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M. A., Chin D., Wagner A. E., Rimbach G., <i>Angew. Chem. Int. Ed. Engl.<\/i>, <b>51<\/b>, 5308\u20135332 (2012).","DOI":"10.1002\/anie.201107724"},{"key":"2","unstructured":"2) Sharma R. A., McLelland H. R., Hill K. A., Ireson C. R., Euden S. A., Manson M. M., Pirmohamed M., Marnett L. J., Gescher A. J., Steward W. P., <i>Clin. Cancer Res.<\/i>, <b>7<\/b>, 1894\u20131900 (2001)."},{"key":"3","doi-asserted-by":"crossref","unstructured":"3) Dhillon N., Aggarwal B. B., Newman R. A., Wolff R. A., Kunnumakkara A. B., Abbruzzese J. L., Ng C. S., Badmaev V., Kurzrock R., <i>Clin. Cancer Res.<\/i>, <b>14<\/b>, 4491\u20134499 (2008).","DOI":"10.1158\/1078-0432.CCR-08-0024"},{"key":"4","doi-asserted-by":"crossref","unstructured":"4) Moreira J., Saraiva L., Pinto M. M., Cidade H., <i>Eur. J. Med. Chem.<\/i>, <b>192<\/b>, 112177 (2020).","DOI":"10.1016\/j.ejmech.2020.112177"},{"key":"5","unstructured":"5) Nomura H., Hotta S., <i>Science Reports of the Tohoku Imperial University<\/i>, <b>14<\/b>, 119\u2013125 (1925)."},{"key":"6","doi-asserted-by":"crossref","unstructured":"6) Schraufstatter E., Bernt H., <i>Nature<\/i> (London), <b>164<\/b>, 456\u2013457 (1949).","DOI":"10.1038\/164456a0"},{"key":"7","doi-asserted-by":"crossref","unstructured":"7) Masuda T., Jitoe A., Isobe J., Nakatani N., Yonemori S., <i>Phytochemistry<\/i>, <b>32<\/b>, 1557\u20131560 (1993).","DOI":"10.1016\/0031-9422(93)85179-U"},{"key":"8","doi-asserted-by":"crossref","unstructured":"8) Ohori H., Yamakoshi H., Tomizawa M., Shibuya M., Kakudo Y., Takahashi A., Takahashi S., Kato S., Suzuki T., Ishioka C., Iwabuchi Y., Shibata H., <i>Mol. Cancer Ther.<\/i>, <b>5<\/b>, 2563\u20132571 (2006).","DOI":"10.1158\/1535-7163.MCT-06-0174"},{"key":"9","doi-asserted-by":"crossref","unstructured":"9) Baell J., Walters M. A., <i>Nature<\/i> (London), <b>513<\/b>, 481\u2013483 (2014).","DOI":"10.1038\/513481a"},{"key":"10","doi-asserted-by":"crossref","unstructured":"10) Baell J. B., Holloway G. A., <i>J. Med. Chem.<\/i>, <b>53<\/b>, 2719\u20132740 (2010).","DOI":"10.1021\/jm901137j"},{"key":"11","doi-asserted-by":"crossref","unstructured":"11) Bisson J., McAlpine J. B., Friesen J. B., Chen S.-N., Graham J., Pauli G. F., <i>J. Med. Chem.<\/i>, <b>59<\/b>, 1671\u20131690 (2016).","DOI":"10.1021\/acs.jmedchem.5b01009"},{"key":"12","doi-asserted-by":"crossref","unstructured":"12) McGovern S. L., Caselli E., Grigorieff N., Shoichet B. K., <i>J. Med. Chem.<\/i>, <b>45<\/b>, 1712\u20131722 (2002).","DOI":"10.1021\/jm010533y"},{"key":"13","doi-asserted-by":"crossref","unstructured":"13) Nelson K. M., Dahlin J. L., Bisson J., Graham J., Pauli G. F., Walters M. A., <i>J. Med. Chem.<\/i>, <b>60<\/b>, 1620\u20131637 (2017).","DOI":"10.1021\/acs.jmedchem.6b00975"},{"key":"14","doi-asserted-by":"crossref","unstructured":"14) Shibata H., Yamakoshi H., Sato A., Ohori H., Kakudo Y., Kudo C., Takahashi Y., Watanabe M., Takano H., Ishioka C., Noda T., Iwabuchi Y., <i>Cancer Sci.<\/i>, <b>100<\/b>, 956\u2013960 (2009).","DOI":"10.1111\/j.1349-7006.2009.01127.x"},{"key":"15","unstructured":"15) Kudo C., Yamakoshi H., Sato A., Ohori H., Ishioka C., Iwabuchi Y., Shibata H., <i>Anticancer Res.<\/i>, <b>31<\/b>, 3719\u20133726 (2011)."},{"key":"16","doi-asserted-by":"crossref","unstructured":"16) Adams B. K., Ferstl E. M., Davis M. C., Herold M., Kurtkaya S., Camalier R. F., Hollingshead M. G., Kaur G., Sausville E. A., Rickles F. R., Snyder J. P., Liotta D. C., Shoji M., <i>Bioorg. Med. Chem.<\/i>, <b>12<\/b>, 3871\u20133883 (2004).","DOI":"10.1016\/j.bmc.2004.05.006"},{"key":"17","doi-asserted-by":"crossref","unstructured":"17) Costi R., Di Santo R., Artico M., Miele G., Valentini P., Novellino E., Cereseto A., <i>J. Med. Chem.<\/i>, <b>50<\/b>, 1973\u20131977 (2007).","DOI":"10.1021\/jm060943s"},{"key":"18","doi-asserted-by":"crossref","unstructured":"18) Kudo C., Yamakoshi H., Sato A., Nanjo H., Ohori H., Ishioka C., Iwabuchi Y., Shibata H., <i>BMC Pharmacol.<\/i>, <b>11<\/b>, 4 (2011).","DOI":"10.1186\/1471-2210-11-4"},{"key":"19","doi-asserted-by":"crossref","unstructured":"19) Kohyama A., Fukuda M., Sugiyama S., Yamakoshi H., Kanoh N., Ishioka C., Shibata H., Iwabuchi Y., <i>Org. Biomol. Chem.<\/i>, <b>14<\/b>, 10683\u201310687 (2016).","DOI":"10.1039\/C6OB01771A"},{"key":"20","unstructured":"20) Snyder <i>et al.<\/i> reported the development of a thia-Michael adduct as a C5-curcuminoid prodrug with water-soluble thiols. This prodrug gradually releases C5-curcuminoids (ref. 21)."},{"key":"21","doi-asserted-by":"crossref","unstructured":"21) Sun A., Lu Y. J., Hu H., Shoji M., Liotta D. C., Snyder J. P., <i>Bioorg. Med. Chem. Lett.<\/i>, <b>19<\/b>, 6627\u20136631 (2009).","DOI":"10.1016\/j.bmcl.2009.10.023"},{"key":"22","doi-asserted-by":"crossref","unstructured":"22) Kaminaga Y., Nagatsu A., Akiyama T., Sugimoto N., Yamazaki T., Maitani T., Mizukami H., <i>FEBS Lett.<\/i>, <b>555<\/b>, 311\u2013316 (2003).","DOI":"10.1016\/S0014-5793(03)01265-1"},{"key":"23","doi-asserted-by":"crossref","unstructured":"23) Kakudo Y., Shibata H., Otsuka K., Kato S., Ishioka C., <i>Cancer Res.<\/i>, <b>65<\/b>, 2108\u20132114 (2005).","DOI":"10.1158\/0008-5472.CAN-04-2935"},{"key":"24","doi-asserted-by":"crossref","unstructured":"24) Tanaka T., Nagai H., Noguchi M., Kobayashi A., Shoda S.-I., <i>Chem. 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