Synthesis of Organotin Polyesters from Reaction of the Salt of d-Camphoric Acid and Organotin Dihalides and Initial Anticancer Activity

Abstract

Organotin polyesters were synthesized from d-camphoric acid. Since d-camphoric acid is a natural product, this is part of the green chemistry initiative. Further, synthesis occurred employing commercially available reactants and the interfacial system which is used industrially to synthesize aramids and polycarbonates. Thus, scale-up is straightforward. Polymers were synthesized employing the interfacial reaction between various organotin dihalides and the salt of d-camphoric acid. Reaction was rapid occurring in 30 s and less. Product yield was good except for the product from dioctyltin dichloride. The products are polymeric with chain lengths from 230 to 2200. Structural characterization with infrared spectrometry and MALDI MS are consistent with the formation of organotin polyesters containing the camphoric acid moiety within its backbone. IR shows formation of the Sn–OOC(O) linkage with the polymer having a combination of bridging and non-bridging geometrical arrangements about the tin atom. MALDI MS shows ion fragment to two and three repeat units. The products exhibit good ability to inhibit a battery of cancer cells including those from pancreatic cancer. The effective concentration for inhibition of the cancer cell lines are generally in the same range as those found for cisplatin and in the ng/mL range.