{"status":"ok","message-type":"work","message-version":"1.0.0","message":{"indexed":{"date-parts":[[2025,10,19]],"date-time":"2025-10-19T05:54:00Z","timestamp":1760853240690,"version":"build-2065373602"},"reference-count":36,"publisher":"Wiley","issue":"12","license":[{"start":{"date-parts":[[2006,10,10]],"date-time":"2006-10-10T00:00:00Z","timestamp":1160438400000},"content-version":"vor","delay-in-days":0,"URL":"http:\/\/onlinelibrary.wiley.com\/termsAndConditions#vor"}],"content-domain":{"domain":["chemistry-europe.onlinelibrary.wiley.com"],"crossmark-restriction":true},"short-container-title":["ChemBioChem"],"published-print":{"date-parts":[[2006,12,4]]},"abstract":"<jats:title>Abstract<\/jats:title><jats:p>We describe the synthesis and properties of oligodeoxynucleotides (ODNs) containing 1,8\u2010naphthyridine C\u2010nucleoside (Na\u2010N<jats:sup>O<\/jats:sup>) and imidazo[5\u2032,4\u2032:4,5]pyrido[2,3\u2010<jats:italic>d<\/jats:italic>]pyrimidine nucleoside (Im\u2010O<jats:sup>N<\/jats:sup>) at the termini. The modified ODNs were more resistant (6 to 40 times) than natural DNA to snake venom phosphodiesterase (SVPD). Although incorporation of one pair each of Na\u2010N<jats:sup>O<\/jats:sup>:Im\u2010O<jats:sup>N<\/jats:sup> on the sticky ends of the duplex was insufficient for thermal stabilization (+2.5\u2009\u00b0C per pair relative to the G:C pair), the duplex containing two consecutive Na\u2010N<jats:sup>O<\/jats:sup>:Im\u2010O<jats:sup>N<\/jats:sup> pairs at its sticky ends was markedly stabilized thermally. The stabilizing effect of the incorporation of additional Na\u2010N<jats:sup>O<\/jats:sup>:Im\u2010O<jats:sup>N<\/jats:sup> pairs is estimated to be +7.8\u2009\u00b0C per pair. Application as thermally stabilized decoy molecules to NF\u2010\u03baB (p50) was also demonstrated. The DNA duplexes containing the Na\u2010N<jats:sup>O<\/jats:sup>:Im\u2010O<jats:sup>N<\/jats:sup> pairs (ODN\u2009I:ODN\u2009II and ODN\u2009III:ODN\u2009IV) acted as competitors to the natural NF\u2010\u03baB\u2010binding duplex (ODN\u2009V: ODN\u2009VI), and the calculated IC<jats:sub>50<\/jats:sub> values of ODN\u2009I:ODN\u2009II and ODN\u2009III:ODN\u2009IV were 20.1\u00b113.3 and 10.9\u00b14.8 n<jats:sc>M<\/jats:sc>, respectively, greater than that of ODN\u2009V:ODN\u2009VI.<\/jats:p>","DOI":"10.1002\/cbic.200600318","type":"journal-article","created":{"date-parts":[[2006,10,10]],"date-time":"2006-10-10T08:01:34Z","timestamp":1160467294000},"page":"1970-1975","update-policy":"https:\/\/doi.org\/10.1002\/crossmark_policy","source":"Crossref","is-referenced-by-count":21,"title":["Synthesis and Characterization of Oligodeoxynucleotides Containing Naphthyridine:Imidazopyridopyrimidine Base Pairs at their Sticky Ends. Application as Thermally Stabilized Decoy Molecules"],"prefix":"10.1002","volume":"7","author":[{"given":"Sadao","family":"Hikishima","sequence":"first","affiliation":[],"role":[{"role":"author","vocabulary":"crossref"}]},{"given":"Noriaki","family":"Minakawa","sequence":"additional","affiliation":[],"role":[{"role":"author","vocabulary":"crossref"}]},{"given":"Kazuyuki","family":"Kuramoto","sequence":"additional","affiliation":[],"role":[{"role":"author","vocabulary":"crossref"}]},{"given":"Shintaro","family":"Ogata","sequence":"additional","affiliation":[],"role":[{"role":"author","vocabulary":"crossref"}]},{"given":"Akira","family":"Matsuda","sequence":"additional","affiliation":[],"role":[{"role":"author","vocabulary":"crossref"}]}],"member":"311","published-online":{"date-parts":[[2006,11,27]]},"reference":[{"key":"e_1_2_5_1_2","doi-asserted-by":"publisher","DOI":"10.1021\/ar040004z"},{"key":"e_1_2_5_2_2","doi-asserted-by":"publisher","DOI":"10.1021\/ja0430604"},{"key":"e_1_2_5_3_2","doi-asserted-by":"publisher","DOI":"10.1002\/ange.200500069"},{"key":"e_1_2_5_3_3","doi-asserted-by":"publisher","DOI":"10.1002\/anie.200500069"},{"key":"e_1_2_5_4_2","unstructured":"\u00a0"},{"key":"e_1_2_5_5_2","doi-asserted-by":"publisher","DOI":"10.1021\/ja047201d"},{"key":"e_1_2_5_6_2","doi-asserted-by":"publisher","DOI":"10.1021\/ja0425280"},{"key":"e_1_2_5_7_2","doi-asserted-by":"publisher","DOI":"10.1021\/ar000183u"},{"key":"e_1_2_5_8_2","doi-asserted-by":"publisher","DOI":"10.1016\/j.cbpa.2003.10.011"},{"key":"e_1_2_5_9_2","unstructured":"\u00a0"},{"key":"e_1_2_5_10_2","doi-asserted-by":"publisher","DOI":"10.1021\/ja0025806"},{"key":"e_1_2_5_11_2","doi-asserted-by":"publisher","DOI":"10.1021\/ja020510o"},{"key":"e_1_2_5_12_2","doi-asserted-by":"publisher","DOI":"10.1021\/ja0347686"},{"key":"e_1_2_5_13_2","unstructured":"For the sake of simplicity the aglycons and nucleoside units of imidazopyridopyrimidine derivatives are referred to as Im\u2010NO Im\u2010ON Im\u2010NN and Im\u2010OO and those of naphthyridine derivatives are referred to as Na\u2010NOand Na\u2010ON. As can be seen in Scheme 2 the pairs of Im\u2010NOand Im\u2010ON and Na\u2010NOand Im\u2010ON for example are complementary."},{"key":"e_1_2_5_14_2","doi-asserted-by":"publisher","DOI":"10.1002\/ange.200461857"},{"key":"e_1_2_5_14_3","doi-asserted-by":"publisher","DOI":"10.1002\/anie.200461857"},{"key":"e_1_2_5_15_2","doi-asserted-by":"publisher","DOI":"10.1021\/cr00102a001"},{"key":"e_1_2_5_16_2","doi-asserted-by":"publisher","DOI":"10.1093\/nar\/gkg299"},{"key":"e_1_2_5_17_2","unstructured":"\u00a0"},{"key":"e_1_2_5_18_2","doi-asserted-by":"publisher","DOI":"10.1021\/bc970021r"},{"key":"e_1_2_5_19_2","doi-asserted-by":"publisher","DOI":"10.1021\/bi011725y"},{"key":"e_1_2_5_20_2","doi-asserted-by":"publisher","DOI":"10.1093\/nar\/gkg384"},{"key":"e_1_2_5_21_2","first-page":"386","volume":"1","author":"Cho\u2010Chung Y. S.","year":"1999","journal-title":"Curr. Opin. Mol. Ther."},{"key":"e_1_2_5_22_2","doi-asserted-by":"publisher","DOI":"10.1126\/science.2237444"},{"key":"e_1_2_5_23_2","unstructured":"\u00a0"},{"key":"e_1_2_5_24_2","doi-asserted-by":"publisher","DOI":"10.1093\/nar\/16.8.3209"},{"key":"e_1_2_5_25_2","doi-asserted-by":"publisher","DOI":"10.1021\/ja00154a001"},{"key":"e_1_2_5_26_2","unstructured":"\u00a0"},{"key":"e_1_2_5_27_2","doi-asserted-by":"publisher","DOI":"10.1161\/01.RES.0000023200.19316.D5"},{"key":"e_1_2_5_28_2","doi-asserted-by":"publisher","DOI":"10.1038\/sj.gt.3301849"},{"key":"e_1_2_5_29_2","unstructured":"\u00a0"},{"key":"e_1_2_5_30_2","doi-asserted-by":"publisher","DOI":"10.1021\/bi00427a037"},{"key":"e_1_2_5_31_2","doi-asserted-by":"publisher","DOI":"10.1021\/bi00225a028"},{"key":"e_1_2_5_32_2","doi-asserted-by":"publisher","DOI":"10.1046\/j.0014-2956.2001.02549.x"},{"key":"e_1_2_5_33_2","doi-asserted-by":"publisher","DOI":"10.1093\/nar\/30.11.2435"},{"key":"e_1_2_5_34_2","doi-asserted-by":"publisher","DOI":"10.1016\/j.tet.2006.07.101"}],"container-title":["ChemBioChem"],"original-title":[],"language":"en","link":[{"URL":"https:\/\/api.wiley.com\/onlinelibrary\/tdm\/v1\/articles\/10.1002%2Fcbic.200600318","content-type":"unspecified","content-version":"vor","intended-application":"text-mining"},{"URL":"https:\/\/chemistry-europe.onlinelibrary.wiley.com\/doi\/pdf\/10.1002\/cbic.200600318","content-type":"unspecified","content-version":"vor","intended-application":"similarity-checking"}],"deposited":{"date-parts":[[2025,10,12]],"date-time":"2025-10-12T19:15:34Z","timestamp":1760296534000},"score":1,"resource":{"primary":{"URL":"https:\/\/chemistry-europe.onlinelibrary.wiley.com\/doi\/10.1002\/cbic.200600318"}},"subtitle":[],"short-title":[],"issued":{"date-parts":[[2006,11,27]]},"references-count":36,"journal-issue":{"issue":"12","published-print":{"date-parts":[[2006,12,4]]}},"alternative-id":["10.1002\/cbic.200600318"],"URL":"https:\/\/doi.org\/10.1002\/cbic.200600318","archive":["Portico"],"relation":{},"ISSN":["1439-4227","1439-7633"],"issn-type":[{"type":"print","value":"1439-4227"},{"type":"electronic","value":"1439-7633"}],"subject":[],"published":{"date-parts":[[2006,11,27]]},"assertion":[{"value":"2006-07-25","order":0,"name":"received","label":"Received","group":{"name":"publication_history","label":"Publication History"}},{"value":"2006-11-27","order":3,"name":"published","label":"Published","group":{"name":"publication_history","label":"Publication History"}}]}}