{"status":"ok","message-type":"work","message-version":"1.0.0","message":{"indexed":{"date-parts":[[2025,11,17]],"date-time":"2025-11-17T02:56:54Z","timestamp":1763348214438,"version":"3.40.5"},"reference-count":37,"publisher":"Wiley","issue":"6","license":[{"start":{"date-parts":[[2019,9,12]],"date-time":"2019-09-12T00:00:00Z","timestamp":1568246400000},"content-version":"vor","delay-in-days":0,"URL":"http:\/\/onlinelibrary.wiley.com\/termsAndConditions#vor"}],"funder":[{"DOI":"10.13039\/501100003141","name":"Consejo Nacional de Ciencia y Tecnolog\u00eda","doi-asserted-by":"publisher","award":["574252"],"award-info":[{"award-number":["574252"]}],"id":[{"id":"10.13039\/501100003141","id-type":"DOI","asserted-by":"publisher"}]}],"content-domain":{"domain":["onlinelibrary.wiley.com"],"crossmark-restriction":true},"short-container-title":["Chem Biol Drug Des"],"published-print":{"date-parts":[[2019,12]]},"abstract":"<jats:title>Abstract<\/jats:title><jats:p>There are several drugs for the treatment of giardiasis; however, there is a tendency for patients to abandon treatment because of drug\u2010related adverse effects, resulting in relapses, acquired resistance, and higher rates of treatment failure. Recently, we reported some podophyllotoxin\u2010type lignans from <jats:italic>Bursera fagaroides var. fagaroides<\/jats:italic> showing antigiardial activity. In the present work, we demonstrated that 5\u2032\u2010desmethoxy\u2010peltatin\u2010A\u2010methylether (5\u2010DES), acetylpodophyllotoxin (APOD), and podophyllotoxin (POD) affect the distribution and staining pattern of microtubular structures on <jats:italic>Giardia<\/jats:italic> trophozoites. Virtual screening results revealed that the lignans act via binding in a hydrophobic pocket in the heterodimer interface of tubulin in <jats:italic>Giardia<\/jats:italic>. This study provides useful insight to understand the action mechanism of 5DES, APOD, and POD on <jats:italic>Giardia lamblia<\/jats:italic>. The optimization of these podophyllotoxin\u2010type lignans will lead to promising candidates for antigiardial drugs.<\/jats:p>","DOI":"10.1111\/cbdd.13605","type":"journal-article","created":{"date-parts":[[2019,8,22]],"date-time":"2019-08-22T15:17:55Z","timestamp":1566487075000},"page":"2031-2040","update-policy":"https:\/\/doi.org\/10.1002\/crossmark_policy","source":"Crossref","is-referenced-by-count":5,"title":["Identification and molecular characterization of the tubulin\u2010podophyllotoxin\u2010type lignans binding site on <i>Giardia lamblia<\/i>"],"prefix":"10.1111","volume":"94","author":[{"given":"Filiberto","family":"Guti\u00e9rrez\u2010Guti\u00e9rrez","sequence":"first","affiliation":[{"name":"Departamento de Qu\u00edmica Centro Universitario de Ciencias Exactas e Ingenier\u00edas Universidad de Guadalajara Guadalajara M\u00e9xico"}],"role":[{"role":"author","vocabulary":"crossref"}]},{"ORCID":"https:\/\/orcid.org\/0000-0003-2869-588X","authenticated-orcid":false,"given":"Antonio","family":"Romo\u2010Mancillas","sequence":"additional","affiliation":[{"name":"Laboratorio de Dise\u00f1o Asistido por Computadora y S\u00edntesis de F\u00e1rmacos Facultad de Qu\u00edmica Universidad Aut\u00f3noma de Quer\u00e9taro Santiago de Quer\u00e9taro M\u00e9xico"}],"role":[{"role":"author","vocabulary":"crossref"}]},{"given":"Ana Mar\u00eda","family":"Puebla\u2010P\u00e9rez","sequence":"additional","affiliation":[{"name":"Departamento de Qu\u00edmica Centro Universitario de Ciencias Exactas e Ingenier\u00edas Universidad de Guadalajara Guadalajara M\u00e9xico"}],"role":[{"role":"author","vocabulary":"crossref"}]},{"given":"Jos\u00e9 Manuel","family":"Hern\u00e1ndez\u2010Hern\u00e1ndez","sequence":"additional","affiliation":[{"name":"Departamento de Biolog\u00eda Celular Centro de Investigaci\u00f3n y Estudios Avanzados del Instituto Polit\u00e9cnico Nacional Ciudad de M\u00e9xico M\u00e9xico"}],"role":[{"role":"author","vocabulary":"crossref"}]},{"ORCID":"https:\/\/orcid.org\/0000-0002-4461-7673","authenticated-orcid":false,"given":"Araceli","family":"Castillo\u2010Romero","sequence":"additional","affiliation":[{"name":"Departamento de Microbiolog\u00eda y Patolog\u00eda Centro Universitario de Ciencias de la Salud Universidad de Guadalajara Guadalajara M\u00e9xico"}],"role":[{"role":"author","vocabulary":"crossref"}]}],"member":"311","published-online":{"date-parts":[[2019,9,12]]},"reference":[{"key":"e_1_2_10_2_1","doi-asserted-by":"publisher","DOI":"10.1128\/CMR.14.3.447-475.2001"},{"key":"e_1_2_10_3_1","doi-asserted-by":"publisher","DOI":"10.1016\/j.jmgm.2013.07.008"},{"key":"e_1_2_10_4_1","doi-asserted-by":"publisher","DOI":"10.11604\/pamj.2016.24.217.8012"},{"key":"e_1_2_10_5_1","doi-asserted-by":"publisher","DOI":"10.1016\/j.biotechadv.2015.04.009"},{"key":"e_1_2_10_6_1","doi-asserted-by":"publisher","DOI":"10.1021\/acs.jnatprod.6b00428"},{"key":"e_1_2_10_7_1","doi-asserted-by":"publisher","DOI":"10.1093\/bioinformatics\/btq662"},{"key":"e_1_2_10_8_1","doi-asserted-by":"publisher","DOI":"10.1093\/nar\/gkp322"},{"key":"e_1_2_10_9_1","doi-asserted-by":"publisher","DOI":"10.1063\/1.448118"},{"key":"e_1_2_10_10_1","doi-asserted-by":"publisher","DOI":"10.1093\/nar\/gku340"},{"key":"e_1_2_10_11_1","doi-asserted-by":"publisher","DOI":"10.1016\/j.jep.2016.09.055"},{"key":"e_1_2_10_12_1","doi-asserted-by":"publisher","DOI":"10.1002\/pro.5560020916"},{"key":"e_1_2_10_13_1","doi-asserted-by":"publisher","DOI":"10.1016\/S0076-6879(97)77022-8"},{"key":"e_1_2_10_14_1","doi-asserted-by":"publisher","DOI":"10.1016\/j.ijpddr.2017.06.003"},{"key":"e_1_2_10_15_1","doi-asserted-by":"publisher","DOI":"10.26508\/lsa.201800054"},{"key":"e_1_2_10_16_1","doi-asserted-by":"publisher","DOI":"10.1016\/j.actatropica.2017.04.027"},{"key":"e_1_2_10_17_1","doi-asserted-by":"publisher","DOI":"10.3390\/molecules22050799"},{"key":"e_1_2_10_18_1","doi-asserted-by":"publisher","DOI":"10.3389\/fpls.2014.00511"},{"key":"e_1_2_10_19_1","doi-asserted-by":"publisher","DOI":"10.1016\/j.bmc.2014.07.031"},{"key":"e_1_2_10_20_1","doi-asserted-by":"publisher","DOI":"10.1016\/0035-9203(83)90120-7"},{"key":"e_1_2_10_21_1","doi-asserted-by":"publisher","DOI":"10.2174\/187152610791591610"},{"key":"e_1_2_10_22_1","doi-asserted-by":"publisher","DOI":"10.1007\/s40475-015-0051-1"},{"key":"e_1_2_10_23_1","doi-asserted-by":"publisher","DOI":"10.1002\/prot.10286"},{"key":"e_1_2_10_24_1","doi-asserted-by":"publisher","DOI":"10.1371\/journal.pone.0077970"},{"key":"e_1_2_10_25_1","doi-asserted-by":"publisher","DOI":"10.1038\/s41594-018-0087-8"},{"key":"e_1_2_10_26_1","doi-asserted-by":"publisher","DOI":"10.1002\/jcc.21256"},{"key":"e_1_2_10_27_1","doi-asserted-by":"publisher","DOI":"10.1016\/j.jmgm.2013.09.005"},{"key":"e_1_2_10_28_1","doi-asserted-by":"publisher","DOI":"10.1103\/PhysRevLett.45.1196"},{"key":"e_1_2_10_29_1","doi-asserted-by":"publisher","DOI":"10.1007\/s00436-013-3521-1"},{"key":"e_1_2_10_30_1","doi-asserted-by":"publisher","DOI":"10.1021\/jm0307685"},{"volume-title":"ImageJ","year":"1999","author":"Rasband W. S.","key":"e_1_2_10_31_1"},{"key":"e_1_2_10_32_1","doi-asserted-by":"publisher","DOI":"10.1038\/nature02393"},{"key":"e_1_2_10_33_1","doi-asserted-by":"publisher","DOI":"10.1007\/s00436-015-4465-4"},{"key":"e_1_2_10_34_1","doi-asserted-by":"publisher","DOI":"10.1016\/j.exppara.2008.04.003"},{"key":"e_1_2_10_35_1","doi-asserted-by":"publisher","DOI":"10.1017\/S0031182011002162"},{"key":"e_1_2_10_36_1","doi-asserted-by":"publisher","DOI":"10.21829\/abm70.2005.989"},{"key":"e_1_2_10_37_1","doi-asserted-by":"publisher","DOI":"10.1073\/pnas.76.9.4350"},{"key":"e_1_2_10_38_1","doi-asserted-by":"publisher","DOI":"10.1016\/j.jmgm.2015.10.012"}],"container-title":["Chemical Biology &amp; Drug Design"],"original-title":[],"language":"en","link":[{"URL":"https:\/\/onlinelibrary.wiley.com\/doi\/pdf\/10.1111\/cbdd.13605","content-type":"application\/pdf","content-version":"vor","intended-application":"text-mining"},{"URL":"https:\/\/onlinelibrary.wiley.com\/doi\/full-xml\/10.1111\/cbdd.13605","content-type":"application\/xml","content-version":"vor","intended-application":"text-mining"},{"URL":"https:\/\/onlinelibrary.wiley.com\/doi\/pdf\/10.1111\/cbdd.13605","content-type":"unspecified","content-version":"vor","intended-application":"similarity-checking"}],"deposited":{"date-parts":[[2023,9,8]],"date-time":"2023-09-08T12:26:14Z","timestamp":1694175974000},"score":1,"resource":{"primary":{"URL":"https:\/\/onlinelibrary.wiley.com\/doi\/10.1111\/cbdd.13605"}},"subtitle":[],"short-title":[],"issued":{"date-parts":[[2019,9,12]]},"references-count":37,"journal-issue":{"issue":"6","published-print":{"date-parts":[[2019,12]]}},"alternative-id":["10.1111\/cbdd.13605"],"URL":"https:\/\/doi.org\/10.1111\/cbdd.13605","archive":["Portico"],"relation":{},"ISSN":["1747-0277","1747-0285"],"issn-type":[{"type":"print","value":"1747-0277"},{"type":"electronic","value":"1747-0285"}],"subject":[],"published":{"date-parts":[[2019,9,12]]},"assertion":[{"value":"2019-01-25","order":0,"name":"received","label":"Received","group":{"name":"publication_history","label":"Publication History"}},{"value":"2019-07-27","order":1,"name":"accepted","label":"Accepted","group":{"name":"publication_history","label":"Publication History"}},{"value":"2019-09-12","order":2,"name":"published","label":"Published","group":{"name":"publication_history","label":"Publication History"}}]}}