{"doi":"10.1021/jacs.8b05093","title":"Bioorthogonal Removal of 3-Isocyanopropyl Groups Enables the Controlled Release of Fluorophores and Drugs in Vivo","abstract":null,"journal":"Journal of the American Chemical Society","year":2018,"id":650268,"datarank":0.7694848072384611,"base_score":5.1298987149230735,"endowment":5.1298987149230735,"self_citation_contribution":0.7694848072384611,"citation_network_contribution":0.0,"self_endowment_contribution":0.7694848072384611,"citer_contribution":0.0,"corpus_percentile":null,"corpus_rank":null,"citation_count":168,"citer_count":0,"citers_with_citation_signal":0,"citers_with_endowment":0,"datacite_reuse_total":0,"is_dataset":false,"is_dataset_confidence":null,"is_data_producer":false,"deposit_databanks":null,"is_oa":false,"file_count":0,"downloads":0,"has_version_chain":false,"published_date":null,"fair_score":null,"fair_percentile":null,"algorithm_id":"datarank_citation_only_1hop_v6","ranking_scope":"data_only","authors":[{"id":550980,"name":"Minghao Xu","orcid":"0000-0002-7684-4926","position":1,"is_corresponding":false},{"id":644023,"name":"Saba Parvez","orcid":"0000-0001-8608-1494","position":2,"is_corresponding":false},{"id":268421,"name":"Randall T. Peterson","orcid":"0000-0003-0727-3469","position":3,"is_corresponding":false},{"id":416690,"name":"Raphael M. Franzini","orcid":"0000-0001-6772-5119","position":4,"is_corresponding":false},{"id":1355104,"name":"Julian Tu","orcid":"0000-0002-5645-8577","position":0,"is_corresponding":false}],"reference_count":0,"raw_metadata":{"has_enrichment":true,"resolved":true,"title":"Bioorthogonal Removal of 3-Isocyanopropyl Groups Enables the Controlled Release of Fluorophores and Drugs in Vivo","abstract":"Dissociative bioorthogonal reactions allow for chemically controlling the release of bioactive agents and reporter probes. Here we describe 3-isocyanopropyl substituents as masking groups that can be effectively removed in biological systems. 3-Isocyanopropyl derivatives react with tetrazines to afford 3-oxopropyl groups that eliminate diverse functionalities. The study shows that the reaction is rapid and can liberate phenols and amines near-quantitatively under physiological conditions. The reaction is compatible with living organisms as demonstrated by the release of a resorufin fluorophore and a mexiletine drug in zebrafish embryos implanted with tetrazine-modified beads. The combined benefits of synthetic ease, rapid kinetics, diversity of leaving groups, high release yields, and structural compactness, make 3-isocyanopropyl derivatives attractive chemical caging moieties for uses in chemical biology and drug delivery.","is_dataset_classified":null,"base_score":5.1298987149230735,"endowment":5.1298987149230735,"datacite_reuse_total":0,"file_count":0,"downloads":0,"views":0,"has_version_chain":false,"is_dataset":false,"is_oa":false,"pmid":"29927585","pmcid":null,"openalex_id":"https://openalex.org/W2808739041","authors":[],"funders":[{"funder_name":"Huntsman Cancer Institute","grant_id":"","title":null},{"funder_name":"Utah Science Technology and Research","grant_id":"","title":null},{"funder_name":"University of Utah","grant_id":"","title":null}],"total_grants":3,"fwci":7.1284,"citation_percentile":0.9828788,"influential_citations":0,"citation_trend":[{"year":2018,"count":2},{"year":2019,"count":21},{"year":2020,"count":21},{"year":2021,"count":24},{"year":2022,"count":13},{"year":2023,"count":25},{"year":2024,"count":19},{"year":2025,"count":23},{"year":2026,"count":20}],"oa_status":"closed","license":null,"oa_locations":[{"url":"https://pubs.acs.org/doi/pdf/10.1021/jacs.8b05093","host_type":"publisher"},{"url":"https://doi.org/10.1021/jacs.8b05093","host_type":"journal"},{"url":"https://pubmed.ncbi.nlm.nih.gov/29927585","host_type":"repository"}],"fields_of_study":["Click Chemistry and Applications","Chemical Synthesis and Analysis","Advanced biosensing and bioanalysis techniques"],"mesh_terms":["Animals","Anti-Arrhythmia Agents","Delayed-Action Preparations","Fluorescent Dyes","Mexiletine","Oxazines","Zebrafish","Isocyanates","Drug Liberation"],"keywords":["Bioorthogonal chemistry","Chemistry","Tetrazine","Combinatorial chemistry","Fluorophore","Drug delivery","In vivo","Fluorescence","Biophysics","Organic chemistry","Click chemistry"],"sdg_mappings":[],"linked_datasets":[],"clinical_trials":[],"software_tools":[],"database_accessions":[],"source":"live","citation_network_status":"fetched"},"created_at":"2026-08-10T05:10:33.817582Z","pmid":null,"pmcid":null,"fwci":null,"citation_percentile":null,"influential_citations":0,"oa_status":null,"license":null,"views":0,"total_file_size_bytes":0,"version_count":0,"fair_f":null,"fair_a":null,"fair_i":null,"fair_r":null,"fair_zscore":null,"fair_rationale":null,"fair_model":null,"fair_agent_version":null,"fair_fulltext_source":null,"fair_has_llm":null,"fair_computed_at":null,"clinical_trials":[],"software_tools":[],"db_accessions":[],"linked_datasets":[],"topics":[]}