{"status":"ok","message-type":"work","message-version":"1.0.0","message":{"indexed":{"date-parts":[[2026,10,1]],"date-time":"2026-10-01T00:59:09Z","timestamp":1790816349894,"version":"4.1.0"},"reference-count":70,"publisher":"Wiley","license":[{"start":{"date-parts":[[2026,9,30]],"date-time":"2026-09-30T00:00:00Z","timestamp":1790726400000},"content-version":"vor","delay-in-days":0,"URL":"http:\/\/onlinelibrary.wiley.com\/termsAndConditions#vor"},{"start":{"date-parts":[[2026,9,30]],"date-time":"2026-09-30T00:00:00Z","timestamp":1790726400000},"content-version":"tdm","delay-in-days":0,"URL":"http:\/\/doi.wiley.com\/10.1002\/tdm_license_1.1"}],"content-domain":{"domain":["onlinelibrary.wiley.com"],"crossmark-restriction":true},"short-container-title":["Angew Chem Int Ed"],"abstract":"<jats:title>ABSTRACT<\/jats:title>\n                  <jats:p>Lipid\u2010bound nanoparticles (LBNs), including extracellular vesicles and lipoproteins, are characterized by distinct membrane architectures that modulate biological functions. However, optical probes capable of directly distinguishing lipid bilayers from monolayers remain limited. Here, we establish conjugated oligoelectrolytes (COEs) as molecular transducers of lipid membrane architecture capable of converting differences in supramolecular organization into distinct optical signatures. Using model systems, we show that COEs intercalate across lipid bilayers but preferentially adsorb onto lipid monolayers. Employing COE\u2010KP, a probe sensitive to water contact, enabled direct interrogation of membrane microenvironments. Fluorescence lifetime imaging microscopy (FLIM) revealed that COE\u2010KP exhibits shorter fluorescence lifetimes when associated with lipid monolayers relative to bilayers. Atomistic molecular dynamics simulations corroborate these observations by revealing distinct insertion energetics at monolayer and bilayer interfaces. Guided by this mechanistic framework, we applied COEs in nano\u2010flow cytometry to discriminate red blood cell\u2010derived extracellular vesicles from very\u2010low\u2010density lipoproteins. These results demonstrate that COEs adopt distinct binding orientations depending on lipid organization and highlight their utility as optical probes for analyzing LBNs. Beyond enabling analysis of biologically relevant LBNs, this work establishes a general molecular framework linking membrane architecture to probe orientation and photophysics, providing a strategy for designing optical reporters that decode membrane organization.<\/jats:p>","DOI":"10.1002\/anie.9487218","type":"journal-article","created":{"date-parts":[[2026,10,1]],"date-time":"2026-10-01T00:02:09Z","timestamp":1790812929000},"update-policy":"https:\/\/doi.org\/10.1002\/crossmark_policy","source":"Crossref","is-referenced-by-count":0,"title":["Membrane Architecture\u2010Dependent Photophysics of Conjugated Oligoelectrolytes Distinguishes Extracellular Vesicles From Lipoproteins"],"prefix":"10.1002","author":[{"ORCID":"https:\/\/orcid.org\/0009-0007-0796-5891","authenticated-orcid":false,"given":"Sean Carey","family":"Winoto","sequence":"first","affiliation":[{"name":"Department of Chemistry National University of Singapore  Singapore Singapore"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"ORCID":"https:\/\/orcid.org\/0009-0001-6475-3971","authenticated-orcid":false,"given":"Samuel J. W.","family":"Chan","sequence":"additional","affiliation":[{"name":"Institute for Functional Intelligent Materials National University of Singapore  Singapore Singapore"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Ji\u2010Yu","family":"Zhu","sequence":"additional","affiliation":[{"name":"Institute for Digital Molecular Analytics and Science Nanyang Technological University Singapore Singapore"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"ORCID":"https:\/\/orcid.org\/0000-0001-8030-0000","authenticated-orcid":false,"given":"Mohammad Firdaus","family":"Akmal","sequence":"additional","affiliation":[{"name":"Department of Chemistry National University of Singapore  Singapore Singapore"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Chuan Xiang Alvin","family":"Tan","sequence":"additional","affiliation":[{"name":"Institute for Functional Intelligent Materials National University of Singapore  Singapore Singapore"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Fernando","family":"Lopez\u2010Garcia","sequence":"additional","affiliation":[{"name":"Institute for Functional Intelligent Materials National University of Singapore  Singapore Singapore"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"ORCID":"https:\/\/orcid.org\/0000-0003-2162-1220","authenticated-orcid":false,"given":"Ming Wah","family":"Wong","sequence":"additional","affiliation":[{"name":"Department of Chemistry National University of Singapore  Singapore Singapore"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"ORCID":"https:\/\/orcid.org\/0000-0002-6077-1566","authenticated-orcid":false,"given":"Minh T. N.","family":"Le","sequence":"additional","affiliation":[{"name":"Department of Pharmacology Yong Loo Lin School of Medicine National University of Singapore  Singapore Singapore"},{"name":"Institute for Digital Medicine Yong Loo Lin School of Medicine National University of Singapore  Singapore Singapore"},{"name":"Agency for Science Technology and Research Institute of Molecular and Cell Biology  Singapore Singapore"},{"name":"Department of Surgery Yong Loo Lin School of Medicine National University of Singapore  Singapore Singapore"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"ORCID":"https:\/\/orcid.org\/0000-0002-2537-0310","authenticated-orcid":false,"given":"Guillermo C.","family":"Bazan","sequence":"additional","affiliation":[{"name":"Department of Chemistry National University of Singapore  Singapore Singapore"},{"name":"Institute for Functional Intelligent Materials National University of Singapore  Singapore Singapore"},{"name":"Institute for Digital Molecular Analytics and Science Nanyang Technological University Singapore Singapore"},{"name":"Department of Chemical and Biomolecular Engineering National University of Singapore  Singapore Singapore"}],"role":[{"vocabulary":"crossref","role":"author"}]}],"member":"311","published-online":{"date-parts":[[2026,9,30]]},"reference":[{"key":"e_1_2_8_2_1","doi-asserted-by":"publisher","DOI":"10.3390\/cells13060495"},{"key":"e_1_2_8_3_1","first-page":"435","article-title":"Lipid Droplets and the Management of Cellular Stress","volume":"92","author":"Jarc E.","year":"2019","journal-title":"Yale Journal of Biology and Medicine"},{"key":"e_1_2_8_4_1","doi-asserted-by":"publisher","DOI":"10.1007\/s11060\u2010013\u20101084\u20108"},{"key":"e_1_2_8_5_1","doi-asserted-by":"publisher","DOI":"10.1002\/ange.202305668"},{"key":"e_1_2_8_6_1","doi-asserted-by":"publisher","DOI":"10.1016\/j.tem.2024.07.015"},{"key":"e_1_2_8_7_1","doi-asserted-by":"publisher","DOI":"10.1002\/advs.202514290"},{"key":"e_1_2_8_8_1","doi-asserted-by":"publisher","DOI":"10.1126\/sciadv.adw0730"},{"key":"e_1_2_8_9_1","doi-asserted-by":"publisher","DOI":"10.1016\/j.copbio.2021.09.016"},{"key":"e_1_2_8_10_1","doi-asserted-by":"publisher","DOI":"10.1002\/anie.202417165"},{"key":"e_1_2_8_11_1","doi-asserted-by":"publisher","DOI":"10.1016\/j.jprot.2010.06.006"},{"key":"e_1_2_8_12_1","doi-asserted-by":"publisher","DOI":"10.1016\/j.cell.2016.01.043"},{"key":"e_1_2_8_13_1","doi-asserted-by":"publisher","DOI":"10.3389\/fimmu.2021.566299"},{"key":"e_1_2_8_14_1","doi-asserted-by":"publisher","DOI":"10.1038\/nrneurol.2016.68"},{"key":"e_1_2_8_15_1","doi-asserted-by":"publisher","DOI":"10.1002\/anie.202506744"},{"key":"e_1_2_8_16_1","doi-asserted-by":"publisher","DOI":"10.1002\/anie.202207037"},{"key":"e_1_2_8_17_1","doi-asserted-by":"publisher","DOI":"10.1002\/smtd.202001131"},{"key":"e_1_2_8_18_1","doi-asserted-by":"publisher","DOI":"10.7150\/thno.39486"},{"key":"e_1_2_8_19_1","doi-asserted-by":"publisher","DOI":"10.1038\/nri3622"},{"key":"e_1_2_8_20_1","doi-asserted-by":"publisher","DOI":"10.1002\/anie.202404889"},{"key":"e_1_2_8_21_1","doi-asserted-by":"publisher","DOI":"10.1016\/j.nantod.2015.04.004"},{"key":"e_1_2_8_22_1","doi-asserted-by":"publisher","DOI":"10.3389\/fcell.2021.734720"},{"key":"e_1_2_8_23_1","doi-asserted-by":"publisher","DOI":"10.1161\/CIRCRESAHA.117.311767"},{"key":"e_1_2_8_24_1","doi-asserted-by":"publisher","DOI":"10.1021\/acs.accounts.7b00339"},{"key":"e_1_2_8_25_1","doi-asserted-by":"publisher","DOI":"10.1021\/acs.nanolett.3c03579"},{"key":"e_1_2_8_26_1","doi-asserted-by":"publisher","DOI":"10.3402\/jev.v3.23262"},{"key":"e_1_2_8_27_1","doi-asserted-by":"publisher","DOI":"10.1002\/jex2.100"},{"key":"e_1_2_8_28_1","doi-asserted-by":"publisher","DOI":"10.1002\/jev2.12200"},{"key":"e_1_2_8_29_1","doi-asserted-by":"publisher","DOI":"10.1021\/ja100351w"},{"key":"e_1_2_8_30_1","doi-asserted-by":"publisher","DOI":"10.1016\/j.cbpa.2022.102161"},{"key":"e_1_2_8_31_1","doi-asserted-by":"publisher","DOI":"10.1016\/j.chembiol.2019.01.009"},{"key":"e_1_2_8_32_1","doi-asserted-by":"publisher","DOI":"10.1021\/acs.analchem.2c02312"},{"key":"e_1_2_8_33_1","doi-asserted-by":"publisher","DOI":"10.1021\/acs.analchem.8b00590"},{"key":"e_1_2_8_34_1","doi-asserted-by":"publisher","DOI":"10.1021\/la501226v"},{"key":"e_1_2_8_35_1","doi-asserted-by":"publisher","DOI":"10.1021\/acs.analchem.1c05268"},{"key":"e_1_2_8_36_1","doi-asserted-by":"publisher","DOI":"10.1002\/ange.202217868"},{"key":"e_1_2_8_37_1","doi-asserted-by":"publisher","DOI":"10.1002\/ange.202016105"},{"key":"e_1_2_8_38_1","article-title":"Monitoring Changes in Membrane Polarity, Membrane Integrity, and Intracellular Ion Concentrations in Streptococcus pneumoniae Using Fluorescent Dyes","volume":"84","author":"Clementi E. 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