{"status":"ok","message-type":"work","message-version":"1.0.0","message":{"indexed":{"date-parts":[[2026,9,1]],"date-time":"2026-09-01T13:20:29Z","timestamp":1788268829186,"version":"build-2803163510"},"reference-count":40,"publisher":"American Chemical Society (ACS)","issue":"6","license":[{"start":{"date-parts":[[2015,2,24]],"date-time":"2015-02-24T00:00:00Z","timestamp":1424736000000},"content-version":"vor","delay-in-days":365,"URL":"https:\/\/pubs.acs.org\/page\/policy\/authorchoice_termsofuse.html"}],"funder":[{"DOI":"10.13039\/100000002","name":"National Institutes of Health","doi-asserted-by":"publisher","award":["CA76497"],"award-info":[{"award-number":["CA76497"]}],"id":[{"id":"10.13039\/100000002","id-type":"DOI","asserted-by":"publisher"}]},{"DOI":"10.13039\/100000002","name":"National Institutes of Health","doi-asserted-by":"publisher","award":["NIBIB EB011671"],"award-info":[{"award-number":["NIBIB EB011671"]}],"id":[{"id":"10.13039\/100000002","id-type":"DOI","asserted-by":"publisher"}]}],"content-domain":{"domain":[],"crossmark-restriction":false},"short-container-title":[],"published-print":{"date-parts":[[2014,3,27]]},"abstract":"<jats:title>Abstract<\/jats:title>\n                  <jats:p>We report here the synthesis and selected properties of various silicate ester derivatives (tetraalkoxysilanes) of the taxanes paclitaxel (PTX) and docetaxel (DTX) [i.e., PTX-OSi(OR)3 and DTX-OSi(OR)3]. Both the hydrophobicity and hydrolytic lability of these silicates can be (independently) controlled by choice of the alkyl group (R). The synthesis, structural characterization, hydrolytic reactivity, and in vitro cytotoxicity against the MDA-MB-231 breast cancer cell line of most of these derivatives are described. We envision that the greater hydrophobicity of these silicates (vis-a\u0300-vis PTX or DTX itself) should be advantageous from the perspective of preparation of stable aqueous dispersions of amphiphilic block-copolymer-based nanoparticle formulations.<\/jats:p>","DOI":"10.1021\/jm401708f","type":"journal-article","created":{"date-parts":[[2014,2,24]],"date-time":"2014-02-24T08:51:51Z","timestamp":1393231911000},"page":"2368-2379","source":"Crossref","is-referenced-by-count":27,"title":["Silicate Esters of Paclitaxel\nand Docetaxel: Synthesis,\nHydrophobicity, Hydrolytic Stability, Cytotoxicity, and Prodrug Potential"],"prefix":"10.1021","volume":"57","author":[{"given":"Adam R.","family":"Wohl","sequence":"first","affiliation":[{"name":"University of Minnesota , Departments of, , , Departments of, , Departments of, , , , ,","place":["Minneapolis, Minnesota, United States, 55455"]}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Andrew R.","family":"Michel","sequence":"additional","affiliation":[{"name":"University of Minnesota , Departments of, , , Departments of, , Departments of, , , , ,","place":["Minneapolis, Minnesota, United States, 55455"]}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Stephen","family":"Kalscheuer","sequence":"additional","affiliation":[{"name":"University of Minnesota , Departments of, , , Departments of, , Departments of, , , , ,","place":["Minneapolis, Minnesota, United States, 55455"]}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Christopher W.","family":"Macosko","sequence":"additional","affiliation":[{"name":"University of Minnesota , Departments of, , , Departments of, , Departments of, , , , ,","place":["Minneapolis, Minnesota, United States, 55455"]}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Jayanth","family":"Panyam","sequence":"additional","affiliation":[{"name":"University of Minnesota , Departments of, , , Departments of, , Departments of, , , , ,","place":["Minneapolis, Minnesota, United States, 55455"]}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Thomas R.","family":"Hoye","sequence":"additional","affiliation":[{"name":"University of Minnesota , Departments of, , , Departments of, , Departments of, , , , ,","place":["Minneapolis, Minnesota, United States, 55455"]}],"role":[{"vocabulary":"crossref","role":"author"}]}],"member":"316","published-online":{"date-parts":[[2014,2,24]]},"reference":[{"key":"2026090108460389500_cit1","doi-asserted-by":"crossref","first-page":"81","DOI":"10.1016\/j.ctrv.2007.08.001","article-title":"Novel cytotoxic drugs:\nold challenges, new solutions","volume":"34","author":"Ismael","year":"2008","journal-title":"Cancer Treat.\nRev."},{"key":"2026090108460389500_cit2","doi-asserted-by":"crossref","first-page":"735","DOI":"10.1093\/annonc\/mdj100","article-title":"New formulations of\ntaxanes: a review. Old wine in\na new bottle?","volume":"17","author":"Hennenfent","year":"2006","journal-title":"Ann. Oncol."},{"key":"2026090108460389500_cit3","doi-asserted-by":"crossref","first-page":"2264","DOI":"10.1002\/aic.690490905","article-title":"Chemical processing\nand micromixing in confined impinging\njets","volume":"49","author":"Johnson","year":"2003","journal-title":"AIChE J."},{"key":"2026090108460389500_cit4","doi-asserted-by":"crossref","first-page":"1021","DOI":"10.1071\/CH03115","article-title":"Flash nanoprecipitation of organic actives and block\ncopolymers using a confined impinging jets mixer","volume":"56","author":"Johnson","year":"2003","journal-title":"Aust. J. Chem."},{"key":"2026090108460389500_cit5","doi-asserted-by":"crossref","first-page":"4018","DOI":"10.1002\/jps.23259","article-title":"A simple confined impingement jets mixer for flash\nnanoprecipitation","volume":"101","author":"Han","year":"2012","journal-title":"J. Pharm. 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Ph.D. Thesis, University of Minnesota,\nMinneapolis, MN, 2010."},{"key":"2026090108460389500_cit9","doi-asserted-by":"crossref","first-page":"79","DOI":"10.1016\/S0022-328X(98)00365-9","article-title":"Synthesis and reactivity of bis(triethoxysilyl)methane,\ntris(triethoxysilyl)methane and some derivatives","volume":"562","author":"Corriu","year":"1998","journal-title":"J. Organomet. Chem."},{"key":"2026090108460389500_cit10","unstructured":"Hoye, T. R.; Wohl, A. W.; Macosko, C. W.; Panyam, J.\n          Silicate prodrugs\nand nanoparticles. U.S. Patent Application PCT\/US2012\/040247, May 31, 2012."},{"key":"2026090108460389500_cit11","doi-asserted-by":"crossref","first-page":"957","DOI":"10.1038\/ki.1992.373","article-title":"Renal handling of silicon in normals\nand patients with renal insufficiency","volume":"42","author":"Gitelman","year":"1992","journal-title":"Kidney\nInt."},{"key":"2026090108460389500_cit12","first-page":"52","article-title":"Oxalate, silicon, and vanadium in\nacquired cystic kidney disease","volume":"35","author":"Marco-Franco","year":"1991","journal-title":"Clin. Nephrol."},{"key":"2026090108460389500_cit13","doi-asserted-by":"crossref","first-page":"1266","DOI":"10.1016\/j.addr.2008.03.017","article-title":"Porous silicon in\ndrug delivery devices and materials","volume":"60","author":"Anglin","year":"2008","journal-title":"Adv. Drug\nDelivery Rev."},{"key":"2026090108460389500_cit14","doi-asserted-by":"crossref","first-page":"7978","DOI":"10.1021\/ja301710z","article-title":"Incorporation and controlled release\nof silyl ether prodrugs from PRINT nanoparticles","volume":"134","author":"Parrott","year":"2012","journal-title":"J. Am. Chem. Soc."},{"key":"2026090108460389500_cit15","doi-asserted-by":"crossref","first-page":"7253","DOI":"10.1021\/jm0602155","article-title":"Paclitaxel prodrugs: toward smarter\ndelivery of anticancer agents","volume":"49","author":"Skwarczynski","year":"2006","journal-title":"J. Med. Chem."},{"key":"2026090108460389500_cit16","doi-asserted-by":"crossref","first-page":"1357","DOI":"10.1016\/S0960-894X(00)80348-0","article-title":"Tumor targeting\nby covalent conjugation\nof a natural fatty acid to paclitaxel","volume":"3","author":"Vyas","year":"1993","journal-title":"Bioorg.\nMed. Chem. 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U.S. Patent 5,534,499, July 9, 1996."},{"key":"2026090108460389500_cit23","doi-asserted-by":"crossref","first-page":"93","DOI":"10.1016\/S0168-3659(02)00323-1","article-title":"A lipophilic paclitaxel\nderivative incorporated in a lipid emulsion for parenteral administration","volume":"86","author":"Lundberg","year":"2003","journal-title":"J. Controlled Release"},{"key":"2026090108460389500_cit24","doi-asserted-by":"crossref","first-page":"565","DOI":"10.1007\/s00280-004-0930-y","article-title":"Improvement of paclitaxel therapeutic\nindex by derivatization and association to a cholesterol-rich microemulsion:\nin vitro and in vivo studies","volume":"55","author":"Rodrigues","year":"2005","journal-title":"Cancer Chemother.\nPharmacol."},{"key":"2026090108460389500_cit25","doi-asserted-by":"crossref","first-page":"3288","DOI":"10.1021\/jm800002y","article-title":"Modulating the therapeutic activity of nanoparticle\ndelivered paclitaxel by manipulating the hydrophobicity of prodrug\nconjugates","volume":"51","author":"Ansell","year":"2008","journal-title":"J. Med. Chem."},{"key":"2026090108460389500_cit26","doi-asserted-by":"crossref","first-page":"615","DOI":"10.1038\/nrd2591","article-title":"Strategies in the design of nanoparticles\nfor therapeutic\napplications","volume":"9","author":"Petros","year":"2010","journal-title":"Nat. Rev. Drug Discovery"},{"key":"2026090108460389500_cit27","doi-asserted-by":"crossref","first-page":"185","DOI":"10.1146\/annurev-med-040210-162544","article-title":"Nanoparticle\ndelivery of cancer drugs","volume":"63","author":"Wang","year":"2012","journal-title":"Annu. Rev. 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Chem."},{"key":"2026090108460389500_cit40","doi-asserted-by":"crossref","first-page":"4443","DOI":"10.1158\/0008-5472.CAN-09-4362","article-title":"Injectable\nsustained release microparticles of curcumin:\na new concept for cancer chemoprevention","volume":"70","author":"Shahani","year":"2010","journal-title":"Cancer\nRes."}],"container-title":["Journal of\nMedicinal Chemistry"],"original-title":[],"language":"en","link":[{"URL":"https:\/\/pubs.acs.org\/doi\/pdf\/10.1021\/jm401708f","content-type":"application\/pdf","content-version":"vor","intended-application":"unspecified"},{"URL":"https:\/\/pubs.acs.org\/jmcmar\/article-pdf\/57\/6\/2368\/12877404\/jm401708f.pdf","content-type":"application\/pdf","content-version":"vor","intended-application":"syndication"},{"URL":"https:\/\/pubs.acs.org\/jmcmar\/article-pdf\/57\/6\/2368\/12877404\/jm401708f.pdf","content-type":"unspecified","content-version":"vor","intended-application":"similarity-checking"}],"deposited":{"date-parts":[[2026,9,1]],"date-time":"2026-09-01T12:46:14Z","timestamp":1788266774000},"score":1,"resource":{"primary":{"URL":"https:\/\/pubs.acs.org\/jmcmar\/article\/57\/6\/2368\/1300566\/Silicate-Esters-of-Paclitaxel-and-Docetaxel"}},"subtitle":[],"short-title":[],"issued":{"date-parts":[[2014,2,24]]},"references-count":40,"journal-issue":{"issue":"6","published-online":{"date-parts":[[2014,2,24]]},"published-print":{"date-parts":[[2014,3,27]]}},"URL":"https:\/\/doi.org\/10.1021\/jm401708f","relation":{},"ISSN":["0022-2623","1520-4804"],"issn-type":[{"value":"0022-2623","type":"print"},{"value":"1520-4804","type":"electronic"}],"subject":[],"published":{"date-parts":[[2014,2,24]]}}}