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Although all of the compounds are antiproliferative, surprisingly the carbamates (<jats:bold>1<\/jats:bold> and <jats:bold>2<\/jats:bold>) are more effective against the hormone\u2010independent cell lines DU145 and PC3 than toward other cancer cell lines we examined. This selectivity was not observed with the dicarbamates (<jats:bold>3<\/jats:bold> and <jats:bold>4<\/jats:bold>). Phosphocholine carbamate analogue <jats:bold>5<\/jats:bold> is as effective against the prostate cancer cell lines as the corresponding phosphonocholine analogue <jats:bold>1<\/jats:bold>. Cell death induced by 2\u2032\u2010(trimethylammonio)ethyl 4\u2010hexadecyloxy\u20103(<\/jats:italic>R<jats:italic>)\u2010<\/jats:italic>N<jats:italic>\u2010methylcarbamoyl\u20101\u2010butanephosphonate (carbamate analogue <jats:bold>2<\/jats:bold>) appeared to be mediated by apoptosis, as assessed by caspase activation and loss of mitochondrial membrane potential. The in\u2005vivo activity of <jats:bold>2<\/jats:bold> was evaluated in a murine prostate cancer xenograft model. Oral and intravenous administration showed that <jats:bold>2<\/jats:bold> is effective in inhibiting the growth of PC3 tumors in Rag2M mice. Our studies show that the glycerolipid carbamates reported herein represent a class of prostate\u2010cancer\u2010selective cytotoxic agents.<\/jats:italic><\/jats:p>","DOI":"10.1002\/cmdc.201000060","type":"journal-article","created":{"date-parts":[[2010,6,8]],"date-time":"2010-06-08T04:39:10Z","timestamp":1275971950000},"page":"1045-1052","update-policy":"https:\/\/doi.org\/10.1002\/crossmark_policy","source":"Crossref","is-referenced-by-count":7,"title":["Synthesis and Antitumor Activity of Ether Glycerophospholipids Bearing a Carbamate Moiety at the <i>sn<\/i>\u20102 Position: Selective Sensitivity Against Prostate Cancer Cell Lines"],"prefix":"10.1002","volume":"5","author":[{"given":"Hoe\u2010Sup","family":"Byun","sequence":"first","affiliation":[],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Robert","family":"Bittman","sequence":"additional","affiliation":[],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Pranati","family":"Samadder","sequence":"additional","affiliation":[],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Gilbert","family":"Arthur","sequence":"additional","affiliation":[],"role":[{"vocabulary":"crossref","role":"author"}]}],"member":"311","published-online":{"date-parts":[[2010,6,25]]},"reference":[{"key":"e_1_2_6_1_2","doi-asserted-by":"publisher","DOI":"10.3322\/canjclin.53.1.5"},{"key":"e_1_2_6_2_2","doi-asserted-by":"publisher","DOI":"10.1002\/1097-0142(19841215)54:12<3078::AID-CNCR2820541245>3.0.CO;2-U"},{"key":"e_1_2_6_3_2","doi-asserted-by":"publisher","DOI":"10.1016\/0090-4295(83)90147-4"},{"key":"e_1_2_6_4_2","doi-asserted-by":"publisher","DOI":"10.1002\/pros.2990070105"},{"key":"e_1_2_6_5_2","doi-asserted-by":"publisher","DOI":"10.1111\/j.1742-1241.2007.01551.x"},{"key":"e_1_2_6_6_2","doi-asserted-by":"publisher","DOI":"10.1016\/j.critrevonc.2006.10.002"},{"key":"e_1_2_6_7_2","doi-asserted-by":"publisher","DOI":"10.1002\/pros.21116"},{"key":"e_1_2_6_8_2","doi-asserted-by":"publisher","DOI":"10.1016\/S0005-2760(97)00163-X"},{"key":"e_1_2_6_9_2","doi-asserted-by":"publisher","DOI":"10.1124\/mol.53.4.602"},{"key":"e_1_2_6_10_2","doi-asserted-by":"publisher","DOI":"10.1021\/jm0302748"},{"key":"e_1_2_6_11_2","doi-asserted-by":"publisher","DOI":"10.1038\/sj.onc.1210816"},{"key":"e_1_2_6_12_2","doi-asserted-by":"publisher","DOI":"10.1158\/0008-5472.CAN-07-0278"},{"key":"e_1_2_6_13_2","doi-asserted-by":"publisher","DOI":"10.1182\/blood-2006-04-016824"},{"key":"e_1_2_6_14_2","doi-asserted-by":"publisher","DOI":"10.2174\/0929867043363703"},{"key":"e_1_2_6_15_2","doi-asserted-by":"publisher","DOI":"10.1038\/bjc.1991.277"},{"key":"e_1_2_6_16_2","first-page":"4808","volume":"59","author":"Samadder P.","year":"1999","journal-title":"Cancer Res."},{"key":"e_1_2_6_17_2","doi-asserted-by":"publisher","DOI":"10.2174\/138161208785294636"},{"key":"e_1_2_6_18_2","doi-asserted-by":"publisher","DOI":"10.1002\/med.2610150302"},{"key":"e_1_2_6_19_2","first-page":"1813","volume":"16","author":"Ashagbley A.","year":"1996","journal-title":"Anticancer Res."},{"key":"e_1_2_6_20_2","first-page":"41","volume-title":"Phospholipids and Cellular Regulation, Vol.\u20052","author":"Berdel W. 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