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All conjugates feature single\u2010bonded and hydrophobic linkages between the fluorophore and sterol that are devoid of heteroatoms. Using HeLa cells, we show that these BODIPY\u2013cholesterol analogues can be used simultaneously with the parent BODIPY\u2013cholesterol for cell imaging and flow cytometry. The BODIPY\u2013cholesterol analogues exhibit similar cellular localization in HeLa cells and show similar cholesterol efflux properties from THP\u20101 cells to HDL acceptors. These results demonstrate that the red\u2010shifted BODIPY\u2013cholesterol analogues behave in a manner similar to unlabeled cholesterol and are useful probes for simultaneous visualization of intracellular cholesterol pools and for monitoring cholesterol efflux from cells to extracellular acceptors.<\/jats:p>","DOI":"10.1002\/cbic.201402042","type":"journal-article","created":{"date-parts":[[2014,8,22]],"date-time":"2014-08-22T11:29:59Z","timestamp":1408706999000},"page":"2087-2096","update-policy":"https:\/\/doi.org\/10.1002\/crossmark_policy","source":"Crossref","is-referenced-by-count":20,"title":["Synthesis of Cholesterol Analogues Bearing BODIPY Fluorophores by Suzuki or Liebeskind\u2013Srogl Cross\u2010Coupling and Evaluation of Their Potential for Visualization of Cholesterol Pools"],"prefix":"10.1002","volume":"15","author":[{"given":"Zheng","family":"Liu","sequence":"first","affiliation":[],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Seth G","family":"Thacker","sequence":"additional","affiliation":[],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Sara","family":"Fernandez\u2010Castillejo","sequence":"additional","affiliation":[],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Edward B.","family":"Neufeld","sequence":"additional","affiliation":[],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Alan T.","family":"Remaley","sequence":"additional","affiliation":[],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Robert","family":"Bittman","sequence":"additional","affiliation":[],"role":[{"vocabulary":"crossref","role":"author"}]}],"member":"311","published-online":{"date-parts":[[2014,8,22]]},"reference":[{"key":"e_1_2_6_1_2","doi-asserted-by":"publisher","DOI":"10.1016\/j.steroids.2010.11.001"},{"key":"e_1_2_6_2_2","doi-asserted-by":"publisher","DOI":"10.1007\/s00418-008-0509-5"},{"key":"e_1_2_6_3_2","doi-asserted-by":"publisher","DOI":"10.1016\/B978-0-12-386487-1.00017-1"},{"key":"e_1_2_6_4_2","doi-asserted-by":"publisher","DOI":"10.1111\/j.1600-0854.2008.00801.x"},{"key":"e_1_2_6_5_2","doi-asserted-by":"publisher","DOI":"10.1194\/jlr.D018051"},{"key":"e_1_2_6_6_2","doi-asserted-by":"publisher","DOI":"10.1172\/JCI63685"},{"key":"e_1_2_6_7_2","doi-asserted-by":"publisher","DOI":"10.1371\/journal.pone.0023834"},{"key":"e_1_2_6_8_2","doi-asserted-by":"publisher","DOI":"10.1016\/j.chembiol.2012.05.018"},{"key":"e_1_2_6_9_2","doi-asserted-by":"publisher","DOI":"10.1371\/journal.ppat.1003109"},{"key":"e_1_2_6_10_2","doi-asserted-by":"publisher","DOI":"10.1021\/jo052029x"},{"key":"e_1_2_6_11_2","doi-asserted-by":"publisher","DOI":"10.1016\/j.bpj.2008.12.3922"},{"key":"e_1_2_6_12_2","doi-asserted-by":"publisher","DOI":"10.1186\/2046-1682-5-20"},{"key":"e_1_2_6_13_2","doi-asserted-by":"publisher","DOI":"10.1016\/j.bbamem.2012.03.007"},{"key":"e_1_2_6_14_2","doi-asserted-by":"publisher","DOI":"10.1016\/j.chemphyslip.2011.01.004"},{"key":"e_1_2_6_15_2","doi-asserted-by":"publisher","DOI":"10.1021\/cr00039a007"},{"key":"e_1_2_6_16_2","doi-asserted-by":"publisher","DOI":"10.1002\/anie.200802842"},{"key":"e_1_2_6_16_3","doi-asserted-by":"publisher","DOI":"10.1002\/ange.200802842"},{"key":"e_1_2_6_17_2","doi-asserted-by":"publisher","DOI":"10.1081\/SCC-120027294"},{"key":"e_1_2_6_18_2","doi-asserted-by":"publisher","DOI":"10.1002\/1521-3773(20011217)40:24<4544::AID-ANIE4544>3.0.CO;2-N"},{"key":"e_1_2_6_18_3","doi-asserted-by":"publisher","DOI":"10.1002\/1521-3757(20011217)113:24<4676::AID-ANGE4676>3.0.CO;2-B"},{"key":"e_1_2_6_19_2","doi-asserted-by":"publisher","DOI":"10.1002\/anie.200902520"},{"key":"e_1_2_6_19_3","doi-asserted-by":"publisher","DOI":"10.1002\/ange.200902520"},{"key":"e_1_2_6_20_2","doi-asserted-by":"publisher","DOI":"10.1021\/jo802519b"},{"key":"e_1_2_6_21_2","doi-asserted-by":"publisher","DOI":"10.1039\/B818390B"},{"key":"e_1_2_6_22_2","unstructured":"The formation of the corresponding phenol was also observed but it was avoided by degassing with nitrogen."},{"key":"e_1_2_6_23_2","doi-asserted-by":"publisher","DOI":"10.1002\/anie.200701551"},{"key":"e_1_2_6_23_3","doi-asserted-by":"publisher","DOI":"10.1002\/ange.200701551"},{"key":"e_1_2_6_24_2","doi-asserted-by":"publisher","DOI":"10.1016\/j.tet.2006.03.036"},{"key":"e_1_2_6_25_2","doi-asserted-by":"publisher","DOI":"10.1039\/j39670000431"},{"key":"e_1_2_6_26_2","doi-asserted-by":"publisher","DOI":"10.1021\/jo701475q"},{"key":"e_1_2_6_27_2","doi-asserted-by":"publisher","DOI":"10.1021\/jo201754m"},{"key":"e_1_2_6_28_2","doi-asserted-by":"publisher","DOI":"10.1021\/ol200799u"},{"key":"e_1_2_6_29_2","doi-asserted-by":"publisher","DOI":"10.1016\/j.tetlet.2009.09.163"},{"key":"e_1_2_6_30_2","doi-asserted-by":"publisher","DOI":"10.1021\/jo201413b"},{"key":"e_1_2_6_31_2","first-page":"477","volume-title":"Subcellular Biochemistry, Vol. 28","author":"Severs N. 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