{"status":"ok","message-type":"work","message-version":"1.0.0","message":{"indexed":{"date-parts":[[2026,3,23]],"date-time":"2026-03-23T20:49:09Z","timestamp":1774298949427,"version":"3.50.1"},"reference-count":37,"publisher":"Wiley","issue":"23","license":[{"start":{"date-parts":[[2023,10,12]],"date-time":"2023-10-12T00:00:00Z","timestamp":1697068800000},"content-version":"vor","delay-in-days":0,"URL":"http:\/\/creativecommons.org\/licenses\/by-nc\/4.0\/"}],"content-domain":{"domain":["chemistry-europe.onlinelibrary.wiley.com"],"crossmark-restriction":true},"short-container-title":["ChemBioChem"],"published-print":{"date-parts":[[2023,12]]},"abstract":"<jats:title>Abstract<\/jats:title><jats:p>We recently reported that some adenosine binding aptamers can also bind caffeine and theophylline with around 20\u2010fold lower affinities. This discovery led to the current work to examine the cross\u2010binding of adenosine to theophylline aptamers. For the DNA aptamer for theophylline, cross\u2010binding to adenosine was observed, and the affinity was 18 to 38\u2010fold lower for adenosine based on assays using isothermal titration calorimetry and ThT fluorescence spectroscopy. The binding complexes were characterized using NMR spectroscopy, and both adenosine and theophylline showed an overall similar binding structure to the DNA theophylline aptamer, although small differences were also observed. In contrast, the RNA aptamer did not show binding to adenosine, although both aptamers have very similar relative selectivity for various methylxanthines including caffeine. After a negative selection, a few new aptamers with completely different primary sequences for theophylline were obtained and they did not show binding to adenosine. Thus, there are many ways for aptamers to bind theophylline and some can have cross\u2010binding to adenosine. In biology, theophylline, caffeine, and adenosine can bind to the same protein receptors to regulate sleep, and their binding to the same DNA motifs may suggest an early role of nucleic acids in similar regulatory functions.<\/jats:p>","DOI":"10.1002\/cbic.202300566","type":"journal-article","created":{"date-parts":[[2023,9,25]],"date-time":"2023-09-25T13:39:35Z","timestamp":1695649175000},"update-policy":"https:\/\/doi.org\/10.1002\/crossmark_policy","source":"Crossref","is-referenced-by-count":5,"title":["Cross\u2010Binding of Adenosine by Aptamers Selected Using Theophylline"],"prefix":"10.1002","volume":"24","author":[{"given":"Po\u2010Jung Jimmy","family":"Huang","sequence":"first","affiliation":[{"name":"Department of Chemistry University of Waterloo  Waterloo Ontario N2\u2005L 3G1 Canada"},{"name":"Waterloo Institute for Nanotechnology University of Waterloo  Waterloo Ontario N2\u2005L 3G1 Canada"}],"role":[{"role":"author","vocabulary":"crossref"}]},{"given":"Natasha M.","family":"Evans","sequence":"additional","affiliation":[{"name":"Department of Chemistry University of Waterloo  Waterloo Ontario N2\u2005L 3G1 Canada"}],"role":[{"role":"author","vocabulary":"crossref"}]},{"given":"Chang","family":"Lu","sequence":"additional","affiliation":[{"name":"Department of Chemistry University of Waterloo  Waterloo Ontario N2\u2005L 3G1 Canada"}],"role":[{"role":"author","vocabulary":"crossref"}]},{"given":"Albert Zehan","family":"Li","sequence":"additional","affiliation":[{"name":"Department of Chemistry University of Waterloo  Waterloo Ontario N2\u2005L 3G1 Canada"}],"role":[{"role":"author","vocabulary":"crossref"}]},{"given":"Thorsten","family":"Dieckmann","sequence":"additional","affiliation":[{"name":"Department of Chemistry University of Waterloo  Waterloo Ontario N2\u2005L 3G1 Canada"}],"role":[{"role":"author","vocabulary":"crossref"}]},{"ORCID":"https:\/\/orcid.org\/0000-0001-5918-9336","authenticated-orcid":false,"given":"Juewen","family":"Liu","sequence":"additional","affiliation":[{"name":"Department of Chemistry University of Waterloo  Waterloo Ontario N2\u2005L 3G1 Canada"},{"name":"Waterloo Institute for Nanotechnology University of Waterloo  Waterloo Ontario N2\u2005L 3G1 Canada"}],"role":[{"role":"author","vocabulary":"crossref"}]}],"member":"311","published-online":{"date-parts":[[2023,10,12]]},"reference":[{"key":"e_1_2_8_1_1","doi-asserted-by":"publisher","DOI":"10.3233\/JAD-2010-1379"},{"key":"e_1_2_8_2_1","doi-asserted-by":"publisher","DOI":"10.1016\/0304-3940(82)90290-7"},{"key":"e_1_2_8_3_1","doi-asserted-by":"publisher","DOI":"10.3389\/fmolb.2021.673170"},{"key":"e_1_2_8_4_1","doi-asserted-by":"publisher","DOI":"10.1016\/j.str.2011.06.014"},{"key":"e_1_2_8_5_1","doi-asserted-by":"publisher","DOI":"10.1039\/D0CS00617C"},{"key":"e_1_2_8_6_1","doi-asserted-by":"publisher","DOI":"10.1016\/j.cbpa.2017.09.017"},{"key":"e_1_2_8_7_1","doi-asserted-by":"publisher","DOI":"10.1126\/science.287.5454.820"},{"key":"e_1_2_8_8_1","doi-asserted-by":"publisher","DOI":"10.1146\/annurev.biochem.78.070507.135656"},{"key":"e_1_2_8_9_1","author":"Wu D.","year":"2022","journal-title":"Acc. Chem. Res."},{"key":"e_1_2_8_10_1","doi-asserted-by":"publisher","DOI":"10.1021\/acs.chemrev.0c01140"},{"key":"e_1_2_8_11_1","doi-asserted-by":"publisher","DOI":"10.1002\/anie.202008663"},{"key":"e_1_2_8_12_1","doi-asserted-by":"publisher","DOI":"10.1021\/acs.accounts.9b00419"},{"key":"e_1_2_8_13_1","doi-asserted-by":"publisher","DOI":"10.1016\/j.isci.2019.100815"},{"key":"e_1_2_8_14_1","doi-asserted-by":"publisher","DOI":"10.1039\/D1CS00240F"},{"key":"e_1_2_8_15_1","doi-asserted-by":"publisher","DOI":"10.1021\/acs.biochem.3c00260"},{"key":"e_1_2_8_16_1","doi-asserted-by":"publisher","DOI":"10.1021\/cr0306743"},{"key":"e_1_2_8_17_1","doi-asserted-by":"publisher","DOI":"10.1038\/s41570-017-0076"},{"key":"e_1_2_8_18_1","doi-asserted-by":"publisher","DOI":"10.1126\/science.7510417"},{"key":"e_1_2_8_19_1","doi-asserted-by":"publisher","DOI":"10.1021\/acssynbio.9b00475"},{"key":"e_1_2_8_20_1","doi-asserted-by":"publisher","DOI":"10.1021\/acschembio.2c00179"},{"key":"e_1_2_8_21_1","doi-asserted-by":"publisher","DOI":"10.1016\/0022-2364(87)90269-1"},{"key":"e_1_2_8_22_1","doi-asserted-by":"publisher","DOI":"10.1063\/1.438208"},{"key":"e_1_2_8_23_1","doi-asserted-by":"publisher","DOI":"10.1016\/0006-291X(80)90695-6"},{"key":"e_1_2_8_24_1","doi-asserted-by":"publisher","DOI":"10.1016\/0022-2364(88)90178-3"},{"key":"e_1_2_8_25_1","doi-asserted-by":"publisher","DOI":"10.1016\/0022-2364(83)90226-3"},{"key":"e_1_2_8_26_1","doi-asserted-by":"publisher","DOI":"10.1016\/0076-6879(89)80091-6"},{"key":"e_1_2_8_27_1","first-page":"45","volume":"2","author":"Slavkovic S.","year":"2018","journal-title":"Aptamers"},{"key":"e_1_2_8_28_1","doi-asserted-by":"publisher","DOI":"10.1021\/bi00002a033"},{"key":"e_1_2_8_29_1","doi-asserted-by":"publisher","DOI":"10.1093\/nar\/gkx517"},{"key":"e_1_2_8_30_1","doi-asserted-by":"publisher","DOI":"10.1016\/j.trac.2018.09.013"},{"key":"e_1_2_8_31_1","doi-asserted-by":"publisher","DOI":"10.1126\/science.abn9859"},{"key":"e_1_2_8_32_1","doi-asserted-by":"publisher","DOI":"10.1021\/ja900695m"},{"key":"e_1_2_8_33_1","doi-asserted-by":"publisher","DOI":"10.1016\/0014-5793(93)81000-P"},{"key":"e_1_2_8_34_1","doi-asserted-by":"publisher","DOI":"10.1016\/0022-2364(85)90207-0"},{"key":"e_1_2_8_35_1","doi-asserted-by":"publisher","DOI":"10.1021\/ja00389a085"},{"key":"e_1_2_8_36_1","doi-asserted-by":"publisher","DOI":"10.1016\/j.jmb.2004.06.084"},{"key":"e_1_2_8_37_1","doi-asserted-by":"publisher","DOI":"10.1016\/j.pnmrs.2006.03.001"}],"container-title":["ChemBioChem"],"original-title":[],"language":"en","link":[{"URL":"https:\/\/chemistry-europe.onlinelibrary.wiley.com\/doi\/pdf\/10.1002\/cbic.202300566","content-type":"unspecified","content-version":"vor","intended-application":"similarity-checking"}],"deposited":{"date-parts":[[2025,10,12]],"date-time":"2025-10-12T13:32:18Z","timestamp":1760275938000},"score":1,"resource":{"primary":{"URL":"https:\/\/chemistry-europe.onlinelibrary.wiley.com\/doi\/10.1002\/cbic.202300566"}},"subtitle":[],"short-title":[],"issued":{"date-parts":[[2023,10,12]]},"references-count":37,"journal-issue":{"issue":"23","published-print":{"date-parts":[[2023,12]]}},"alternative-id":["10.1002\/cbic.202300566"],"URL":"https:\/\/doi.org\/10.1002\/cbic.202300566","archive":["Portico"],"relation":{},"ISSN":["1439-4227","1439-7633"],"issn-type":[{"value":"1439-4227","type":"print"},{"value":"1439-7633","type":"electronic"}],"subject":[],"published":{"date-parts":[[2023,10,12]]},"assertion":[{"value":"2023-08-11","order":0,"name":"received","label":"Received","group":{"name":"publication_history","label":"Publication History"}},{"value":"2023-10-12","order":3,"name":"published","label":"Published","group":{"name":"publication_history","label":"Publication History"}}],"article-number":"e202300566"}}