{"status":"ok","message-type":"work","message-version":"1.0.0","message":{"indexed":{"date-parts":[[2026,8,23]],"date-time":"2026-08-23T16:05:54Z","timestamp":1787501154351,"version":"build-2736575974"},"reference-count":28,"publisher":"Elsevier BV","license":[{"start":{"date-parts":[[2021,5,1]],"date-time":"2021-05-01T00:00:00Z","timestamp":1619827200000},"content-version":"tdm","delay-in-days":0,"URL":"https:\/\/www.elsevier.com\/tdm\/userlicense\/1.0\/"},{"start":{"date-parts":[[2021,5,1]],"date-time":"2021-05-01T00:00:00Z","timestamp":1619827200000},"content-version":"tdm","delay-in-days":0,"URL":"https:\/\/www.elsevier.com\/legal\/tdmrep-license"},{"start":{"date-parts":[[2021,5,1]],"date-time":"2021-05-01T00:00:00Z","timestamp":1619827200000},"content-version":"stm-asf","delay-in-days":0,"URL":"https:\/\/doi.org\/10.15223\/policy-017"},{"start":{"date-parts":[[2021,5,1]],"date-time":"2021-05-01T00:00:00Z","timestamp":1619827200000},"content-version":"stm-asf","delay-in-days":0,"URL":"https:\/\/doi.org\/10.15223\/policy-037"},{"start":{"date-parts":[[2021,5,1]],"date-time":"2021-05-01T00:00:00Z","timestamp":1619827200000},"content-version":"stm-asf","delay-in-days":0,"URL":"https:\/\/doi.org\/10.15223\/policy-012"},{"start":{"date-parts":[[2021,5,1]],"date-time":"2021-05-01T00:00:00Z","timestamp":1619827200000},"content-version":"stm-asf","delay-in-days":0,"URL":"https:\/\/doi.org\/10.15223\/policy-029"},{"start":{"date-parts":[[2021,5,1]],"date-time":"2021-05-01T00:00:00Z","timestamp":1619827200000},"content-version":"stm-asf","delay-in-days":0,"URL":"https:\/\/doi.org\/10.15223\/policy-004"}],"funder":[{"DOI":"10.13039\/501100001691","name":"Japan Society for the Promotion of Science","doi-asserted-by":"publisher","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 & Medicinal Chemistry Letters"],"published-print":{"date-parts":[[2021,5]]},"DOI":"10.1016\/j.bmcl.2021.127918","type":"journal-article","created":{"date-parts":[[2021,3,10]],"date-time":"2021-03-10T23:41:40Z","timestamp":1615419700000},"page":"127918","update-policy":"https:\/\/doi.org\/10.1016\/elsevier_cm_policy","source":"Crossref","is-referenced-by-count":7,"special_numbering":"C","title":["Addition of hydrophobic side chains improve the apoptosis inducibility of the human glyoxalase I inhibitor, TLSC702"],"prefix":"10.1016","volume":"40","author":[{"given":"Miku","family":"Azuma","sequence":"first","affiliation":[],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Manami","family":"Inoue","sequence":"additional","affiliation":[],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Aya","family":"Nishida","sequence":"additional","affiliation":[],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Haruka","family":"Akahane","sequence":"additional","affiliation":[],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Masataka","family":"Kitajima","sequence":"additional","affiliation":[],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Shunsuke","family":"Natani","sequence":"additional","affiliation":[],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Ryusei","family":"Chimori","sequence":"additional","affiliation":[],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Atsushi","family":"Yoshimori","sequence":"additional","affiliation":[],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Yasunari","family":"Mano","sequence":"additional","affiliation":[],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Hiromi","family":"Uchiro","sequence":"additional","affiliation":[],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Sei-ichi","family":"Tanuma","sequence":"additional","affiliation":[],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Ryoko","family":"Takasawa","sequence":"additional","affiliation":[],"role":[{"vocabulary":"crossref","role":"author"}]}],"member":"78","reference":[{"key":"10.1016\/j.bmcl.2021.127918_b0005","doi-asserted-by":"crossref","first-page":"1","DOI":"10.1042\/bj2690001","article-title":"The glyoxalase system: new developments towards functional characterization of a metabolic pathway fundamental to biological life","volume":"269","author":"Thornalley","year":"1990","journal-title":"Biochem J"},{"issue":"5","key":"10.1016\/j.bmcl.2021.127918_b0010","doi-asserted-by":"crossref","first-page":"397","DOI":"10.1016\/0145-2126(95)00162-X","article-title":"Effect of methylglyoxal on human leukaemia 60 cell growth: Modification of DNA, G1 growth arrest and induction of apoptosis","volume":"20","author":"Kang","year":"1996","journal-title":"Leuk Res"},{"issue":"3","key":"10.1016\/j.bmcl.2021.127918_b0015","doi-asserted-by":"crossref","first-page":"311","DOI":"10.1016\/0925-4439(93)90074-B","article-title":"Analysis of glyoxalase-I from normal and tumor tissue","volume":"1182","author":"Ranganathan","year":"1993","journal-title":"Biochim Biophys Acta"},{"key":"10.1016\/j.bmcl.2021.127918_b0020","first-page":"3219","article-title":"Glyoxalase I (GLO1) is up-regulated in pancreatic cancerous tissues compared with related non-cancerous tissues","volume":"32","author":"Wang","year":"2012","journal-title":"Anticancer Res"},{"issue":"3","key":"10.1016\/j.bmcl.2021.127918_b0025","doi-asserted-by":"crossref","first-page":"e34352","DOI":"10.1371\/journal.pone.0034352","article-title":"Glyoxalase-I is a novel prognosis factor associated with gastric cancer progression","volume":"7","author":"Cheng","year":"2012","journal-title":"PLoS ONE"},{"issue":"15","key":"10.1016\/j.bmcl.2021.127918_b0030","doi-asserted-by":"crossref","first-page":"1528","DOI":"10.1002\/pros.23431","article-title":"High-Level Glyoxalase 1 (GLO1) expression is linked to poor prognosis in prostate cancer","volume":"77","author":"Burdelski","year":"2017","journal-title":"Prostate"},{"issue":"1","key":"10.1016\/j.bmcl.2021.127918_b0035","doi-asserted-by":"crossref","first-page":"67","DOI":"10.1023\/A:1010632919129","article-title":"Expression of glyoxalase I and II in normal and breast cancer tissues","volume":"66","author":"Rulli","year":"2001","journal-title":"Breast Cancer Res Treat"},{"issue":"92","key":"10.1016\/j.bmcl.2021.127918_b0040","doi-asserted-by":"crossref","first-page":"36515","DOI":"10.18632\/oncotarget.26369","article-title":"Glyoxalase 1 gene is highly expressed in basal-like human breast cancers and contributes to survival of ALDH1-positive breast cancer stem cells","volume":"9","author":"Tamori","year":"2018","journal-title":"Oncotarget"},{"key":"10.1016\/j.bmcl.2021.127918_b0045","first-page":"2513","article-title":"Selective activation of apoptosis program by S-p-bromobenzylglutathione cyclopentyl diester in glyoxalase I-overexpressing human lung cancer cells","volume":"7","author":"Sakamoto","year":"2001","journal-title":"Clin Cancer Res"},{"key":"10.1016\/j.bmcl.2021.127918_b0050","doi-asserted-by":"crossref","first-page":"85","DOI":"10.1097\/CMR.0b013e3283364903","article-title":"GLO1 overexpression in human malignant melanoma","volume":"20","author":"Bair","year":"2010","journal-title":"Melanoma Res"},{"key":"10.1016\/j.bmcl.2021.127918_b0055","doi-asserted-by":"crossref","first-page":"3214","DOI":"10.1182\/blood.V95.10.3214","article-title":"Glyoxalase I is involved in resistance of human leukemia cells to antitumor agent-induced apoptosis","volume":"95","author":"Sakamoto","year":"2000","journal-title":"Blood"},{"issue":"5","key":"10.1016\/j.bmcl.2021.127918_b0060","doi-asserted-by":"crossref","first-page":"593","DOI":"10.1016\/0006-291X(69)90445-8","article-title":"Glyoxalase inhibitors as potential anticancer agents","volume":"35","author":"Vince","year":"1969","journal-title":"Biochem Biophys Res Commun"},{"key":"10.1016\/j.bmcl.2021.127918_b0065","doi-asserted-by":"crossref","first-page":"1378","DOI":"10.1042\/bst0311378","article-title":"Glyoxalase I inhibitors in cancer chemotherapy","volume":"31","author":"Creighton","year":"2003","journal-title":"Biochem Soc Trans"},{"issue":"4","key":"10.1016\/j.bmcl.2021.127918_b0070","doi-asserted-by":"crossref","first-page":"115243","DOI":"10.1016\/j.bmc.2019.115243","article-title":"Recent advances in the discovery and development of glyoxalase I inhibitors","volume":"28","author":"Jin","year":"2020","journal-title":"Bioorg Med Chem"},{"issue":"14","key":"10.1016\/j.bmcl.2021.127918_b0075","doi-asserted-by":"crossref","first-page":"4337","DOI":"10.1016\/j.bmcl.2011.05.046","article-title":"Discovery of a new type inhibitor of human glyoxalase I by myricetin-based 4-point pharmacophore","volume":"21","author":"Takasawa","year":"2011","journal-title":"Bioorg Med Chem Lett"},{"issue":"5","key":"10.1016\/j.bmcl.2021.127918_b0080","doi-asserted-by":"crossref","first-page":"869","DOI":"10.1248\/bpb.b15-00710","article-title":"TLSC702, a novel inhibitor of human glyoxalase I, induces apoptosis in tumor cells","volume":"39","author":"Takasawa","year":"2016","journal-title":"Biol Pharm Bull"},{"issue":"13","key":"10.1016\/j.bmcl.2021.127918_b0085","doi-asserted-by":"crossref","first-page":"3793","DOI":"10.1016\/j.bmcl.2006.12.056","article-title":"Design, synthesis, and binding studies of bidentate Zn-chelating peptidic inhibitors of glyoxalase-I","volume":"17","author":"More","year":"2007","journal-title":"Bioorg Med Chem Lett"},{"key":"10.1016\/j.bmcl.2021.127918_b0090","doi-asserted-by":"crossref","first-page":"13740","DOI":"10.3390\/molecules171213740","article-title":"Generation of the first structure-based pharmacophore model containing a selective \u201czinc binding group\u201d feature to identify potential glyoxalase-1 inhibitors","volume":"17","author":"Al-Balas","year":"2012","journal-title":"Molecules"},{"issue":"3","key":"10.1016\/j.bmcl.2021.127918_b0095","doi-asserted-by":"crossref","first-page":"1609","DOI":"10.1021\/acs.jmedchem.8b01868","article-title":"Metal-binding pharmacophore library yields the discovery of a glyoxalase 1 inhibitor","volume":"62","author":"Perez","year":"2019","journal-title":"J Med Chem"},{"issue":"8","key":"10.1016\/j.bmcl.2021.127918_b0100","doi-asserted-by":"crossref","first-page":"711","DOI":"10.1002\/gcc.20784","article-title":"GLO1\u2014A novel amplified gene in human cancer","volume":"49","author":"Santarius","year":"2010","journal-title":"Genes Chromosomes Cancer"},{"issue":"5","key":"10.1016\/j.bmcl.2021.127918_b0105","doi-asserted-by":"crossref","first-page":"1169","DOI":"10.1016\/j.bmcl.2017.01.070","article-title":"Piceatannol, a natural trans-stilbene compound, inhibits human glyoxalase I","volume":"27","author":"Takasawa","year":"2017","journal-title":"Bioorg Med Chem Lett"},{"issue":"10","key":"10.1016\/j.bmcl.2021.127918_b0110","doi-asserted-by":"crossref","first-page":"1365","DOI":"10.1016\/0006-2952(96)00059-7","article-title":"Antitumour activity of S-p-bromobenzylglutathione cyclopentyl diester in vitro and in vivo: Inhibition of glyoxalase I and induction of apoptosis","volume":"51","author":"Thornalley","year":"1996","journal-title":"Biochem Pharmacol"},{"issue":"7","key":"10.1016\/j.bmcl.2021.127918_b0115","doi-asserted-by":"crossref","first-page":"3969","DOI":"10.1016\/j.bmc.2008.01.031","article-title":"Structure\u2013activity relationship of human GLO I inhibitory natural flavonoids and their growth inhibitory effects","volume":"16","author":"Takasawa","year":"2008","journal-title":"Bioorg Med Chem"},{"issue":"19","key":"10.1016\/j.bmcl.2021.127918_b0120","doi-asserted-by":"crossref","first-page":"7029","DOI":"10.1016\/j.bmc.2010.08.012","article-title":"Delphinidin, a dietary anthocyanidin in berry fruits, inhibits human glyoxalase I","volume":"18","author":"Takasawa","year":"2010","journal-title":"Bioorg Med Chem"},{"issue":"2","key":"10.1016\/j.bmcl.2021.127918_b0125","doi-asserted-by":"crossref","first-page":"171","DOI":"10.1006\/abio.1996.0271","article-title":"Method for determination of free intracellular and extracellular methylglyoxal in animal cells grown in culture","volume":"238","author":"Chaplen","year":"1996","journal-title":"Anal Biochem"},{"key":"10.1016\/j.bmcl.2021.127918_b0130","first-page":"1581","article-title":"Inhibitory effect of isoflavones from erythrina poeppigiana on the growth of HL-60 human leukemia cells through inhibition of glyoxalase I","volume":"10","author":"Hikita","year":"2015","journal-title":"Nat Prod Commun"},{"key":"10.1016\/j.bmcl.2021.127918_b0135","doi-asserted-by":"crossref","first-page":"455","DOI":"10.1002\/jcc.21334","article-title":"AutoDock Vina: improving the speed and accuracy of docking with a new scoring function, efficient optimization, and multithreading","volume":"31","author":"Trott","year":"2010","journal-title":"J Comput Chem"},{"key":"10.1016\/j.bmcl.2021.127918_b0140","doi-asserted-by":"crossref","first-page":"2981","DOI":"10.1093\/bioinformatics\/btu426","article-title":"YASARA View - molecular graphics for all devices \u2013 from smartphones to workstations","volume":"30","author":"Krieger","year":"2014","journal-title":"Bioinfomatics"}],"container-title":["Bioorganic & Medicinal Chemistry Letters"],"original-title":[],"language":"en","link":[{"URL":"https:\/\/api.elsevier.com\/content\/article\/PII:S0960894X2100144X?httpAccept=text\/xml","content-type":"text\/xml","content-version":"vor","intended-application":"text-mining"},{"URL":"https:\/\/api.elsevier.com\/content\/article\/PII:S0960894X2100144X?httpAccept=text\/plain","content-type":"text\/plain","content-version":"vor","intended-application":"text-mining"}],"deposited":{"date-parts":[[2025,10,18]],"date-time":"2025-10-18T07:42:39Z","timestamp":1760773359000},"score":1,"resource":{"primary":{"URL":"https:\/\/linkinghub.elsevier.com\/retrieve\/pii\/S0960894X2100144X"}},"subtitle":[],"short-title":[],"issued":{"date-parts":[[2021,5]]},"references-count":28,"alternative-id":["S0960894X2100144X"],"URL":"https:\/\/doi.org\/10.1016\/j.bmcl.2021.127918","relation":{},"ISSN":["0960-894X"],"issn-type":[{"value":"0960-894X","type":"print"}],"subject":[],"published":{"date-parts":[[2021,5]]},"assertion":[{"value":"Elsevier","name":"publisher","label":"This article is maintained by"},{"value":"Addition of hydrophobic side chains improve the apoptosis inducibility of the human glyoxalase I inhibitor, TLSC702","name":"articletitle","label":"Article Title"},{"value":"Bioorganic & Medicinal Chemistry Letters","name":"journaltitle","label":"Journal Title"},{"value":"https:\/\/doi.org\/10.1016\/j.bmcl.2021.127918","name":"articlelink","label":"CrossRef DOI link to publisher maintained version"},{"value":"article","name":"content_type","label":"Content Type"},{"value":"\u00a9 2021 Elsevier Ltd. All rights reserved.","name":"copyright","label":"Copyright"}],"article-number":"127918"}}