSREF","@value":"10.1021/bi9620161"},{"@type":"CIA","@value":"30010852646"},{"@type":"OPENAIRE","@value":"doi_dedup___::4ab6531906956eda30f93dfa3a467b31"},{"@type":"CROSSREF","@value":"10.1039/c3ra44290j_references_DOI_SQjGg179lJJvZx6qCHbrs1XZ0cZ"},{"@type":"CROSSREF","@value":"10.3164/jcbn.08-157_references_DOI_SQjGg179lJJvZx6qCHbrs1XZ0cZ"},{"@type":"CROSSREF","@value":"10.1016/j.bmcl.2015.05.050_references_DOI_SQjGg179lJJvZx6qCHbrs1XZ0cZ"},{"@type":"CROSSREF","@value":"10.3390/biom4010140_references_DOI_SQjGg179lJJvZx6qCHbrs1XZ0cZ"},{"@type":"CROSSREF","@value":"10.1186/s41021-017-0081-0_references_DOI_SQjGg179lJJvZx6qCHbrs1XZ0cZ"}]}