{"id":"https://openalex.org/W4221124952","doi":"https://doi.org/10.1021/jacs.2c01136","title":"Self-Immolative Hydroxybenzylamine Linkers for Traceless Protein Modification","display_name":"Self-Immolative Hydroxybenzylamine Linkers for Traceless Protein Modification","publication_year":2022,"publication_date":"2022-03-24","ids":{"openalex":"https://openalex.org/W4221124952","doi":"https://doi.org/10.1021/jacs.2c01136","pmid":"https://pubmed.ncbi.nlm.nih.gov/35321547"},"language":"en","primary_location":{"id":"doi:10.1021/jacs.2c01136","doi":"https://doi.org/10.1021/jacs.2c01136","is_oa":false,"landing_page_url":"https://doi.org/10.1021/jacs.2c01136","pdf_url":null,"source":{"id":"https://openalex.org/S111155417","display_name":"Journal of the American Chemical Society","issn_l":"0002-7863","issn":["0002-7863","1520-5126","1943-2984"],"is_oa":false,"is_in_doaj":false,"is_core":true,"listed_in":["cwts-core","dongbi-a","jufo-3","ki-jl-3","medline","norway-2","poland-200","russia-white-list-1","vabb-shw"],"host_organization":"https://openalex.org/P4310320006","host_organization_name":"American Chemical Society","host_organization_lineage":["https://openalex.org/P4310320006"],"host_organization_lineage_names":["American Chemical Society"],"type":"journal"},"license":null,"license_id":null,"version":"publishedVersion","is_accepted":true,"is_published":true,"raw_source_name":"Journal of the American Chemical Society","raw_type":"journal-article"},"volume":null,"type":"article","indexed_in":["crossref","pubmed"],"open_access":{"is_oa":false,"oa_status":"closed","oa_url":null,"any_repository_has_fulltext":false},"authorships":[{"author_position":"first","author":{"id":"https://openalex.org/A5072973197","display_name":"Douglas A. Rose","orcid":null,"observed_orcids":[]},"institutions":[{"id":"https://openalex.org/I142207940","display_name":"California NanoSystems Institute","ror":"https://ror.org/00q7fqf35","country_code":"US","type":"facility","lineage":["https://openalex.org/I142207940","https://openalex.org/I154570441","https://openalex.org/I161318765"]},{"id":"https://openalex.org/I161318765","display_name":"University of California, Los Angeles","ror":"https://ror.org/046rm7j60","country_code":"US","type":"education","lineage":["https://openalex.org/I161318765"]}],"countries":["US"],"is_corresponding":false,"raw_author_name":"Douglas A. Rose","raw_affiliation_strings":["Department of Chemistry and Biochemistry and California NanoSystems Institute, University of California, Los Angeles, 607 Charles E. Young Drive East, Los Angeles, California 90095-1569, United States"],"raw_orcid":null,"affiliations":[{"raw_affiliation_string":"Department of Chemistry and Biochemistry and California NanoSystems Institute, University of California, Los Angeles, 607 Charles E. Young Drive East, Los Angeles, California 90095-1569, United States","institution_ids":["https://openalex.org/I142207940","https://openalex.org/I161318765"]}]},{"author_position":"middle","author":{"id":"https://openalex.org/A5011597703","display_name":"Joseph W. Treacy","orcid":"https://orcid.org/0000-0002-8597-0246","observed_orcids":["https://orcid.org/0000-0002-8597-0246"]},"institutions":[{"id":"https://openalex.org/I142207940","display_name":"California NanoSystems Institute","ror":"https://ror.org/00q7fqf35","country_code":"US","type":"facility","lineage":["https://openalex.org/I142207940","https://openalex.org/I154570441","https://openalex.org/I161318765"]},{"id":"https://openalex.org/I161318765","display_name":"University of California, Los Angeles","ror":"https://ror.org/046rm7j60","country_code":"US","type":"education","lineage":["https://openalex.org/I161318765"]}],"countries":["US"],"is_corresponding":false,"raw_author_name":"Joseph W. Treacy","raw_affiliation_strings":["Department of Chemistry and Biochemistry and California NanoSystems Institute, University of California, Los Angeles, 607 Charles E. Young Drive East, Los Angeles, California 90095-1569, United States"],"raw_orcid":null,"affiliations":[{"raw_affiliation_string":"Department of Chemistry and Biochemistry and California NanoSystems Institute, University of California, Los Angeles, 607 Charles E. Young Drive East, Los Angeles, California 90095-1569, United States","institution_ids":["https://openalex.org/I142207940","https://openalex.org/I161318765"]}]},{"author_position":"middle","author":{"id":"https://openalex.org/A5055785990","display_name":"Zhongyue John Yang","orcid":"https://orcid.org/0000-0003-0395-6617","observed_orcids":["https://orcid.org/0000-0003-0395-6617"]},"institutions":[{"id":"https://openalex.org/I142207940","display_name":"California NanoSystems Institute","ror":"https://ror.org/00q7fqf35","country_code":"US","type":"facility","lineage":["https://openalex.org/I142207940","https://openalex.org/I154570441","https://openalex.org/I161318765"]},{"id":"https://openalex.org/I161318765","display_name":"University of California, Los Angeles","ror":"https://ror.org/046rm7j60","country_code":"US","type":"education","lineage":["https://openalex.org/I161318765"]}],"countries":["US"],"is_corresponding":false,"raw_author_name":"Zhongyue J. Yang","raw_affiliation_strings":["Department of Chemistry and Biochemistry and California NanoSystems Institute, University of California, Los Angeles, 607 Charles E. Young Drive East, Los Angeles, California 90095-1569, United States"],"raw_orcid":"https://orcid.org/0000-0003-0395-6617","affiliations":[{"raw_affiliation_string":"Department of Chemistry and Biochemistry and California NanoSystems Institute, University of California, Los Angeles, 607 Charles E. Young Drive East, Los Angeles, California 90095-1569, United States","institution_ids":["https://openalex.org/I142207940","https://openalex.org/I161318765"]}]},{"author_position":"middle","author":{"id":"https://openalex.org/A5070853748","display_name":"Jeong Hoon Ko","orcid":"https://orcid.org/0000-0003-2000-3789","observed_orcids":["https://orcid.org/0000-0003-2000-3789"]},"institutions":[{"id":"https://openalex.org/I142207940","display_name":"California NanoSystems Institute","ror":"https://ror.org/00q7fqf35","country_code":"US","type":"facility","lineage":["https://openalex.org/I142207940","https://openalex.org/I154570441","https://openalex.org/I161318765"]},{"id":"https://openalex.org/I161318765","display_name":"University of California, Los Angeles","ror":"https://ror.org/046rm7j60","country_code":"US","type":"education","lineage":["https://openalex.org/I161318765"]}],"countries":["US"],"is_corresponding":true,"raw_author_name":"Jeong Hoon Ko","raw_affiliation_strings":["Department of Chemistry and Biochemistry and California NanoSystems Institute, University of California, Los Angeles, 607 Charles E. Young Drive East, Los Angeles, California 90095-1569, United States"],"raw_orcid":"https://orcid.org/0000-0003-2000-3789","affiliations":[{"raw_affiliation_string":"Department of Chemistry and Biochemistry and California NanoSystems Institute, University of California, Los Angeles, 607 Charles E. Young Drive East, Los Angeles, California 90095-1569, United States","institution_ids":["https://openalex.org/I142207940","https://openalex.org/I161318765"]}]},{"author_position":"middle","author":{"id":"https://openalex.org/A5042178740","display_name":"Kendall N. Houk","orcid":"https://orcid.org/0000-0002-8387-5261","observed_orcids":["https://orcid.org/0000-0002-8387-5261"]},"institutions":[{"id":"https://openalex.org/I142207940","display_name":"California NanoSystems Institute","ror":"https://ror.org/00q7fqf35","country_code":"US","type":"facility","lineage":["https://openalex.org/I142207940","https://openalex.org/I154570441","https://openalex.org/I161318765"]},{"id":"https://openalex.org/I161318765","display_name":"University of California, Los Angeles","ror":"https://ror.org/046rm7j60","country_code":"US","type":"education","lineage":["https://openalex.org/I161318765"]}],"countries":["US"],"is_corresponding":true,"raw_author_name":"K. N. Houk","raw_affiliation_strings":["Department of Chemistry and Biochemistry and California NanoSystems Institute, University of California, Los Angeles, 607 Charles E. Young Drive East, Los Angeles, California 90095-1569, United States"],"raw_orcid":"https://orcid.org/0000-0002-8387-5261","affiliations":[{"raw_affiliation_string":"Department of Chemistry and Biochemistry and California NanoSystems Institute, University of California, Los Angeles, 607 Charles E. Young Drive East, Los Angeles, California 90095-1569, United States","institution_ids":["https://openalex.org/I142207940","https://openalex.org/I161318765"]}]},{"author_position":"last","author":{"id":"https://openalex.org/A5035180870","display_name":"Heather D. Maynard","orcid":"https://orcid.org/0000-0003-3692-6289","observed_orcids":["https://orcid.org/0000-0003-3692-6289"]},"institutions":[{"id":"https://openalex.org/I142207940","display_name":"California NanoSystems Institute","ror":"https://ror.org/00q7fqf35","country_code":"US","type":"facility","lineage":["https://openalex.org/I142207940","https://openalex.org/I154570441","https://openalex.org/I161318765"]},{"id":"https://openalex.org/I161318765","display_name":"University of California, Los Angeles","ror":"https://ror.org/046rm7j60","country_code":"US","type":"education","lineage":["https://openalex.org/I161318765"]}],"countries":["US"],"is_corresponding":true,"raw_author_name":"Heather D. Maynard","raw_affiliation_strings":["Department of Chemistry and Biochemistry and California NanoSystems Institute, University of California, Los Angeles, 607 Charles E. Young Drive East, Los Angeles, California 90095-1569, United States"],"raw_orcid":"https://orcid.org/0000-0003-3692-6289","affiliations":[{"raw_affiliation_string":"Department of Chemistry and Biochemistry and California NanoSystems Institute, University of California, Los Angeles, 607 Charles E. Young Drive East, Los Angeles, California 90095-1569, United States","institution_ids":["https://openalex.org/I142207940","https://openalex.org/I161318765"]}]}],"institutions":[],"countries_distinct_count":1,"institutions_distinct_count":2,"corresponding_author_ids":["https://openalex.org/A5035180870","https://openalex.org/A5042178740","https://openalex.org/A5070853748"],"corresponding_institution_ids":["https://openalex.org/I142207940","https://openalex.org/I161318765"],"apc_list":{"value":5000,"currency":"USD","value_usd":5000},"apc_paid":null,"fwci":3.2627,"has_fulltext":false,"cited_by_count":49,"citation_normalized_percentile":{"value":0.94287913,"is_in_top_1_percent":false,"is_in_top_10_percent":true},"cited_by_percentile_year":{"min":97,"max":100},"biblio":{"volume":"144","issue":"13","first_page":"6050","last_page":"6058"},"is_retracted":false,"is_paratext":false,"is_xpac":false,"primary_topic":{"id":"https://openalex.org/T10911","display_name":"Chemical Synthesis and Analysis","score":0.426800012588501,"subfield":{"id":"https://openalex.org/subfields/1312","display_name":"Molecular Biology"},"field":{"id":"https://openalex.org/fields/13","display_name":"Biochemistry, Genetics and Molecular Biology"},"domain":{"id":"https://openalex.org/domains/1","display_name":"Life Sciences"}},"topics":[{"id":"https://openalex.org/T10911","display_name":"Chemical Synthesis and Analysis","score":0.426800012588501,"subfield":{"id":"https://openalex.org/subfields/1312","display_name":"Molecular Biology"},"field":{"id":"https://openalex.org/fields/13","display_name":"Biochemistry, Genetics and Molecular Biology"},"domain":{"id":"https://openalex.org/domains/1","display_name":"Life Sciences"}},{"id":"https://openalex.org/T11440","display_name":"Click Chemistry and Applications","score":0.2865999937057495,"subfield":{"id":"https://openalex.org/subfields/1605","display_name":"Organic Chemistry"},"field":{"id":"https://openalex.org/fields/16","display_name":"Chemistry"},"domain":{"id":"https://openalex.org/domains/3","display_name":"Physical Sciences"}},{"id":"https://openalex.org/T10405","display_name":"Advanced Polymer Synthesis and Characterization","score":0.11379999667406082,"subfield":{"id":"https://openalex.org/subfields/1605","display_name":"Organic Chemistry"},"field":{"id":"https://openalex.org/fields/16","display_name":"Chemistry"},"domain":{"id":"https://openalex.org/domains/3","display_name":"Physical Sciences"}}],"keywords":[{"id":"https://openalex.org/keywords/self-immolative-linker","display_name":"self-immolative linker","score":0.9240000247955322},{"id":"https://openalex.org/keywords/quinone-methide-intermediate","display_name":"quinone methide intermediate","score":0.9319999814033508},{"id":"https://openalex.org/keywords/electron-donating-substituents","display_name":"electron-donating substituents","score":0.9549999833106995},{"id":"https://openalex.org/keywords/bioconjugation","display_name":"bioconjugation","score":0.8840000033378601}],"concepts":[{"id":"https://openalex.org/C185592680","wikidata":"https://www.wikidata.org/wiki/Q2329","display_name":"Chemistry","level":0,"score":0.9431365728378296},{"id":"https://openalex.org/C23963754","wikidata":"https://www.wikidata.org/wiki/Q4914729","display_name":"Bioconjugation","level":2,"score":0.9312742948532104},{"id":"https://openalex.org/C2780557392","wikidata":"https://www.wikidata.org/wiki/Q523796","display_name":"Linker","level":2,"score":0.7602090239524841},{"id":"https://openalex.org/C75079739","wikidata":"https://www.wikidata.org/wiki/Q1571801","display_name":"Intramolecular force","level":2,"score":0.7551751136779785},{"id":"https://openalex.org/C2779149719","wikidata":"https://www.wikidata.org/wiki/Q682252","display_name":"PEGylation","level":3,"score":0.718582034111023},{"id":"https://openalex.org/C21951064","wikidata":"https://www.wikidata.org/wiki/Q899212","display_name":"Combinatorial chemistry","level":1,"score":0.6617664098739624},{"id":"https://openalex.org/C197336794","wikidata":"https://www.wikidata.org/wiki/Q5161150","display_name":"Conjugate","level":2,"score":0.5177630186080933},{"id":"https://openalex.org/C2776964284","wikidata":"https://www.wikidata.org/wiki/Q410083","display_name":"Polyethylene glycol","level":2,"score":0.3665177822113037},{"id":"https://openalex.org/C71240020","wikidata":"https://www.wikidata.org/wiki/Q186011","display_name":"Stereochemistry","level":1,"score":0.2136351466178894},{"id":"https://openalex.org/C178790620","wikidata":"https://www.wikidata.org/wiki/Q11351","display_name":"Organic chemistry","level":1,"score":0.20803800225257874},{"id":"https://openalex.org/C111919701","wikidata":"https://www.wikidata.org/wiki/Q9135","display_name":"Operating system","level":1,"score":0.0},{"id":"https://openalex.org/C33923547","wikidata":"https://www.wikidata.org/wiki/Q395","display_name":"Mathematics","level":0,"score":0.0},{"id":"https://openalex.org/C41008148","wikidata":"https://www.wikidata.org/wiki/Q21198","display_name":"Computer science","level":0,"score":0.0},{"id":"https://openalex.org/C134306372","wikidata":"https://www.wikidata.org/wiki/Q7754","display_name":"Mathematical analysis","level":1,"score":0.0}],"mesh":[{"descriptor_ui":"D011092","descriptor_name":"Polyethylene Glycols","qualifier_ui":null,"qualifier_name":null,"is_major_topic":true},{"descriptor_ui":"D011108","descriptor_name":"Polymers","qualifier_ui":"Q000737","qualifier_name":"chemistry","is_major_topic":true},{"descriptor_ui":"D011506","descriptor_name":"Proteins","qualifier_ui":null,"qualifier_name":null,"is_major_topic":false}],"locations_count":2,"locations":[{"id":"doi:10.1021/jacs.2c01136","doi":"https://doi.org/10.1021/jacs.2c01136","is_oa":false,"landing_page_url":"https://doi.org/10.1021/jacs.2c01136","pdf_url":null,"source":{"id":"https://openalex.org/S111155417","display_name":"Journal of the American Chemical Society","issn_l":"0002-7863","issn":["0002-7863","1520-5126","1943-2984"],"is_oa":false,"is_in_doaj":false,"is_core":true,"listed_in":["cwts-core","dongbi-a","jufo-3","ki-jl-3","medline","norway-2","poland-200","russia-white-list-1","vabb-shw"],"host_organization":"https://openalex.org/P4310320006","host_organization_name":"American Chemical Society","host_organization_lineage":["https://openalex.org/P4310320006"],"host_organization_lineage_names":["American Chemical Society"],"type":"journal"},"license":null,"license_id":null,"version":"publishedVersion","is_accepted":true,"is_published":true,"raw_source_name":"Journal of the American Chemical Society","raw_type":"journal-article"},{"id":"pmid:35321547","doi":null,"is_oa":false,"landing_page_url":"https://pubmed.ncbi.nlm.nih.gov/35321547","pdf_url":null,"source":{"id":"https://openalex.org/S4306525036","display_name":"PubMed","issn_l":null,"issn":null,"is_oa":false,"is_in_doaj":false,"is_core":false,"listed_in":[],"host_organization":"https://openalex.org/I1299303238","host_organization_name":"National Institutes of Health","host_organization_lineage":["https://openalex.org/I1299303238"],"host_organization_lineage_names":[],"type":"repository"},"license":null,"license_id":null,"version":"publishedVersion","is_accepted":true,"is_published":true,"raw_source_name":"Journal of the American Chemical Society","raw_type":"Journal Article"}],"best_oa_location":null,"sustainable_development_goals":[],"study_designs":[],"awards":[{"id":"https://openalex.org/G3284329834","display_name":null,"funder_award_id":"CHE 2003946","funder_id":"https://openalex.org/F4320337393","funder_display_name":"Division of Chemistry"},{"id":"https://openalex.org/G8364527723","display_name":"Trehalose Glycopolymers to Enhance both Pharmacokinetics and Stability of Therapeutic Proteins","funder_award_id":"R01EB020676","funder_id":"https://openalex.org/F4320337363","funder_display_name":"National Institute of Biomedical Imaging and Bioengineering"}],"funders":[{"id":"https://openalex.org/F4320337363","display_name":"National Institute of Biomedical Imaging and Bioengineering","ror":"https://ror.org/00372qc85"},{"id":"https://openalex.org/F4320337393","display_name":"Division of Chemistry","ror":"https://ror.org/01ar8dr59"}],"has_content":{"grobid_xml":false,"pdf":false},"content_urls":null,"referenced_works_count":33,"referenced_works":["https://openalex.org/W768713857","https://openalex.org/W1775469721","https://openalex.org/W1945627170","https://openalex.org/W1951491916","https://openalex.org/W1987645139","https://openalex.org/W2021001311","https://openalex.org/W2025920006","https://openalex.org/W2032071899","https://openalex.org/W2034931543","https://openalex.org/W2051096170","https://openalex.org/W2055610164","https://openalex.org/W2065025587","https://openalex.org/W2085952412","https://openalex.org/W2087777969","https://openalex.org/W2092850986","https://openalex.org/W2151063961","https://openalex.org/W2160790360","https://openalex.org/W2258704515","https://openalex.org/W2315302880","https://openalex.org/W2323190196","https://openalex.org/W2323232713","https://openalex.org/W2329663744","https://openalex.org/W2334236480","https://openalex.org/W2470831393","https://openalex.org/W2516173104","https://openalex.org/W2533801509","https://openalex.org/W2566202925","https://openalex.org/W2568910234","https://openalex.org/W2742118221","https://openalex.org/W2800128426","https://openalex.org/W2890904427","https://openalex.org/W2946755811","https://openalex.org/W2951034389"],"related_works":["https://openalex.org/W2943258021","https://openalex.org/W7203936012","https://openalex.org/W2078695337","https://openalex.org/W2332109986","https://openalex.org/W2941518649","https://openalex.org/W7126160045","https://openalex.org/W1998751694","https://openalex.org/W2944582686","https://openalex.org/W7015505813","https://openalex.org/W3084705282"],"abstract_inverted_index":{"Traceless":[0],"self-immolative":[1,135],"linkers":[2,22,74,149,182,190],"are":[3],"widely":[4],"used":[5],"for":[6,47,150,192],"the":[7,35,39,56,60,63,79,93,108,118,130,176,188],"reversible":[8,152],"modification":[9],"of":[10,20,31,65,72,92,112,120,132,140,175,181,195],"proteins":[11],"and":[12,107,122],"peptides.":[13],"This":[14,127,178],"article":[15],"describes":[16],"a":[17,45,69,133,138,157,193],"new":[18,179],"class":[19,180],"traceless":[21,148,173,189],"based":[23],"on":[24,34],"ortho-":[25],"or":[26],"para":[27],"-hydroxybenzylamines.":[28],"The":[29],"introduction":[30],"electron-donating":[32],"substituents":[33],"aromatic":[36,80],"core":[37],"stabilizes":[38],"quinone":[40],"methide":[41],"intermediate,":[42],"thus":[43],"providing":[44],"platform":[46],"payload":[48],"release":[49,174,185],"that":[50],"can":[51],"be":[52],"modulated.":[53],"To":[54,143],"determine":[55],"extent":[57],"to":[58,88],"which":[59,163],"electronics":[61,77],"affect":[62],"rate":[64],"release,":[66],"we":[67],"prepared":[68],"small":[70],"library":[71],"hydroxybenzylamine":[73],"with":[75,99,137,156,183],"varied":[76],"in":[78,83,109,129],"core,":[81],"resulting":[82],"half-lives":[84],"ranging":[85],"from":[86,102],"20":[87],"144":[89],"h.":[90,142],"Optimization":[91],"linker":[94,136],"design":[95,111],"was":[96],"carried":[97],"out":[98],"mechanistic":[100],"insights":[101],"density":[103],"functional":[104],"theory":[105],"(DFT)":[106],"silico":[110],"an":[113],"intramolecular":[114,123],"trapping":[115],"agent":[116],"through":[117],"use":[119],"DFT":[121],"distortion":[124],"energy":[125],"calculations.":[126],"resulted":[128],"development":[131],"faster":[134],"half-life":[139],"4.6":[141],"demonstrate":[144],"their":[145],"effectiveness":[146],"as":[147],"bioconjugation,":[151],"protein\u2013polyethylene":[153],"glycol":[154],"conjugates":[155],"model":[158],"protein":[159,166],"lysozyme":[160],"were":[161],"prepared,":[162],"had":[164],"reduced":[165],"activity":[167,171],"but":[168],"recovered":[169],"\u226594%":[170],"upon":[172],"polymer.":[177],"tunable":[184],"rates":[186],"expands":[187],"toolbox":[191],"variety":[194],"bioconjugation":[196],"applications.":[197]},"counts_by_year":[{"year":2026,"cited_by_count":9},{"year":2025,"cited_by_count":9},{"year":2024,"cited_by_count":18},{"year":2023,"cited_by_count":5},{"year":2022,"cited_by_count":8}],"updated_date":"2026-10-31T12:09:11.096373","created_date":"2022-04-03T00:00:00"}