Synthesis and study of new polyethyleneglycol-functionalized sapphyrin and texaphyrins

ORGN 539

Wen-hao Wei, weiw@mail.cm.utexas.edu1, Darren Magda, DMagda@pcyc.com2, Zhong Wang, ZWang@pcyc.com2, Louie Naumovskib, LNaumovski@pcyc.com2, and Jonathan L. Sessler, sessler@mail.utexas.edu3. (1) Department of Chemistry and Biochemistry, The University of Texas at Austin, 1 University Station-A5300, Austin, TX 78712-016, (2) Pharmacyclics, Inc, 995 East Arques Avenue, Sunnyvale, CA 94085, (3) Department of Chemistry and Biochemistry, University of Texas at Austin, 1 University Station-A5300, Austin, TX 78712-0165
Motexafin gadolinium (Xcytrinš) is currently undergoing Phase III clinical testing as an agent for treating brain metastases from non-small cell lung cancer in conjunction with whole brain radiation therapy. Recently, we also found that sapphyrins, pentapyrrolic expanded porphyrins, have tumor-localizing capabilities, and antiproliferative activity. In this poster, 1) a novel synthetic route for meso-dipolyethyleneglycol-functionalized sapphyrin 1 is described; 2) the synthesis of four new gadolinium texaphyrin analogues 2-5 is presented that were found to be quite active in vitro as judged by cell proliferation assays using PC3 prostate, A549 lung cancer, and Ramos lymphoma cell lines.

 

Heterocycles, Aromatics, Metal-Mediated Reactions and Syntheses, Materials, Devices, and Switches
8:00 PM-10:00 PM, Wednesday, 29 March 2006 Georgia World Congress Center -- Ex. Hall B4, Poster

Division of Organic Chemistry

The 231st ACS National Meeting, Atlanta, GA, March 26-30, 2006