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Amino acid\u2010based surfactants are especially promising amphiphiles due to their enhanced biocompatibility compared to conventional surfactants. They can self\u2010organize into micelles, vesicles and complex hierarchical structures, such as fibers, twisted and coiled ribbons, and tubules. In this work, we investigated the self\u2010assembly and drug loading properties of a family of novel anionic double\u2010tailed lysine\u2010derived surfactants, with variable degree of tail length mismatch, designated as <jats:italic>m<\/jats:italic>Lys10 and 10Lys<jats:italic>n<\/jats:italic>, where <jats:italic>m<\/jats:italic> and <jats:italic>n<\/jats:italic> are the number of carbon atoms in the tails. These surfactants form tubular aggregates with assorted morphologies in water that undergo gelation due to dense entanglement, as evidenced by light and electron microscopy. Lysozyme (LZM), an enzyme with antimicrobial properties, was selected as model protein for loading. After the characterization of the interfacial properties and phase behavior of the amphiphiles, the LZM\u2010loading ability of the tubules was investigated, under varying experimental conditions, to assess the efficiency of the aggregates as pH\u2010 and temperature\u2010sensitive nanocarriers. Further, the toxicological profile of the surfactants <jats:italic>per se<\/jats:italic> and surfactant\/LZM hydrogels was obtained, using human skin fibroblasts (BJ\u20105ta cell line). Overall, the results show that the tubule\u2010based hydrogels exhibit very interesting properties for the transport and controlled release of molecules of therapeutic interest.<\/jats:p>","DOI":"10.1002\/chem.202003320","type":"journal-article","created":{"date-parts":[[2020,8,23]],"date-time":"2020-08-23T22:21:23Z","timestamp":1598221283000},"page":"692-704","update-policy":"https:\/\/doi.org\/10.1002\/crossmark_policy","source":"Crossref","is-referenced-by-count":9,"title":["Stimuli\u2010Sensitive Self\u2010Assembled Tubules Based on Lysine\u2010Derived Surfactants for Delivery of Antimicrobial Proteins"],"prefix":"10.1002","volume":"27","author":[{"ORCID":"https:\/\/orcid.org\/0000-0002-0515-9470","authenticated-orcid":false,"given":"Isabel S.","family":"Oliveira","sequence":"first","affiliation":[{"name":"CIQUP, Departamento de Qu\u00edmica e Bioqu\u00edmica, Faculdade de Ci\u00eancias Universidade do Porto  Rua do Campo Alegre s\/n 4169-007 Porto Portugal"}]},{"given":"Rui L.","family":"Machado","sequence":"additional","affiliation":[{"name":"CIQUP, Departamento de Qu\u00edmica e Bioqu\u00edmica, Faculdade de Ci\u00eancias Universidade do Porto  Rua do Campo Alegre s\/n 4169-007 Porto Portugal"}]},{"ORCID":"https:\/\/orcid.org\/0000-0002-3106-4205","authenticated-orcid":false,"given":"Maria J.","family":"Ara\u00fajo","sequence":"additional","affiliation":[{"name":"LAQV-REQUIMTE, Departamento de Qu\u00edmica e Bioqu\u00edmica, Faculdade de Ci\u00eancias Universidade do Porto  Rua do Campo Alegre s\/n 4169-007 Porto Portugal"}]},{"ORCID":"https:\/\/orcid.org\/0000-0002-0567-064X","authenticated-orcid":false,"given":"Andreia C.","family":"Gomes","sequence":"additional","affiliation":[{"name":"CBMA\u2014Centro de Biologia Molecular e Ambiental Departamento de Biologia Universidade do Minho  Campus de Gualtar 4710-057 Braga Portugal"}]},{"ORCID":"https:\/\/orcid.org\/0000-0002-3892-9216","authenticated-orcid":false,"given":"Eduardo F.","family":"Marques","sequence":"additional","affiliation":[{"name":"CIQUP, Departamento de Qu\u00edmica e Bioqu\u00edmica, Faculdade de Ci\u00eancias Universidade do Porto  Rua do Campo Alegre s\/n 4169-007 Porto Portugal"}]}],"member":"311","published-online":{"date-parts":[[2020,12,2]]},"reference":[{"key":"e_1_2_7_1_1","unstructured":"\u00a0"},{"key":"e_1_2_7_2_2","doi-asserted-by":"publisher","DOI":"10.1039\/b608348j"},{"key":"e_1_2_7_3_2","doi-asserted-by":"publisher","DOI":"10.1016\/j.addr.2012.07.015"},{"key":"e_1_2_7_4_2","doi-asserted-by":"publisher","DOI":"10.1002\/anie.201005662"},{"key":"e_1_2_7_4_3","doi-asserted-by":"publisher","DOI":"10.1002\/ange.201005662"},{"key":"e_1_2_7_5_2","doi-asserted-by":"publisher","DOI":"10.1039\/C5SM02397A"},{"key":"e_1_2_7_6_1","unstructured":"\u00a0"},{"key":"e_1_2_7_7_2","doi-asserted-by":"publisher","DOI":"10.1586\/14737159.6.3.307"},{"key":"e_1_2_7_8_2","doi-asserted-by":"publisher","DOI":"10.1038\/nrc1566"},{"key":"e_1_2_7_9_1","unstructured":"\u00a0"},{"key":"e_1_2_7_10_2","doi-asserted-by":"publisher","DOI":"10.1002\/cphc.201402187"},{"key":"e_1_2_7_11_2","doi-asserted-by":"publisher","DOI":"10.1002\/smll.201402075"},{"key":"e_1_2_7_12_1","doi-asserted-by":"publisher","DOI":"10.2967\/jnumed.107.043216"},{"key":"e_1_2_7_13_1","doi-asserted-by":"publisher","DOI":"10.1007\/s10439-005-9002-7"},{"key":"e_1_2_7_14_1","doi-asserted-by":"publisher","DOI":"10.1562\/2005-12-14-RA-754"},{"key":"e_1_2_7_15_1","unstructured":"\u00a0"},{"key":"e_1_2_7_16_2","doi-asserted-by":"publisher","DOI":"10.1002\/wnan.1272"},{"key":"e_1_2_7_17_2","doi-asserted-by":"publisher","DOI":"10.1016\/j.ijpharm.2003.07.014"},{"key":"e_1_2_7_18_1","unstructured":"\u00a0"},{"key":"e_1_2_7_19_2","first-page":"591325","author":"Wagner A.","year":"2011","journal-title":"J. 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