{"status":"ok","message-type":"work","message-version":"1.0.0","message":{"indexed":{"date-parts":[[2026,9,8]],"date-time":"2026-09-08T16:09:18Z","timestamp":1788883758485,"version":"build-2803163510"},"reference-count":87,"publisher":"Wiley","issue":"18","license":[{"start":{"date-parts":[[2026,1,20]],"date-time":"2026-01-20T00:00:00Z","timestamp":1768867200000},"content-version":"vor","delay-in-days":0,"URL":"http:\/\/creativecommons.org\/licenses\/by\/4.0\/"},{"start":{"date-parts":[[2026,1,20]],"date-time":"2026-01-20T00:00:00Z","timestamp":1768867200000},"content-version":"tdm","delay-in-days":0,"URL":"http:\/\/doi.wiley.com\/10.1002\/tdm_license_1.1"}],"funder":[{"DOI":"10.13039\/100000060","name":"National Institute of Allergy and Infectious Diseases","doi-asserted-by":"publisher","award":["R01 AI168918"],"award-info":[{"award-number":["R01 AI168918"]}],"id":[{"id":"10.13039\/100000060","id-type":"DOI","asserted-by":"publisher"}]}],"content-domain":{"domain":["advanced.onlinelibrary.wiley.com"],"crossmark-restriction":true},"short-container-title":["Advanced Science"],"published-print":{"date-parts":[[2026,3]]},"abstract":"<jats:title>ABSTRACT<\/jats:title>\n                  <jats:p>Self\u2010assembled peptide\u2010based biomaterials provide versatile platforms for biomedical uses, featuring customizable physicochemical properties, biocompatibility, and dynamic capabilities. This self\u2010assembly process is primarily dictated by primary sequence features, such as hydrophobicity, length, and charge, leading to the formation of fibrils and hydrogels. Amphipathic peptides, with alternating polar and hydrophobic residues, are especially effective in forming supramolecular nanofibers stabilized by \u03c0\u2013\u03c0 interactions and hydrogen bonds. Chemical modifications on aromatic side chains are promising for controlling assembly morphology, stability, and biological activity. However, the influence of these substituents on peptide packing and immunogenicity remains relatively unexplored. Herein, we examine the effect of substituents on benzyl groups attached to short amphipathic peptides. By introducing different electron\u2010donating and withdrawing groups at the para\u2010position of benzyl rings and modifying the chain length connecting the backbone to the aromatic moiety, we observe notable effects on fibril formation, molecular packing, and immunogenicity both in vitro and in vivo. Our results show that subtle chemical modifications are practical tools for designing tailored peptide nanomaterials with promising potential in vaccine delivery, tissue engineering, and regenerative medicine.<\/jats:p>","DOI":"10.1002\/advs.202518567","type":"journal-article","created":{"date-parts":[[2026,1,21]],"date-time":"2026-01-21T06:15:51Z","timestamp":1768976151000},"update-policy":"https:\/\/doi.org\/10.1002\/crossmark_policy","source":"Crossref","is-referenced-by-count":3,"title":["Substituent\u2010Based Modulation of Self\u2010Assembly and Immunogenicity of Amphipathic Peptides"],"prefix":"10.1002","volume":"13","author":[{"ORCID":"https:\/\/orcid.org\/0000-0003-0641-0935","authenticated-orcid":false,"given":"Anirban","family":"Das","sequence":"first","affiliation":[{"name":"Department of Biomedical Engineering Washington University in St. Louis  St. Louis Missouri USA"},{"name":"Department of Chemistry Washington University in St. Louis  St. Louis Missouri USA"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"ORCID":"https:\/\/orcid.org\/0000-0002-2991-3685","authenticated-orcid":false,"given":"Ushasi","family":"Pramanik","sequence":"additional","affiliation":[{"name":"Department of Biomedical Engineering Washington University in St. Louis  St. Louis Missouri USA"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Elise M.","family":"Brown","sequence":"additional","affiliation":[{"name":"Department of Biomedical Engineering Washington University in St. Louis  St. Louis Missouri USA"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Chih\u2010Yun","family":"Liu","sequence":"additional","affiliation":[{"name":"Department of Biomedical Engineering Washington University in St. Louis  St. Louis Missouri USA"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Huan","family":"Gong","sequence":"additional","affiliation":[{"name":"Department of Pharmaceutical Chemistry The University of Kansas  Lawrence Kansas USA"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Jonathan","family":"Fascetti","sequence":"additional","affiliation":[{"name":"Department of Biomedical Engineering Washington University in St. Louis  St. Louis Missouri USA"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Mark","family":"Gibson","sequence":"additional","affiliation":[{"name":"Department of Biomedical Engineering Washington University in St. Louis  St. Louis Missouri USA"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Samuel","family":"Stealey","sequence":"additional","affiliation":[{"name":"Department of Biomedical Engineering Saint Louis University  St. Louis Missouri USA"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Silviya P.","family":"Zustiak","sequence":"additional","affiliation":[{"name":"Department of Biomedical Engineering Saint Louis University  St. Louis Missouri USA"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Cory","family":"Berkland","sequence":"additional","affiliation":[{"name":"Department of Biomedical Engineering Washington University in St. Louis  St. Louis Missouri USA"},{"name":"Department of Chemistry Washington University in St. Louis  St. Louis Missouri USA"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"ORCID":"https:\/\/orcid.org\/0000-0002-1102-8602","authenticated-orcid":false,"given":"Piyoosh","family":"Sharma","sequence":"additional","affiliation":[{"name":"Department of Biomedical Engineering Washington University in St. Louis  St. Louis Missouri USA"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Meredith E.","family":"Jackrel","sequence":"additional","affiliation":[{"name":"Department of Chemistry Washington University in St. Louis  St. Louis Missouri USA"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Mark A.","family":"White","sequence":"additional","affiliation":[{"name":"Sealy Center for Structural Biology and Molecular Biophysics &amp; Department of Biochemistry and Molecular Biology University of Texas Medical Branch  Galveston Texas USA"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"ORCID":"https:\/\/orcid.org\/0000-0002-7837-4980","authenticated-orcid":false,"given":"Jai S.","family":"Rudra","sequence":"additional","affiliation":[{"name":"Department of Biomedical Engineering Washington University in St. Louis  St. Louis Missouri USA"}],"role":[{"vocabulary":"crossref","role":"author"}]}],"member":"311","published-online":{"date-parts":[[2026,1,20]]},"reference":[{"key":"e_1_2_9_2_1","doi-asserted-by":"publisher","DOI":"10.1016\/j.bioactmat.2021.09.029"},{"key":"e_1_2_9_3_1","doi-asserted-by":"publisher","DOI":"10.1021\/jacs.4c06447"},{"key":"e_1_2_9_4_1","doi-asserted-by":"publisher","DOI":"10.1016\/j.biomaterials.2021.120825"},{"key":"e_1_2_9_5_1","doi-asserted-by":"publisher","DOI":"10.1021\/acs.langmuir.5b03227"},{"key":"e_1_2_9_6_1","doi-asserted-by":"publisher","DOI":"10.1039\/C6CC09888F"},{"key":"e_1_2_9_7_1","doi-asserted-by":"publisher","DOI":"10.1039\/D4SM00117F"},{"key":"e_1_2_9_8_1","doi-asserted-by":"publisher","DOI":"10.1016\/j.actbio.2023.08.015"},{"key":"e_1_2_9_9_1","doi-asserted-by":"publisher","DOI":"10.1038\/nmat4474"},{"key":"e_1_2_9_10_1","doi-asserted-by":"publisher","DOI":"10.1126\/sciadv.abf7668"},{"key":"e_1_2_9_11_1","doi-asserted-by":"publisher","DOI":"10.1126\/science.1082387"},{"key":"e_1_2_9_12_1","doi-asserted-by":"publisher","DOI":"10.1038\/369301a0"},{"key":"e_1_2_9_13_1","doi-asserted-by":"publisher","DOI":"10.1002\/adma.200401849"},{"key":"e_1_2_9_14_1","doi-asserted-by":"publisher","DOI":"10.1021\/acsomega.7b01871"},{"key":"e_1_2_9_15_1","doi-asserted-by":"publisher","DOI":"10.1021\/jacs.9b09755"},{"key":"e_1_2_9_16_1","doi-asserted-by":"publisher","DOI":"10.1039\/b700434f"},{"key":"e_1_2_9_17_1","doi-asserted-by":"publisher","DOI":"10.1021\/nl015697g"},{"key":"e_1_2_9_18_1","doi-asserted-by":"publisher","DOI":"10.1039\/c0sm01218a"},{"key":"e_1_2_9_19_1","doi-asserted-by":"publisher","DOI":"10.1002\/bip.22058"},{"key":"e_1_2_9_20_1","doi-asserted-by":"publisher","DOI":"10.1021\/bm400876s"},{"key":"e_1_2_9_21_1","doi-asserted-by":"publisher","DOI":"10.1021\/ja9088764"},{"key":"e_1_2_9_22_1","doi-asserted-by":"publisher","DOI":"10.1002\/bip.21328"},{"key":"e_1_2_9_23_1","doi-asserted-by":"publisher","DOI":"10.1016\/j.ccr.2020.213242"},{"key":"e_1_2_9_24_1","doi-asserted-by":"publisher","DOI":"10.1021\/cr3002824"},{"key":"e_1_2_9_25_1","doi-asserted-by":"publisher","DOI":"10.1038\/s41467-024-54391-y"},{"key":"e_1_2_9_26_1","doi-asserted-by":"publisher","DOI":"10.1039\/B208871A"},{"key":"e_1_2_9_27_1","doi-asserted-by":"publisher","DOI":"10.1021\/ja802849j"},{"key":"e_1_2_9_28_1","doi-asserted-by":"publisher","DOI":"10.1039\/c2sc20045g"},{"key":"e_1_2_9_29_1","doi-asserted-by":"publisher","DOI":"10.1038\/s41428-019-0301-5"},{"key":"e_1_2_9_30_1","doi-asserted-by":"publisher","DOI":"10.1002\/adma.200501765"},{"key":"e_1_2_9_31_1","doi-asserted-by":"publisher","DOI":"10.1039\/C1SM06929B"},{"key":"e_1_2_9_32_1","doi-asserted-by":"publisher","DOI":"10.1039\/C7NR03263C"},{"key":"e_1_2_9_33_1","doi-asserted-by":"publisher","DOI":"10.1002\/psc.3227"},{"key":"e_1_2_9_34_1","doi-asserted-by":"publisher","DOI":"10.1039\/D5NR01182E"},{"key":"e_1_2_9_35_1","doi-asserted-by":"publisher","DOI":"10.1039\/D1MA00455G"},{"key":"e_1_2_9_36_1","doi-asserted-by":"publisher","DOI":"10.1016\/j.matt.2021.06.037"},{"key":"e_1_2_9_37_1","doi-asserted-by":"publisher","DOI":"10.1063\/1.1524618"},{"key":"e_1_2_9_38_1","doi-asserted-by":"publisher","DOI":"10.1002\/chem.202404603"},{"key":"e_1_2_9_39_1","doi-asserted-by":"publisher","DOI":"10.1039\/D5SC01163A"},{"key":"e_1_2_9_40_1","doi-asserted-by":"publisher","DOI":"10.1016\/S0040-4020(02)01362-5"},{"key":"e_1_2_9_41_1","doi-asserted-by":"publisher","DOI":"10.1016\/j.jsb.2007.06.004"},{"key":"e_1_2_9_42_1","doi-asserted-by":"publisher","DOI":"10.1021\/acs.analchem.0c00379"},{"key":"e_1_2_9_43_1","doi-asserted-by":"publisher","DOI":"10.1002\/cphc.202200155"},{"key":"e_1_2_9_44_1","doi-asserted-by":"publisher","DOI":"10.1039\/D5RA03251B"},{"key":"e_1_2_9_45_1","doi-asserted-by":"publisher","DOI":"10.1016\/j.actbio.2021.05.003"},{"key":"e_1_2_9_46_1","doi-asserted-by":"publisher","DOI":"10.1038\/s41541-022-00466-0"},{"key":"e_1_2_9_47_1","doi-asserted-by":"publisher","DOI":"10.1039\/D0BM00521E"},{"key":"e_1_2_9_48_1","doi-asserted-by":"publisher","DOI":"10.1126\/science.1227157"},{"key":"e_1_2_9_49_1","doi-asserted-by":"publisher","DOI":"10.1021\/acschemneuro.5b00345"},{"key":"e_1_2_9_50_1","doi-asserted-by":"publisher","DOI":"10.1021\/acsbiomaterials.5b00139"},{"key":"e_1_2_9_51_1","doi-asserted-by":"publisher","DOI":"10.1038\/s41598-018-31089-y"},{"key":"e_1_2_9_52_1","doi-asserted-by":"publisher","DOI":"10.1186\/s12951-022-01545-z"},{"key":"e_1_2_9_53_1","doi-asserted-by":"publisher","DOI":"10.1021\/acsnano.6b03409"},{"key":"e_1_2_9_54_1","doi-asserted-by":"publisher","DOI":"10.1016\/j.biomaterials.2010.07.068"},{"key":"e_1_2_9_55_1","doi-asserted-by":"publisher","DOI":"10.1126\/sciadv.abm7833"},{"key":"e_1_2_9_56_1","doi-asserted-by":"publisher","DOI":"10.1039\/D4CP02889A"},{"key":"e_1_2_9_57_1","doi-asserted-by":"publisher","DOI":"10.1039\/D3CY00758H"},{"key":"e_1_2_9_58_1","doi-asserted-by":"publisher","DOI":"10.1021\/acs.jpca.6b03119"},{"key":"e_1_2_9_59_1","doi-asserted-by":"publisher","DOI":"10.1039\/C9CC10079B"},{"key":"e_1_2_9_60_1","doi-asserted-by":"publisher","DOI":"10.1021\/acs.jpcb.7b10233"},{"key":"e_1_2_9_61_1","doi-asserted-by":"publisher","DOI":"10.1016\/j.bbamem.2012.03.001"},{"key":"e_1_2_9_62_1","doi-asserted-by":"publisher","DOI":"10.1007\/s11224-016-0825-7"},{"key":"e_1_2_9_63_1","doi-asserted-by":"publisher","DOI":"10.1039\/C8SM02430H"},{"key":"e_1_2_9_64_1","doi-asserted-by":"publisher","DOI":"10.1021\/acs.jcim.6b00761"},{"key":"e_1_2_9_65_1","doi-asserted-by":"publisher","DOI":"10.1074\/jbc.M112.362921"},{"key":"e_1_2_9_66_1","doi-asserted-by":"publisher","DOI":"10.1021\/acs.langmuir.4c03936"},{"key":"e_1_2_9_67_1","doi-asserted-by":"publisher","DOI":"10.1021\/acsnano.0c06041"},{"key":"e_1_2_9_68_1","doi-asserted-by":"publisher","DOI":"10.1039\/c0sm00018c"},{"key":"e_1_2_9_69_1","doi-asserted-by":"publisher","DOI":"10.1002\/adhm.202404795"},{"key":"e_1_2_9_70_1","doi-asserted-by":"publisher","DOI":"10.1016\/j.addr.2021.114022"},{"key":"e_1_2_9_71_1","doi-asserted-by":"publisher","DOI":"10.1002\/adma.202003310"},{"key":"e_1_2_9_72_1","doi-asserted-by":"publisher","DOI":"10.3389\/fimmu.2014.00520"},{"key":"e_1_2_9_73_1","doi-asserted-by":"publisher","DOI":"10.1073\/pnas.1309613110"},{"key":"e_1_2_9_74_1","doi-asserted-by":"publisher","DOI":"10.3390\/ijms22094828"},{"key":"e_1_2_9_75_1","doi-asserted-by":"publisher","DOI":"10.1039\/D1SC06562A"},{"key":"e_1_2_9_76_1","doi-asserted-by":"publisher","DOI":"10.1021\/acs.chemrev.0c00690"},{"key":"e_1_2_9_77_1","doi-asserted-by":"publisher","DOI":"10.1073\/pnas.1509313112"},{"key":"e_1_2_9_78_1","doi-asserted-by":"publisher","DOI":"10.1016\/j.bbabio.2007.06.004"},{"key":"e_1_2_9_79_1","doi-asserted-by":"publisher","DOI":"10.3109\/10409239509085140"},{"key":"e_1_2_9_80_1","doi-asserted-by":"publisher","DOI":"10.1021\/bi00465a022"},{"key":"e_1_2_9_81_1","doi-asserted-by":"publisher","DOI":"10.1073\/pnas.1500851112"},{"key":"e_1_2_9_82_1","doi-asserted-by":"publisher","DOI":"10.1107\/S1600576720013412"},{"key":"e_1_2_9_83_1","doi-asserted-by":"publisher","DOI":"10.1111\/1468-0262.00124"},{"key":"e_1_2_9_84_1","doi-asserted-by":"publisher","DOI":"10.1107\/S1600576721006877"},{"key":"e_1_2_9_85_1","doi-asserted-by":"publisher","DOI":"10.1073\/pnas.1411649111"},{"key":"e_1_2_9_86_1","doi-asserted-by":"publisher","DOI":"10.4049\/jimmunol.153.11.4925"},{"key":"e_1_2_9_87_1","doi-asserted-by":"publisher","DOI":"10.1007\/s13346-025-01798-9"},{"key":"e_1_2_9_88_1","doi-asserted-by":"publisher","DOI":"10.1093\/nar\/gkac194"}],"container-title":["Advanced Science"],"original-title":[],"language":"en","link":[{"URL":"https:\/\/advanced.onlinelibrary.wiley.com\/doi\/pdf\/10.1002\/advs.202518567","content-type":"application\/pdf","content-version":"vor","intended-application":"text-mining"},{"URL":"https:\/\/advanced.onlinelibrary.wiley.com\/doi\/full-xml\/10.1002\/advs.202518567","content-type":"application\/xml","content-version":"vor","intended-application":"text-mining"},{"URL":"https:\/\/advanced.onlinelibrary.wiley.com\/doi\/pdf\/10.1002\/advs.202518567","content-type":"unspecified","content-version":"vor","intended-application":"similarity-checking"}],"deposited":{"date-parts":[[2026,3,27]],"date-time":"2026-03-27T08:07:00Z","timestamp":1774598820000},"score":1,"resource":{"primary":{"URL":"https:\/\/advanced.onlinelibrary.wiley.com\/doi\/10.1002\/advs.202518567"}},"subtitle":[],"short-title":[],"issued":{"date-parts":[[2026,1,20]]},"references-count":87,"journal-issue":{"issue":"18","published-print":{"date-parts":[[2026,3]]}},"alternative-id":["10.1002\/advs.202518567"],"URL":"https:\/\/doi.org\/10.1002\/advs.202518567","archive":["Portico"],"relation":{},"ISSN":["2198-3844","2198-3844"],"issn-type":[{"value":"2198-3844","type":"print"},{"value":"2198-3844","type":"electronic"}],"subject":[],"published":{"date-parts":[[2026,1,20]]},"assertion":[{"value":"2025-09-21","order":0,"name":"received","label":"Received","group":{"name":"publication_history","label":"Publication History"}},{"value":"2026-01-13","order":2,"name":"accepted","label":"Accepted","group":{"name":"publication_history","label":"Publication History"}},{"value":"2026-01-20","order":3,"name":"published","label":"Published","group":{"name":"publication_history","label":"Publication History"}}],"article-number":"e18567"}}