Synthesis and Characterization, Including Cancer Cell Line Inhibition, of Group VA (Group 15)-Containing Polyesters from Reaction with Camphoric Acid

Abstract

Polyesters were rapidly synthesized employing interfacial polymerization from reaction of the salt of camphoric acid with Group VA (Group 15) triphenylmetallic dihalides. Yields range from 25 to 46 percent with chain lengths about 250. Infrared spectroscopy shows the formation of two new bands one assigned to the symmetrical M–O stretching and the second assigned to the asymmetrical M–O stretching. The bridging structure about the metal atom increases as the metal atom size increases. MALDI MS and proton NMR are consistent with the formation of the polyester structure. Ion fragment clusters to four to six units are identified. The polymers show good inhibition of a group of cancer cell lines including two pancreatic human cancer cell lines. In comparison with other metal/camphoric acid polymers, the metallocene polymers exhibit low EC50 to the nanogram/ml range, and CI50 values greater than one thousand for the hafnocene and zirconocene products. If this trend continues, the emphasis should be on the Group IVB metallocenes with respect to efforts to create anticancer drugs.