{"id":"https://openalex.org/W2053660332","doi":"https://doi.org/10.1021/jm900078f","title":"Fructose-1,6-bisphosphatase Inhibitors. 1. Purine Phosphonic Acids as Novel AMP Mimics","display_name":"Fructose-1,6-bisphosphatase Inhibitors. 1. Purine Phosphonic Acids as Novel AMP Mimics","publication_year":2009,"publication_date":"2009-04-06","ids":{"openalex":"https://openalex.org/W2053660332","doi":"https://doi.org/10.1021/jm900078f","mag":"2053660332","pmid":"https://pubmed.ncbi.nlm.nih.gov/19348494"},"language":"en","primary_location":{"id":"doi:10.1021/jm900078f","doi":"https://doi.org/10.1021/jm900078f","is_oa":false,"landing_page_url":"https://doi.org/10.1021/jm900078f","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/A5014550332","display_name":"Qun Dang","orcid":"https://orcid.org/0000-0001-5338-7761","observed_orcids":["https://orcid.org/0000-0001-5338-7761","https://orcid.org/0000-0003-1153-3358"]},"institutions":[],"countries":[],"is_corresponding":true,"raw_author_name":"Qun Dang","raw_affiliation_strings":["Departments of Medicinal Chemistry and Biochemistry, Metabasis Therapeutics, Inc., 11119 North Torrey Pines Road, La Jolla, California 92037"],"raw_orcid":null,"affiliations":[{"raw_affiliation_string":"Departments of Medicinal Chemistry and Biochemistry, Metabasis Therapeutics, Inc., 11119 North Torrey Pines Road, La Jolla, California 92037","institution_ids":[]}]},{"author_position":"middle","author":{"id":"https://openalex.org/A5043161866","display_name":"Brian S. Brown","orcid":"https://orcid.org/0000-0002-0366-0528","observed_orcids":["https://orcid.org/0000-0002-0366-0528"]},"institutions":[],"countries":[],"is_corresponding":false,"raw_author_name":"Brian S. Brown","raw_affiliation_strings":["Departments of Medicinal Chemistry and Biochemistry, Metabasis Therapeutics, Inc., 11119 North Torrey Pines Road, La Jolla, California 92037"],"raw_orcid":null,"affiliations":[{"raw_affiliation_string":"Departments of Medicinal Chemistry and Biochemistry, Metabasis Therapeutics, Inc., 11119 North Torrey Pines Road, La Jolla, California 92037","institution_ids":[]}]},{"author_position":"middle","author":{"id":null,"display_name":"Yan Liu","orcid":null,"observed_orcids":[]},"institutions":[],"countries":[],"is_corresponding":false,"raw_author_name":"Yan Liu","raw_affiliation_strings":["Departments of Medicinal Chemistry and Biochemistry, Metabasis Therapeutics, Inc., 11119 North Torrey Pines Road, La Jolla, California 92037"],"raw_orcid":null,"affiliations":[{"raw_affiliation_string":"Departments of Medicinal Chemistry and Biochemistry, Metabasis Therapeutics, Inc., 11119 North Torrey Pines Road, La Jolla, California 92037","institution_ids":[]}]},{"author_position":"middle","author":{"id":"https://openalex.org/A5006662504","display_name":"Robert M. Rydzewski","orcid":null,"observed_orcids":[]},"institutions":[],"countries":[],"is_corresponding":false,"raw_author_name":"Robert M. Rydzewski","raw_affiliation_strings":["Departments of Medicinal Chemistry and Biochemistry, Metabasis Therapeutics, Inc., 11119 North Torrey Pines Road, La Jolla, California 92037"],"raw_orcid":null,"affiliations":[{"raw_affiliation_string":"Departments of Medicinal Chemistry and Biochemistry, Metabasis Therapeutics, Inc., 11119 North Torrey Pines Road, La Jolla, California 92037","institution_ids":[]}]},{"author_position":"middle","author":{"id":"https://openalex.org/A5008252579","display_name":"Edward D. Robinson","orcid":null,"observed_orcids":[]},"institutions":[],"countries":[],"is_corresponding":false,"raw_author_name":"Edward D. Robinson","raw_affiliation_strings":["Departments of Medicinal Chemistry and Biochemistry, Metabasis Therapeutics, Inc., 11119 North Torrey Pines Road, La Jolla, California 92037"],"raw_orcid":null,"affiliations":[{"raw_affiliation_string":"Departments of Medicinal Chemistry and Biochemistry, Metabasis Therapeutics, Inc., 11119 North Torrey Pines Road, La Jolla, California 92037","institution_ids":[]}]},{"author_position":"middle","author":{"id":"https://openalex.org/A5030063103","display_name":"Paul D. van Poelje","orcid":null,"observed_orcids":[]},"institutions":[],"countries":[],"is_corresponding":false,"raw_author_name":"Paul D. van Poelje","raw_affiliation_strings":["Departments of Medicinal Chemistry and Biochemistry, Metabasis Therapeutics, Inc., 11119 North Torrey Pines Road, La Jolla, California 92037"],"raw_orcid":null,"affiliations":[{"raw_affiliation_string":"Departments of Medicinal Chemistry and Biochemistry, Metabasis Therapeutics, Inc., 11119 North Torrey Pines Road, La Jolla, California 92037","institution_ids":[]}]},{"author_position":"middle","author":{"id":"https://openalex.org/A5019969242","display_name":"M. Rami Reddy","orcid":"https://orcid.org/0000-0001-8371-8306","observed_orcids":["https://orcid.org/0000-0001-8371-8306"]},"institutions":[],"countries":[],"is_corresponding":false,"raw_author_name":"M. Rami Reddy","raw_affiliation_strings":["Departments of Medicinal Chemistry and Biochemistry, Metabasis Therapeutics, Inc., 11119 North Torrey Pines Road, La Jolla, California 92037"],"raw_orcid":null,"affiliations":[{"raw_affiliation_string":"Departments of Medicinal Chemistry and Biochemistry, Metabasis Therapeutics, Inc., 11119 North Torrey Pines Road, La Jolla, California 92037","institution_ids":[]}]},{"author_position":"last","author":{"id":"https://openalex.org/A5110461190","display_name":"Mark D. Erion","orcid":null,"observed_orcids":[]},"institutions":[],"countries":[],"is_corresponding":false,"raw_author_name":"Mark D. Erion","raw_affiliation_strings":["Departments of Medicinal Chemistry and Biochemistry, Metabasis Therapeutics, Inc., 11119 North Torrey Pines Road, La Jolla, California 92037"],"raw_orcid":null,"affiliations":[{"raw_affiliation_string":"Departments of Medicinal Chemistry and Biochemistry, Metabasis Therapeutics, Inc., 11119 North Torrey Pines Road, La Jolla, California 92037","institution_ids":[]}]}],"institutions":[],"countries_distinct_count":0,"institutions_distinct_count":0,"corresponding_author_ids":["https://openalex.org/A5014550332"],"corresponding_institution_ids":[],"apc_list":{"value":4500,"currency":"USD","value_usd":4500},"apc_paid":null,"fwci":1.7763,"has_fulltext":false,"cited_by_count":55,"citation_normalized_percentile":{"value":0.83900302,"is_in_top_1_percent":false,"is_in_top_10_percent":false},"cited_by_percentile_year":{"min":88,"max":99},"biblio":{"volume":"52","issue":"9","first_page":"2880","last_page":"2898"},"is_retracted":false,"is_paratext":false,"is_xpac":false,"primary_topic":{"id":"https://openalex.org/T12827","display_name":"Biochemical and Molecular Research","score":0.38989999890327454,"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/T12827","display_name":"Biochemical and Molecular Research","score":0.38989999890327454,"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/T11748","display_name":"Organophosphorus compounds synthesis","score":0.1964000016450882,"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/T11339","display_name":"Metabolism, Diabetes, and Cancer","score":0.15469999611377716,"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"}}],"keywords":[{"id":"https://openalex.org/keywords/hepatic-gluconeogenesis","display_name":"hepatic gluconeogenesis","score":0.9549999833106995},{"id":"https://openalex.org/keywords/type-2-diabetes","display_name":"type 2 diabetes","score":0.9869999885559082},{"id":"https://openalex.org/keywords/structure-based-drug-design","display_name":"structure-based drug design","score":0.8600000143051147},{"id":"https://openalex.org/keywords/glucose-lowering-activity","display_name":"glucose-lowering activity","score":0.8550000190734863},{"id":"https://openalex.org/keywords/hepatocytes","display_name":"hepatocytes","score":0.7419999837875366},{"id":"https://openalex.org/keywords/blood-glucose-reduction","display_name":"blood glucose reduction","score":0.734000027179718}],"concepts":[{"id":"https://openalex.org/C189909181","wikidata":"https://www.wikidata.org/wiki/Q899507","display_name":"Fructose 1,6-bisphosphatase","level":3,"score":0.9040992259979248},{"id":"https://openalex.org/C185592680","wikidata":"https://www.wikidata.org/wiki/Q2329","display_name":"Chemistry","level":0,"score":0.8512917757034302},{"id":"https://openalex.org/C2776476023","wikidata":"https://www.wikidata.org/wiki/Q188261","display_name":"Purine","level":3,"score":0.759610652923584},{"id":"https://openalex.org/C20904676","wikidata":"https://www.wikidata.org/wiki/Q191835","display_name":"Gluconeogenesis","level":3,"score":0.6149685978889465},{"id":"https://openalex.org/C55493867","wikidata":"https://www.wikidata.org/wiki/Q7094","display_name":"Biochemistry","level":1,"score":0.5857531428337097},{"id":"https://openalex.org/C207001950","wikidata":"https://www.wikidata.org/wiki/Q141124","display_name":"In vivo","level":2,"score":0.5676386952400208},{"id":"https://openalex.org/C512185932","wikidata":"https://www.wikidata.org/wiki/Q28745","display_name":"Nucleotide","level":3,"score":0.5600975751876831},{"id":"https://openalex.org/C2776970464","wikidata":"https://www.wikidata.org/wiki/Q122043","display_name":"Fructose","level":2,"score":0.4483463168144226},{"id":"https://openalex.org/C57992300","wikidata":"https://www.wikidata.org/wiki/Q2066956","display_name":"Potency","level":3,"score":0.44008877873420715},{"id":"https://openalex.org/C202751555","wikidata":"https://www.wikidata.org/wiki/Q221681","display_name":"In vitro","level":2,"score":0.42453664541244507},{"id":"https://openalex.org/C181199279","wikidata":"https://www.wikidata.org/wiki/Q8047","display_name":"Enzyme","level":2,"score":0.411630243062973},{"id":"https://openalex.org/C86803240","wikidata":"https://www.wikidata.org/wiki/Q420","display_name":"Biology","level":0,"score":0.07090869545936584},{"id":"https://openalex.org/C150903083","wikidata":"https://www.wikidata.org/wiki/Q7108","display_name":"Biotechnology","level":1,"score":0.0},{"id":"https://openalex.org/C104317684","wikidata":"https://www.wikidata.org/wiki/Q7187","display_name":"Gene","level":2,"score":0.0}],"mesh":[{"descriptor_ui":"D000249","descriptor_name":"Adenosine Monophosphate","qualifier_ui":"Q000378","qualifier_name":"metabolism","is_major_topic":true},{"descriptor_ui":"D000284","descriptor_name":"Administration, Oral","qualifier_ui":null,"qualifier_name":null,"is_major_topic":false},{"descriptor_ui":"D000818","descriptor_name":"Animals","qualifier_ui":null,"qualifier_name":null,"is_major_topic":false},{"descriptor_ui":"D001682","descriptor_name":"Biological Availability","qualifier_ui":null,"qualifier_name":null,"is_major_topic":false},{"descriptor_ui":"D003924","descriptor_name":"Diabetes Mellitus, Type 2","qualifier_ui":"Q000188","qualifier_name":"drug therapy","is_major_topic":false},{"descriptor_ui":"D004791","descriptor_name":"Enzyme Inhibitors","qualifier_ui":"Q000138","qualifier_name":"chemical synthesis","is_major_topic":false},{"descriptor_ui":"D004791","descriptor_name":"Enzyme Inhibitors","qualifier_ui":"Q000493","qualifier_name":"pharmacokinetics","is_major_topic":false},{"descriptor_ui":"D004791","descriptor_name":"Enzyme Inhibitors","qualifier_ui":"Q000494","qualifier_name":"pharmacology","is_major_topic":false},{"descriptor_ui":"D004791","descriptor_name":"Enzyme Inhibitors","qualifier_ui":"Q000627","qualifier_name":"therapeutic use","is_major_topic":false},{"descriptor_ui":"D005947","descriptor_name":"Glucose","qualifier_ui":"Q000378","qualifier_name":"metabolism","is_major_topic":false},{"descriptor_ui":"D006597","descriptor_name":"Fructose-Bisphosphatase","qualifier_ui":"Q000037","qualifier_name":"antagonists & inhibitors","is_major_topic":true},{"descriptor_ui":"D006597","descriptor_name":"Fructose-Bisphosphatase","qualifier_ui":"Q000378","qualifier_name":"metabolism","is_major_topic":false},{"descriptor_ui":"D006597","descriptor_name":"Fructose-Bisphosphatase","qualifier_ui":"Q000737","qualifier_name":"chemistry","is_major_topic":false},{"descriptor_ui":"D006801","descriptor_name":"Humans","qualifier_ui":null,"qualifier_name":null,"is_major_topic":false},{"descriptor_ui":"D008099","descriptor_name":"Liver","qualifier_ui":"Q000201","qualifier_name":"enzymology","is_major_topic":false},{"descriptor_ui":"D011687","descriptor_name":"Purines","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":"D013379","descriptor_name":"Substrate Specificity","qualifier_ui":null,"qualifier_name":null,"is_major_topic":false},{"descriptor_ui":"D015195","descriptor_name":"Drug Design","qualifier_ui":null,"qualifier_name":null,"is_major_topic":false},{"descriptor_ui":"D017207","descriptor_name":"Rats, Sprague-Dawley","qualifier_ui":null,"qualifier_name":null,"is_major_topic":false},{"descriptor_ui":"D020128","descriptor_name":"Inhibitory Concentration 50","qualifier_ui":null,"qualifier_name":null,"is_major_topic":false},{"descriptor_ui":"D032701","descriptor_name":"Biomimetics","qualifier_ui":null,"qualifier_name":null,"is_major_topic":true},{"descriptor_ui":"D051381","descriptor_name":"Rats","qualifier_ui":null,"qualifier_name":null,"is_major_topic":false},{"descriptor_ui":"D063065","descriptor_name":"Organophosphonates","qualifier_ui":"Q000493","qualifier_name":"pharmacokinetics","is_major_topic":false},{"descriptor_ui":"D063065","descriptor_name":"Organophosphonates","qualifier_ui":"Q000494","qualifier_name":"pharmacology","is_major_topic":true},{"descriptor_ui":"D063065","descriptor_name":"Organophosphonates","qualifier_ui":"Q000627","qualifier_name":"therapeutic use","is_major_topic":false},{"descriptor_ui":"D063065","descriptor_name":"Organophosphonates","qualifier_ui":"Q000737","qualifier_name":"chemistry","is_major_topic":true}],"locations_count":2,"locations":[{"id":"doi:10.1021/jm900078f","doi":"https://doi.org/10.1021/jm900078f","is_oa":false,"landing_page_url":"https://doi.org/10.1021/jm900078f","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:19348494","doi":null,"is_oa":false,"landing_page_url":"https://pubmed.ncbi.nlm.nih.gov/19348494","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":[{"display_name":"Good health and well-being","score":0.9391000270843506,"id":"https://metadata.un.org/sdg/3"}],"study_designs":[],"awards":[],"funders":[],"has_content":{"grobid_xml":false,"pdf":false},"content_urls":null,"referenced_works_count":43,"referenced_works":["https://openalex.org/W1569135515","https://openalex.org/W1572025105","https://openalex.org/W1587358923","https://openalex.org/W1977095493","https://openalex.org/W1984316322","https://openalex.org/W1986178361","https://openalex.org/W1990762981","https://openalex.org/W2004891935","https://openalex.org/W2007272260","https://openalex.org/W2025859941","https://openalex.org/W2028212562","https://openalex.org/W2040535923","https://openalex.org/W2041827468","https://openalex.org/W2048360890","https://openalex.org/W2048854640","https://openalex.org/W2050289195","https://openalex.org/W2050645048","https://openalex.org/W2052605851","https://openalex.org/W2052847048","https://openalex.org/W2053099783","https://openalex.org/W2056865735","https://openalex.org/W2057831386","https://openalex.org/W2058859643","https://openalex.org/W2063416692","https://openalex.org/W2072482644","https://openalex.org/W2088551222","https://openalex.org/W2088879148","https://openalex.org/W2089543391","https://openalex.org/W2092446346","https://openalex.org/W2093453823","https://openalex.org/W2095016472","https://openalex.org/W2095727423","https://openalex.org/W2110487370","https://openalex.org/W2114989762","https://openalex.org/W2128282444","https://openalex.org/W2136427955","https://openalex.org/W2136906985","https://openalex.org/W2142504521","https://openalex.org/W2163179316","https://openalex.org/W2179287997","https://openalex.org/W2209685769","https://openalex.org/W2416145179","https://openalex.org/W4285719527"],"related_works":["https://openalex.org/W1990371346","https://openalex.org/W2095016472","https://openalex.org/W2040535923","https://openalex.org/W7166463794","https://openalex.org/W2043624103","https://openalex.org/W58124373","https://openalex.org/W2088551222","https://openalex.org/W2759945994","https://openalex.org/W179456212","https://openalex.org/W1984316322"],"abstract_inverted_index":{"Inhibition":[0],"of":[1,29,32,43],"FBPase":[2,59,88,108],"is":[3],"considered":[4],"a":[5,16,30,49,61,90],"promising":[6],"way":[7],"to":[8,19,107],"reduce":[9],"hepatic":[10],"gluconeogenesis":[11],"and":[12,64,78,98,120],"therefore":[13],"could":[14],"be":[15],"potential":[17],"approach":[18],"treat":[20],"type":[21],"2":[22],"diabetes.":[23],"Herein":[24],"we":[25],"report":[26],"the":[27,40],"discovery":[28,92],"series":[31],"purine":[33,56,73],"phosphonic":[34],"acids":[35],"as":[36,68,89,101,103],"AMP":[37,41,104],"mimics":[38],"targeting":[39],"site":[42],"FBPase,":[44],"which":[45],"was":[46],"achieved":[47],"using":[48],"structure-guided":[50],"drug":[51,91],"design":[52],"approach.":[53],"These":[54],"non-nucleotide":[55],"analogues":[57,74],"inhibit":[58],"in":[60,79,116,126],"similar":[62,66],"manner":[63],"with":[65,105],"potency":[67],"AMP.":[69],"More":[70],"importantly,":[71],"several":[72],"exhibited":[75],"potent":[76],"cellular":[77],"vivo":[80],"glucose-lowering":[81],"activities,":[82],"thus":[83],"achieving":[84],"proof-of-concept":[85],"for":[86],"inhibiting":[87],"target.":[93],"For":[94],"example,":[95],"compounds":[96],"4.11":[97,112],"4.13":[99],"are":[100],"equipotent":[102],"regard":[106],"inhibition.":[109],"Furthermore,":[110],"compound":[111],"inhibited":[113],"glucose":[114,124],"production":[115],"primary":[117],"rat":[118],"hepatocytes":[119],"significantly":[121],"lowered":[122],"blood":[123],"levels":[125],"fasted":[127],"rats.":[128]},"counts_by_year":[{"year":2026,"cited_by_count":1},{"year":2023,"cited_by_count":1},{"year":2022,"cited_by_count":2},{"year":2021,"cited_by_count":4},{"year":2020,"cited_by_count":9},{"year":2019,"cited_by_count":2},{"year":2018,"cited_by_count":6},{"year":2017,"cited_by_count":5},{"year":2016,"cited_by_count":2},{"year":2014,"cited_by_count":7},{"year":2013,"cited_by_count":1},{"year":2012,"cited_by_count":4}],"updated_date":"2026-11-06T12:05:46.655746","created_date":"2016-06-24T00:00:00"}
