{"status":"ok","message-type":"work","message-version":"1.0.0","message":{"indexed":{"date-parts":[[2026,3,20]],"date-time":"2026-03-20T12:18:10Z","timestamp":1774009090664,"version":"3.50.1"},"reference-count":45,"publisher":"Wiley","issue":"13","license":[{"start":{"date-parts":[[2016,6,14]],"date-time":"2016-06-14T00:00:00Z","timestamp":1465862400000},"content-version":"vor","delay-in-days":0,"URL":"http:\/\/onlinelibrary.wiley.com\/termsAndConditions#vor"}],"funder":[{"name":"JSPS","award":["26000007"],"award-info":[{"award-number":["26000007"]}]},{"name":"Advanced Research for Medical Products Mining Program of the National Institute of Biomedical Innovation of the National Institute of Biomedical Innovation","award":["NIBIO, 10-22"],"award-info":[{"award-number":["NIBIO, 10-22"]}]},{"DOI":"10.13039\/501100001700","name":"Ministry of Education, Culture, Sports, Science and Technology, Japan","doi-asserted-by":"crossref","id":[{"id":"10.13039\/501100001700","id-type":"DOI","asserted-by":"crossref"}]}],"content-domain":{"domain":[],"crossmark-restriction":false},"short-container-title":["Chemistry \u0097 An Asian Journal"],"published-print":{"date-parts":[[2016,7,5]]},"abstract":"<jats:title>Abstract<\/jats:title><jats:p>The expansion of CAG repeats in the human genome causes the neurological disorder Huntington's disease. The small\u2010molecule naphthyridine\u2010azaquinolone <jats:bold>NA<\/jats:bold> we reported earlier bound to the CAG\/CAG motif in the hairpin structure of the CAG repeat DNA. In order to investigate and improve <jats:bold>NA<\/jats:bold>\u2010binding to the CAG repeat DNA and RNA, we conducted systematic structure\u2010binding studies of <jats:bold>NA<\/jats:bold> to CAG repeats. Among the five new <jats:bold>NA<\/jats:bold> derivatives we synthesized, surface plasmon resonance (SPR) assay showed that all of the derivatives modified from amide linkages in <jats:bold>NA<\/jats:bold> to a carbamate linkage failed to bind to CAG repeat DNA and RNA. One derivative, <jats:bold>NBzA<\/jats:bold>, modified by incorporating an additional ring to the azaquinolone was found to bind to both d(CAG)<jats:sub>9<\/jats:sub> and r(CAG)<jats:sub>9<\/jats:sub>. <jats:bold>NBzA<\/jats:bold> binding to d(CAG)<jats:sub>9<\/jats:sub> was similar to <jats:bold>NA<\/jats:bold> binding in terms of large changes in the SPR assay and circular dichroism (CD) as well as pairwise binding, as assessed by electron spray ionization time\u2010of\u2010flight (ESI\u2010TOF) mass spectrometry. For the binding to r(CAG)<jats:sub>9<\/jats:sub>, both <jats:bold>NA<\/jats:bold> and <jats:bold>NBzA<\/jats:bold> showed stepwise binding in ESI\u2010TOF MS, and <jats:bold>NBzA<\/jats:bold>\u2010binding to r(CAG)<jats:sub>9<\/jats:sub> induced more extensive conformational change than <jats:bold>NA<\/jats:bold>\u2010binding. The tricyclic system in <jats:bold>NBzA<\/jats:bold> did not show significant effects on the binding, selectivity, and translation, but provides a large chemical space for further modification to gain higher affinity and selectivity. These studies revealed that the linker structure in <jats:bold>NA<\/jats:bold> and <jats:bold>NBzA<\/jats:bold> was suitable for the binding to CAG DNA and RNA, and that the tricyclic benzoazaquinolone did not interfere with the binding.<\/jats:p>","DOI":"10.1002\/asia.201600527","type":"journal-article","created":{"date-parts":[[2016,5,4]],"date-time":"2016-05-04T20:59:52Z","timestamp":1462395592000},"page":"1971-1981","source":"Crossref","is-referenced-by-count":21,"title":["Naphthyridine\u2010Benzoazaquinolone: Evaluation of a Tricyclic System for the Binding to (CAG)<sub><i>n<\/i><\/sub> Repeat DNA and RNA"],"prefix":"10.1002","volume":"11","author":[{"given":"Jinxing","family":"Li","sequence":"first","affiliation":[{"name":"Department of Regulatory Bioorganic Chemistry The Institute of Scientific and Industrial Research Osaka University  8-1 Mihogaoka Ibaraki 567-0047 Japan"}],"role":[{"role":"author","vocabulary":"crossref"}]},{"given":"Akihiro","family":"Sakata","sequence":"additional","affiliation":[{"name":"Department of Regulatory Bioorganic Chemistry The Institute of Scientific and Industrial Research Osaka University  8-1 Mihogaoka Ibaraki 567-0047 Japan"}],"role":[{"role":"author","vocabulary":"crossref"}]},{"given":"Hanping","family":"He","sequence":"additional","affiliation":[{"name":"Chemistry and Chemical Engineering College Hubei University  Road Youyi 368, Wuchang, Wuhan Hubei 430062 China"}],"role":[{"role":"author","vocabulary":"crossref"}]},{"given":"Li\u2010Ping","family":"Bai","sequence":"additional","affiliation":[{"name":"State Key Laboratory of Quality Research in Chinese Medicine, and Macau Institute for Applied Research in Medicine and Health Macau University of Science and Technology  Avenida Wai Long, Taipa Macau China"}],"role":[{"role":"author","vocabulary":"crossref"}]},{"given":"Asako","family":"Murata","sequence":"additional","affiliation":[{"name":"Department of Regulatory Bioorganic Chemistry The Institute of Scientific and Industrial Research Osaka University  8-1 Mihogaoka Ibaraki 567-0047 Japan"}],"role":[{"role":"author","vocabulary":"crossref"}]},{"given":"Chikara","family":"Dohno","sequence":"additional","affiliation":[{"name":"Department of Regulatory Bioorganic Chemistry The Institute of Scientific and Industrial Research Osaka University  8-1 Mihogaoka Ibaraki 567-0047 Japan"}],"role":[{"role":"author","vocabulary":"crossref"}]},{"given":"Kazuhiko","family":"Nakatani","sequence":"additional","affiliation":[{"name":"Department of Regulatory Bioorganic Chemistry The Institute of Scientific and Industrial Research Osaka University  8-1 Mihogaoka Ibaraki 567-0047 Japan"}],"role":[{"role":"author","vocabulary":"crossref"}]}],"member":"311","published-online":{"date-parts":[[2016,6,14]]},"reference":[{"key":"e_1_2_7_1_1","first-page":"3","volume-title":"Genetic Instabilities and hereditary neurological diseases","author":"Wilmot G. 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