{"status":"ok","message-type":"work","message-version":"1.0.0","message":{"indexed":{"date-parts":[[2026,5,1]],"date-time":"2026-05-01T14:46:49Z","timestamp":1777646809361,"version":"3.51.4"},"reference-count":36,"publisher":"Wiley","issue":"3","license":[{"start":{"date-parts":[[2014,11,27]],"date-time":"2014-11-27T00:00:00Z","timestamp":1417046400000},"content-version":"vor","delay-in-days":0,"URL":"http:\/\/onlinelibrary.wiley.com\/termsAndConditions#vor"}],"content-domain":{"domain":[],"crossmark-restriction":false},"short-container-title":["Angew Chem Int Ed"],"published-print":{"date-parts":[[2015,1,12]]},"abstract":"<jats:title>Abstract<\/jats:title><jats:p>Apoptolidin\u2005A has been described among the top 0.1\u2009% most\u2010cell\u2010selective cytotoxic agents to be evaluated in the NCI 60 cell line panel. The molecular structure of apoptolidin\u2005A consists of a 20\u2010membered macrolide with mono\u2010 and disaccharide moieties. In contrast to apoptolidin\u2005A, the aglycone (apoptolidinone) shows no cytotoxicity (&gt;10\u2005\u03bc<jats:sc>M<\/jats:sc>) when evaluated against several tumor cell lines. Apoptolidin\u2005H, the C27 deglycosylated analogue of apoptolidin\u2005A, displayed sub\u2010micromolar activity against H292 lung carcinoma cells. Selective esterification of apoptolidins\u2005A and H with 5\u2010azidopentanoic acid afforded azido\u2010functionalized derivatives of potency equal to that of the parent macrolide. They also underwent strain\u2010promoted alkyne\u2013azido cycloaddition reactions to provide access to fluorescent and biotin\u2010functionalized probes. Microscopy studies demonstrate apoptolidins\u2005A and H localize in the mitochondria of H292 human lung carcinoma cells.<\/jats:p>","DOI":"10.1002\/anie.201408906","type":"journal-article","created":{"date-parts":[[2014,11,28]],"date-time":"2014-11-28T14:24:17Z","timestamp":1417184657000},"page":"961-964","source":"Crossref","is-referenced-by-count":20,"title":["Fluorescent Probes of the Apoptolidins and their Utility in Cellular Localization Studies"],"prefix":"10.1002","volume":"54","author":[{"given":"Sean M.","family":"DeGuire","sequence":"first","affiliation":[],"role":[{"role":"author","vocabulary":"crossref"}]},{"given":"David C.","family":"Earl","sequence":"additional","affiliation":[],"role":[{"role":"author","vocabulary":"crossref"}]},{"given":"Yu","family":"Du","sequence":"additional","affiliation":[],"role":[{"role":"author","vocabulary":"crossref"}]},{"given":"Brenda A.","family":"Crews","sequence":"additional","affiliation":[],"role":[{"role":"author","vocabulary":"crossref"}]},{"given":"Aaron T.","family":"Jacobs","sequence":"additional","affiliation":[],"role":[{"role":"author","vocabulary":"crossref"}]},{"given":"Alessandro","family":"Ustione","sequence":"additional","affiliation":[],"role":[{"role":"author","vocabulary":"crossref"}]},{"given":"Cristina","family":"Daniel","sequence":"additional","affiliation":[],"role":[{"role":"author","vocabulary":"crossref"}]},{"given":"Katherine M.","family":"Chong","sequence":"additional","affiliation":[],"role":[{"role":"author","vocabulary":"crossref"}]},{"given":"Lawrence J.","family":"Marnett","sequence":"additional","affiliation":[],"role":[{"role":"author","vocabulary":"crossref"}]},{"given":"David W.","family":"Piston","sequence":"additional","affiliation":[],"role":[{"role":"author","vocabulary":"crossref"}]},{"given":"Brian O.","family":"Bachmann","sequence":"additional","affiliation":[],"role":[{"role":"author","vocabulary":"crossref"}]},{"given":"Gary A.","family":"Sulikowski","sequence":"additional","affiliation":[],"role":[{"role":"author","vocabulary":"crossref"}]}],"member":"311","published-online":{"date-parts":[[2014,11,27]]},"reference":[{"key":"e_1_2_2_1_2","doi-asserted-by":"publisher","DOI":"10.1021\/ja9732643"},{"key":"e_1_2_2_2_2","doi-asserted-by":"publisher","DOI":"10.7164\/antibiotics.50.628"},{"key":"e_1_2_2_3_2","doi-asserted-by":"publisher","DOI":"10.1002\/anie.200502698"},{"key":"e_1_2_2_3_3","doi-asserted-by":"publisher","DOI":"10.1002\/ange.200502698"},{"key":"e_1_2_2_4_2","unstructured":"\u00a0"},{"key":"e_1_2_2_5_2","doi-asserted-by":"publisher","DOI":"10.1073\/pnas.97.26.14766"},{"key":"e_1_2_2_6_2","doi-asserted-by":"publisher","DOI":"10.1016\/S1074-5521(00)00057-0"},{"key":"e_1_2_2_7_2","unstructured":"\u00a0"},{"key":"e_1_2_2_8_2","doi-asserted-by":"publisher","DOI":"10.1021\/ol0630245"},{"key":"e_1_2_2_9_2","doi-asserted-by":"publisher","DOI":"10.1021\/ol902308v"},{"key":"e_1_2_2_10_2","doi-asserted-by":"publisher","DOI":"10.1021\/ol051074o"},{"key":"e_1_2_2_11_2","unstructured":"\u00a0"},{"key":"e_1_2_2_12_2","doi-asserted-by":"publisher","DOI":"10.1021\/ol0266222"},{"key":"e_1_2_2_13_2","doi-asserted-by":"publisher","DOI":"10.1021\/ol026829v"},{"key":"e_1_2_2_14_2","doi-asserted-by":"publisher","DOI":"10.1021\/ol1009398"},{"key":"e_1_2_2_15_2","unstructured":"\u00a0"},{"key":"e_1_2_2_16_2","doi-asserted-by":"publisher","DOI":"10.1021\/ol027366w"},{"key":"e_1_2_2_17_2","doi-asserted-by":"publisher","DOI":"10.1021\/np9004932"},{"key":"e_1_2_2_18_2","unstructured":"\u00a0"},{"key":"e_1_2_2_19_2","doi-asserted-by":"publisher","DOI":"10.1021\/ja0304953"},{"key":"e_1_2_2_20_2","doi-asserted-by":"publisher","DOI":"10.1002\/chem.200600462"},{"key":"e_1_2_2_21_2","doi-asserted-by":"publisher","DOI":"10.1021\/jo800545r"},{"key":"e_1_2_2_22_2","doi-asserted-by":"publisher","DOI":"10.1021\/ol901045v"},{"key":"e_1_2_2_23_2","doi-asserted-by":"publisher","DOI":"10.1002\/chem.200600461"},{"key":"e_1_2_2_24_2","doi-asserted-by":"publisher","DOI":"10.1016\/j.tet.2011.05.106"},{"key":"e_1_2_2_25_2","unstructured":"The13C\u2005NMR spectra of apoptolidin\u2005H and synthetic material reported by Koert and co\u2010workers (Ref.\u2005[8b]) compare favorably (see Table\u2005S2 in the Supporting Information). The13C\u2005NMR spectra of apoptolidin\u2005H and F (Ref.\u2005[5b]) differ."},{"key":"e_1_2_2_26_2","doi-asserted-by":"publisher","DOI":"10.1247\/csf.23.85"},{"key":"e_1_2_2_27_2","unstructured":"\u00a0"},{"key":"e_1_2_2_28_2","doi-asserted-by":"publisher","DOI":"10.1021\/jm901577g"},{"key":"e_1_2_2_29_2","doi-asserted-by":"publisher","DOI":"10.1016\/j.bmcl.2010.04.015"},{"key":"e_1_2_2_30_2","doi-asserted-by":"publisher","DOI":"10.1038\/nchembio.1060"},{"key":"e_1_2_2_31_2","doi-asserted-by":"publisher","DOI":"10.1002\/anie.200900942"},{"key":"e_1_2_2_31_3","doi-asserted-by":"publisher","DOI":"10.1002\/ange.200900942"},{"key":"e_1_2_2_32_2","doi-asserted-by":"publisher","DOI":"10.1002\/anie.201003761"},{"key":"e_1_2_2_32_3","doi-asserted-by":"publisher","DOI":"10.1002\/ange.201003761"},{"key":"e_1_2_2_33_2","doi-asserted-by":"publisher","DOI":"10.1021\/ja906862g"}],"container-title":["Angewandte Chemie International Edition"],"original-title":[],"language":"en","link":[{"URL":"https:\/\/api.wiley.com\/onlinelibrary\/tdm\/v1\/articles\/10.1002%2Fanie.201408906","content-type":"unspecified","content-version":"vor","intended-application":"text-mining"},{"URL":"https:\/\/onlinelibrary.wiley.com\/doi\/pdf\/10.1002\/anie.201408906","content-type":"unspecified","content-version":"vor","intended-application":"similarity-checking"}],"deposited":{"date-parts":[[2023,10,16]],"date-time":"2023-10-16T09:26:14Z","timestamp":1697448374000},"score":1,"resource":{"primary":{"URL":"https:\/\/onlinelibrary.wiley.com\/doi\/10.1002\/anie.201408906"}},"subtitle":[],"short-title":[],"issued":{"date-parts":[[2014,11,27]]},"references-count":36,"journal-issue":{"issue":"3","published-print":{"date-parts":[[2015,1,12]]}},"alternative-id":["10.1002\/anie.201408906"],"URL":"https:\/\/doi.org\/10.1002\/anie.201408906","archive":["Portico"],"relation":{},"ISSN":["1433-7851","1521-3773"],"issn-type":[{"value":"1433-7851","type":"print"},{"value":"1521-3773","type":"electronic"}],"subject":[],"published":{"date-parts":[[2014,11,27]]}}}