{"status":"ok","message-type":"work","message-version":"1.0.0","message":{"indexed":{"date-parts":[[2026,9,24]],"date-time":"2026-09-24T22:06:21Z","timestamp":1790287581791,"version":"4.1.0"},"reference-count":33,"publisher":"Elsevier BV","license":[{"start":{"date-parts":[[2023,1,1]],"date-time":"2023-01-01T00:00:00Z","timestamp":1672531200000},"content-version":"tdm","delay-in-days":0,"URL":"https:\/\/www.elsevier.com\/tdm\/userlicense\/1.0\/"},{"start":{"date-parts":[[2023,1,1]],"date-time":"2023-01-01T00:00:00Z","timestamp":1672531200000},"content-version":"tdm","delay-in-days":0,"URL":"https:\/\/www.elsevier.com\/legal\/tdmrep-license"},{"start":{"date-parts":[[2022,12,24]],"date-time":"2022-12-24T00:00:00Z","timestamp":1671840000000},"content-version":"vor","delay-in-days":0,"URL":"http:\/\/creativecommons.org\/licenses\/by\/4.0\/"}],"funder":[{"DOI":"10.13039\/501100001700","name":"Ministry of Education, Culture, Sports, Science and Technology","doi-asserted-by":"publisher","id":[{"id":"10.13039\/501100001700","id-type":"DOI","asserted-by":"publisher"}]},{"DOI":"10.13039\/100009619","name":"Japan Agency for Medical Research and Development","doi-asserted-by":"publisher","award":["JP21am0401003"],"award-info":[{"award-number":["JP21am0401003"]}],"id":[{"id":"10.13039\/100009619","id-type":"DOI","asserted-by":"publisher"}]},{"DOI":"10.13039\/100009619","name":"Japan Agency for Medical Research and Development","doi-asserted-by":"publisher","award":["JP21fk0108461"],"award-info":[{"award-number":["JP21fk0108461"]}],"id":[{"id":"10.13039\/100009619","id-type":"DOI","asserted-by":"publisher"}]},{"DOI":"10.13039\/100009619","name":"Japan Agency for Medical Research and Development","doi-asserted-by":"publisher","award":["JP21ae0121022"],"award-info":[{"award-number":["JP21ae0121022"]}],"id":[{"id":"10.13039\/100009619","id-type":"DOI","asserted-by":"publisher"}]},{"DOI":"10.13039\/100009619","name":"Japan Agency for Medical Research and Development","doi-asserted-by":"publisher","award":["JP20fk0108507"],"award-info":[{"award-number":["JP20fk0108507"]}],"id":[{"id":"10.13039\/100009619","id-type":"DOI","asserted-by":"publisher"}]},{"DOI":"10.13039\/501100001691","name":"Japan Society for the Promotion of Science","doi-asserted-by":"publisher","award":["JP20K15401"],"award-info":[{"award-number":["JP20K15401"]}],"id":[{"id":"10.13039\/501100001691","id-type":"DOI","asserted-by":"publisher"}]}],"content-domain":{"domain":["elsevier.com","sciencedirect.com"],"crossmark-restriction":true},"short-container-title":["Bioorganic &amp; Medicinal Chemistry"],"published-print":{"date-parts":[[2023,1]]},"DOI":"10.1016\/j.bmc.2022.117149","type":"journal-article","created":{"date-parts":[[2022,12,26]],"date-time":"2022-12-26T02:19:58Z","timestamp":1672021198000},"page":"117149","update-policy":"https:\/\/doi.org\/10.1016\/elsevier_cm_policy","source":"Crossref","is-referenced-by-count":4,"special_numbering":"C","title":["Synthesis and biophysical properties of tetravalent PEG-conjugated antisense oligonucleotide"],"prefix":"10.1016","volume":"78","author":[{"given":"Taslima","family":"Rahman Chowdhury","sequence":"first","affiliation":[],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Tahia","family":"Taufiq","sequence":"additional","affiliation":[],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Kenta","family":"Ishida","sequence":"additional","affiliation":[],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Md","family":"Ariful Islam","sequence":"additional","affiliation":[],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Yuuya","family":"Kasahara","sequence":"additional","affiliation":[],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Takashi","family":"Osawa","sequence":"additional","affiliation":[],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Satoshi","family":"Obika","sequence":"additional","affiliation":[],"role":[{"vocabulary":"crossref","role":"author"}]}],"member":"78","reference":[{"key":"10.1016\/j.bmc.2022.117149_b0005","doi-asserted-by":"crossref","first-page":"13993","DOI":"10.1021\/acsnano.1c05099","article-title":"Delivery of oligonucleotide therapeutics: Chemical modifications, lipid nanoparticles, and extracellular vesicles","volume":"15","author":"Bost","year":"2021","journal-title":"ACS Nano"},{"key":"10.1016\/j.bmc.2022.117149_b0010","doi-asserted-by":"crossref","DOI":"10.1016\/j.jbc.2021.100416","article-title":"Antisense technology: a review","volume":"296","author":"Crooke","year":"2021","journal-title":"J Biol Chem"},{"key":"10.1016\/j.bmc.2022.117149_b0015","doi-asserted-by":"crossref","first-page":"673","DOI":"10.1038\/s41573-020-0075-7","article-title":"Advances in oligonucleotide drug delivery","volume":"19","author":"Roberts","year":"2020","journal-title":"Nat Rev Drug Discov"},{"key":"10.1016\/j.bmc.2022.117149_b0020","doi-asserted-by":"crossref","first-page":"2004","DOI":"10.3390\/jcm9062004","article-title":"Antisense oligonucleotides: An emerging area in drug discovery and development","volume":"9","author":"Dhuri","year":"2020","journal-title":"J Clin Med"},{"key":"10.1016\/j.bmc.2022.117149_b0025","doi-asserted-by":"crossref","first-page":"433","DOI":"10.3390\/biomedicines9040433","article-title":"The challenges and strategies of antisense oligonucleotide drug delivery","volume":"9","author":"Gagliardi","year":"2021","journal-title":"Biomedicines."},{"key":"10.1016\/j.bmc.2022.117149_b0030","doi-asserted-by":"crossref","first-page":"46","DOI":"10.1124\/jpet.113.212407","article-title":"Pharmacology of a central nervous system delivered 2'-O-methoxyethyl-modified survival of motor neuron splicing oligonucleotide in mice and nonhuman primates","volume":"350","author":"Rigo","year":"2014","journal-title":"J Pharmacol Exp Ther"},{"key":"10.1016\/j.bmc.2022.117149_b0035","doi-asserted-by":"crossref","first-page":"e323","DOI":"10.1212\/NXG.0000000000000323","article-title":"Antisense oligonucleotides: a primer","volume":"5","author":"Scoles","year":"2019","journal-title":"Neurol Genet"},{"key":"10.1016\/j.bmc.2022.117149_b0040","doi-asserted-by":"crossref","first-page":"72","DOI":"10.1002\/jimd.12251","article-title":"Opportunities and challenges for antisense oligonucleotide therapies","volume":"44","author":"Kuijper","year":"2021","journal-title":"J Inherit Metab Dis"},{"key":"10.1016\/j.bmc.2022.117149_b0045","doi-asserted-by":"crossref","first-page":"2286","DOI":"10.1529\/biophysj.104.054080","article-title":"Molecular and cellular barriers limiting the effectiveness of antisense oligonucleotides","volume":"89","author":"Roth","year":"2005","journal-title":"Biophys J"},{"key":"10.1016\/j.bmc.2022.117149_b0050","doi-asserted-by":"crossref","first-page":"100","DOI":"10.1016\/j.jconrel.2006.04.014","article-title":"Toxicity of cationic lipids and cationic polymers in gene delivery","volume":"114","author":"Lv","year":"2006","journal-title":"J Contr Rel."},{"key":"10.1016\/j.bmc.2022.117149_b0055","doi-asserted-by":"crossref","unstructured":"Zhang L, Wang Y, Chen P, et al. A mechanistic study on the cellular uptake, intracellular trafficking, and antisense gene regulation of bottlebrush polymer-conjugated oligonucleotides. bioRxiv. https:\/\/doi.org\/10.1101\/2022.06.15.496353.","DOI":"10.1101\/2022.06.15.496353"},{"key":"10.1016\/j.bmc.2022.117149_b0060","doi-asserted-by":"crossref","first-page":"214","DOI":"10.1038\/nrd1033","article-title":"Effect of PEGylation on pharmaceuticals","volume":"2","author":"Harris","year":"2003","journal-title":"Nat Rev Drug Discov"},{"key":"10.1016\/j.bmc.2022.117149_b0065","doi-asserted-by":"crossref","first-page":"5519","DOI":"10.1007\/s12274-018-2131-8","article-title":"PEGylation of therapeutic oligonucletides: From linear to highly branched PEG architectures","volume":"11","author":"Lu","year":"2018","journal-title":"Nano Res"},{"key":"10.1016\/j.bmc.2022.117149_b0070","doi-asserted-by":"crossref","first-page":"448","DOI":"10.1080\/09205063.2017.1422853","article-title":"PEG-modification on the endo-position of an antisense oligonucleotide increases tumor accumulation via the EPR effect","volume":"29","author":"Hagiwara","year":"2018","journal-title":"J Biomater Sci Polym Ed"},{"key":"10.1016\/j.bmc.2022.117149_b0075","doi-asserted-by":"crossref","first-page":"143","DOI":"10.1016\/j.jconrel.2006.12.021","article-title":"Delivery of G3139 using releasable PEG-linkers: Impact on pharmacokinetic profile and anti-tumor efficacy","volume":"119","author":"Zhao","year":"2007","journal-title":"J Contr Rel."},{"key":"10.1016\/j.bmc.2022.117149_b0080","doi-asserted-by":"crossref","first-page":"381","DOI":"10.1517\/17425250902877680","article-title":"Antisense oligonucleotide pharmacokinetics and metabolism","volume":"5","author":"Geary","year":"2009","journal-title":"Expert Opin Drug Metab Toxicol"},{"key":"10.1016\/j.bmc.2022.117149_b0085","doi-asserted-by":"crossref","first-page":"421","DOI":"10.1016\/j.progpolymsci.2012.07.006","article-title":"Current drug research on PEGylation with small molecular agents","volume":"38","author":"Li","year":"2013","journal-title":"Prog Polym Sci"},{"key":"10.1016\/j.bmc.2022.117149_b0090","doi-asserted-by":"crossref","first-page":"45830","DOI":"10.1021\/acsami.0c13995","article-title":"Self-assembled DNA\u2013PEG bottlebrushes enhance antisense activity and pharmacokinetics of oligonucleotides","volume":"12","author":"Wang","year":"2020","journal-title":"ACS Appl Mater Interfaces"},{"key":"10.1016\/j.bmc.2022.117149_b0095","article-title":"Targeting oncogenic KRAS with molecular brush-conjugated antisense oligonucleotides","volume":"119","author":"Wang","year":"2022","journal-title":"Proc Natl Acad Sci U S A."},{"key":"10.1016\/j.bmc.2022.117149_b0100","doi-asserted-by":"crossref","first-page":"2754","DOI":"10.1002\/(SICI)1521-3773(19981102)37:20<2754::AID-ANIE2754>3.0.CO;2-3","article-title":"Polyvalent interactions in biological systems: Implications for design and use of multivalent ligands and inhibitors","volume":"37","author":"Mammen","year":"1998","journal-title":"Angew Chem Int Ed Engl"},{"key":"10.1016\/j.bmc.2022.117149_b0105","doi-asserted-by":"crossref","first-page":"565","DOI":"10.1016\/j.jconrel.2020.04.039","article-title":"Application of star poly(ethylene glycol) derivatives in drug delivery and controlled release","volume":"323","author":"Zhao","year":"2020","journal-title":"J Contr Rel."},{"key":"10.1016\/j.bmc.2022.117149_b0110","doi-asserted-by":"crossref","first-page":"e202100583","DOI":"10.1002\/cbic.202100583","article-title":"Enhanced immunostimulatory activity of covalent DNA dendrons","volume":"23","author":"Kawamoto","year":"2022","journal-title":"Chembiochem"},{"key":"10.1016\/j.bmc.2022.117149_b0115","doi-asserted-by":"crossref","first-page":"1673","DOI":"10.1021\/bc200235q","article-title":"Multivalent cyclic RGD conjugates for targeted delivery of small interfering RNA","volume":"22","author":"Alam","year":"2011","journal-title":"Bioconjug Chem"},{"key":"10.1016\/j.bmc.2022.117149_b0120","doi-asserted-by":"crossref","DOI":"10.1016\/j.bmc.2022.116972","article-title":"Synthesis and physical and biological properties of 1,3-diaza-2-oxophenoxazine-conjugated oligonucleotides","volume":"72","author":"Yamaji","year":"2022","journal-title":"Bioorg Med Chem"},{"key":"10.1016\/j.bmc.2022.117149_b0125","doi-asserted-by":"crossref","first-page":"4810","DOI":"10.1093\/nar\/22.22.4810","article-title":"Synthesis and properties of oligodeoxyribonucleotide-polyethylene glycol conjugates","volume":"22","author":"J\u00e4schke","year":"1994","journal-title":"Nucleic Acids Res"},{"key":"10.1016\/j.bmc.2022.117149_b0130","doi-asserted-by":"crossref","first-page":"1589","DOI":"10.1007\/s10337-014-2766-x","article-title":"The effects of stationary phases on retention and selectivity of oligonucleotides in IP-RP-HPLC","volume":"77","author":"Studzi\u0144ska","year":"2014","journal-title":"Chromatographia"},{"key":"10.1016\/j.bmc.2022.117149_b0135","doi-asserted-by":"crossref","first-page":"563","DOI":"10.3390\/vaccines9060563","article-title":"Chemical conjugation strategies for the development of protein-based subunit nanovaccines","volume":"9","author":"Lu","year":"2021","journal-title":"Vaccines"},{"key":"10.1016\/j.bmc.2022.117149_b0140","doi-asserted-by":"crossref","first-page":"8584","DOI":"10.1021\/acs.analchem.0c01567","article-title":"Characterization of high molecular weight multi-arm functionalized PEG\u2013maleimide for protein conjugation by charge-reduction mass spectrometry coupled to two-dimensional liquid chromatography","volume":"92","author":"Yang","year":"2020","journal-title":"Anal Chem"},{"key":"10.1016\/j.bmc.2022.117149_b0145","doi-asserted-by":"crossref","first-page":"2136","DOI":"10.1021\/bc200411n","article-title":"Stabilization and photochemical regulation of antisense agents through PEGylation","volume":"22","author":"Govan","year":"2011","journal-title":"Bioconjug Chem"},{"key":"10.1016\/j.bmc.2022.117149_b0150","doi-asserted-by":"crossref","first-page":"5758","DOI":"10.1016\/j.bmcl.2014.10.045","article-title":"Oligonucleotides conjugated with short chemically defined polyethylene glycol chains are efficient antisense agents","volume":"24","author":"Shokrzadeh","year":"2014","journal-title":"Bioorg Med Chem Lett"},{"key":"10.1016\/j.bmc.2022.117149_b0155","doi-asserted-by":"crossref","first-page":"12466","DOI":"10.1021\/jacs.5b08069","article-title":"Providing oligonucleotides with steric selectivity by brush-polymer-assisted compaction","volume":"137","author":"Lu","year":"2015","journal-title":"J Am Chem Soc"},{"key":"10.1016\/j.bmc.2022.117149_b0160","doi-asserted-by":"crossref","first-page":"57","DOI":"10.1016\/j.jconrel.2016.02.007","article-title":"Evaluation of the effects of chemically different linkers on hepatic accumulations, cell tropism and gene silencing ability of cholesterol-conjugated antisense oligonucleotides","volume":"226","author":"Wada","year":"2016","journal-title":"J Contr Rel."},{"key":"10.1016\/j.bmc.2022.117149_b0165","doi-asserted-by":"crossref","first-page":"26","DOI":"10.1016\/j.bmc.2015.11.036","article-title":"Serial incorporation of a monovalent GalNAc phosphoramidite unit into hepatocyte-targeting antisense oligonucleotides","volume":"24","author":"Yamamoto","year":"2016","journal-title":"Bioorg Med Chem"}],"container-title":["Bioorganic &amp; Medicinal Chemistry"],"original-title":[],"language":"en","link":[{"URL":"https:\/\/api.elsevier.com\/content\/article\/PII:S0968089622005429?httpAccept=text\/xml","content-type":"text\/xml","content-version":"vor","intended-application":"text-mining"},{"URL":"https:\/\/api.elsevier.com\/content\/article\/PII:S0968089622005429?httpAccept=text\/plain","content-type":"text\/plain","content-version":"vor","intended-application":"text-mining"}],"deposited":{"date-parts":[[2026,5,12]],"date-time":"2026-05-12T08:29:53Z","timestamp":1778574593000},"score":1,"resource":{"primary":{"URL":"https:\/\/linkinghub.elsevier.com\/retrieve\/pii\/S0968089622005429"}},"subtitle":[],"short-title":[],"issued":{"date-parts":[[2023,1]]},"references-count":33,"alternative-id":["S0968089622005429"],"URL":"https:\/\/doi.org\/10.1016\/j.bmc.2022.117149","relation":{},"ISSN":["0968-0896"],"issn-type":[{"value":"0968-0896","type":"print"}],"subject":[],"published":{"date-parts":[[2023,1]]},"assertion":[{"value":"Elsevier","name":"publisher","label":"This article is maintained by"},{"value":"Synthesis and biophysical properties of tetravalent PEG-conjugated antisense oligonucleotide","name":"articletitle","label":"Article Title"},{"value":"Bioorganic & Medicinal Chemistry","name":"journaltitle","label":"Journal Title"},{"value":"https:\/\/doi.org\/10.1016\/j.bmc.2022.117149","name":"articlelink","label":"CrossRef DOI link to publisher maintained version"},{"value":"article","name":"content_type","label":"Content Type"},{"value":"\u00a9 2022 The Author(s). Published by Elsevier Ltd.","name":"copyright","label":"Copyright"}],"article-number":"117149"}}