Abstract

SYNTHESIS AND STRUCTURAL CHARACTERIZATION OF POLYETHERS FROM ISOMANNIDE AND ORGANOTIN DIHALIDES AND THEIR ABILITY TO INHIBIT HUMAN CANCER CELL LINES, ESPECIALLY PANCREATIC CANCER CELL LINE PANC-1

Charles E. Carraher Jr.*, Michael R. Roner, Tiasha Arnold, Kimberly Shahi, Paul Slawek, Francesca Mosca and Jessica Frank

Abstract

Polyethers were synthesized from the interfacial polycondensation of isomannide and organotin dihalides with yield increasing as the size of the organotin alkyl group increases. The polymers are of moderate molecular weight ranging from 50 to 230 units in length. Infrared spectral analysis shows the formation of Sn-O bands and absence of the R-OH consistent with polyether formation. MALDI MS shows ion fragments from 3 to 6 repeat units long with good isotopic abundance matches for the presence of tin atoms within the ion fragments. NMR shows the presence of both reactants and the loss of the isomannide protons, as expected. Human cancer cell analysis shows inhibition focusing on the pancreatic cancer line PANC-1 to the picogram/mL for the dimethyltin polymer which is the lowest observed by us. Selected polymers show inhibition of all of the cancer cell lines to the nanogram/mL for breast, lung, colon, prostate and pancreatic cancer cell lines.

Keywords: Organotin polyethers, interfacial polymerization, isomannide, pancreatic cancer, breast cancer, fiber formation, MALDI MS, PANC-1 pancreatic cancer.