{"id":"https://openalex.org/W2154149779","doi":"https://doi.org/10.1034/j.1399-3011.1999.00071.x","title":"Synthesis and evaluation of the physicochemical properties of esterase\u2010sensitive cyclic prodrugs of opioid peptides using coumarinic acid and phenylpropionic acid linkers","display_name":"Synthesis and evaluation of the physicochemical properties of esterase\u2010sensitive cyclic prodrugs of opioid peptides using coumarinic acid and phenylpropionic acid linkers","publication_year":1999,"publication_date":"1999-04-01","ids":{"openalex":"https://openalex.org/W2154149779","doi":"https://doi.org/10.1034/j.1399-3011.1999.00071.x","mag":"2154149779","pmid":"https://pubmed.ncbi.nlm.nih.gov/10406215"},"language":"en","primary_location":{"id":"doi:10.1034/j.1399-3011.1999.00071.x","doi":"https://doi.org/10.1034/j.1399-3011.1999.00071.x","is_oa":false,"landing_page_url":"https://doi.org/10.1034/j.1399-3011.1999.00071.x","pdf_url":null,"source":{"id":"https://openalex.org/S122310368","display_name":"Journal of Peptide Research","issn_l":"1397-002X","issn":["1397-002X","1399-3011"],"is_oa":false,"is_in_doaj":false,"is_core":true,"listed_in":["cwts-core"],"host_organization":"https://openalex.org/P4310320595","host_organization_name":"Wiley","host_organization_lineage":["https://openalex.org/P4310320595"],"host_organization_lineage_names":["Wiley"],"type":"journal"},"license":null,"license_id":null,"version":"publishedVersion","is_accepted":true,"is_published":true,"raw_source_name":"The Journal of Peptide Research","raw_type":"journal-article"},"volume":null,"type":"article","is_traditional":true,"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/A5044174487","display_name":"Binghe Wang","orcid":"https://orcid.org/0000-0002-2200-5270","observed_orcids":["https://orcid.org/0000-0002-2200-5270"]},"institutions":[{"id":"https://openalex.org/I137902535","display_name":"North Carolina State University","ror":"https://ror.org/04tj63d06","country_code":"US","type":"education","lineage":["https://openalex.org/I137902535"]}],"countries":["US"],"is_corresponding":true,"raw_author_name":"B. Wang","raw_affiliation_strings":["Department of Chemistry, North Carolina State University, Raleigh 27695-8204, USA. binghe_wang@ncsu.edu","Department of Chemistry, North Carolina State University, Raleigh, NC 27695\u20138204, USA"],"raw_orcid":null,"affiliations":[{"raw_affiliation_string":"Department of Chemistry, North Carolina State University, Raleigh 27695-8204, USA. binghe_wang@ncsu.edu","institution_ids":["https://openalex.org/I137902535"]},{"raw_affiliation_string":"Department of Chemistry, North Carolina State University, Raleigh, NC 27695\u20138204, USA","institution_ids":["https://openalex.org/I137902535"]}]},{"author_position":"middle","author":{"id":null,"display_name":"W. Wang","orcid":null,"observed_orcids":[]},"institutions":[{"id":"https://openalex.org/I137902535","display_name":"North Carolina State University","ror":"https://ror.org/04tj63d06","country_code":"US","type":"education","lineage":["https://openalex.org/I137902535"]}],"countries":["US"],"is_corresponding":true,"raw_author_name":"W. Wang","raw_affiliation_strings":["Department of Chemistry, North Carolina State University, Raleigh, NC 27695\u20138204, USA"],"raw_orcid":null,"affiliations":[{"raw_affiliation_string":"Department of Chemistry, North Carolina State University, Raleigh, NC 27695\u20138204, USA","institution_ids":["https://openalex.org/I137902535"]}]},{"author_position":"middle","author":{"id":null,"display_name":"H. Zhang","orcid":null,"observed_orcids":[]},"institutions":[{"id":"https://openalex.org/I114027177","display_name":"University of North Carolina at Chapel Hill","ror":"https://ror.org/0130frc33","country_code":"US","type":"education","lineage":["https://openalex.org/I114027177"]}],"countries":["US"],"is_corresponding":false,"raw_author_name":"H. Zhang","raw_affiliation_strings":["H. Zhang, Department of Chemistry, University of North Carolina, Chapel Hill, NC"],"raw_orcid":null,"affiliations":[{"raw_affiliation_string":"H. Zhang, Department of Chemistry, University of North Carolina, Chapel Hill, NC","institution_ids":["https://openalex.org/I114027177"]}]},{"author_position":"middle","author":{"id":"https://openalex.org/A5046902431","display_name":"Daxian Shan","orcid":null,"observed_orcids":[]},"institutions":[],"countries":[],"is_corresponding":false,"raw_author_name":"D. Shan","raw_affiliation_strings":["D. Shan, Chiron Corporation, Thousand Oaks, CA"],"raw_orcid":null,"affiliations":[{"raw_affiliation_string":"D. Shan, Chiron Corporation, Thousand Oaks, CA","institution_ids":[]}]},{"author_position":"middle","author":{"id":"https://openalex.org/A5033910570","display_name":"Kalpana S. Nimkar","orcid":null,"observed_orcids":[]},"institutions":[{"id":"https://openalex.org/I146416000","display_name":"University of Kansas","ror":"https://ror.org/001tmjg57","country_code":"US","type":"education","lineage":["https://openalex.org/I146416000"]}],"countries":["US"],"is_corresponding":false,"raw_author_name":"K. Nimkar","raw_affiliation_strings":["Department of Pharmaceutical Chemistry, The University of Kansas, Lawrence, KS 66047, USA\n\nPresent addresses:"],"raw_orcid":null,"affiliations":[{"raw_affiliation_string":"Department of Pharmaceutical Chemistry, The University of Kansas, Lawrence, KS 66047, USA\n\nPresent addresses:","institution_ids":["https://openalex.org/I146416000"]}]},{"author_position":"middle","author":{"id":null,"display_name":"O. Gudmundsson","orcid":null,"observed_orcids":[]},"institutions":[{"id":"https://openalex.org/I146416000","display_name":"University of Kansas","ror":"https://ror.org/001tmjg57","country_code":"US","type":"education","lineage":["https://openalex.org/I146416000"]},{"id":"https://openalex.org/I4210091812","display_name":"Bristol-Myers Squibb (United States)","ror":"https://ror.org/00gtmwv55","country_code":"US","type":"company","lineage":["https://openalex.org/I4210091812"]}],"countries":["US"],"is_corresponding":false,"raw_author_name":"O. Gudmundsson","raw_affiliation_strings":["Department of Pharmaceutical Chemistry, The University of Kansas, Lawrence, KS 66047, USA\n\nPresent addresses:","O. Gudmundsson, Bristol-Myers Squibb, New Brunswick, NJ"],"raw_orcid":null,"affiliations":[{"raw_affiliation_string":"Department of Pharmaceutical Chemistry, The University of Kansas, Lawrence, KS 66047, USA\n\nPresent addresses:","institution_ids":["https://openalex.org/I146416000"]},{"raw_affiliation_string":"O. Gudmundsson, Bristol-Myers Squibb, New Brunswick, NJ","institution_ids":["https://openalex.org/I4210091812"]}]},{"author_position":"middle","author":{"id":"https://openalex.org/A5037761580","display_name":"Sanjeev Gangwar","orcid":"https://orcid.org/0000-0001-6285-4915","observed_orcids":["https://orcid.org/0000-0001-6285-4915"]},"institutions":[{"id":"https://openalex.org/I146416000","display_name":"University of Kansas","ror":"https://ror.org/001tmjg57","country_code":"US","type":"education","lineage":["https://openalex.org/I146416000"]}],"countries":["US"],"is_corresponding":false,"raw_author_name":"S. Gangwar","raw_affiliation_strings":["Department of Pharmaceutical Chemistry, The University of Kansas, Lawrence, KS 66047, USA\n\nPresent addresses:","S. Gangwar, Prolix, Inc., Bothell, WA, USA"],"raw_orcid":null,"affiliations":[{"raw_affiliation_string":"Department of Pharmaceutical Chemistry, The University of Kansas, Lawrence, KS 66047, USA\n\nPresent addresses:","institution_ids":["https://openalex.org/I146416000"]},{"raw_affiliation_string":"S. Gangwar, Prolix, Inc., Bothell, WA, USA","institution_ids":[]}]},{"author_position":"middle","author":{"id":"https://openalex.org/A5003956897","display_name":"Teruna J. Siahaan","orcid":"https://orcid.org/0000-0001-7250-0627","observed_orcids":["https://orcid.org/0000-0001-7250-0627"]},"institutions":[{"id":"https://openalex.org/I146416000","display_name":"University of Kansas","ror":"https://ror.org/001tmjg57","country_code":"US","type":"education","lineage":["https://openalex.org/I146416000"]}],"countries":["US"],"is_corresponding":false,"raw_author_name":"T. Siahaan","raw_affiliation_strings":["Department of Pharmaceutical Chemistry, The University of Kansas, Lawrence, KS 66047, USA\n\nPresent addresses:"],"raw_orcid":null,"affiliations":[{"raw_affiliation_string":"Department of Pharmaceutical Chemistry, The University of Kansas, Lawrence, KS 66047, USA\n\nPresent addresses:","institution_ids":["https://openalex.org/I146416000"]}]},{"author_position":"last","author":{"id":"https://openalex.org/A5110194225","display_name":"Ronald T. Borchardt","orcid":null,"observed_orcids":[]},"institutions":[{"id":"https://openalex.org/I146416000","display_name":"University of Kansas","ror":"https://ror.org/001tmjg57","country_code":"US","type":"education","lineage":["https://openalex.org/I146416000"]}],"countries":["US"],"is_corresponding":false,"raw_author_name":"R.T. Borchardt","raw_affiliation_strings":["Department of Pharmaceutical Chemistry, The University of Kansas, Lawrence, KS 66047, USA\n\nPresent addresses:"],"raw_orcid":null,"affiliations":[{"raw_affiliation_string":"Department of Pharmaceutical Chemistry, The University of Kansas, Lawrence, KS 66047, USA\n\nPresent addresses:","institution_ids":["https://openalex.org/I146416000"]}]}],"institutions":[],"countries_distinct_count":1,"institutions_distinct_count":4,"corresponding_author_ids":["https://openalex.org/A5044174487"],"corresponding_institution_ids":["https://openalex.org/I137902535"],"apc_list":null,"apc_paid":null,"fwci":6.1407,"has_fulltext":false,"cited_by_count":57,"citation_normalized_percentile":{"value":0.97821293,"is_in_top_1_percent":false,"is_in_top_10_percent":true},"cited_by_percentile_year":{"min":88,"max":97},"biblio":{"volume":"53","issue":"4","first_page":"370","last_page":"382"},"is_retracted":false,"is_paratext":false,"is_xpac":false,"primary_topic":{"id":"https://openalex.org/T10911","display_name":"Chemical Synthesis and Analysis","score":0.70169997215271,"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"}},"topics":[{"id":"https://openalex.org/T10911","display_name":"Chemical Synthesis and Analysis","score":0.70169997215271,"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/T10814","display_name":"Neuropeptides and Animal Physiology","score":0.17589999735355377,"subfield":{"id":"https://openalex.org/subfields/2804","display_name":"Cellular and Molecular Neuroscience"},"field":{"id":"https://openalex.org/fields/28","display_name":"Neuroscience"},"domain":{"id":"https://openalex.org/domains/1","display_name":"Life Sciences"}},{"id":"https://openalex.org/T10920","display_name":"Advanced Drug Delivery Systems","score":0.02710000053048134,"subfield":{"id":"https://openalex.org/subfields/3003","display_name":"Pharmaceutical Science"},"field":{"id":"https://openalex.org/fields/30","display_name":"Pharmacology, Toxicology and Pharmaceutics"},"domain":{"id":"https://openalex.org/domains/1","display_name":"Life Sciences"}}],"keywords":[{"id":"https://openalex.org/keywords/opioid-peptides","display_name":"opioid peptides","score":0.9909999966621399},{"id":"https://openalex.org/keywords/leu-enkephalin","display_name":"leu-enkephalin","score":0.9629999995231628},{"id":"https://openalex.org/keywords/dadle","display_name":"DADLE","score":0.9980000257492065},{"id":"https://openalex.org/keywords/membrane-permeability","display_name":"membrane permeability","score":0.921999990940094},{"id":"https://openalex.org/keywords/intestinal-permeation","display_name":"intestinal permeation","score":0.6769999861717224},{"id":"https://openalex.org/keywords/caco-2-cells","display_name":"Caco-2 cells","score":0.8730000257492065},{"id":"https://openalex.org/keywords/lipophilicity","display_name":"lipophilicity","score":0.8080000281333923},{"id":"https://openalex.org/keywords/hydrogen-bonding","display_name":"hydrogen bonding","score":0.753000020980835},{"id":"https://openalex.org/keywords/peptide-cyclization","display_name":"peptide cyclization","score":0.5559999942779541}],"concepts":[{"id":"https://openalex.org/C108215921","wikidata":"https://www.wikidata.org/wiki/Q603741","display_name":"Prodrug","level":2,"score":0.8382619619369507},{"id":"https://openalex.org/C185592680","wikidata":"https://www.wikidata.org/wiki/Q2329","display_name":"Chemistry","level":0,"score":0.8237439393997192},{"id":"https://openalex.org/C60984968","wikidata":"https://www.wikidata.org/wiki/Q389172","display_name":"Cyclic peptide","level":3,"score":0.5626757144927979},{"id":"https://openalex.org/C201399114","wikidata":"https://www.wikidata.org/wiki/Q898401","display_name":"Lipophilicity","level":2,"score":0.543982982635498},{"id":"https://openalex.org/C515207424","wikidata":"https://www.wikidata.org/wiki/Q8066","display_name":"Amino acid","level":2,"score":0.5258738994598389},{"id":"https://openalex.org/C2779281246","wikidata":"https://www.wikidata.org/wiki/Q172847","display_name":"Peptide","level":2,"score":0.4796179234981537},{"id":"https://openalex.org/C71240020","wikidata":"https://www.wikidata.org/wiki/Q186011","display_name":"Stereochemistry","level":1,"score":0.45235660672187805},{"id":"https://openalex.org/C2778680407","wikidata":"https://www.wikidata.org/wiki/Q424905","display_name":"DADLE","level":5,"score":0.4451540410518646},{"id":"https://openalex.org/C88016717","wikidata":"https://www.wikidata.org/wiki/Q417189","display_name":"Opioid peptide","level":4,"score":0.41834068298339844},{"id":"https://openalex.org/C55493867","wikidata":"https://www.wikidata.org/wiki/Q7094","display_name":"Biochemistry","level":1,"score":0.21490421891212463},{"id":"https://openalex.org/C2781063702","wikidata":"https://www.wikidata.org/wiki/Q427523","display_name":"Opioid","level":3,"score":0.12695050239562988},{"id":"https://openalex.org/C170493617","wikidata":"https://www.wikidata.org/wiki/Q208467","display_name":"Receptor","level":2,"score":0.0}],"mesh":[{"descriptor_ui":"D000595","descriptor_name":"Amino Acid Sequence","qualifier_ui":null,"qualifier_name":null,"is_major_topic":false},{"descriptor_ui":"D002463","descriptor_name":"Cell Membrane Permeability","qualifier_ui":"Q000187","qualifier_name":"drug effects","is_major_topic":false},{"descriptor_ui":"D002627","descriptor_name":"Chemistry, Physical","qualifier_ui":null,"qualifier_name":null,"is_major_topic":false},{"descriptor_ui":"D003373","descriptor_name":"Coumaric Acids","qualifier_ui":"Q000737","qualifier_name":"chemistry","is_major_topic":false},{"descriptor_ui":"D004743","descriptor_name":"Enkephalin, Leucine","qualifier_ui":"Q000494","qualifier_name":"pharmacology","is_major_topic":false},{"descriptor_ui":"D004743","descriptor_name":"Enkephalin, Leucine","qualifier_ui":"Q000737","qualifier_name":"chemistry","is_major_topic":false},{"descriptor_ui":"D004950","descriptor_name":"Esterases","qualifier_ui":"Q000378","qualifier_name":"metabolism","is_major_topic":false},{"descriptor_ui":"D008567","descriptor_name":"Membranes, Artificial","qualifier_ui":null,"qualifier_name":null,"is_major_topic":false},{"descriptor_ui":"D008954","descriptor_name":"Models, Biological","qualifier_ui":null,"qualifier_name":null,"is_major_topic":false},{"descriptor_ui":"D010456","descriptor_name":"Peptides, Cyclic","qualifier_ui":"Q000138","qualifier_name":"chemical synthesis","is_major_topic":false},{"descriptor_ui":"D010456","descriptor_name":"Peptides, Cyclic","qualifier_ui":"Q000378","qualifier_name":"metabolism","is_major_topic":false},{"descriptor_ui":"D010456","descriptor_name":"Peptides, Cyclic","qualifier_ui":"Q000737","qualifier_name":"chemistry","is_major_topic":true},{"descriptor_ui":"D010539","descriptor_name":"Permeability","qualifier_ui":null,"qualifier_name":null,"is_major_topic":false},{"descriptor_ui":"D010666","descriptor_name":"Phenylpropionates","qualifier_ui":"Q000737","qualifier_name":"chemistry","is_major_topic":false},{"descriptor_ui":"D011355","descriptor_name":"Prodrugs","qualifier_ui":"Q000138","qualifier_name":"chemical synthesis","is_major_topic":true},{"descriptor_ui":"D011355","descriptor_name":"Prodrugs","qualifier_ui":"Q000378","qualifier_name":"metabolism","is_major_topic":false},{"descriptor_ui":"D011355","descriptor_name":"Prodrugs","qualifier_ui":"Q000494","qualifier_name":"pharmacology","is_major_topic":false},{"descriptor_ui":"D011355","descriptor_name":"Prodrugs","qualifier_ui":"Q000737","qualifier_name":"chemistry","is_major_topic":true},{"descriptor_ui":"D013329","descriptor_name":"Structure-Activity Relationship","qualifier_ui":null,"qualifier_name":null,"is_major_topic":false},{"descriptor_ui":"D016308","descriptor_name":"Enkephalin, Leucine-2-Alanine","qualifier_ui":"Q000494","qualifier_name":"pharmacology","is_major_topic":false},{"descriptor_ui":"D016308","descriptor_name":"Enkephalin, Leucine-2-Alanine","qualifier_ui":"Q000737","qualifier_name":"chemistry","is_major_topic":false},{"descriptor_ui":"D018847","descriptor_name":"Opioid Peptides","qualifier_ui":"Q000138","qualifier_name":"chemical synthesis","is_major_topic":false},{"descriptor_ui":"D018847","descriptor_name":"Opioid Peptides","qualifier_ui":"Q000378","qualifier_name":"metabolism","is_major_topic":false},{"descriptor_ui":"D018847","descriptor_name":"Opioid Peptides","qualifier_ui":"Q000737","qualifier_name":"chemistry","is_major_topic":true},{"descriptor_ui":"D055598","descriptor_name":"Chemical Phenomena","qualifier_ui":null,"qualifier_name":null,"is_major_topic":false}],"locations_count":2,"locations":[{"id":"doi:10.1034/j.1399-3011.1999.00071.x","doi":"https://doi.org/10.1034/j.1399-3011.1999.00071.x","is_oa":false,"landing_page_url":"https://doi.org/10.1034/j.1399-3011.1999.00071.x","pdf_url":null,"source":{"id":"https://openalex.org/S122310368","display_name":"Journal of Peptide Research","issn_l":"1397-002X","issn":["1397-002X","1399-3011"],"is_oa":false,"is_in_doaj":false,"is_core":true,"listed_in":["cwts-core"],"host_organization":"https://openalex.org/P4310320595","host_organization_name":"Wiley","host_organization_lineage":["https://openalex.org/P4310320595"],"host_organization_lineage_names":["Wiley"],"type":"journal"},"license":null,"license_id":null,"version":"publishedVersion","is_accepted":true,"is_published":true,"raw_source_name":"The Journal of Peptide Research","raw_type":"journal-article"},{"id":"pmid:10406215","doi":null,"is_oa":false,"landing_page_url":"https://pubmed.ncbi.nlm.nih.gov/10406215","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":"The journal of peptide research : official journal of the American Peptide Society","raw_type":"Journal Article"}],"best_oa_location":null,"sustainable_development_goals":[{"display_name":"Good health and well-being","score":0.7246000170707703,"id":"https://metadata.un.org/sdg/3"}],"study_designs":[],"awards":[{"id":"https://openalex.org/G5250242095","display_name":"Cyclic Prodrugs of Opioid Peptides","funder_award_id":"R01DA009315","funder_id":"https://openalex.org/F4320337347","funder_display_name":"National Institute on Drug Abuse"}],"funders":[{"id":"https://openalex.org/F4320337347","display_name":"National Institute on Drug Abuse","ror":"https://ror.org/00fq5cm18"}],"has_content":{"pdf":false,"grobid_xml":false},"content_urls":null,"referenced_works_count":51,"referenced_works":["https://openalex.org/W70681129","https://openalex.org/W89465177","https://openalex.org/W112159188","https://openalex.org/W197645179","https://openalex.org/W199876327","https://openalex.org/W251297179","https://openalex.org/W277023688","https://openalex.org/W279922836","https://openalex.org/W573889466","https://openalex.org/W582180302","https://openalex.org/W1486375169","https://openalex.org/W1489745443","https://openalex.org/W1495369518","https://openalex.org/W1530977294","https://openalex.org/W1553691033","https://openalex.org/W1828888750","https://openalex.org/W1963632728","https://openalex.org/W1974963512","https://openalex.org/W1976569662","https://openalex.org/W1987152125","https://openalex.org/W1990028248","https://openalex.org/W2001527051","https://openalex.org/W2006478961","https://openalex.org/W2007554987","https://openalex.org/W2016689621","https://openalex.org/W2019535870","https://openalex.org/W2030965798","https://openalex.org/W2035629108","https://openalex.org/W2044750923","https://openalex.org/W2047901961","https://openalex.org/W2059396938","https://openalex.org/W2063454950","https://openalex.org/W2064767787","https://openalex.org/W2073025812","https://openalex.org/W2073319355","https://openalex.org/W2074062219","https://openalex.org/W2077957449","https://openalex.org/W2084761689","https://openalex.org/W2085156344","https://openalex.org/W2088660160","https://openalex.org/W2108433221","https://openalex.org/W2119073586","https://openalex.org/W2138947171","https://openalex.org/W2145829768","https://openalex.org/W2174417980","https://openalex.org/W2208030924","https://openalex.org/W2225219694","https://openalex.org/W2949424747","https://openalex.org/W3005484640","https://openalex.org/W4253251907","https://openalex.org/W4406065797"],"related_works":["https://openalex.org/W2069913866","https://openalex.org/W2061241957","https://openalex.org/W279922836","https://openalex.org/W277023688","https://openalex.org/W2025673472","https://openalex.org/W2001527051","https://openalex.org/W1489136673","https://openalex.org/W2010554449","https://openalex.org/W1972554701","https://openalex.org/W2504866719"],"abstract_inverted_index":{"In":[0],"an":[1,120],"attempt":[2],"to":[3,61,82,177,192,216],"improve":[4],"the":[5,32,46,49,62,67,72,76,83,88,102,125,130,180,205,210,217],"membrane":[6,160,166,196],"permeabilities":[7,132],"of":[8,16,31,53,71,87,97,124,133,179,209,219],"opioid":[9,54,202],"peptides,":[10],"we":[11,141,157],"have":[12,193],"synthesized":[13],"cyclic":[14,38,103,109,135,171,188,211],"prodrugs":[15,39,104,110,136,172,189,212],"[Leu5]-enkephalin":[17,183],"and":[18,35,66,156,184,222],"DADLE":[19],"using":[20,163],"a":[21,25],"coumarinic":[22,33],"acid":[23,27,79,85,92],"or":[24,93],"phenylpropionic":[26,36],"linker.":[28],"The":[29,170],"synthesis":[30],"acid-":[34],"acid-based":[37],"followed":[40],"similar":[41,176],"strategies.":[42],"Key":[43],"intermediates":[44],"were":[45,152,190],"compounds":[47],"with":[48,137],"C-terminal":[50],"amino":[51,69,78],"acids":[52,70],"peptides":[55],"(L-Leu,":[56],"[Leu5]-enkephalin;":[57],"D-Leu,":[58],"DADLE)":[59],"attached":[60,81],"phenol":[63],"hydroxyl":[64],"group":[65],"remaining":[68],"peptide":[73],"linked":[74],"via":[75],"N-terminal":[77],"(L-Tyr)":[80],"carboxylic":[84],"groups":[86],"prodrug":[89],"moieties":[90],"(coumarinic":[91],"propionic":[94],"acid).":[95],"Cyclization":[96],"these":[98,134,187],"linear":[99],"precursors":[100],"gave":[101],"in":[105,121],"30-50%":[106],"yields.":[107],"These":[108],"exhibited":[111,173],"excellent":[112],"transcellular":[113],"permeation":[114,208],"characteristics":[115],"across":[116],"Caco-2":[117],"cell":[118],"monolayers,":[119],"vitro":[122],"model":[123],"intestinal":[126],"mucosa.":[127],"To":[128],"correlate":[129],"cellular":[131,207],"their":[138,143,148,159,200,220,228],"physicochemical":[139],"properties,":[140],"calculated":[142],"Stokes-Einstein":[144],"molecular":[145,174,229],"radii":[146,175],"from":[147],"diffusion":[149],"coefficients":[150],"which":[151],"determined":[153,158],"by":[154],"NMR":[155],"interaction":[161,197],"potentials":[162,198],"immobilized":[164],"artificial":[165],"(IAM)":[167],"column":[168],"chromatography.":[169],"those":[178],"parent":[181],"compounds,":[182],"DADLE.":[185],"However,":[186],"shown":[191],"much":[194],"higher":[195],"than":[199],"corresponding":[201],"peptides.":[203],"Therefore,":[204],"enhanced":[206],"is":[213],"apparently":[214],"due":[215],"alteration":[218],"lipophilicity":[221],"hydrogen":[223],"bonding":[224],"potential,":[225],"but":[226],"not":[227],"sizes.":[230]},"counts_by_year":[{"year":2024,"cited_by_count":1},{"year":2023,"cited_by_count":2},{"year":2021,"cited_by_count":1},{"year":2018,"cited_by_count":3},{"year":2017,"cited_by_count":2},{"year":2016,"cited_by_count":2},{"year":2014,"cited_by_count":1},{"year":2012,"cited_by_count":3}],"updated_date":"2026-11-06T12:05:46.655746","created_date":"2016-06-24T00:00:00"}