239081-44-8Relevant academic research and scientific papers
Reduction of azides to primary amines in substrates bearing labile ester functionality. Synthesis of a PEG-solubilized, "Y"-shaped iminodiacetic acid reagent for preparation of folate-tethered drugs
Lee, Jae Wook,Fuchs, Philip L.
, p. 179 - 181 (1999)
(equation presented) Anhydride 3 is a useful reagent for the synthesis of triply linked drug conjugates. Examples using paclitaxel are provided. Conversion of the azido moiety to a primary amine in the presence of substrates bearing labile ester functionality requires the use of a tin/mercaptan reducing system which includes methanol exchange equilibration to effect nitrogen-tin bond scission.
Synthesis and evaluation of Taxol-folic acid conjugates as targeted antineoplastics
Lee, Jae Wook,Lu, June Y.,Low,Fuchs
, p. 2397 - 2414 (2007/10/03)
A series of Taxol derivatives tethered at C2′ and C-7 to glutamate and folate have been synthesized for evaluation as prodrugs which release Taxol via hydrolytic lability of their α-alkoxy and α-amino esters. The half-time for hydrolysis of these materials was determined in pH 7 and pH 5 buffer. The in vitro cytotoxicity has been assessed in cell culture against A-549 lung cancer, MCF-7 breast cancer, and HT-29 colon cancer. Selected agents were further screened for folate binding and competitive binding with free folic acid. One agent (54), further evaluated in animal studies was found to increase the lifespan in mice, but was less effective than Taxol itself.
