{"status":"ok","message-type":"work","message-version":"1.0.0","message":{"indexed":{"date-parts":[[2026,1,17]],"date-time":"2026-01-17T21:34:17Z","timestamp":1768685657468,"version":"3.49.0"},"reference-count":60,"publisher":"MDPI AG","issue":"14","license":[{"start":{"date-parts":[[2021,7,10]],"date-time":"2021-07-10T00:00:00Z","timestamp":1625875200000},"content-version":"vor","delay-in-days":0,"URL":"https:\/\/creativecommons.org\/licenses\/by\/4.0\/"}],"funder":[{"DOI":"10.13039\/501100004963","name":"Seventh Framework Programme","doi-asserted-by":"publisher","award":["603240"],"award-info":[{"award-number":["603240"]}],"id":[{"id":"10.13039\/501100004963","id-type":"DOI","asserted-by":"publisher"}]}],"content-domain":{"domain":[],"crossmark-restriction":false},"short-container-title":["Molecules"],"abstract":"<jats:p>A library of seventeen novel ether phospholipid analogues, containing 5-membered heterocyclic rings (1,2,3-triazolyl, isoxazolyl, 1,3,4-oxadiazolyl and 1,2,4-oxadiazolyl) in the lipid portion were designed and synthesized aiming to identify optimised miltefosine analogues. The compounds were evaluated for their in vitro antiparasitic activity against Leishmania infantum and Leishmania donovani intracellular amastigotes, against Trypanosoma brucei brucei and against different developmental stages of Trypanosoma cruzi. The nature of the substituents of the heterocyclic ring (tail) and the oligomethylene spacer between the head group and the heterocyclic ring was found to affect the activity and toxicity of these compounds leading to a significantly improved understanding of their structure\u2013activity relationships. The early ADMET profile of the new derivatives did not reveal major liabilities for the potent compounds. The 1,2,3-triazole derivative 27 substituted by a decyl tail, an undecyl spacer and a choline head group exhibited broad spectrum antiparasitic activity. It possessed low micromolar activity against the intracellular amastigotes of two L. infantum strains and T. cruzi Y strain epimastigotes, intracellular amastigotes and trypomastigotes, while its cytotoxicity concentration (CC50) against THP-1 macrophages ranged between 50 and 100 \u03bcM. Altogether, our work paves the way for the development of improved ether phospholipid derivatives to control neglected tropical diseases.<\/jats:p>","DOI":"10.3390\/molecules26144204","type":"journal-article","created":{"date-parts":[[2021,7,12]],"date-time":"2021-07-12T00:23:36Z","timestamp":1626049416000},"page":"4204","update-policy":"https:\/\/doi.org\/10.3390\/mdpi_crossmark_policy","source":"Crossref","is-referenced-by-count":13,"title":["Design, Synthesis and Antiparasitic Evaluation of Click Phospholipids"],"prefix":"10.3390","volume":"26","author":[{"ORCID":"https:\/\/orcid.org\/0000-0001-8944-1635","authenticated-orcid":false,"given":"George E.","family":"Magoulas","sequence":"first","affiliation":[{"name":"National Hellenic Research Foundation, Institute of Chemical Biology, 11653 Athens, Greece"}]},{"given":"Pantelis","family":"Afroudakis","sequence":"additional","affiliation":[{"name":"National Hellenic Research Foundation, Institute of Chemical Biology, 11653 Athens, Greece"}]},{"given":"Kalliopi","family":"Georgikopoulou","sequence":"additional","affiliation":[{"name":"National Hellenic Research Foundation, Institute of Chemical Biology, 11653 Athens, Greece"}]},{"given":"Marina","family":"Roussaki","sequence":"additional","affiliation":[{"name":"National Hellenic Research Foundation, Institute of Chemical Biology, 11653 Athens, Greece"}]},{"ORCID":"https:\/\/orcid.org\/0000-0002-4688-8362","authenticated-orcid":false,"given":"Chiara","family":"Borsari","sequence":"additional","affiliation":[{"name":"Department of Biomedicine, University of Basel, 4058 Basel, Switzerland"}]},{"given":"Theano","family":"Fotopoulou","sequence":"additional","affiliation":[{"name":"National Hellenic Research Foundation, Institute of Chemical Biology, 11653 Athens, Greece"}]},{"given":"Nuno","family":"Santarem","sequence":"additional","affiliation":[{"name":"i3S\u2013Instituto de Investiga\u00e7\u00e3o e Inova\u00e7\u00e3o em Sa\u00fade, Universidade do Porto, 4200-135 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Germany"}]},{"ORCID":"https:\/\/orcid.org\/0000-0001-5703-3901","authenticated-orcid":false,"given":"Bernhard","family":"Ellinger","sequence":"additional","affiliation":[{"name":"Fraunhofer Institute for Translational Medicine and Pharmacology ITMP, 22525 Hamburg, Germany"},{"name":"Fraunhofer Cluster of Excellence for Immune-Mediated Diseases CIMD, 22525 Hamburg, Germany"}]},{"ORCID":"https:\/\/orcid.org\/0000-0001-8771-1865","authenticated-orcid":false,"given":"Maria","family":"Kuzikov","sequence":"additional","affiliation":[{"name":"Fraunhofer Institute for Translational Medicine and Pharmacology ITMP, 22525 Hamburg, Germany"},{"name":"Fraunhofer Cluster of Excellence for Immune-Mediated Diseases CIMD, 22525 Hamburg, Germany"}]},{"given":"Irini","family":"Fragiadaki","sequence":"additional","affiliation":[{"name":"Department of Clinical Microbiology and Microbial Pathogenesis, Faculty of Medicine, University of Crete, 70013 Heraklion, Greece"}]},{"given":"Effie","family":"Scoulica","sequence":"additional","affiliation":[{"name":"Department of Clinical Microbiology and Microbial Pathogenesis, Faculty of Medicine, University of Crete, 70013 Heraklion, Greece"}]},{"given":"Joachim","family":"Clos","sequence":"additional","affiliation":[{"name":"Bernhard Nocht Institute for Tropical Medicine, 20359 Hamburg, Germany"}]},{"ORCID":"https:\/\/orcid.org\/0000-0003-2543-1643","authenticated-orcid":false,"given":"Sheraz","family":"Gul","sequence":"additional","affiliation":[{"name":"Fraunhofer Institute for Translational Medicine and Pharmacology ITMP, 22525 Hamburg, Germany"},{"name":"Fraunhofer Cluster of Excellence for Immune-Mediated Diseases CIMD, 22525 Hamburg, Germany"}]},{"ORCID":"https:\/\/orcid.org\/0000-0002-0443-5402","authenticated-orcid":false,"given":"Maria Paola","family":"Costi","sequence":"additional","affiliation":[{"name":"Department of Pharmacy, Universit\u00e0 degli Studi di Modena e Reggio Emilia, 41125 Modena, Italy"}]},{"given":"Wanderley","family":"de Souza","sequence":"additional","affiliation":[{"name":"Instituto Nacional de Ci\u00eancia e Tecnologia em Biologia Estrutural e Bioimagens, Universidade Federal do Rio de Janeiro, Rio de Janeiro 21941-902, Brazil"},{"name":"Instituto de Biof\u00edsica Carlos Chagas Filho, Universidade Federal do Rio de Janeiro, Ilha do Fund\u00e3o, Rio Janeiro 21941-902, Brazil"}]},{"given":"Kyriakos C.","family":"Prousis","sequence":"additional","affiliation":[{"name":"National Hellenic Research Foundation, Institute of Chemical Biology, 11653 Athens, Greece"}]},{"ORCID":"https:\/\/orcid.org\/0000-0003-2392-6087","authenticated-orcid":false,"given":"Anabela","family":"Cordeiro da Silva","sequence":"additional","affiliation":[{"name":"i3S\u2013Instituto de Investiga\u00e7\u00e3o e Inova\u00e7\u00e3o em Sa\u00fade, Universidade do Porto, 4200-135 Porto, Portugal"},{"name":"Parasite Disease Group, IBMC-Instituto de Biologia Molecular e Celular, 4150-180 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