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Lengthening the alkyl spacer between the pentylpyridinium headgroups from 12 to 16 methylene units resulted in increased antifungal activity against <jats:italic>C.\u2005neoformans<\/jats:italic> and <jats:italic>C.\u2005albicans<\/jats:italic>, but also resulted in increased hemolytic activity and cytotoxicity against mammalian cells. However, inclusion of an <jats:italic>ortho<\/jats:italic>\u2010substituted benzene ring in the centre of the alkyl spacer resulted in decreased cytotoxicity and hemolytic activity, while maintaining antifungal potency. Replacement of the alkyl and aromatic\u2010containing spacers by more hydrophilic ethylene glycol groups resulted in a loss of antifungal activity. Some of the compounds inhibited fungal PLB1 activity, but the low correlation of this inhibition with antifungal potency indicates PLB1 inhibition is unlikely to be the predominant mode of antifungal action of this class of compounds, with preliminary studies suggesting they may act via disruption of fungal mitochondrial function.<\/jats:p>","DOI":"10.1002\/cmdc.201800331","type":"journal-article","created":{"date-parts":[[2018,5,21]],"date-time":"2018-05-21T01:58:50Z","timestamp":1526867930000},"page":"1421-1436","update-policy":"https:\/\/doi.org\/10.1002\/crossmark_policy","source":"Crossref","is-referenced-by-count":19,"title":["Synthesis and Evaluation of a Series of Bis(pentylpyridinium) Compounds as Antifungal Agents"],"prefix":"10.1002","volume":"13","author":[{"given":"Daniel","family":"Obando","sequence":"first","affiliation":[{"name":"School of Chemistry The University of Sydney  2006 NSW Australia"}],"role":[{"role":"author","vocabulary":"crossref"}]},{"given":"Yasuko","family":"Koda","sequence":"additional","affiliation":[{"name":"School of Chemistry The University of Sydney  2006 NSW Australia"},{"name":"The University of Sydney Marie Bashir Institute for Infectious Diseases and Biosecurity Centre for Infectious Diseases and Microbiology, Westmead Institute for Medical Research  Westmead 2145 NSW Australia"}],"role":[{"role":"author","vocabulary":"crossref"}]},{"given":"Namfon","family":"Pantarat","sequence":"additional","affiliation":[{"name":"The University of Sydney Marie Bashir Institute for Infectious Diseases and Biosecurity Centre for Infectious Diseases and Microbiology, Westmead Institute for Medical Research  Westmead 2145 NSW Australia"}],"role":[{"role":"author","vocabulary":"crossref"}]},{"given":"Sophie","family":"Lev","sequence":"additional","affiliation":[{"name":"The University of Sydney Marie Bashir Institute for Infectious Diseases and Biosecurity Centre for Infectious Diseases and Microbiology, Westmead Institute for Medical Research  Westmead 2145 NSW Australia"}],"role":[{"role":"author","vocabulary":"crossref"}]},{"given":"Xiaoming","family":"Zuo","sequence":"additional","affiliation":[{"name":"The University of Sydney Marie Bashir Institute for Infectious Diseases and Biosecurity Centre for Infectious Diseases and Microbiology, Westmead Institute for Medical Research  Westmead 2145 NSW Australia"}],"role":[{"role":"author","vocabulary":"crossref"}]},{"given":"Johanes","family":"Bijosono\u2005Oei","sequence":"additional","affiliation":[{"name":"The University of Sydney Marie Bashir Institute for Infectious Diseases and Biosecurity Centre for Infectious Diseases and Microbiology, Westmead Institute for Medical Research  Westmead 2145 NSW Australia"}],"role":[{"role":"author","vocabulary":"crossref"}]},{"given":"Fred","family":"Widmer","sequence":"additional","affiliation":[{"name":"The University of Sydney Marie Bashir Institute for Infectious Diseases and Biosecurity Centre for Infectious Diseases and Microbiology, Westmead Institute for Medical Research  Westmead 2145 NSW Australia"}],"role":[{"role":"author","vocabulary":"crossref"}]},{"given":"Julianne T.","family":"Djordjevic","sequence":"additional","affiliation":[{"name":"The University of Sydney Marie Bashir Institute for Infectious Diseases and Biosecurity Centre for Infectious Diseases and Microbiology, Westmead Institute for Medical Research  Westmead 2145 NSW Australia"}],"role":[{"role":"author","vocabulary":"crossref"}]},{"given":"Tania C.","family":"Sorrell","sequence":"additional","affiliation":[{"name":"The University of Sydney Marie Bashir Institute for Infectious Diseases and Biosecurity Centre for Infectious Diseases and Microbiology, Westmead Institute for Medical Research  Westmead 2145 NSW Australia"}],"role":[{"role":"author","vocabulary":"crossref"}]},{"ORCID":"https:\/\/orcid.org\/0000-0003-1100-4544","authenticated-orcid":false,"given":"Katrina A.","family":"Jolliffe","sequence":"additional","affiliation":[{"name":"School of Chemistry The University of Sydney  2006 NSW Australia"}],"role":[{"role":"author","vocabulary":"crossref"}]}],"member":"311","published-online":{"date-parts":[[2018,6,19]]},"reference":[{"key":"e_1_2_7_1_1","unstructured":"\u00a0"},{"key":"e_1_2_7_2_2","first-page":"16","volume":"51","author":"Chakrabati A.","year":"2005","journal-title":"J. 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