{"status":"ok","message-type":"work","message-version":"1.0.0","message":{"indexed":{"date-parts":[[2026,8,28]],"date-time":"2026-08-28T21:02:18Z","timestamp":1787950938895,"version":"build-2784847793"},"reference-count":33,"publisher":"Japanese Society of Toxicology","issue":"12","content-domain":{"domain":[],"crossmark-restriction":false},"short-container-title":["J. Toxicol. Sci."],"published-print":{"date-parts":[[2022]]},"DOI":"10.2131\/jts.47.539","type":"journal-article","created":{"date-parts":[[2022,11,30]],"date-time":"2022-11-30T17:17:37Z","timestamp":1669828657000},"page":"539-546","source":"Crossref","is-referenced-by-count":7,"title":["Triphenylbismuth dichloride inhibits human glyoxalase I and induces cytotoxicity in cultured cancer cell lines"],"prefix":"10.2131","volume":"47","author":[{"given":"Ryoko","family":"Takasawa","sequence":"first","affiliation":[{"name":"Faculty of Pharmaceutical Sciences, Tokyo University of Science"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Akane","family":"Jona","sequence":"additional","affiliation":[{"name":"Faculty of Pharmaceutical Sciences, Tokyo University of Science"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Manami","family":"Inoue","sequence":"additional","affiliation":[{"name":"Faculty of Pharmaceutical Sciences, Tokyo University of Science"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Miku","family":"Azuma","sequence":"additional","affiliation":[{"name":"Faculty of Pharmaceutical Sciences, Tokyo University of Science"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Haruka","family":"Akahane","sequence":"additional","affiliation":[{"name":"Faculty of Pharmaceutical Sciences, Tokyo University of Science"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Yuto","family":"Ueno","sequence":"additional","affiliation":[{"name":"Faculty of Pharmaceutical Sciences, Tokyo University of Science"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Yuki","family":"Nakagawa","sequence":"additional","affiliation":[{"name":"Faculty of Pharmaceutical Sciences, Tokyo University of Science"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Ryusei","family":"Chimori","sequence":"additional","affiliation":[{"name":"Faculty of Pharmaceutical Sciences, Tokyo University of Science"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Yasunari","family":"Mano","sequence":"additional","affiliation":[{"name":"Faculty of Pharmaceutical Sciences, Tokyo University of Science"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Yuki","family":"Murata","sequence":"additional","affiliation":[{"name":"School of Pharmaceutical Sciences, Aichi Gakuin University"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Shuji","family":"Yasuike","sequence":"additional","affiliation":[{"name":"School of Pharmaceutical Sciences, Aichi Gakuin University"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Toshiyuki","family":"Kaji","sequence":"additional","affiliation":[{"name":"Faculty of Pharmaceutical Sciences, Tokyo University of Science"}],"role":[{"vocabulary":"crossref","role":"author"}]}],"member":"898","reference":[{"key":"1","doi-asserted-by":"crossref","unstructured":"Azuma, M., Inoue, M., Nishida, A., Akahane, H., Kitajima, M., Natani, S., Chimori, R., Yoshimori, A., Mano, Y., Uchiro, H., Tanuma, S.I. and Takasawa, R. (2021): Addition of hydrophobic side chains improve the apoptosis inducibility of the human glyoxalase I inhibitor, TLSC702. Bioorg. Med. Chem. Lett., <b>40<\/b>, 127918.","DOI":"10.1016\/j.bmcl.2021.127918"},{"key":"2","doi-asserted-by":"crossref","unstructured":"Bair, W.B. 3rd, Cabello, C.M., Uchida, K., Bause, A.S. and Wondrak, G.T. (2010): GLO1 overexpression in human malignant melanoma. Melanoma Res., <b>20<\/b>, 85-96.","DOI":"10.1097\/CMR.0b013e3283364903"},{"key":"3","doi-asserted-by":"publisher","unstructured":"Burdelski, C., Shihada, R., Hinsch, A., Angerer, A., G\u00f6bel, C., Friedrich, E., Hube-Magg, C., Burdak-Rothkamm, S., Kluth, M., Simon, R., M\u00f6ller-Koop, C., Sauter, G., B\u00fcscheck, F., Wittmer, C., Clauditz, T.S., Krech, T., Tsourlakis, M.C., Minner, S., Graefen, M., Schlomm, T., Wilczak, W. and Jacobsen, F. (2017): High-Level Glyoxalase 1 (GLO1) expression is linked to poor prognosis in prostate cancer. Prostate, <b>77<\/b>, 1528-1538.","DOI":"10.1002\/pros.23431"},{"key":"4","doi-asserted-by":"crossref","unstructured":"Cameron, A.D., Olin, B., Ridderstr\u00f6m, M., Mannervik, B. and Jones, T.A. (1997): Crystal structure of human glyoxalase I--evidence for gene duplication and 3D domain swapping. EMBO J., <b>16<\/b>, 3386-3395.","DOI":"10.1093\/emboj\/16.12.3386"},{"key":"5","doi-asserted-by":"crossref","unstructured":"Cheng, W.L., Tsai, M.M., Tsai, C.Y., Huang, Y.H., Chen, C.Y., Chi, H.C., Tseng, Y.H., Chao, I.W., Lin, W.C., Wu, S.M., Liang, Y., Liao, C.J., Lin, Y.H., Chung, I.H., Chen, W.J., Lin, P.Y., Wang, C.S. and Lin, K.H. (2012): Glyoxalase-I is a novel prognosis factor associated with gastric cancer progression. PLoS One, <b>7<\/b>, e34352.","DOI":"10.1371\/journal.pone.0034352"},{"key":"6","doi-asserted-by":"crossref","unstructured":"Hikita, K., Yamada, S., Shibata, R., Katoh, M., Murata, T., Kato, K., Tanaka, H. and Kaneda, N. (2015): Inhibitory effect of isoflavones from <i>Erythrina poeppigiana<\/i> on the growth of HL-60 human leukemia cells through inhibition of glyoxalase I. Nat. Prod. Commun., <b>10<\/b>, 1581-1584.","DOI":"10.1177\/1934578X1501000924"},{"key":"7","doi-asserted-by":"crossref","unstructured":"Islam, A., Rodrigues, B.L., Marzano, I.M., Perreira-Maia, E.C., Dittz, D., Paz Lopes, M.T., Ishfaq, M., Fr\u00e9zard, F. and Demicheli, C. (2016): Cytotoxicity and apoptotic activity of novel organobismuth(V) and organoantimony(V) complexes in different cancer cell lines. Eur. J. Med. Chem., <b>109<\/b>, 254-267.","DOI":"10.1016\/j.ejmech.2016.01.003"},{"key":"8","doi-asserted-by":"crossref","unstructured":"Iuchi, K., Hatano, Y. and Yagura, T. (2008): Heterocyclic organobismuth(III) induces apoptosis of human promyelocytic leukemic cells through activation of caspases and mitochondrial perturbation. Biochem. Pharmacol., <b>76<\/b>, 974-986.","DOI":"10.1016\/j.bcp.2008.07.038"},{"key":"9","doi-asserted-by":"crossref","unstructured":"Iuchi, K., Akagi, K. and Yagura, T. (2009): Heterocyclic organobismuth(III) compound targets tubulin to induce G2\/M arrest in HeLa cells. J. Pharmacol. Sci., <b>109<\/b>, 573-582.","DOI":"10.1254\/jphs.09020FP"},{"key":"10","doi-asserted-by":"crossref","unstructured":"Jin, T., Zhao, L., Wang, H.P., Huang, M.L., Yue, Y., Lu, C. and Zheng, Z.B. (2020): Recent advances in the discovery and development of glyoxalase I inhibitors. Bioorg. Med. Chem., <b>28<\/b>, 115243.","DOI":"10.1016\/j.bmc.2019.115243"},{"key":"11","doi-asserted-by":"crossref","unstructured":"Kamepalli, S., Carmalt, C.J., Culp, R.D., Cowley, A.H., Jones, R.A. and Norman, N.C. (1996): Synthesis and structures of intramolecularly base-coordinated aryl group 15 compounds. Inorg. Chem., <b>35<\/b>, 6179-6183.","DOI":"10.1021\/ic960516c"},{"key":"12","doi-asserted-by":"crossref","unstructured":"Kang, Y., Edwards, L.G. and Thornalley, P.J. (1996): Effect of methylglyoxal on human leukaemia 60 cell growth: modification of DNA G1 growth arrest and induction of apoptosis. Leuk. Res., <b>20<\/b>, 397-405.","DOI":"10.1016\/0145-2126(95)00162-X"},{"key":"13","doi-asserted-by":"crossref","unstructured":"Kohri, K., Yoshida, E., Yasuike, S., Fujie, T., Yamamoto, C. and Kaji, T. (2015): The cytotoxicity of organobismuth compounds with certain molecular structures can be diminished by replacing the bismuth atom with an antimony atom in the molecules. J. Toxicol. Sci., <b>40<\/b>, 321-327.","DOI":"10.2131\/jts.40.321"},{"key":"14","doi-asserted-by":"publisher","unstructured":"Lee, J.H., Subedi, L. and Kim, S.Y. (2020): Effect of cysteine on methylglyoxal-induced renal damage in mesangial cells. Cells, <b>9<\/b>, 234.","DOI":"10.3390\/cells9010234"},{"key":"15","doi-asserted-by":"crossref","unstructured":"Liu, Y.P., Lei, J., Tang, L.W., Peng, Y., Au, C.T., Chen, Y. and Yin, S.F. (2017): Studies on the cytotoxicity and anticancer performance of heterocyclic hypervalent organobismuth(III) compounds. Eur. J. Med. Chem., <b>139<\/b>, 826-835.","DOI":"10.1016\/j.ejmech.2017.08.043"},{"key":"16","doi-asserted-by":"crossref","unstructured":"Murafuji, T., Azuma, T., Miyoshi, Y., Ishibashi, M., Rahman, A.F., Migita, K., Sugihara, Y. and Mikata, Y. (2006): Inhibition of jack bean urease by organobismuth compounds. Bioorg. Med. Chem. Lett., <b>16<\/b>, 1510-1513.","DOI":"10.1016\/j.bmcl.2005.12.034"},{"key":"17","doi-asserted-by":"crossref","unstructured":"Ohtaka, K., Takemoto, S., Ohnishi, M. and Akiba, K. (1989): Synthesis and chemical behaviors of 12-substituted dibenz[<i>c,f<\/i>][1,5]azastibocine and dibenz[<i>c,f<\/i>][1,5]azabismocine derivatives: evidences of 10-Pn-4 type hypervalent interaction. Tetrahedron Lett., <b>30<\/b>, 4841-4844.","DOI":"10.1016\/S0040-4039(01)80523-2"},{"key":"18","doi-asserted-by":"crossref","unstructured":"Onishi, K., Douke, M., Nakamura, T., Ochiai, Y., Kakusawa, N., Yasuike, S., Kurita, J., Yamamoto, C., Kawahata, M., Yamaguchi, K. and Yagura, T. (2012): A novel organobismuth compound, 1-[(2-di-<i>p<\/i>-tolylbismuthanophenyl)diazenyl]pyrrolidine, induces apoptosis in the human acute promyelocytic leukemia cell line NB4 via reactive oxygen species. J. Inorg. Biochem., <b>117<\/b>, 77-84.","DOI":"10.1016\/j.jinorgbio.2012.09.009"},{"key":"19","doi-asserted-by":"crossref","unstructured":"Ranganathan, S. and Tew, K.D. (1993): Analysis of glyoxalase-I from normal and tumor tissue from human colon. Biochim. Biophys. Acta, <b>1182<\/b>, 311-316.","DOI":"10.1016\/0925-4439(93)90074-B"},{"key":"20","doi-asserted-by":"crossref","first-page":"3214","DOI":"10.1182\/blood.V95.10.3214","author":"H. Sakamoto","year":"2000","unstructured":"Sakamoto, H., Mashima, T., Kizaki, A., Dan, S., Hashimoto, Y., Naito, M. and Tsuruo, T. (2000): Glyoxalase I is involved in resistance of human leukemia cells to antitumor agent-induced apoptosis. Blood, <b>95<\/b>, 3214-3218.","journal-title":"Blood","ISSN":"https:\/\/id.crossref.org\/issn\/0006-4971","issn-type":"print"},{"key":"21","unstructured":"Sakamoto, H., Mashima, T., Sato, S., Hashimoto, Y., Yamori, T. and Tsuruo, T. (2001): Selective activation of apoptosis program by <i>S<\/i>-<i>p<\/i>-bromobenzylglutathione cyclopentyl diester in glyoxalase I-overexpressing human lung cancer cells. Clin. Cancer Res., <b>7<\/b>, 2513-2518."},{"key":"22","doi-asserted-by":"crossref","unstructured":"Santarius, T., Bignell, G.R., Greenman, C.D., Widaa, S., Chen, L., Mahoney, C.L., Butler, A., Edkins, S., Waris, S., Thornalley, P.J., Futreal, P.A. and Stratton, M.R. (2010): GLO1-A novel amplified gene in human cancer. Genes Chromosomes Cancer, <b>49<\/b>, 711-725.","DOI":"10.1002\/gcc.20784"},{"key":"23","doi-asserted-by":"crossref","unstructured":"Takasawa, R., Takahashi, S., Saeki, K., Sunaga, S., Yoshimori, A. and Tanuma, S. (2008): Structure-activity relationship of human GLO I inhibitory natural flavonoids and their growth inhibitory effects. Bioorg. Med. Chem., <b>16<\/b>, 3969-3975.","DOI":"10.1016\/j.bmc.2008.01.031"},{"key":"24","doi-asserted-by":"crossref","unstructured":"Takasawa, R., Saeki, K., Tao, A., Yoshimori, A., Uchiro, H., Fujiwara, M. and Tanuma, S. (2010): Delphinidin, a dietary anthocyanidin in berry fruits, inhibits human glyoxalase I. Bioorg. Med. Chem., <b>18<\/b>, 7029-7033.","DOI":"10.1016\/j.bmc.2010.08.012"},{"key":"25","doi-asserted-by":"crossref","unstructured":"Takasawa, R., Tao, A., Saeki, K., Shionozaki, N., Tanaka, R., Uchiro, H., Takahashi, S., Yoshimori, A. and Tanuma, S. (2011): Discovery of a new type inhibitor of human glyoxalase I by myricetin-based 4-point pharmacophore. Bioorg. Med. Chem. Lett., <b>21<\/b>, 4337-4342.","DOI":"10.1016\/j.bmcl.2011.05.046"},{"key":"26","doi-asserted-by":"crossref","unstructured":"Takasawa, R., Shimada, N., Uchiro, H., Takahashi, S., Yoshimori, A. and Tanuma, S. (2016): TLSC702, a novel inhibitor of human glyoxalase I, induces apoptosis in tumor cells. Biol. Pharm. Bull., <b>39<\/b>, 869-873.","DOI":"10.1248\/bpb.b15-00710"},{"key":"27","doi-asserted-by":"crossref","unstructured":"Takasawa, R., Akahane, H., Tanaka, H., Shimada, N., Yamamoto, T., Uchida-Maruki, H., Sai, M., Yoshimori, A. and Tanuma, S.I. (2017): Piceatannol, a natural trans-stilbene compound, inhibits human glyoxalase I. Bioorg. Med. Chem. Lett., <b>27<\/b>, 1169-1174.","DOI":"10.1016\/j.bmcl.2017.01.070"},{"key":"28","doi-asserted-by":"publisher","unstructured":"Tamori, S., Nozaki, Y., Motomura, H., Nakane, H., Katayama, R., Onaga, C., Kikuchi, E., Shimada, N., Suzuki, Y., Noike, M., Hara, Y., Sato, K., Sato, T., Yamamoto, K., Hanawa, T., Imai, M., Abe, R., Yoshimori, A., Takasawa, R., Tanuma, S.I. and Akimoto, K. (2018): Glyoxalase 1 gene is highly expressed in basal-like human breast cancers and contributes to survival of ALDH1-positive breast cancer stem cells. Oncotarget, <b>9<\/b>, 36515-36529.","DOI":"10.18632\/oncotarget.26369"},{"key":"29","doi-asserted-by":"crossref","unstructured":"Thornalley, P.J. (1990): The glyoxalase system: new developments towards functional characterization of a metabolic pathway fundamental to biological life. Biochem. J., <b>269<\/b>, 1-11.","DOI":"10.1042\/bj2690001"},{"key":"30","doi-asserted-by":"crossref","unstructured":"Thornalley, P.J., Edwards, L.G., Kang, Y., Wyatt, C., Davies, N., Ladan, M.J. and Double, J. (1996): Antitumour activity of S-p-bromobenzylglutathione cyclopentyl diester <i>in vitro<\/i> and <i>in vivo<\/i>. Inhibition of glyoxalase I and induction of apoptosis. Biochem. Pharmacol., <b>51<\/b>, 1365-1372.","DOI":"10.1016\/0006-2952(96)00059-7"},{"key":"31","unstructured":"Wang, Y., Kuramitsu, Y., Ueno, T., Suzuki, N., Yoshino, S., Iizuka, N., Akada, J., Kitagawa, T., Oka, M. and Nakamura, K. (2012): Glyoxalase I (GLO1) is up-regulated in pancreatic cancerous tissues compared with related non-cancerous tissues. Anticancer Res., <b>32<\/b>, 3219-3222."},{"key":"32","doi-asserted-by":"publisher","unstructured":"Zhang, L., Mulrooney, S.B., Leung, A.F., Zeng, Y., Ko, B.B., Hausinger, R.P. and Sun, H. (2006): Inhibition of urease by bismuth(III): implications for the mechanism of action of bismuth drugs. Biometals, <b>19<\/b>, 503-511.","DOI":"10.1007\/s10534-005-5449-0"},{"key":"33","doi-asserted-by":"crossref","unstructured":"Zhitkovich, A. (2019): N-Acetylcysteine: antioxidant, aldehyde scavenger, and more. Chem. Res. Toxicol., <b>32<\/b>, 1318-1319.","DOI":"10.1021\/acs.chemrestox.9b00152"}],"container-title":["The Journal of Toxicological Sciences"],"original-title":[],"language":"en","link":[{"URL":"https:\/\/www.jstage.jst.go.jp\/article\/jts\/47\/12\/47_539\/_pdf","content-type":"unspecified","content-version":"vor","intended-application":"similarity-checking"}],"deposited":{"date-parts":[[2022,12,2]],"date-time":"2022-12-02T23:30:15Z","timestamp":1670023815000},"score":1,"resource":{"primary":{"URL":"https:\/\/www.jstage.jst.go.jp\/article\/jts\/47\/12\/47_539\/_article"}},"subtitle":[],"short-title":[],"issued":{"date-parts":[[2022]]},"references-count":33,"journal-issue":{"issue":"12","published-print":{"date-parts":[[2022]]}},"URL":"https:\/\/doi.org\/10.2131\/jts.47.539","relation":{},"ISSN":["0388-1350","1880-3989"],"issn-type":[{"value":"0388-1350","type":"print"},{"value":"1880-3989","type":"electronic"}],"subject":[],"published":{"date-parts":[[2022]]}}}