{"status":"ok","message-type":"work","message-version":"1.0.0","message":{"indexed":{"date-parts":[[2026,4,13]],"date-time":"2026-04-13T23:21:15Z","timestamp":1776122475540,"version":"3.50.1"},"reference-count":24,"publisher":"Wiley","issue":"18","license":[{"start":{"date-parts":[[2016,11,11]],"date-time":"2016-11-11T00:00:00Z","timestamp":1478822400000},"content-version":"vor","delay-in-days":10,"URL":"http:\/\/onlinelibrary.wiley.com\/termsAndConditions#vor"}],"content-domain":{"domain":["chemistry-europe.onlinelibrary.wiley.com"],"crossmark-restriction":true},"short-container-title":["ChemistrySelect"],"published-print":{"date-parts":[[2016,11]]},"abstract":"<jats:title>Abstract<\/jats:title>\n                  <jats:p>\n                    Antibiotic resistance is a global public health concern. The choline\u2010based ionic liquids (ILs) have raised particular attention in the design of \u201cgreener\u201d ILs and can exert a broad\u2010spectrum of antimicrobial activity. To improve antimicrobial chemotherapy, we herein tested the antimicrobial activity and toxicity of a wide range of choline\u2010based ILs. Two series of compounds were synthesized \u2010dimethylethanolamine monoquaternary ammonium salts (Series A) and \u2010methyl diethanolamine, diethanolamine and triethanolamine monoquaternary ammonium salts (Series B). The antimicrobial screening revealed that compounds\n                    <jats:italic>N<\/jats:italic>\n                    \u2010(2\u2010hydroxyethyl)\u2010\n                    <jats:italic>N,N<\/jats:italic>\n                    \u2010dimethyl\u20101\u2010tetradecanaminium bromide (\n                    <jats:italic>\n                      <jats:bold>[N<\/jats:bold>\n                    <\/jats:italic>\n                    <jats:sub>\n                      <jats:italic>\n                        <jats:bold>1,1,14,2(OH)<\/jats:bold>\n                      <\/jats:italic>\n                    <\/jats:sub>\n                    <jats:italic>\n                      <jats:bold>]Br<\/jats:bold>\n                    <\/jats:italic>\n                    ),\n                    <jats:italic>N<\/jats:italic>\n                    \u2010(2\u2010hydroxyethyl)\u2010\n                    <jats:italic>N,N<\/jats:italic>\n                    \u2010dimethyl\u20101\u2010hexadecanaminium bromide (\n                    <jats:italic>\n                      <jats:bold>[N<\/jats:bold>\n                    <\/jats:italic>\n                    <jats:sub>\n                      <jats:italic>\n                        <jats:bold>1,1,16,2(OH)<\/jats:bold>\n                      <\/jats:italic>\n                    <\/jats:sub>\n                    <jats:italic>\n                      <jats:bold>]Br<\/jats:bold>\n                    <\/jats:italic>\n                    ) and\n                    <jats:italic>N<\/jats:italic>\n                    \u2010(2\u2010hydroxyethyl)\u2010\n                    <jats:italic>N,N<\/jats:italic>\n                    \u2010dimethyl\u20101\u2010octadecanaminium bromide (\n                    <jats:italic>\n                      <jats:bold>[N<\/jats:bold>\n                    <\/jats:italic>\n                    <jats:sub>\n                      <jats:italic>\n                        <jats:bold>1,1,18,2(OH)<\/jats:bold>\n                      <\/jats:italic>\n                    <\/jats:sub>\n                    <jats:italic>\n                      <jats:bold>]Br<\/jats:bold>\n                    <\/jats:italic>\n                    ) are potent antimicrobial agents. The presence of a hydroxyethyl group and as mention previously in the literature, the C\n                    <jats:sub>14<\/jats:sub>\n                    to C\n                    <jats:sub>16<\/jats:sub>\n                    linker in a choline compound improves the antimicrobial activity and lowers the cytotoxic properties of this class of compounds.\n                  <\/jats:p>","DOI":"10.1002\/slct.201600864","type":"journal-article","created":{"date-parts":[[2016,11,16]],"date-time":"2016-11-16T15:15:55Z","timestamp":1479309355000},"page":"5909-5916","update-policy":"https:\/\/doi.org\/10.1002\/crossmark_policy","source":"Crossref","is-referenced-by-count":43,"title":["Choline\u2010Based Ionic Liquids: Improvement of Antimicrobial Activity"],"prefix":"10.1002","volume":"1","author":[{"given":"Filipa","family":"Siopa","sequence":"first","affiliation":[{"name":"Instituto de Investiga\u00e7\u00e3o do Medicamento (iMed.ULisboa) Faculdade de Farm\u00e1cia da Universidade de Lisboa  Av. Prof. Gama Pinto 1649-003 Lisboa Portugal"}]},{"given":"Teresa","family":"Figueiredo","sequence":"additional","affiliation":[{"name":"UCIBIO@REQUIMTE, Departamento de Ci\u00eancias da Vida, Faculdade de Ci\u00eancias e Tecnologia Universidade Nova de Lisboa"},{"name":"Laboratory of Molecular Genetics Instituto de Tecnologia Qu\u00edmica e Biol\u00f3gica da Universidade Nova de Lisboa"}]},{"given":"Raquel F. M.","family":"Frade","sequence":"additional","affiliation":[{"name":"Instituto de Investiga\u00e7\u00e3o do Medicamento (iMed.ULisboa) Faculdade de Farm\u00e1cia da Universidade de Lisboa  Av. Prof. Gama Pinto 1649-003 Lisboa Portugal"}]},{"given":"Iris","family":"Neto","sequence":"additional","affiliation":[{"name":"Center for Research in Biosciences &amp; Health Technologies (CBIOS) Universidade Lus\u00f3fona de Humanidades e Tecnologias  Campo Grande 376 1749-024 Lisboa Portugal"}]},{"given":"Ana","family":"Meirinhos","sequence":"additional","affiliation":[{"name":"Instituto de Investiga\u00e7\u00e3o do Medicamento (iMed.ULisboa) Faculdade de Farm\u00e1cia da Universidade de Lisboa  Av. Prof. Gama Pinto 1649-003 Lisboa Portugal"}]},{"given":"Catarina P.","family":"Reis","sequence":"additional","affiliation":[{"name":"Center for Research in Biosciences &amp; Health Technologies (CBIOS) Universidade Lus\u00f3fona de Humanidades e Tecnologias  Campo Grande 376 1749-024 Lisboa Portugal"}]},{"given":"Rita G.","family":"Sobral","sequence":"additional","affiliation":[{"name":"UCIBIO@REQUIMTE, Departamento de Ci\u00eancias da Vida, Faculdade de Ci\u00eancias e Tecnologia Universidade Nova de Lisboa"}]},{"given":"Carlos A. M.","family":"Afonso","sequence":"additional","affiliation":[{"name":"Instituto de Investiga\u00e7\u00e3o do Medicamento (iMed.ULisboa) Faculdade de Farm\u00e1cia da Universidade de Lisboa  Av. Prof. Gama Pinto 1649-003 Lisboa Portugal"}]},{"given":"Patr\u00edcia","family":"Rijo","sequence":"additional","affiliation":[{"name":"Instituto de Investiga\u00e7\u00e3o do Medicamento (iMed.ULisboa) Faculdade de Farm\u00e1cia da Universidade de Lisboa  Av. Prof. Gama Pinto 1649-003 Lisboa Portugal"},{"name":"Center for Research in Biosciences &amp; Health Technologies (CBIOS) Universidade Lus\u00f3fona de Humanidades e Tecnologias  Campo Grande 376 1749-024 Lisboa Portugal"}]}],"member":"311","published-online":{"date-parts":[[2016,11,11]]},"reference":[{"key":"e_1_2_5_1_1","doi-asserted-by":"publisher","DOI":"10.1002\/chem.200700285"},{"key":"e_1_2_5_2_1","doi-asserted-by":"publisher","DOI":"10.1111\/j.1753-4887.2009.00246.x"},{"key":"e_1_2_5_3_1","doi-asserted-by":"publisher","DOI":"10.1128\/AAC.39.1.50"},{"key":"e_1_2_5_4_1","doi-asserted-by":"publisher","DOI":"10.1016\/j.ejmech.2003.09.004"},{"key":"e_1_2_5_5_1","doi-asserted-by":"publisher","DOI":"10.1016\/j.ecoenv.2014.07.003"},{"key":"e_1_2_5_6_1","doi-asserted-by":"publisher","DOI":"10.1177\/0960327110371259"},{"key":"e_1_2_5_7_1","doi-asserted-by":"publisher","DOI":"10.1016\/j.ijantimicag.2015.02.016"},{"key":"e_1_2_5_8_1","doi-asserted-by":"publisher","DOI":"10.1021\/acsinfecdis.5b00047"},{"key":"e_1_2_5_9_1","doi-asserted-by":"publisher","DOI":"10.1111\/cbdd.12427"},{"key":"e_1_2_5_10_1","doi-asserted-by":"publisher","DOI":"10.4236\/jsemat.2013.33032"},{"key":"e_1_2_5_11_1","doi-asserted-by":"publisher","DOI":"10.1039\/C4RA05295A"},{"key":"e_1_2_5_12_1","volume":"8","author":"Hou X. 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