{"status":"ok","message-type":"work","message-version":"1.0.0","message":{"indexed":{"date-parts":[[2026,10,5]],"date-time":"2026-10-05T20:06:47Z","timestamp":1791230807435,"version":"4.1.0"},"reference-count":66,"publisher":"Wiley","issue":"5","license":[{"start":{"date-parts":[[2015,9,24]],"date-time":"2015-09-24T00:00:00Z","timestamp":1443052800000},"content-version":"vor","delay-in-days":23,"URL":"http:\/\/onlinelibrary.wiley.com\/termsAndConditions#vor"}],"content-domain":{"domain":[],"crossmark-restriction":false},"short-container-title":["Biopolymers"],"published-print":{"date-parts":[[2015,9]]},"abstract":"<jats:title>ABSTRACT<\/jats:title><jats:p>The extracellular deposition of insoluble amyloid fibrils resulting from the aggregation of the amyloid\u2010\u03b2 (A\u03b2) is a pathological feature of neuronal loss in Alzheimer's disease (AD). Numerous small molecules have been reported to interfere with the process of A\u03b2 aggregation. Compounds containing aromatic structures, hydrophobic amino acids and\/or the \u03b1\u2010aminoisobutyric acid (Aib) as \u03b2\u2010sheet breaker elements have been reported to be effective inhibitors of A\u03b2 aggregation. We synthesized two peptides, one containing the Aib amino acid and the other including its trifluoromethylated analog (R)\u2010\u03b1\u2010Trifluoromethylalanine ((R)\u2010Tfm\u2010Alanine) and we evaluated the impact of these peptides on A\u03b2 amyloid formation. The compounds were tested by standard methods such as thioflavin\u2010T fluorescence spectroscopy and transmission electron microscopy but also by circular dichroism, liquid state nuclear magnetic resonance (NMR) and NMR saturation transfer difference (STD) experiments to further characterize the effect of the two molecules on A\u03b2 structure and on the kinetics of depletion of monomeric, soluble A\u03b2. Our results demonstrate that the peptide containing Aib reduces the quantity of aggregates containing \u03b2\u2010sheet structure but slightly inhibits A\u03b2 fibril formation, while the molecule including the trifluoromethyl (Tfm) group slows down the kinetics of A\u03b2 fibril formation, delays the random coil to \u03b2\u2010sheet structure transition and induces a change in the oligomerization pathway. These results suggest that the hydrophobic Tfm group has a better affinity with A\u03b2 than the methyl groups of the Aib and that this Tfm group is effective and important in preventing the A\u03b2 aggregation. \u00a9 2015 Wiley Periodicals, Inc. Biopolymers (Pept Sci) 104: 601\u2013610, 2015.<\/jats:p>","DOI":"10.1002\/bip.22670","type":"journal-article","created":{"date-parts":[[2015,5,13]],"date-time":"2015-05-13T09:54:07Z","timestamp":1431510847000},"page":"601-610","source":"Crossref","is-referenced-by-count":22,"title":["(<i>R<\/i>)\u2010\u03b1\u2010trifluoromethylalanine containing short peptide in the inhibition of amyloid peptide fibrillation"],"prefix":"10.1002","volume":"104","author":[{"given":"Alexandra","family":"Botz","sequence":"first","affiliation":[{"name":"Sorbonne Universit\u00e9s, UPMC Univ Paris 06, Laboratoire des Biomol\u00e9cules 4 Place Jussieu F\u201075005 Paris France"},{"name":"Ecole Normale Sup\u00e9rieure\u2010PSL Research University, D\u00e9partement De Chimie 24 rue Lhomond F\u201075005 Paris France"},{"name":"CNRS, UMR 7203 Laboratoire Des Biomol\u00e9cules F\u201075005 Paris France"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Vincent","family":"Gasparik","sequence":"additional","affiliation":[{"name":"Laboratoire De Chimie Biologique, Universit\u00e9 De Cergy\u2010Pontoise EA 4505, 5 Mail Gay\u2010Lussac 95000 Cergy\u2010Pontoise France"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Emmanuelle","family":"Devillers","sequence":"additional","affiliation":[{"name":"Laboratoire De Chimie Biologique, Universit\u00e9 De Cergy\u2010Pontoise EA 4505, 5 Mail Gay\u2010Lussac 95000 Cergy\u2010Pontoise France"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Anais R. F.","family":"Hoffmann","sequence":"additional","affiliation":[{"name":"Sorbonne Universit\u00e9s, UPMC Univ Paris 06, Laboratoire des Biomol\u00e9cules 4 Place Jussieu F\u201075005 Paris France"},{"name":"Ecole Normale Sup\u00e9rieure\u2010PSL Research University, D\u00e9partement De Chimie 24 rue Lhomond F\u201075005 Paris France"},{"name":"CNRS, UMR 7203 Laboratoire Des Biomol\u00e9cules F\u201075005 Paris France"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Lucie","family":"Caillon","sequence":"additional","affiliation":[{"name":"Sorbonne Universit\u00e9s, UPMC Univ Paris 06, Laboratoire des Biomol\u00e9cules 4 Place Jussieu F\u201075005 Paris France"},{"name":"Ecole Normale Sup\u00e9rieure\u2010PSL Research University, D\u00e9partement De Chimie 24 rue Lhomond F\u201075005 Paris France"},{"name":"CNRS, UMR 7203 Laboratoire Des Biomol\u00e9cules F\u201075005 Paris France"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Evelyne","family":"Chelain","sequence":"additional","affiliation":[{"name":"Laboratoire De Chimie Biologique, Universit\u00e9 De Cergy\u2010Pontoise EA 4505, 5 Mail Gay\u2010Lussac 95000 Cergy\u2010Pontoise France"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Olivier","family":"Lequin","sequence":"additional","affiliation":[{"name":"Sorbonne Universit\u00e9s, UPMC Univ Paris 06, Laboratoire des Biomol\u00e9cules 4 Place Jussieu F\u201075005 Paris France"},{"name":"Ecole Normale Sup\u00e9rieure\u2010PSL Research University, D\u00e9partement De Chimie 24 rue Lhomond F\u201075005 Paris France"},{"name":"CNRS, UMR 7203 Laboratoire Des Biomol\u00e9cules F\u201075005 Paris France"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Thierry","family":"Brigaud","sequence":"additional","affiliation":[{"name":"Laboratoire De Chimie Biologique, Universit\u00e9 De Cergy\u2010Pontoise EA 4505, 5 Mail Gay\u2010Lussac 95000 Cergy\u2010Pontoise France"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Lucie","family":"Khemtemourian","sequence":"additional","affiliation":[{"name":"Sorbonne Universit\u00e9s, UPMC Univ Paris 06, Laboratoire des Biomol\u00e9cules 4 Place Jussieu F\u201075005 Paris France"},{"name":"Ecole Normale Sup\u00e9rieure\u2010PSL Research University, D\u00e9partement De Chimie 24 rue Lhomond F\u201075005 Paris France"},{"name":"CNRS, UMR 7203 Laboratoire Des Biomol\u00e9cules F\u201075005 Paris France"}],"role":[{"vocabulary":"crossref","role":"author"}]}],"member":"311","published-online":{"date-parts":[[2015,9,24]]},"reference":[{"key":"e_1_2_6_2_1","doi-asserted-by":"publisher","DOI":"10.1038\/nature02264"},{"key":"e_1_2_6_3_1","doi-asserted-by":"publisher","DOI":"10.1126\/science.1079469"},{"key":"e_1_2_6_4_1","doi-asserted-by":"publisher","DOI":"10.1111\/j.1471-4159.1993.tb09841.x"},{"key":"e_1_2_6_5_1","doi-asserted-by":"publisher","DOI":"10.1038\/361260a0"},{"key":"e_1_2_6_6_1","doi-asserted-by":"publisher","DOI":"10.1007\/s00702-006-0537-z"},{"key":"e_1_2_6_7_1","doi-asserted-by":"publisher","DOI":"10.1002\/1531-8249(199904)45:4<504::AID-ANA12>3.0.CO;2-9"},{"key":"e_1_2_6_8_1","doi-asserted-by":"publisher","DOI":"10.1016\/S0002-9440(10)65184-X"},{"key":"e_1_2_6_9_1","doi-asserted-by":"publisher","DOI":"10.1074\/jbc.M201750200"},{"key":"e_1_2_6_10_1","doi-asserted-by":"publisher","DOI":"10.1074\/jbc.M110.172411"},{"key":"e_1_2_6_11_1","doi-asserted-by":"publisher","DOI":"10.1016\/j.bbrc.2011.06.133"},{"key":"e_1_2_6_12_1","doi-asserted-by":"publisher","DOI":"10.1021\/bi051952q"},{"key":"e_1_2_6_13_1","doi-asserted-by":"publisher","DOI":"10.1021\/bi802046n"},{"key":"e_1_2_6_14_1","doi-asserted-by":"publisher","DOI":"10.1016\/S1074-5521(97)90255-6"},{"key":"e_1_2_6_15_1","doi-asserted-by":"publisher","DOI":"10.1016\/0092-8674(93)90635-4"},{"key":"e_1_2_6_16_1","doi-asserted-by":"publisher","DOI":"10.1126\/science.1566067"},{"key":"e_1_2_6_17_1","doi-asserted-by":"publisher","DOI":"10.1126\/science.1072994"},{"key":"e_1_2_6_18_1","doi-asserted-by":"publisher","DOI":"10.1074\/jbc.M110.172411"},{"key":"e_1_2_6_18_2","doi-asserted-by":"publisher","DOI":"10.1016\/j.jmb.2005.11.091"},{"key":"e_1_2_6_19_1","doi-asserted-by":"publisher","DOI":"10.1073\/pnas.0708354105"},{"key":"e_1_2_6_20_1","doi-asserted-by":"publisher","DOI":"10.1074\/jbc.M110.173856"},{"key":"e_1_2_6_21_1","doi-asserted-by":"publisher","DOI":"10.1002\/cmdc.200700140"},{"key":"e_1_2_6_21_2","doi-asserted-by":"publisher","DOI":"10.1016\/j.ejmech.2014.09.031"},{"key":"e_1_2_6_21_3","doi-asserted-by":"publisher","DOI":"10.1016\/j.ejmech.2011.10.008"},{"key":"e_1_2_6_22_1","doi-asserted-by":"publisher","DOI":"10.1074\/jbc.272.19.12601"},{"key":"e_1_2_6_23_1","doi-asserted-by":"publisher","DOI":"10.1021\/bi002734u"},{"key":"e_1_2_6_24_1","doi-asserted-by":"publisher","DOI":"10.1021\/bi0156254"},{"key":"e_1_2_6_25_1","doi-asserted-by":"publisher","DOI":"10.1021\/ja0600678"},{"key":"e_1_2_6_26_1","doi-asserted-by":"publisher","DOI":"10.1002\/anie.200802123"},{"key":"e_1_2_6_26_2","doi-asserted-by":"publisher","DOI":"10.1002\/anie.200353565"},{"key":"e_1_2_6_27_1","doi-asserted-by":"publisher","DOI":"10.1021\/bi002416v"},{"key":"e_1_2_6_28_1","doi-asserted-by":"publisher","DOI":"10.1038\/nm0798-822"},{"key":"e_1_2_6_29_1","doi-asserted-by":"publisher","DOI":"10.1016\/j.bbrc.2014.04.041"},{"key":"e_1_2_6_29_2","doi-asserted-by":"publisher","DOI":"10.1039\/C3CC48473D"},{"key":"e_1_2_6_29_3","doi-asserted-by":"publisher","DOI":"10.1002\/anie.201007824"},{"key":"e_1_2_6_29_4","first-page":"21990\u221221995","volume":"107","author":"Choi J. \u2010S.","year":"2010","journal-title":"Proc Natl Acad Sci U. S. A."},{"key":"e_1_2_6_30_1","doi-asserted-by":"publisher","DOI":"10.1002\/9781444312096"},{"key":"e_1_2_6_30_2","doi-asserted-by":"publisher","DOI":"10.1142\/p746"},{"key":"e_1_2_6_30_3","doi-asserted-by":"publisher","DOI":"10.1021\/cr4002879"},{"key":"e_1_2_6_31_1","doi-asserted-by":"publisher","DOI":"10.1039\/C1CS15241F"},{"key":"e_1_2_6_31_2","doi-asserted-by":"publisher","DOI":"10.1002\/(SICI)1099-1387(199705)3:3<157::AID-PSC94>3.0.CO;2-W"},{"key":"e_1_2_6_31_3","doi-asserted-by":"publisher","DOI":"10.1007\/s00726-014-1819-7"},{"key":"e_1_2_6_31_4","doi-asserted-by":"publisher","DOI":"10.1021\/ja075373f"},{"key":"e_1_2_6_32_1","doi-asserted-by":"publisher","DOI":"10.1016\/j.jfluchem.2004.09.014"},{"key":"e_1_2_6_32_2","doi-asserted-by":"publisher","DOI":"10.1039\/b405955g"},{"key":"e_1_2_6_32_3","doi-asserted-by":"publisher","DOI":"10.1021\/jp300284u"},{"key":"e_1_2_6_33_1","doi-asserted-by":"publisher","DOI":"10.1142\/9781848166363_0004"},{"key":"e_1_2_6_33_2","doi-asserted-by":"publisher","DOI":"10.1016\/j.drudis.2012.03.014"},{"key":"e_1_2_6_33_3","doi-asserted-by":"publisher","DOI":"10.1016\/S1359-6446(04)03161-7"},{"key":"e_1_2_6_34_1","doi-asserted-by":"publisher","DOI":"10.1021\/bi3012548"},{"key":"e_1_2_6_34_2","doi-asserted-by":"publisher","DOI":"10.1021\/bi400027y"},{"key":"e_1_2_6_35_1","doi-asserted-by":"publisher","DOI":"10.1021\/jo0607717"},{"key":"e_1_2_6_35_2","doi-asserted-by":"publisher","DOI":"10.1002\/ejoc.200900768"},{"key":"e_1_2_6_35_3","doi-asserted-by":"publisher","DOI":"10.1021\/ol062593"},{"key":"e_1_2_6_35_4","doi-asserted-by":"publisher","DOI":"10.1021\/ol8024567"},{"key":"e_1_2_6_36_1","doi-asserted-by":"publisher","DOI":"10.1016\/j.ejmech.2012.12.041"},{"key":"e_1_2_6_37_1","doi-asserted-by":"publisher","DOI":"10.1016\/S0076-6879(99)09020-5"},{"key":"e_1_2_6_38_1","doi-asserted-by":"publisher","DOI":"10.1002\/cbic.200700427"},{"key":"e_1_2_6_39_1","doi-asserted-by":"publisher","DOI":"10.1016\/j.bbamem.2013.05.014"},{"key":"e_1_2_6_40_1","first-page":"239","volume":"7","author":"Caillon L.","year":"2015","journal-title":"Mol Membr Biol"},{"key":"e_1_2_6_41_1","doi-asserted-by":"publisher","DOI":"10.1002\/anie.200390233"},{"key":"e_1_2_6_42_1","doi-asserted-by":"publisher","DOI":"10.2174\/157340708786305970"},{"key":"e_1_2_6_42_2","doi-asserted-by":"publisher","DOI":"10.1002\/cmdc.201100569"},{"key":"e_1_2_6_43_1","doi-asserted-by":"publisher","DOI":"10.1039\/C1CS15241F"},{"key":"e_1_2_6_44_1","doi-asserted-by":"publisher","DOI":"10.1039\/C3SC52932K"},{"key":"e_1_2_6_45_1","doi-asserted-by":"publisher","DOI":"10.1039\/C3TB21483D"},{"key":"e_1_2_6_46_1","doi-asserted-by":"publisher","DOI":"10.1007\/s00249-006-0111-5"}],"container-title":["Peptide Science"],"original-title":[],"language":"en","link":[{"URL":"https:\/\/api.wiley.com\/onlinelibrary\/tdm\/v1\/articles\/10.1002%2Fbip.22670","content-type":"unspecified","content-version":"vor","intended-application":"text-mining"},{"URL":"https:\/\/onlinelibrary.wiley.com\/doi\/pdf\/10.1002\/bip.22670","content-type":"unspecified","content-version":"vor","intended-application":"similarity-checking"}],"deposited":{"date-parts":[[2023,9,13]],"date-time":"2023-09-13T20:53:25Z","timestamp":1694638405000},"score":1,"resource":{"primary":{"URL":"https:\/\/onlinelibrary.wiley.com\/doi\/10.1002\/bip.22670"}},"subtitle":[],"short-title":[],"issued":{"date-parts":[[2015,9]]},"references-count":66,"journal-issue":{"issue":"5","published-print":{"date-parts":[[2015,9]]}},"alternative-id":["10.1002\/bip.22670"],"URL":"https:\/\/doi.org\/10.1002\/bip.22670","archive":["Portico"],"relation":{},"ISSN":["0006-3525"],"issn-type":[{"value":"0006-3525","type":"print"}],"subject":[],"published":{"date-parts":[[2015,9]]}}}