{"id":"https://openalex.org/W2063043885","doi":"https://doi.org/10.1021/jm058184l","title":"Replacement of Phe6, Phe7, and Phe11of d -Trp8-Somatostatin-14 with l -Pyrazinylalanine. Predicted and Observed Effects on Binding Affinities at hSST2 and hSST4. An Unexpected Effect of the Chirality of Trp8on NMR Spectra in Methanol","display_name":"Replacement of Phe6, Phe7, and Phe11of d -Trp8-Somatostatin-14 with l -Pyrazinylalanine. Predicted and Observed Effects on Binding Affinities at hSST2 and hSST4. An Unexpected Effect of the Chirality of Trp8on NMR Spectra in Methanol","publication_year":2005,"publication_date":"2005-05-21","ids":{"openalex":"https://openalex.org/W2063043885","doi":"https://doi.org/10.1021/jm058184l","mag":"2063043885","pmid":"https://pubmed.ncbi.nlm.nih.gov/15943475"},"language":"en","primary_location":{"id":"doi:10.1021/jm058184l","doi":"https://doi.org/10.1021/jm058184l","is_oa":false,"landing_page_url":"https://doi.org/10.1021/jm058184l","pdf_url":null,"source":{"id":"https://openalex.org/S162030435","display_name":"Journal of Medicinal Chemistry","issn_l":"0022-2623","issn":["0022-2623","1520-4804"],"is_oa":false,"is_in_doaj":false,"is_core":true,"listed_in":["anvur-scientific","cwts-core","dongbi-a","jufo-3","ki-jl-2","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 Medicinal Chemistry","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/A5009205253","display_name":"Santhosh F. Neelamkavil","orcid":"https://orcid.org/0000-0001-9836-3472","observed_orcids":["https://orcid.org/0000-0001-9836-3472"]},"institutions":[{"id":"https://openalex.org/I79576946","display_name":"University of Pennsylvania","ror":"https://ror.org/00b30xv10","country_code":"US","type":"education","lineage":["https://openalex.org/I79576946"]}],"countries":["US"],"is_corresponding":false,"raw_author_name":"Santhosh Neelamkavil","raw_affiliation_strings":["Department of Chemistry, University of Pennsylvania, Philadelphia, Pennsylvania 19104, Merck Research Laboratories, Rahway, New Jersey 07065, MDS Pharma Services-Taiwan Ltd., Pharmacology Laboratories, 158 Li-Teh Road, Peitou, Taipei, Taiwan 112, and MDS Pharma Services, 22011 30th Drive SE Bothell, Washington 98021"],"raw_orcid":null,"affiliations":[{"raw_affiliation_string":"Department of Chemistry, University of Pennsylvania, Philadelphia, Pennsylvania 19104, Merck Research Laboratories, Rahway, New Jersey 07065, MDS Pharma Services-Taiwan Ltd., Pharmacology Laboratories, 158 Li-Teh Road, Peitou, Taipei, Taiwan 112, and MDS Pharma Services, 22011 30th Drive SE Bothell, Washington 98021","institution_ids":["https://openalex.org/I79576946"]}]},{"author_position":"middle","author":{"id":"https://openalex.org/A5038151500","display_name":"Byron H. Arison","orcid":null,"observed_orcids":[]},"institutions":[{"id":"https://openalex.org/I79576946","display_name":"University of Pennsylvania","ror":"https://ror.org/00b30xv10","country_code":"US","type":"education","lineage":["https://openalex.org/I79576946"]}],"countries":["US"],"is_corresponding":false,"raw_author_name":"Byron Arison","raw_affiliation_strings":["Department of Chemistry, University of Pennsylvania, Philadelphia, Pennsylvania 19104, Merck Research Laboratories, Rahway, New Jersey 07065, MDS Pharma Services-Taiwan Ltd., Pharmacology Laboratories, 158 Li-Teh Road, Peitou, Taipei, Taiwan 112, and MDS Pharma Services, 22011 30th Drive SE Bothell, Washington 98021"],"raw_orcid":null,"affiliations":[{"raw_affiliation_string":"Department of Chemistry, University of Pennsylvania, Philadelphia, Pennsylvania 19104, Merck Research Laboratories, Rahway, New Jersey 07065, MDS Pharma Services-Taiwan Ltd., Pharmacology Laboratories, 158 Li-Teh Road, Peitou, Taipei, Taiwan 112, and MDS Pharma Services, 22011 30th Drive SE Bothell, Washington 98021","institution_ids":["https://openalex.org/I79576946"]}]},{"author_position":"middle","author":{"id":"https://openalex.org/A5017198901","display_name":"Elizabeth T. Birzin","orcid":null,"observed_orcids":[]},"institutions":[{"id":"https://openalex.org/I79576946","display_name":"University of Pennsylvania","ror":"https://ror.org/00b30xv10","country_code":"US","type":"education","lineage":["https://openalex.org/I79576946"]}],"countries":["US"],"is_corresponding":false,"raw_author_name":"Elizabeth Birzin","raw_affiliation_strings":["Department of Chemistry, University of Pennsylvania, Philadelphia, Pennsylvania 19104, Merck Research Laboratories, Rahway, New Jersey 07065, MDS Pharma Services-Taiwan Ltd., Pharmacology Laboratories, 158 Li-Teh Road, Peitou, Taipei, Taiwan 112, and MDS Pharma Services, 22011 30th Drive SE Bothell, Washington 98021"],"raw_orcid":null,"affiliations":[{"raw_affiliation_string":"Department of Chemistry, University of Pennsylvania, Philadelphia, Pennsylvania 19104, Merck Research Laboratories, Rahway, New Jersey 07065, MDS Pharma Services-Taiwan Ltd., Pharmacology Laboratories, 158 Li-Teh Road, Peitou, Taipei, Taiwan 112, and MDS Pharma Services, 22011 30th Drive SE Bothell, Washington 98021","institution_ids":["https://openalex.org/I79576946"]}]},{"author_position":"middle","author":{"id":"https://openalex.org/A5075011254","display_name":"Jin-Jye Feng","orcid":null,"observed_orcids":[]},"institutions":[{"id":"https://openalex.org/I79576946","display_name":"University of Pennsylvania","ror":"https://ror.org/00b30xv10","country_code":"US","type":"education","lineage":["https://openalex.org/I79576946"]}],"countries":["US"],"is_corresponding":false,"raw_author_name":"Jin-Jye Feng","raw_affiliation_strings":["Department of Chemistry, University of Pennsylvania, Philadelphia, Pennsylvania 19104, Merck Research Laboratories, Rahway, New Jersey 07065, MDS Pharma Services-Taiwan Ltd., Pharmacology Laboratories, 158 Li-Teh Road, Peitou, Taipei, Taiwan 112, and MDS Pharma Services, 22011 30th Drive SE Bothell, Washington 98021"],"raw_orcid":null,"affiliations":[{"raw_affiliation_string":"Department of Chemistry, University of Pennsylvania, Philadelphia, Pennsylvania 19104, Merck Research Laboratories, Rahway, New Jersey 07065, MDS Pharma Services-Taiwan Ltd., Pharmacology Laboratories, 158 Li-Teh Road, Peitou, Taipei, Taiwan 112, and MDS Pharma Services, 22011 30th Drive SE Bothell, Washington 98021","institution_ids":["https://openalex.org/I79576946"]}]},{"author_position":"middle","author":{"id":"https://openalex.org/A5036235270","display_name":"Kuo-Hsin Chen","orcid":"https://orcid.org/0000-0003-3947-1400","observed_orcids":["https://orcid.org/0000-0003-3947-1400"]},"institutions":[{"id":"https://openalex.org/I79576946","display_name":"University of Pennsylvania","ror":"https://ror.org/00b30xv10","country_code":"US","type":"education","lineage":["https://openalex.org/I79576946"]}],"countries":["US"],"is_corresponding":false,"raw_author_name":"Kuo-Hsin Chen","raw_affiliation_strings":["Department of Chemistry, University of Pennsylvania, Philadelphia, Pennsylvania 19104, Merck Research Laboratories, Rahway, New Jersey 07065, MDS Pharma Services-Taiwan Ltd., Pharmacology Laboratories, 158 Li-Teh Road, Peitou, Taipei, Taiwan 112, and MDS Pharma Services, 22011 30th Drive SE Bothell, Washington 98021"],"raw_orcid":null,"affiliations":[{"raw_affiliation_string":"Department of Chemistry, University of Pennsylvania, Philadelphia, Pennsylvania 19104, Merck Research Laboratories, Rahway, New Jersey 07065, MDS Pharma Services-Taiwan Ltd., Pharmacology Laboratories, 158 Li-Teh Road, Peitou, Taipei, Taiwan 112, and MDS Pharma Services, 22011 30th Drive SE Bothell, Washington 98021","institution_ids":["https://openalex.org/I79576946"]}]},{"author_position":"middle","author":{"id":"https://openalex.org/A5100894671","display_name":"Atsui Lin","orcid":null,"observed_orcids":[]},"institutions":[{"id":"https://openalex.org/I79576946","display_name":"University of Pennsylvania","ror":"https://ror.org/00b30xv10","country_code":"US","type":"education","lineage":["https://openalex.org/I79576946"]}],"countries":["US"],"is_corresponding":false,"raw_author_name":"Atsui Lin","raw_affiliation_strings":["Department of Chemistry, University of Pennsylvania, Philadelphia, Pennsylvania 19104, Merck Research Laboratories, Rahway, New Jersey 07065, MDS Pharma Services-Taiwan Ltd., Pharmacology Laboratories, 158 Li-Teh Road, Peitou, Taipei, Taiwan 112, and MDS Pharma Services, 22011 30th Drive SE Bothell, Washington 98021"],"raw_orcid":null,"affiliations":[{"raw_affiliation_string":"Department of Chemistry, University of Pennsylvania, Philadelphia, Pennsylvania 19104, Merck Research Laboratories, Rahway, New Jersey 07065, MDS Pharma Services-Taiwan Ltd., Pharmacology Laboratories, 158 Li-Teh Road, Peitou, Taipei, Taiwan 112, and MDS Pharma Services, 22011 30th Drive SE Bothell, Washington 98021","institution_ids":["https://openalex.org/I79576946"]}]},{"author_position":"middle","author":{"id":"https://openalex.org/A5100834751","display_name":"Fong\u2010Chi Cheng","orcid":null,"observed_orcids":[]},"institutions":[{"id":"https://openalex.org/I79576946","display_name":"University of Pennsylvania","ror":"https://ror.org/00b30xv10","country_code":"US","type":"education","lineage":["https://openalex.org/I79576946"]}],"countries":["US"],"is_corresponding":false,"raw_author_name":"Fong-Chi Cheng","raw_affiliation_strings":["Department of Chemistry, University of Pennsylvania, Philadelphia, Pennsylvania 19104, Merck Research Laboratories, Rahway, New Jersey 07065, MDS Pharma Services-Taiwan Ltd., Pharmacology Laboratories, 158 Li-Teh Road, Peitou, Taipei, Taiwan 112, and MDS Pharma Services, 22011 30th Drive SE Bothell, Washington 98021"],"raw_orcid":null,"affiliations":[{"raw_affiliation_string":"Department of Chemistry, University of Pennsylvania, Philadelphia, Pennsylvania 19104, Merck Research Laboratories, Rahway, New Jersey 07065, MDS Pharma Services-Taiwan Ltd., Pharmacology Laboratories, 158 Li-Teh Road, Peitou, Taipei, Taiwan 112, and MDS Pharma Services, 22011 30th Drive SE Bothell, Washington 98021","institution_ids":["https://openalex.org/I79576946"]}]},{"author_position":"middle","author":{"id":"https://openalex.org/A5016637321","display_name":"Laurie L. Taylor","orcid":null,"observed_orcids":[]},"institutions":[{"id":"https://openalex.org/I79576946","display_name":"University of Pennsylvania","ror":"https://ror.org/00b30xv10","country_code":"US","type":"education","lineage":["https://openalex.org/I79576946"]}],"countries":["US"],"is_corresponding":false,"raw_author_name":"Laurie Taylor","raw_affiliation_strings":["Department of Chemistry, University of Pennsylvania, Philadelphia, Pennsylvania 19104, Merck Research Laboratories, Rahway, New Jersey 07065, MDS Pharma Services-Taiwan Ltd., Pharmacology Laboratories, 158 Li-Teh Road, Peitou, Taipei, Taiwan 112, and MDS Pharma Services, 22011 30th Drive SE Bothell, Washington 98021"],"raw_orcid":null,"affiliations":[{"raw_affiliation_string":"Department of Chemistry, University of Pennsylvania, Philadelphia, Pennsylvania 19104, Merck Research Laboratories, Rahway, New Jersey 07065, MDS Pharma Services-Taiwan Ltd., Pharmacology Laboratories, 158 Li-Teh Road, Peitou, Taipei, Taiwan 112, and MDS Pharma Services, 22011 30th Drive SE Bothell, Washington 98021","institution_ids":["https://openalex.org/I79576946"]}]},{"author_position":"middle","author":{"id":"https://openalex.org/A5072310503","display_name":"Edward R. Thornton","orcid":null,"observed_orcids":[]},"institutions":[{"id":"https://openalex.org/I79576946","display_name":"University of Pennsylvania","ror":"https://ror.org/00b30xv10","country_code":"US","type":"education","lineage":["https://openalex.org/I79576946"]}],"countries":["US"],"is_corresponding":false,"raw_author_name":"Edward R Thornton","raw_affiliation_strings":["Department of Chemistry, University of Pennsylvania, Philadelphia, Pennsylvania 19104, Merck Research Laboratories, Rahway, New Jersey 07065, MDS Pharma Services-Taiwan Ltd., Pharmacology Laboratories, 158 Li-Teh Road, Peitou, Taipei, Taiwan 112, and MDS Pharma Services, 22011 30th Drive SE Bothell, Washington 98021"],"raw_orcid":null,"affiliations":[{"raw_affiliation_string":"Department of Chemistry, University of Pennsylvania, Philadelphia, Pennsylvania 19104, Merck Research Laboratories, Rahway, New Jersey 07065, MDS Pharma Services-Taiwan Ltd., Pharmacology Laboratories, 158 Li-Teh Road, Peitou, Taipei, Taiwan 112, and MDS Pharma Services, 22011 30th Drive SE Bothell, Washington 98021","institution_ids":["https://openalex.org/I79576946"]}]},{"author_position":"middle","author":{"id":"https://openalex.org/A5066527875","display_name":"Amos B. Smith","orcid":"https://orcid.org/0000-0002-1712-8567","observed_orcids":["https://orcid.org/0000-0002-1712-8567"]},"institutions":[{"id":"https://openalex.org/I79576946","display_name":"University of Pennsylvania","ror":"https://ror.org/00b30xv10","country_code":"US","type":"education","lineage":["https://openalex.org/I79576946"]}],"countries":["US"],"is_corresponding":false,"raw_author_name":"Amos B. Smith","raw_affiliation_strings":["Department of Chemistry, University of Pennsylvania, Philadelphia, Pennsylvania 19104, Merck Research Laboratories, Rahway, New Jersey 07065, MDS Pharma Services-Taiwan Ltd., Pharmacology Laboratories, 158 Li-Teh Road, Peitou, Taipei, Taiwan 112, and MDS Pharma Services, 22011 30th Drive SE Bothell, Washington 98021"],"raw_orcid":null,"affiliations":[{"raw_affiliation_string":"Department of Chemistry, University of Pennsylvania, Philadelphia, Pennsylvania 19104, Merck Research Laboratories, Rahway, New Jersey 07065, MDS Pharma Services-Taiwan Ltd., Pharmacology Laboratories, 158 Li-Teh Road, Peitou, Taipei, Taiwan 112, and MDS Pharma Services, 22011 30th Drive SE Bothell, Washington 98021","institution_ids":["https://openalex.org/I79576946"]}]},{"author_position":"last","author":{"id":"https://openalex.org/A5072463303","display_name":"Ralph F. Hirschmann","orcid":null,"observed_orcids":[]},"institutions":[{"id":"https://openalex.org/I79576946","display_name":"University of Pennsylvania","ror":"https://ror.org/00b30xv10","country_code":"US","type":"education","lineage":["https://openalex.org/I79576946"]}],"countries":["US"],"is_corresponding":false,"raw_author_name":"Ralph Hirschmann","raw_affiliation_strings":["Department of Chemistry, University of Pennsylvania, Philadelphia, Pennsylvania 19104, Merck Research Laboratories, Rahway, New Jersey 07065, MDS Pharma Services-Taiwan Ltd., Pharmacology Laboratories, 158 Li-Teh Road, Peitou, Taipei, Taiwan 112, and MDS Pharma Services, 22011 30th Drive SE Bothell, Washington 98021"],"raw_orcid":null,"affiliations":[{"raw_affiliation_string":"Department of Chemistry, University of Pennsylvania, Philadelphia, Pennsylvania 19104, Merck Research Laboratories, Rahway, New Jersey 07065, MDS Pharma Services-Taiwan Ltd., Pharmacology Laboratories, 158 Li-Teh Road, Peitou, Taipei, Taiwan 112, and MDS Pharma Services, 22011 30th Drive SE Bothell, Washington 98021","institution_ids":["https://openalex.org/I79576946"]}]}],"institutions":[],"countries_distinct_count":1,"institutions_distinct_count":1,"corresponding_author_ids":[],"corresponding_institution_ids":["https://openalex.org/I79576946"],"apc_list":{"value":4500,"currency":"USD","value_usd":4500},"apc_paid":null,"fwci":0.7617,"has_fulltext":false,"cited_by_count":17,"citation_normalized_percentile":{"value":0.63743042,"is_in_top_1_percent":false,"is_in_top_10_percent":false},"cited_by_percentile_year":{"min":88,"max":96},"biblio":{"volume":"48","issue":"12","first_page":"4025","last_page":"4030"},"is_retracted":false,"is_paratext":false,"is_xpac":false,"primary_topic":{"id":"https://openalex.org/T10911","display_name":"Chemical Synthesis and Analysis","score":0.8012999892234802,"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":0.8012999892234802,"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/T11178","display_name":"Receptor Mechanisms and Signaling","score":0.06040000170469284,"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/T10814","display_name":"Neuropeptides and Animal Physiology","score":0.05290000140666962,"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"}}],"keywords":[{"id":"https://openalex.org/keywords/somatostatin-analogs","display_name":"somatostatin analogues","score":0.8259999752044678},{"id":"https://openalex.org/keywords/receptor-binding-affinity","display_name":"receptor binding affinity","score":0.7770000100135803},{"id":"https://openalex.org/keywords/structure-activity-relationship","display_name":"structure-activity relationship","score":0.6850000023841858},{"id":"https://openalex.org/keywords/pi-bonding","display_name":"\u03c0-bonding","score":0.5410000085830688},{"id":"https://openalex.org/keywords/chirality","display_name":"chirality","score":0.45500001311302185},{"id":"https://openalex.org/keywords/alanine-scanning","display_name":"alanine scanning","score":0.6299999952316284}],"concepts":[{"id":"https://openalex.org/C185592680","wikidata":"https://www.wikidata.org/wiki/Q2329","display_name":"Chemistry","level":0,"score":0.8876640796661377},{"id":"https://openalex.org/C71240020","wikidata":"https://www.wikidata.org/wiki/Q186011","display_name":"Stereochemistry","level":1,"score":0.6411029100418091},{"id":"https://openalex.org/C2779856020","wikidata":"https://www.wikidata.org/wiki/Q218642","display_name":"Alanine","level":3,"score":0.6226168870925903},{"id":"https://openalex.org/C67787023","wikidata":"https://www.wikidata.org/wiki/Q6954755","display_name":"NMR spectra database","level":3,"score":0.47753989696502686},{"id":"https://openalex.org/C2776297358","wikidata":"https://www.wikidata.org/wiki/Q407166","display_name":"Somatostatin","level":2,"score":0.4604722857475281},{"id":"https://openalex.org/C2778439535","wikidata":"https://www.wikidata.org/wiki/Q188777","display_name":"Amide","level":2,"score":0.43007349967956543},{"id":"https://openalex.org/C80115893","wikidata":"https://www.wikidata.org/wiki/Q2067077","display_name":"Somatostatin receptor","level":3,"score":0.4285407066345215},{"id":"https://openalex.org/C170493617","wikidata":"https://www.wikidata.org/wiki/Q208467","display_name":"Receptor","level":2,"score":0.3481820225715637},{"id":"https://openalex.org/C515207424","wikidata":"https://www.wikidata.org/wiki/Q8066","display_name":"Amino acid","level":2,"score":0.24672704935073853},{"id":"https://openalex.org/C55493867","wikidata":"https://www.wikidata.org/wiki/Q7094","display_name":"Biochemistry","level":1,"score":0.15557745099067688},{"id":"https://openalex.org/C4839761","wikidata":"https://www.wikidata.org/wiki/Q212111","display_name":"Spectral line","level":2,"score":0.12895768880844116},{"id":"https://openalex.org/C86803240","wikidata":"https://www.wikidata.org/wiki/Q420","display_name":"Biology","level":0,"score":0.0},{"id":"https://openalex.org/C169760540","wikidata":"https://www.wikidata.org/wiki/Q207011","display_name":"Neuroscience","level":1,"score":0.0},{"id":"https://openalex.org/C1276947","wikidata":"https://www.wikidata.org/wiki/Q333","display_name":"Astronomy","level":1,"score":0.0},{"id":"https://openalex.org/C121332964","wikidata":"https://www.wikidata.org/wiki/Q413","display_name":"Physics","level":0,"score":0.0}],"mesh":[{"descriptor_ui":"D000409","descriptor_name":"Alanine","qualifier_ui":"Q000031","qualifier_name":"analogs & derivatives","is_major_topic":true},{"descriptor_ui":"D000409","descriptor_name":"Alanine","qualifier_ui":"Q000737","qualifier_name":"chemistry","is_major_topic":true},{"descriptor_ui":"D000432","descriptor_name":"Methanol","qualifier_ui":null,"qualifier_name":null,"is_major_topic":false},{"descriptor_ui":"D001665","descriptor_name":"Binding Sites","qualifier_ui":null,"qualifier_name":null,"is_major_topic":false},{"descriptor_ui":"D008565","descriptor_name":"Membrane Proteins","qualifier_ui":"Q000737","qualifier_name":"chemistry","is_major_topic":true},{"descriptor_ui":"D008958","descriptor_name":"Models, Molecular","qualifier_ui":null,"qualifier_name":null,"is_major_topic":false},{"descriptor_ui":"D009682","descriptor_name":"Magnetic Resonance Spectroscopy","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":"Q000737","qualifier_name":"chemistry","is_major_topic":false},{"descriptor_ui":"D010649","descriptor_name":"Phenylalanine","qualifier_ui":"Q000737","qualifier_name":"chemistry","is_major_topic":true},{"descriptor_ui":"D011719","descriptor_name":"Pyrazines","qualifier_ui":"Q000737","qualifier_name":"chemistry","is_major_topic":true},{"descriptor_ui":"D012997","descriptor_name":"Solvents","qualifier_ui":null,"qualifier_name":null,"is_major_topic":false},{"descriptor_ui":"D013004","descriptor_name":"Somatostatin","qualifier_ui":"Q000031","qualifier_name":"analogs & derivatives","is_major_topic":true},{"descriptor_ui":"D013004","descriptor_name":"Somatostatin","qualifier_ui":"Q000138","qualifier_name":"chemical synthesis","is_major_topic":true},{"descriptor_ui":"D013004","descriptor_name":"Somatostatin","qualifier_ui":"Q000737","qualifier_name":"chemistry","is_major_topic":false},{"descriptor_ui":"D013237","descriptor_name":"Stereoisomerism","qualifier_ui":null,"qualifier_name":null,"is_major_topic":false},{"descriptor_ui":"D013329","descriptor_name":"Structure-Activity Relationship","qualifier_ui":null,"qualifier_name":null,"is_major_topic":false},{"descriptor_ui":"D017481","descriptor_name":"Receptors, Somatostatin","qualifier_ui":"Q000737","qualifier_name":"chemistry","is_major_topic":true}],"locations_count":2,"locations":[{"id":"doi:10.1021/jm058184l","doi":"https://doi.org/10.1021/jm058184l","is_oa":false,"landing_page_url":"https://doi.org/10.1021/jm058184l","pdf_url":null,"source":{"id":"https://openalex.org/S162030435","display_name":"Journal of Medicinal Chemistry","issn_l":"0022-2623","issn":["0022-2623","1520-4804"],"is_oa":false,"is_in_doaj":false,"is_core":true,"listed_in":["anvur-scientific","cwts-core","dongbi-a","jufo-3","ki-jl-2","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 Medicinal Chemistry","raw_type":"journal-article"},{"id":"pmid:15943475","doi":null,"is_oa":false,"landing_page_url":"https://pubmed.ncbi.nlm.nih.gov/15943475","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 medicinal chemistry","raw_type":"Journal Article"}],"best_oa_location":null,"sustainable_development_goals":[],"study_designs":[],"awards":[{"id":"https://openalex.org/G8392424091","display_name":"Non-Peptide Peptidomimetics","funder_award_id":"R01GM041821","funder_id":"https://openalex.org/F4320337354","funder_display_name":"National Institute of General Medical Sciences"}],"funders":[{"id":"https://openalex.org/F4320337354","display_name":"National Institute of General Medical Sciences","ror":"https://ror.org/04q48ey07"}],"has_content":{"pdf":false,"grobid_xml":false},"content_urls":null,"referenced_works_count":23,"referenced_works":["https://openalex.org/W160707011","https://openalex.org/W1585963184","https://openalex.org/W1970344662","https://openalex.org/W1971013393","https://openalex.org/W1979231788","https://openalex.org/W1985974805","https://openalex.org/W1990332976","https://openalex.org/W1995922082","https://openalex.org/W1996738050","https://openalex.org/W2008357770","https://openalex.org/W2011447313","https://openalex.org/W2019426425","https://openalex.org/W2028987798","https://openalex.org/W2031544977","https://openalex.org/W2040127137","https://openalex.org/W2041559752","https://openalex.org/W2057740793","https://openalex.org/W2062714484","https://openalex.org/W2074106705","https://openalex.org/W2084687677","https://openalex.org/W2090051214","https://openalex.org/W2094186244","https://openalex.org/W2330066175"],"related_works":["https://openalex.org/W1982304619","https://openalex.org/W2001258610","https://openalex.org/W2416173352","https://openalex.org/W2060038932","https://openalex.org/W2051625564","https://openalex.org/W7100733356","https://openalex.org/W1573064166","https://openalex.org/W2016368229","https://openalex.org/W2017622012","https://openalex.org/W2078082468"],"abstract_inverted_index":{"An":[0],"alanine":[1,208],"scan":[2],"performed":[3],"in":[4,65,85,88,120,143,158,310],"the":[5,15,36,45,53,93,102,109,125,136,151,161,165,170,195,199,203,207,224,238,245,262,284,287,291,295],"1970s":[6],"suggested":[7],"that":[8,48,61,77,167,180,192,216,252],"Phe(6)":[9,26,49,64,128,145],"and":[10,23,27,50,97,108,129,146,160,179],"Phe(11)":[11,28,51,62,130,147,168],"are":[12,228],"required":[13],"for":[14,106],"binding":[16,104],"of":[17,25,38,56,95,111,127,138,141,206,223,233,242,286,297],"somatostatin":[18],"(SRIF-14).":[19],"Molecular":[20],"modeling":[21],"studies":[22,59,232],"replacement":[24],"with":[29,35,198,202,219,261],"a":[30,66,71,258,304],"cystine":[31],"bridge":[32],"affording":[33],"ligands":[34],"retention":[37],"high":[39],"biological":[40],"activity,":[41],"however,":[42],"led":[43],"to":[44,100,113,302],"alternate":[46],"conclusion":[47],"stabilize":[52],"bioactive":[54,171],"conformation":[55,172],"SRIF-14.":[57],"Subsequent":[58],"revealed":[60],"shields":[63],"\"herringbone\"":[67],"arrangement.":[68],"More":[69],"recently,":[70],"report":[72,134],"from":[73],"this":[74],"laboratory":[75],"demonstrated":[76],"Spartan":[78,274],"3-21G":[79,275],"MO":[80,276],"calculations":[81],"can":[82,182],"be":[83,183],"invaluable":[84],"explaining":[86],"SARs":[87],"medicinal":[89],"chemistry.":[90],"For":[91],"example,":[92],"ability":[94],"benzene":[96],"indole":[98],"rings":[99],"bind":[101],"Trp(8)":[103,298],"pocket":[105],"SRIF-14":[107],"inability":[110],"pyrazine":[112],"do":[114],"so":[115],"was":[116,299],"explained":[117],"through":[118,173],"differences":[119],"electrostatic":[121],"potentials.":[122],"To":[123],"investigate":[124],"role":[126],"more":[131],"fully,":[132],"we":[133],"here":[135],"synthesis":[137],"two":[139],"analogues":[140],"D-Trp(8)-SRIF":[142],"which":[144],"were":[148],"replaced":[149],"by":[150,185,230],"pryazinylalanine":[152],"congeners,":[153],"respectively.":[154],"The":[155,187],"NMR":[156,308],"spectra":[157,309],"D(2)O":[159],"K(i)s":[162,241],"fully":[163],"support":[164],"proposition":[166],"stabilizes":[169],"pi-bonding":[174],"or":[175],"aromatic":[176],"edge-to-face":[177],"interaction":[178,260,289],"pyrazinylalanine(6)":[181],"shielded":[184],"Phe(11).":[186],"data":[188],"also":[189,250,279],"show":[190],"unexpectedly":[191,300],"Phe(6),":[193],"via":[194],"pi-bond,":[196],"interacts":[197,218],"receptor,":[200],"consistent":[201],"original":[204],"interpretation":[205],"scan.":[209],"Heretofore":[210],"it":[211],"had":[212],"only":[213,269],"been":[214],"known":[215],"Lys(9)":[217],"an":[220],"aspartate":[221],"anion":[222],"receptor.":[225,263],"These":[226],"conclusions":[227],"supported":[229],"recent":[231],"Lewis":[234],"et":[235],"al.":[236],"on":[237,240,273,307],"effects":[239],"Ala(6)-SRIF-14-amide":[243],"at":[244,290,313],"five":[246],"receptor":[247,288],"subtargets.":[248],"We":[249],"found":[251,301],"pyrazinylalanine(7)-D-Trp(8)-SRIF-14":[253],"does":[254],"not":[255,268],"bind,":[256],"suggesting":[257],"repulsive":[259],"Taken":[264],"together,":[265],"our":[266],"results":[267],"validate":[270],"predictions":[271],"based":[272],"analysis":[277],"but":[278],"provide":[280],"valuable":[281],"information":[282],"about":[283],"nature":[285],"molecular":[292],"level.":[293],"Finally,":[294],"chirality":[296],"have":[303],"striking":[305],"effect":[306],"methanol,":[311],"especially":[312],"lower":[314],"temperatures.":[315]},"counts_by_year":[{"year":2024,"cited_by_count":1},{"year":2018,"cited_by_count":1},{"year":2016,"cited_by_count":2},{"year":2014,"cited_by_count":1},{"year":2013,"cited_by_count":2}],"updated_date":"2026-11-06T12:05:46.655746","created_date":"2016-06-24T00:00:00"}
