{"status":"ok","message-type":"work","message-version":"1.0.0","message":{"indexed":{"date-parts":[[2026,10,9]],"date-time":"2026-10-09T19:53:05Z","timestamp":1791575585611,"version":"4.3.4"},"reference-count":84,"publisher":"Wiley","issue":"16","license":[{"start":{"date-parts":[[2019,2,28]],"date-time":"2019-02-28T00:00:00Z","timestamp":1551312000000},"content-version":"vor","delay-in-days":0,"URL":"http:\/\/onlinelibrary.wiley.com\/termsAndConditions#vor"}],"funder":[{"DOI":"10.13039\/501100006389","name":"Universit\u00e9 de Gen\u00e8ve","doi-asserted-by":"publisher","award":["Unige"],"award-info":[{"award-number":["Unige"]}],"id":[{"id":"10.13039\/501100006389","id-type":"DOI","asserted-by":"publisher"}]}],"content-domain":{"domain":["chemistry-europe.onlinelibrary.wiley.com"],"crossmark-restriction":true},"short-container-title":["Chemistry A European J"],"published-print":{"date-parts":[[2019,3,15]]},"abstract":"<jats:title>Abstract<\/jats:title><jats:p>Cyclic oligochalcogenides are emerging as powerful tools to penetrate cells. With disulfide ring tension maximized, selenium chemistry had to be explored next to enhance speed and selectivity of dynamic covalent exchange on the way into the cytosol. We show that diseleno lipoic acid (DiSeL) delivers a variety of relevant substrates. DiSeL\u2010driven uptake of artificial metalloenzymes enables bioorthogonal fluorophore uncaging within cells. Binding of a bicyclic peptide, phalloidin, to actin fibers evinces targeted delivery to the cytosol. Automated tracking of diffusive compared to directed motility and immobility localizes 79\u2009% of protein\u2010coated quantum dots (QDs) in the cytosol, with little endosomal capture (0.06\u2009%). These results suggest that diselenolanes might act as molecular walkers along disulfide tracks in locally denatured membrane proteins, surrounded by adaptive micellar membrane defects. Miniscule and versatile, DiSeL tags are also readily available, stable, soluble, and non\u2010toxic.<\/jats:p>","DOI":"10.1002\/chem.201805900","type":"journal-article","created":{"date-parts":[[2019,2,28]],"date-time":"2019-02-28T05:02:01Z","timestamp":1551330121000},"page":"4047-4051","update-policy":"https:\/\/doi.org\/10.1002\/crossmark_policy","source":"Crossref","is-referenced-by-count":37,"title":["Diselenolane\u2010Mediated Cellular Uptake: Efficient Cytosolic Delivery of Probes, Peptides, Proteins, Artificial Metalloenzymes and Protein\u2010Coated Quantum Dots"],"prefix":"10.1002","volume":"25","author":[{"given":"Eline","family":"Bartolami","sequence":"first","affiliation":[{"name":"National Centre of Competence in Research (NCCR) Chemical Biology, School of Chemistry and Biochemistry University of Geneva  CH-1211 Geneva Switzerland"},{"name":"National Centre of Competence in Research (NCCR) Molecular Systems Engineering  CH-4002 Basel Switzerland"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Dimitris","family":"Basagiannis","sequence":"additional","affiliation":[{"name":"National Centre of Competence in Research (NCCR) Chemical Biology, School of Chemistry and Biochemistry University of Geneva  CH-1211 Geneva Switzerland"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Lili","family":"Zong","sequence":"additional","affiliation":[{"name":"National Centre of Competence in Research (NCCR) Chemical Biology, School of Chemistry and Biochemistry University of Geneva  CH-1211 Geneva Switzerland"},{"name":"Current Address: School of Chemistry and Chemical Engineering Southeast University  Nanjing 210096 China"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"R\u00e9mi","family":"Martinent","sequence":"additional","affiliation":[{"name":"National Centre of Competence in Research (NCCR) Chemical Biology, School of Chemistry and Biochemistry University of Geneva  CH-1211 Geneva Switzerland"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"ORCID":"https:\/\/orcid.org\/0000-0002-2442-6079","authenticated-orcid":false,"given":"Yasunori","family":"Okamoto","sequence":"additional","affiliation":[{"name":"Department of Chemistry University of Basel  Basel Switzerland"},{"name":"National Centre of Competence in Research (NCCR) Molecular Systems Engineering  CH-4002 Basel Switzerland"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Quentin","family":"Laurent","sequence":"additional","affiliation":[{"name":"National Centre of Competence in Research (NCCR) Chemical Biology, School of Chemistry and Biochemistry University of Geneva  CH-1211 Geneva Switzerland"},{"name":"National Centre of Competence in Research (NCCR) Molecular Systems Engineering  CH-4002 Basel Switzerland"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Thomas R.","family":"Ward","sequence":"additional","affiliation":[{"name":"Department of Chemistry University of Basel  Basel Switzerland"},{"name":"National Centre of Competence in Research (NCCR) Molecular Systems Engineering  CH-4002 Basel Switzerland"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Marcos","family":"Gonzalez\u2010Gaitan","sequence":"additional","affiliation":[{"name":"National Centre of Competence in Research (NCCR) Chemical Biology, School of Chemistry and Biochemistry University of Geneva  CH-1211 Geneva Switzerland"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Naomi","family":"Sakai","sequence":"additional","affiliation":[{"name":"National Centre of Competence in Research (NCCR) Chemical Biology, School of Chemistry and Biochemistry University of Geneva  CH-1211 Geneva Switzerland"},{"name":"National Centre of Competence in Research (NCCR) Molecular Systems Engineering  CH-4002 Basel Switzerland"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"ORCID":"https:\/\/orcid.org\/0000-0002-8537-8349","authenticated-orcid":false,"given":"Stefan","family":"Matile","sequence":"additional","affiliation":[{"name":"National Centre of Competence in Research (NCCR) Chemical Biology, School of Chemistry and Biochemistry University of Geneva  CH-1211 Geneva Switzerland"},{"name":"National Centre of Competence in Research (NCCR) Molecular Systems Engineering  CH-4002 Basel Switzerland"}],"role":[{"vocabulary":"crossref","role":"author"}]}],"member":"311","published-online":{"date-parts":[[2019,2,28]]},"reference":[{"key":"e_1_2_2_1_1","unstructured":"\u00a0"},{"key":"e_1_2_2_2_2","doi-asserted-by":"publisher","DOI":"10.1096\/fj.08-127563"},{"key":"e_1_2_2_3_2","doi-asserted-by":"publisher","DOI":"10.1002\/mabi.201400061"},{"key":"e_1_2_2_4_2","doi-asserted-by":"publisher","DOI":"10.1021\/acs.analchem.7b02084"},{"key":"e_1_2_2_5_2","doi-asserted-by":"publisher","DOI":"10.1021\/acschembio.8b00564"},{"key":"e_1_2_2_6_2","doi-asserted-by":"publisher","DOI":"10.1016\/j.tibtech.2011.12.002"},{"key":"e_1_2_2_7_2","doi-asserted-by":"publisher","DOI":"10.1021\/jacs.5b08948"},{"key":"e_1_2_2_8_2","doi-asserted-by":"publisher","DOI":"10.1039\/C3CC46826G"},{"key":"e_1_2_2_9_2","doi-asserted-by":"publisher","DOI":"10.1016\/j.jconrel.2013.02.014"},{"key":"e_1_2_2_10_2","doi-asserted-by":"publisher","DOI":"10.1021\/bc100045s"},{"key":"e_1_2_2_11_1","unstructured":"\u00a0"},{"key":"e_1_2_2_12_2","doi-asserted-by":"publisher","DOI":"10.1021\/ar4000339"},{"key":"e_1_2_2_13_2","doi-asserted-by":"publisher","DOI":"10.1021\/acscentsci.7b00486"},{"key":"e_1_2_2_14_2","doi-asserted-by":"publisher","DOI":"10.1021\/acsami.6b14639"},{"key":"e_1_2_2_15_2","doi-asserted-by":"publisher","DOI":"10.1039\/C6BM00960C"},{"key":"e_1_2_2_16_1","unstructured":"\u00a0"},{"key":"e_1_2_2_17_2","doi-asserted-by":"publisher","DOI":"10.1021\/jacs.5b13452"},{"key":"e_1_2_2_18_2","doi-asserted-by":"publisher","DOI":"10.1039\/C7SC03918B"},{"key":"e_1_2_2_19_2","doi-asserted-by":"publisher","DOI":"10.1021\/jacs.6b11103"},{"key":"e_1_2_2_20_2","doi-asserted-by":"publisher","DOI":"10.1002\/hlca.201800112"},{"key":"e_1_2_2_21_1","unstructured":"\u00a0"},{"key":"e_1_2_2_22_2","doi-asserted-by":"publisher","DOI":"10.1021\/ja311961k"},{"key":"e_1_2_2_23_2","doi-asserted-by":"publisher","DOI":"10.1021\/ja501581b"},{"key":"e_1_2_2_24_2","doi-asserted-by":"publisher","DOI":"10.1002\/hlca.201600370"},{"key":"e_1_2_2_25_2","doi-asserted-by":"publisher","DOI":"10.1002\/hlca.201700266"},{"key":"e_1_2_2_26_1","doi-asserted-by":"publisher","DOI":"10.1021\/jacs.7b02952"},{"key":"e_1_2_2_27_1","unstructured":"\u00a0"},{"key":"e_1_2_2_28_2","doi-asserted-by":"publisher","DOI":"10.1038\/s41467-018-04440-0"},{"key":"e_1_2_2_29_2","doi-asserted-by":"publisher","DOI":"10.1039\/C8SC00484F"},{"key":"e_1_2_2_30_1","unstructured":"\u00a0"},{"key":"e_1_2_2_31_2","doi-asserted-by":"publisher","DOI":"10.1002\/anie.201711651"},{"key":"e_1_2_2_31_3","doi-asserted-by":"publisher","DOI":"10.1002\/ange.201711651"},{"key":"e_1_2_2_32_2","doi-asserted-by":"publisher","DOI":"10.1021\/jacs.8b06584"},{"key":"e_1_2_2_33_1","unstructured":"\u00a0"},{"key":"e_1_2_2_34_2","doi-asserted-by":"publisher","DOI":"10.1021\/ja5115437"},{"key":"e_1_2_2_35_2","doi-asserted-by":"publisher","DOI":"10.1039\/c0sc00307g"},{"key":"e_1_2_2_36_1","doi-asserted-by":"publisher","DOI":"10.1002\/anie.201502358"},{"key":"e_1_2_2_36_2","doi-asserted-by":"publisher","DOI":"10.1002\/ange.201502358"},{"key":"e_1_2_2_37_1","doi-asserted-by":"publisher","DOI":"10.1021\/acscentsci.7b00080"},{"key":"e_1_2_2_38_1","doi-asserted-by":"publisher","DOI":"10.1039\/C7SC05151D"},{"key":"e_1_2_2_39_1","unstructured":"\u00a0"},{"key":"e_1_2_2_40_2","doi-asserted-by":"publisher","DOI":"10.1039\/C4RP00057A"},{"key":"e_1_2_2_41_2","doi-asserted-by":"publisher","DOI":"10.1002\/anie.201710094"},{"key":"e_1_2_2_41_3","doi-asserted-by":"publisher","DOI":"10.1002\/ange.201710094"},{"key":"e_1_2_2_42_1","unstructured":"\u00a0"},{"key":"e_1_2_2_43_2","doi-asserted-by":"publisher","DOI":"10.1080\/10426507.2016.1250760"},{"key":"e_1_2_2_44_2","doi-asserted-by":"publisher","DOI":"10.1021\/jo1011569"},{"key":"e_1_2_2_45_2","doi-asserted-by":"publisher","DOI":"10.1021\/jo01287a044"},{"key":"e_1_2_2_46_2","doi-asserted-by":"publisher","DOI":"10.1021\/bi8008906"},{"key":"e_1_2_2_47_2","doi-asserted-by":"publisher","DOI":"10.1002\/anie.201307481"},{"key":"e_1_2_2_47_3","doi-asserted-by":"publisher","DOI":"10.1002\/ange.201307481"},{"key":"e_1_2_2_48_1","unstructured":"\u00a0"},{"key":"e_1_2_2_49_2","doi-asserted-by":"publisher","DOI":"10.1021\/jacs.6b09643"},{"key":"e_1_2_2_50_2","doi-asserted-by":"publisher","DOI":"10.1002\/anie.201611772"},{"key":"e_1_2_2_50_3","doi-asserted-by":"publisher","DOI":"10.1002\/ange.201611772"},{"key":"e_1_2_2_51_1","unstructured":"\u00a0"},{"key":"e_1_2_2_52_2","doi-asserted-by":"publisher","DOI":"10.1021\/ja402382n"},{"key":"e_1_2_2_53_2","doi-asserted-by":"publisher","DOI":"10.1002\/anie.201004779"},{"key":"e_1_2_2_53_3","doi-asserted-by":"publisher","DOI":"10.1002\/ange.201004779"},{"key":"e_1_2_2_54_2","doi-asserted-by":"publisher","DOI":"10.1021\/ja047543j"},{"key":"e_1_2_2_55_2","doi-asserted-by":"publisher","DOI":"10.1038\/nature09012"},{"key":"e_1_2_2_56_2","doi-asserted-by":"publisher","DOI":"10.1002\/anie.200902437"},{"key":"e_1_2_2_56_3","doi-asserted-by":"publisher","DOI":"10.1002\/ange.200902437"},{"key":"e_1_2_2_57_1","unstructured":"\u00a0"},{"key":"e_1_2_2_58_2","doi-asserted-by":"publisher","DOI":"10.1039\/C4SC02379J"},{"key":"e_1_2_2_59_2","doi-asserted-by":"publisher","DOI":"10.1021\/cb9002688"},{"key":"e_1_2_2_60_2","doi-asserted-by":"publisher","DOI":"10.1021\/acs.biochem.7b00751"},{"key":"e_1_2_2_61_1","doi-asserted-by":"publisher","DOI":"10.1039\/C5CC03472H"},{"key":"e_1_2_2_62_1","unstructured":"See the Supporting Information."},{"key":"e_1_2_2_63_1","unstructured":"\u00a0"},{"key":"e_1_2_2_64_2","doi-asserted-by":"publisher","DOI":"10.1016\/j.jmb.2013.09.016"},{"key":"e_1_2_2_65_2","doi-asserted-by":"publisher","DOI":"10.1021\/jacs.7b00540"},{"key":"e_1_2_2_66_1","doi-asserted-by":"publisher","DOI":"10.1016\/S1074-5521(02)00284-3"},{"key":"e_1_2_2_67_1","doi-asserted-by":"publisher","DOI":"10.1007\/s10895-010-0752-8"},{"key":"e_1_2_2_68_1","doi-asserted-by":"publisher","DOI":"10.1038\/nchem.981"},{"key":"e_1_2_2_69_1","unstructured":"\u00a0"},{"key":"e_1_2_2_70_2","doi-asserted-by":"publisher","DOI":"10.1177\/002215549704500308"},{"key":"e_1_2_2_71_2","doi-asserted-by":"publisher","DOI":"10.1021\/ol702769n"},{"key":"e_1_2_2_72_1","doi-asserted-by":"publisher","DOI":"10.1038\/natrevmats.2016.14"},{"key":"e_1_2_2_73_1","unstructured":"\u00a0"},{"key":"e_1_2_2_74_2","doi-asserted-by":"publisher","DOI":"10.1091\/mbc.e16-06-0413"},{"key":"e_1_2_2_75_2","doi-asserted-by":"publisher","DOI":"10.1038\/ncomms14772"},{"key":"e_1_2_2_76_2","doi-asserted-by":"publisher","DOI":"10.1021\/nl060921t"},{"key":"e_1_2_2_77_1","doi-asserted-by":"publisher","DOI":"10.1002\/hlca.201800209"}],"container-title":["Chemistry \u2013 A European Journal"],"original-title":[],"language":"en","link":[{"URL":"https:\/\/api.wiley.com\/onlinelibrary\/tdm\/v1\/articles\/10.1002%2Fchem.201805900","content-type":"application\/pdf","content-version":"vor","intended-application":"text-mining"},{"URL":"https:\/\/onlinelibrary.wiley.com\/doi\/pdf\/10.1002\/chem.201805900","content-type":"application\/pdf","content-version":"vor","intended-application":"text-mining"},{"URL":"https:\/\/onlinelibrary.wiley.com\/doi\/full-xml\/10.1002\/chem.201805900","content-type":"application\/xml","content-version":"vor","intended-application":"text-mining"},{"URL":"https:\/\/chemistry-europe.onlinelibrary.wiley.com\/doi\/pdf\/10.1002\/chem.201805900","content-type":"unspecified","content-version":"vor","intended-application":"similarity-checking"}],"deposited":{"date-parts":[[2025,10,12]],"date-time":"2025-10-12T14:16:08Z","timestamp":1760278568000},"score":1,"resource":{"primary":{"URL":"https:\/\/chemistry-europe.onlinelibrary.wiley.com\/doi\/10.1002\/chem.201805900"}},"subtitle":[],"short-title":[],"issued":{"date-parts":[[2019,2,28]]},"references-count":84,"journal-issue":{"issue":"16","published-print":{"date-parts":[[2019,3,15]]}},"alternative-id":["10.1002\/chem.201805900"],"URL":"https:\/\/doi.org\/10.1002\/chem.201805900","archive":["Portico"],"relation":{},"ISSN":["0947-6539","1521-3765"],"issn-type":[{"value":"0947-6539","type":"print"},{"value":"1521-3765","type":"electronic"}],"subject":[],"published":{"date-parts":[[2019,2,28]]},"assertion":[{"value":"2018-11-26","order":0,"name":"received","label":"Received","group":{"name":"publication_history","label":"Publication History"}},{"value":"2019-02-28","order":3,"name":"published","label":"Published","group":{"name":"publication_history","label":"Publication History"}}]}}