{"status":"ok","message-type":"work","message-version":"1.0.0","message":{"indexed":{"date-parts":[[2025,11,13]],"date-time":"2025-11-13T12:22:56Z","timestamp":1763036576531,"version":"build-2065373602"},"reference-count":40,"publisher":"Elsevier BV","issue":"9","license":[{"start":{"date-parts":[[2011,5,1]],"date-time":"2011-05-01T00:00:00Z","timestamp":1304208000000},"content-version":"tdm","delay-in-days":0,"URL":"https:\/\/www.elsevier.com\/tdm\/userlicense\/1.0\/"},{"start":{"date-parts":[[2011,5,1]],"date-time":"2011-05-01T00:00:00Z","timestamp":1304208000000},"content-version":"tdm","delay-in-days":0,"URL":"https:\/\/www.elsevier.com\/legal\/tdmrep-license"}],"content-domain":{"domain":["elsevier.com","sciencedirect.com"],"crossmark-restriction":true},"short-container-title":["Bioorganic &amp; Medicinal Chemistry Letters"],"published-print":{"date-parts":[[2011,5]]},"DOI":"10.1016\/j.bmcl.2011.01.101","type":"journal-article","created":{"date-parts":[[2011,1,28]],"date-time":"2011-01-28T04:40:36Z","timestamp":1296189636000},"page":"2606-2610","update-policy":"https:\/\/doi.org\/10.1016\/elsevier_cm_policy","source":"Crossref","is-referenced-by-count":40,"title":["Potent antiprotozoal activity of a novel semi-synthetic berberine derivative"],"prefix":"10.1016","volume":"21","author":[{"given":"Mark","family":"Bahar","sequence":"first","affiliation":[],"role":[{"role":"author","vocabulary":"crossref"}]},{"given":"Ye","family":"Deng","sequence":"additional","affiliation":[],"role":[{"role":"author","vocabulary":"crossref"}]},{"given":"Xiaohua","family":"Zhu","sequence":"additional","affiliation":[],"role":[{"role":"author","vocabulary":"crossref"}]},{"given":"Shanshan","family":"He","sequence":"additional","affiliation":[],"role":[{"role":"author","vocabulary":"crossref"}]},{"given":"Trupti","family":"Pandharkar","sequence":"additional","affiliation":[],"role":[{"role":"author","vocabulary":"crossref"}]},{"given":"Mark E.","family":"Drew","sequence":"additional","affiliation":[],"role":[{"role":"author","vocabulary":"crossref"}]},{"given":"Armando","family":"Navarro-V\u00e1zquez","sequence":"additional","affiliation":[],"role":[{"role":"author","vocabulary":"crossref"}]},{"given":"Clemens","family":"Anklin","sequence":"additional","affiliation":[],"role":[{"role":"author","vocabulary":"crossref"}]},{"given":"Roberto R.","family":"Gil","sequence":"additional","affiliation":[],"role":[{"role":"author","vocabulary":"crossref"}]},{"given":"Raymond W.","family":"Doskotch","sequence":"additional","affiliation":[],"role":[{"role":"author","vocabulary":"crossref"}]},{"given":"Karl A.","family":"Werbovetz","sequence":"additional","affiliation":[],"role":[{"role":"author","vocabulary":"crossref"}]},{"given":"A. Douglas","family":"Kinghorn","sequence":"additional","affiliation":[],"role":[{"role":"author","vocabulary":"crossref"}]}],"member":"78","reference":[{"key":"10.1016\/j.bmcl.2011.01.101_b0005","doi-asserted-by":"crossref","first-page":"1570","DOI":"10.1016\/S0140-6736(09)60233-6","volume":"373","author":"Hotez","year":"2009","journal-title":"Lancet"},{"key":"10.1016\/j.bmcl.2011.01.101_b0010","doi-asserted-by":"crossref","first-page":"67","DOI":"10.1016\/S0140-6736(09)61749-9","volume":"375","author":"Liese","year":"2010","journal-title":"Lancet"},{"key":"10.1016\/j.bmcl.2011.01.101_b0015","doi-asserted-by":"crossref","first-page":"239","DOI":"10.1016\/S0140-6736(09)61422-7","volume":"375","author":"Conteh","year":"2010","journal-title":"Lancet"},{"key":"10.1016\/j.bmcl.2011.01.101_b0020","doi-asserted-by":"crossref","first-page":"2188","DOI":"10.1016\/S0140-6736(02)09096-7","volume":"359","author":"Trouiller","year":"2002","journal-title":"Lancet"},{"key":"10.1016\/j.bmcl.2011.01.101_b0025","doi-asserted-by":"crossref","first-page":"176","DOI":"10.1136\/bmj.325.7357.176","volume":"325","author":"Yamey","year":"2002","journal-title":"Br. Med. J."},{"year":"2004","series-title":"Needs-based Pharmaceutical R&D Agenda for Neglected Diseases","author":"Toreele","key":"10.1016\/j.bmcl.2011.01.101_b0030"},{"key":"10.1016\/j.bmcl.2011.01.101_b0035","doi-asserted-by":"crossref","first-page":"23","DOI":"10.1007\/0-387-33026-7_3","volume":"582","author":"Hotez","year":"2006","journal-title":"Adv. Exp. Med. Biol."},{"key":"10.1016\/j.bmcl.2011.01.101_b0040","doi-asserted-by":"crossref","first-page":"1018","DOI":"10.1056\/NEJMra064142","volume":"357","author":"Hotez","year":"2007","journal-title":"N. Eng. J. Med."},{"key":"10.1016\/j.bmcl.2011.01.101_b0045","unstructured":"Neglected Tropical Diseases. http:\/\/whqlibdoc.who.int\/publications\/ (accessed Aug 2010)."},{"year":"2002","series-title":"Medicinal Natural Products: A Biosynthetic Approach","author":"Dewick","key":"10.1016\/j.bmcl.2011.01.101_b0050"},{"key":"10.1016\/j.bmcl.2011.01.101_b0055","doi-asserted-by":"crossref","first-page":"13410","DOI":"10.1021\/jp9069515","volume":"113","author":"Sinha","year":"2009","journal-title":"J. Phys. Chem. B"},{"key":"10.1016\/j.bmcl.2011.01.101_b0060","doi-asserted-by":"crossref","first-page":"6004","DOI":"10.1016\/j.bmcl.2009.09.059","volume":"19","author":"Wang","year":"2009","journal-title":"Bioorg. Med. Chem. Lett."},{"key":"10.1016\/j.bmcl.2011.01.101_b0065","doi-asserted-by":"crossref","first-page":"285","DOI":"10.1016\/j.metabol.2009.07.029","volume":"59","author":"Zhang","year":"2010","journal-title":"Metabolism"},{"key":"10.1016\/j.bmcl.2011.01.101_b0070","doi-asserted-by":"crossref","first-page":"165","DOI":"10.1038\/aps.2009.180","volume":"31","author":"Qi","year":"2010","journal-title":"Acta Pharmacol. Sin."},{"key":"10.1016\/j.bmcl.2011.01.101_b0075","doi-asserted-by":"crossref","first-page":"201","DOI":"10.1007\/s10482-009-9394-8","volume":"97","author":"Iwazaki","year":"2010","journal-title":"Antonie van Leeuwenhoek"},{"key":"10.1016\/j.bmcl.2011.01.101_b0080","doi-asserted-by":"crossref","first-page":"404","DOI":"10.1016\/0014-4894(85)90047-5","volume":"60","author":"Ghosh","year":"1985","journal-title":"Exp. Parasitol."},{"key":"10.1016\/j.bmcl.2011.01.101_b0085","doi-asserted-by":"crossref","first-page":"1084","DOI":"10.1021\/jm00401a006","volume":"31","author":"Vennerstrom","year":"1988","journal-title":"J. Med. Chem."},{"key":"10.1016\/j.bmcl.2011.01.101_b0090","doi-asserted-by":"crossref","first-page":"918","DOI":"10.1128\/AAC.34.5.918","volume":"34","author":"Vennerstrom","year":"1990","journal-title":"Antimicrob. Agents Chemother."},{"key":"10.1016\/j.bmcl.2011.01.101_b0095","first-page":"358","volume":"57","author":"Nyasse","year":"2002","journal-title":"Pharmazie"},{"key":"10.1016\/j.bmcl.2011.01.101_b0100","doi-asserted-by":"crossref","first-page":"2462","DOI":"10.3390\/molecules13102462","volume":"13","author":"Rosenkranz","year":"2008","journal-title":"Molecules"},{"key":"10.1016\/j.bmcl.2011.01.101_b0105","doi-asserted-by":"crossref","first-page":"1101","DOI":"10.1080\/10715760903186124","volume":"43","author":"Saha","year":"2009","journal-title":"Free Radical Res."},{"key":"10.1016\/j.bmcl.2011.01.101_b0110","doi-asserted-by":"crossref","first-page":"1144","DOI":"10.1080\/14786410902726241","volume":"23","author":"Nkwengoua","year":"2009","journal-title":"Nat. Prod. Res."},{"key":"10.1016\/j.bmcl.2011.01.101_b0115_1","doi-asserted-by":"crossref","first-page":"705","DOI":"10.1002\/jps.2600680613","volume":"68","author":"Moniot","year":"1979","journal-title":"J. Pharm. Sci."},{"key":"10.1016\/j.bmcl.2011.01.101_b0125","unstructured":"8-Oxoberberine was isolated as pale-yellow needle crystals and characterized spectroscopically: 1H NMR (DMSO-d6) \u03b4 7.49 (1H, d, J=8.7 Hz, H-11), 7.47 (1H, s, H-1), 7.39 (1H, d, J=8.7 Hz, H-12), 7.07 (1H, s, H-13), 6.90 (1H, s, H-4), 6.07 (2H, s, OCH2O-2), 4.11 (2H, t, J=6 Hz, H-6), 3.87 (3H, s, \u2013OCH3, C-10), 3.77 (3H, s, \u2013OCH3, C-9), 2.86 (2H, t, J=6 Hz, H-5); HRESIMS m\/z 374.0978 [M+Na]+(calcd. for [C20H17NO5+Na]+, 374.1004)"},{"key":"10.1016\/j.bmcl.2011.01.101_b0130","unstructured":"8-Chloroberberine chloride was isolated as an orange amorphous solid and characterized spectroscopically: 1H NMR (CF3COOD) \u03b4 8.33 (1H, s, H-13), 7.99 (1H, s, H-11), 7.98 (1H, s, H-12), 7.34 (1H, s, H-1), 6.83 (1H, s, H-4), 6.02 (2H, s, OCH2O-2), 5.09 (2H, t, J=6.3 Hz, H-6), 4.12 (3H, s, \u2013OCH3, \u22129), 4.11 (3H, s, \u2013OCH3, \u221210), 3.18 (2H, t, J=6.0 Hz H-5); HRESIMS m\/z 370.0863 [M+Na]+(calcd. for [C20H17NO5+Na]+, 370.0846)"},{"key":"10.1016\/j.bmcl.2011.01.101_b0135","unstructured":"5,6-Didehydro-8,8-diethyl-13-oxodihydroberberine chloride was isolated as yellow needle crystals (MeOH\/H2O), mp 159 \u00b0C; UV (MeOH) \u03bbmax (log \u03b5) 212 (4.33), 241 (4.18), 287 (4.09) nm; IR (film) \u03bdmax 3417, 1659, 1581, 1460, 1290, 1027 cm\u20131; 1H NMR (300 MHz, MeOD) \u03b4 9.22 (1H, d, J = 7.2 Hz, H-6), 9.09 (1H, s, H-1), 8.61 (1H, d, J = 7.2 Hz, H-5), 8.26 (1H, d, J = 8.9 Hz, H-12), 7.68 (1H,s, H-4), 7.54 (1H, d, J = 8.9 Hz, H-11), 6.45 (2H, s, OCH2O), 4.10 (3H, s, OCH3\/10), 4.03 (3H, s, OCH3\/9), 3.22 (2H, dd, J = 15.4, 7.6 Hz, H-1\u2019\u2019), 2.70 (2H, dd, J = 15.4, 7.4 Hz, H-1\u2019), 0.38 (6H, t, J = 7.4 Hz, H-2\u2019 and H-2\u2019\u2019); 13C NMR (75 MHz, MeOD) \u03b4 178.5 (C-13), 161 (C-10), 158.3 (C-2), 156.1 (C-3), 145.0 (C-9), 142.3 (C-13a), 142.0 (C-4a), 133.3 (C-8a), 132.3 (C-6), 129.3 (C-5), 127.0 (C-13b), 126.6 (C-12), 124.7 (C-12a), 115.8 (C-11), 106.6 (C-1), 106.3 (-OCH2O-), 104.4 (C-4), 81.1 (C-8), 61.7 (OCH3\/9), 57.0 (OCH3\/10), 35.8 (C-1\u2019 and C-1\u2019\u2019), 8.2 (C-2\u2019 and C-2\u2019\u2019); HRESIMS m\/z 406.1650 [M]+ (calcd. for C24H24NO5, 406.1654)"},{"key":"10.1016\/j.bmcl.2011.01.101_b0140","doi-asserted-by":"crossref","first-page":"5037","DOI":"10.1016\/j.tet.2005.03.041","volume":"61","author":"Li","year":"2005","journal-title":"Tetrahedron"},{"key":"10.1016\/j.bmcl.2011.01.101_b0145","doi-asserted-by":"crossref","first-page":"1150","DOI":"10.1021\/np980044+","volume":"61","author":"Iwasa","year":"1998","journal-title":"J. Nat. Prod."},{"key":"10.1016\/j.bmcl.2011.01.101_b0150","doi-asserted-by":"crossref","first-page":"5915","DOI":"10.1016\/j.bmc.2010.06.085","volume":"18","author":"Cheng","year":"2010","journal-title":"Bioorg. Med. Chem."},{"key":"10.1016\/j.bmcl.2011.01.101_b0155","doi-asserted-by":"crossref","first-page":"4849","DOI":"10.1021\/ja00534a056","volume":"102","author":"Bax","year":"1980","journal-title":"J. Am. Chem. Soc."},{"key":"10.1016\/j.bmcl.2011.01.101_b0160","doi-asserted-by":"crossref","first-page":"215","DOI":"10.1007\/s00214-007-0310-x","volume":"120","author":"Zhao","year":"2008","journal-title":"Theor. Chem. Acc."},{"key":"10.1016\/j.bmcl.2011.01.101_b0165","doi-asserted-by":"crossref","first-page":"2999","DOI":"10.1021\/cr9904009","volume":"105","author":"Tomasi","year":"2005","journal-title":"Chem. Rev."},{"key":"10.1016\/j.bmcl.2011.01.101_b0170","unstructured":"gaussian09, Rev. A.02: Frisch, M. J. et al. Gaussian, Wallingford, CT, 2004."},{"key":"10.1016\/j.bmcl.2011.01.101_b0175","doi-asserted-by":"crossref","first-page":"719","DOI":"10.1021\/ct800013z","volume":"4","author":"Jensen","year":"2008","journal-title":"J. Chem. Theor. Comput."},{"key":"10.1016\/j.bmcl.2011.01.101_b0180","doi-asserted-by":"crossref","first-page":"6794","DOI":"10.1021\/jp804583d","volume":"112","author":"Zhao","year":"2008","journal-title":"J. Phys. Chem. A"},{"key":"10.1016\/j.bmcl.2011.01.101_b0185","doi-asserted-by":"crossref","first-page":"3744","DOI":"10.1021\/cr030733c","volume":"107","author":"Bifulco","year":"2007","journal-title":"Chem. Rev."},{"key":"10.1016\/j.bmcl.2011.01.101_b0190","doi-asserted-by":"crossref","first-page":"820","DOI":"10.1016\/j.bmc.2008.11.031","volume":"17","author":"Delf\u00edn","year":"2009","journal-title":"Bioorg. Med. Chem."},{"key":"10.1016\/j.bmcl.2011.01.101_b0195","doi-asserted-by":"crossref","first-page":"1325","DOI":"10.1124\/mol.64.6.1325","volume":"64","author":"Werbovetz","year":"2003","journal-title":"Mol. Pharmacol."},{"key":"10.1016\/j.bmcl.2011.01.101_b0200","doi-asserted-by":"crossref","first-page":"1432","DOI":"10.1074\/jbc.M409740200","volume":"280","author":"Liu","year":"2005","journal-title":"J. Biol. Chem."},{"key":"10.1016\/j.bmcl.2011.01.101_b0205","doi-asserted-by":"crossref","first-page":"108","DOI":"10.1021\/np049682k","volume":"68","author":"Salem","year":"2005","journal-title":"J. Nat. Prod."}],"container-title":["Bioorganic &amp; Medicinal Chemistry Letters"],"original-title":[],"language":"en","link":[{"URL":"https:\/\/api.elsevier.com\/content\/article\/PII:S0960894X11001247?httpAccept=text\/xml","content-type":"text\/xml","content-version":"vor","intended-application":"text-mining"},{"URL":"https:\/\/api.elsevier.com\/content\/article\/PII:S0960894X11001247?httpAccept=text\/plain","content-type":"text\/plain","content-version":"vor","intended-application":"text-mining"}],"deposited":{"date-parts":[[2025,10,18]],"date-time":"2025-10-18T06:22:59Z","timestamp":1760768579000},"score":1,"resource":{"primary":{"URL":"https:\/\/linkinghub.elsevier.com\/retrieve\/pii\/S0960894X11001247"}},"subtitle":[],"short-title":[],"issued":{"date-parts":[[2011,5]]},"references-count":40,"journal-issue":{"issue":"9","published-print":{"date-parts":[[2011,5]]}},"alternative-id":["S0960894X11001247"],"URL":"https:\/\/doi.org\/10.1016\/j.bmcl.2011.01.101","relation":{},"ISSN":["0960-894X"],"issn-type":[{"type":"print","value":"0960-894X"}],"subject":[],"published":{"date-parts":[[2011,5]]},"assertion":[{"value":"Elsevier","name":"publisher","label":"This article is maintained by"},{"value":"Potent antiprotozoal activity of a novel semi-synthetic berberine derivative","name":"articletitle","label":"Article Title"},{"value":"Bioorganic & Medicinal Chemistry Letters","name":"journaltitle","label":"Journal Title"},{"value":"https:\/\/doi.org\/10.1016\/j.bmcl.2011.01.101","name":"articlelink","label":"CrossRef DOI link to publisher maintained version"},{"value":"article","name":"content_type","label":"Content Type"},{"value":"Copyright \u00a9 2011 Published by Elsevier Ltd.","name":"copyright","label":"Copyright"}]}}