{"status":"ok","message-type":"work","message-version":"1.0.0","message":{"indexed":{"date-parts":[[2026,9,3]],"date-time":"2026-09-03T00:53:53Z","timestamp":1788396833825,"version":"build-2803163510"},"reference-count":16,"publisher":"Wiley","issue":"17","license":[{"start":{"date-parts":[[2016,7,14]],"date-time":"2016-07-14T00:00:00Z","timestamp":1468454400000},"content-version":"vor","delay-in-days":0,"URL":"http:\/\/onlinelibrary.wiley.com\/termsAndConditions#vor"}],"funder":[{"name":"National Science Centre in Poland","award":["UMO-2012\/05\/E\/ST5\/03792"],"award-info":[{"award-number":["UMO-2012\/05\/E\/ST5\/03792"]}]}],"content-domain":{"domain":["chemistry-europe.onlinelibrary.wiley.com"],"crossmark-restriction":true},"short-container-title":["ChemMedChem"],"published-print":{"date-parts":[[2016,9,6]]},"abstract":"<jats:title>Abstract<\/jats:title><jats:p>A series of new C13\u2010triazole\u2010bridged and C13\u2010ether leucomycin analogues with a reduced aldehyde group were synthesized. Derivatives with the highest antibacterial [MIC values (<jats:italic>S.\u2005epidermidis<\/jats:italic>, <jats:italic>S.\u2005pneumoniae<\/jats:italic>): \u223c2\u20134\u2005\u03bcg\u2009mL<jats:sup>\u22121<\/jats:sup>; 2.55\u20135.09\u2005\u03bc<jats:sc>m<\/jats:sc>] and cytotoxic [IC<jats:sub>50<\/jats:sub> values (HeLa, KB, MCF\u20107, A549, HepG2 cells): \u223c1.35\u20133.70\u2005\u03bc<jats:sc>m<\/jats:sc>] potencies were those with the best aqueous solubility and bearing a saccharide\u2010triazole arm at the C13 position of the aglycone. These derivatives preferentially bind at the ribosomal tunnel and show the most attractive selectivity indexes [SI; calculated relative to the human dermal fibroblast (HDF) cell line], even higher than that of the reference compound cytarabine. Results of molecular docking studies of this type of macrolide antibiotics at the ribosomal tunnel, together with experimentally determined lipophilicity and aqueous solubility values, as well as biological assay data revealed the importance of the introduced functional group at the aglycone C13 arm to the future design of anticancer and antibacterial drug candidates. Our results clearly indicate that the high antibacterial and anticancer activities of these types of macrolides do not necessarily depend on the presence of the aldehyde group at the aglycone lactone ring.<\/jats:p>","DOI":"10.1002\/cmdc.201600250","type":"journal-article","created":{"date-parts":[[2016,7,14]],"date-time":"2016-07-14T06:50:57Z","timestamp":1468479057000},"page":"1886-1891","update-policy":"https:\/\/doi.org\/10.1002\/crossmark_policy","source":"Crossref","is-referenced-by-count":11,"title":["16\u2010Membered Macrolide Lactone Derivatives Bearing a Triazole\u2010Functionalized Arm at the Aglycone C13 Position as Antibacterial and Anticancer Agents"],"prefix":"10.1002","volume":"11","author":[{"given":"Joanna","family":"Domagalska","sequence":"first","affiliation":[{"name":"Faculty of Chemistry Adam Mickiewicz University  Umultowska\u200589b 61-614 Poznan Poland"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Anna","family":"Janas","sequence":"additional","affiliation":[{"name":"Faculty of Chemistry Adam Mickiewicz University  Umultowska\u200589b 61-614 Poznan Poland"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Krystian","family":"Pyta","sequence":"additional","affiliation":[{"name":"Faculty of Chemistry Adam Mickiewicz University  Umultowska\u200589b 61-614 Poznan Poland"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Paulina","family":"Pecyna","sequence":"additional","affiliation":[{"name":"Department of Genetics and Pharmaceutical Microbiology University of Medical Sciences  Swiecickiego\u20054 60-781 Poznan Poland"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Piotr","family":"Ruszkowski","sequence":"additional","affiliation":[{"name":"Department of Pharmacology University of Medical Sciences  Rokietnicka\u20055a 60-806 Poznan Poland"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Lech","family":"Celewicz","sequence":"additional","affiliation":[{"name":"Faculty of Chemistry Adam Mickiewicz University  Umultowska\u200589b 61-614 Poznan Poland"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Marzena","family":"Gajecka","sequence":"additional","affiliation":[{"name":"Department of Genetics and Pharmaceutical Microbiology University of Medical Sciences  Swiecickiego\u20054 60-781 Poznan Poland"},{"name":"Institute of Human Genetics Polish Academy of Science  Strzeszynska\u200532 60-479 Poznan Poland"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Franz","family":"Bartl","sequence":"additional","affiliation":[{"name":"Institut f\u00fcr Medizinische Physik und Biophysik (CC2) Charit\u00e9-Universit\u00e4tsmedizin Berlin  Charit\u00e9platz\u20051 10117 Berlin Germany"},{"name":"Zentrum f\u00fcr Biophysik und Bioinformatik Humboldt-Universit\u00e4t zu Berlin  Invalidenstrasse\u200542 10115 Berlin Germany"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"ORCID":"https:\/\/orcid.org\/0000-0001-8072-5877","authenticated-orcid":false,"given":"Piotr","family":"Przybylski","sequence":"additional","affiliation":[{"name":"Faculty of Chemistry Adam Mickiewicz University  Umultowska\u200589b 61-614 Poznan Poland"}],"role":[{"vocabulary":"crossref","role":"author"}]}],"member":"311","published-online":{"date-parts":[[2016,7,14]]},"reference":[{"key":"e_1_2_2_1_1","first-page":"5","volume-title":"Macrolides","year":"1993"},{"key":"e_1_2_2_2_1","doi-asserted-by":"publisher","DOI":"10.1128\/AAC.33.9.1419"},{"key":"e_1_2_2_3_1","doi-asserted-by":"publisher","DOI":"10.1016\/S1097-2765(02)00570-1"},{"key":"e_1_2_2_4_1","doi-asserted-by":"publisher","DOI":"10.1016\/S0022-2836(03)00662-4"},{"key":"e_1_2_2_5_1","doi-asserted-by":"publisher","DOI":"10.1128\/AAC.39.3.577"},{"key":"e_1_2_2_6_1","doi-asserted-by":"publisher","DOI":"10.2174\/1568005043340812"},{"key":"e_1_2_2_7_1","doi-asserted-by":"publisher","DOI":"10.1016\/j.bmc.2008.02.064"},{"key":"e_1_2_2_8_1","doi-asserted-by":"publisher","DOI":"10.1016\/j.bmcl.2013.12.029"},{"key":"e_1_2_2_9_1","doi-asserted-by":"publisher","DOI":"10.1016\/j.tetlet.2009.08.118"},{"key":"e_1_2_2_10_1","doi-asserted-by":"publisher","DOI":"10.1016\/j.bmc.2008.01.027"},{"key":"e_1_2_2_11_1","doi-asserted-by":"publisher","DOI":"10.1039\/B922450E"},{"key":"e_1_2_2_12_1","doi-asserted-by":"publisher","DOI":"10.7164\/antibiotics.27.370"},{"key":"e_1_2_2_13_1","doi-asserted-by":"publisher","DOI":"10.1016\/j.tetlet.2011.09.086"},{"key":"e_1_2_2_14_1","doi-asserted-by":"publisher","DOI":"10.1021\/jm00345a014"},{"key":"e_1_2_2_15_1","doi-asserted-by":"publisher","DOI":"10.1007\/s11030-005-1304-z"},{"key":"e_1_2_2_16_1","doi-asserted-by":"publisher","DOI":"10.1016\/j.tetlet.2016.02.113"}],"container-title":["ChemMedChem"],"original-title":[],"language":"en","link":[{"URL":"https:\/\/api.wiley.com\/onlinelibrary\/tdm\/v1\/articles\/10.1002%2Fcmdc.201600250","content-type":"unspecified","content-version":"vor","intended-application":"text-mining"},{"URL":"https:\/\/chemistry-europe.onlinelibrary.wiley.com\/doi\/pdf\/10.1002\/cmdc.201600250","content-type":"unspecified","content-version":"vor","intended-application":"similarity-checking"}],"deposited":{"date-parts":[[2025,10,12]],"date-time":"2025-10-12T20:19:27Z","timestamp":1760300367000},"score":1,"resource":{"primary":{"URL":"https:\/\/chemistry-europe.onlinelibrary.wiley.com\/doi\/10.1002\/cmdc.201600250"}},"subtitle":[],"short-title":[],"issued":{"date-parts":[[2016,7,14]]},"references-count":16,"journal-issue":{"issue":"17","published-print":{"date-parts":[[2016,9,6]]}},"alternative-id":["10.1002\/cmdc.201600250"],"URL":"https:\/\/doi.org\/10.1002\/cmdc.201600250","archive":["Portico"],"relation":{},"ISSN":["1860-7179","1860-7187"],"issn-type":[{"value":"1860-7179","type":"print"},{"value":"1860-7187","type":"electronic"}],"subject":[],"published":{"date-parts":[[2016,7,14]]},"assertion":[{"value":"2016-05-13","order":0,"name":"received","label":"Received","group":{"name":"publication_history","label":"Publication History"}},{"value":"2016-07-14","order":3,"name":"published","label":"Published","group":{"name":"publication_history","label":"Publication History"}}]}}