Organotin compounds

This research is part of a long-term project aimed at elucidating important structural
features, of both ligands and metals, that are needed to produce effective anti-cancer agents.
The specific goal is the synthesis of organotin polymers containing amino acids, in this
case the diamino acid diglycine. The desired materials were synthesized with percent yields
ranging from 32-99%. The products were synthesized employing the interfacial
polymerization technique. The polymers were then characterized utilizing the following
physical characterization techniques: light scattering photometry (LS), Infrared
spectroscopy (IR), nuclear magnetic resonance spectroscopy (NMR), and matrix assisted
laser desorption mass spectroscopy (MALDI). Physical characterization showed evidence
of formation of desired adducts in addition to data that was consistent with the formation
of materials containing multiple repeat units. The materials were then analyzed for
biological activity. The synthesized materials displayed the ability to inhibit tested cancer
cell lines.

Tin-containing polymers were synthesized by reaction of amino acids (4-aminobenzoic acid, ampicillin, glycylglycine and glycyl-D-phenylalanine) with organotin dichloride via the interfacial condensation technique. The products were characterized using Fourier Transform Infrared spectrometry, Ultraviolet spectrometry, light scattering photometry and mass spectral analysis. The biological activities of the products were tested against selected microorganisms and human cells.

Ethylene/vinyl alcohol (EVOH) copolymers are widely used. These copolymers have been reacted with metallic and organometallic groups for various applications. In the present work, organostannane modified EVOH copolymers are synthesized and characterized and their structure-property relationships, especially with respect to their applications as antibacterials and fungicides as well as their film forming ability, are studied. The modified copolymers exhibit "ionomer-like" thermal properties. Some of the properties of the modified EVOH products are also compared to analogous modified polyvinyl alcohol products.

Tin-containing ionomers were synthesized by reaction of poly(ethylene/acrylic acid) with mono, di and trihalo-organostannanes using the interfacial condensation technique. The products contain tin ester bonding as evidenced by infrared and mass spectroscopy. They are insoluble but form tough transparent films on application of heat and pressure. The modified ionomer products were flexible with high degrees of substitution and contained both bridging and nonbridging structures with respect to bonding about the tin atom. The analogous products from poly(acrylic acid) were brittle with lower substitutions and contained on nonbridging structure.

Metal containing polymers were synthesized by reaction of organotin and group IVB metallocene dichlorides with kinetin, a plant growth hormone (PGH), via the interfacial polycondensation process. Product yields were in the range of 40--63% and degrees of polymerization were from 20 to 150. The structures of the products were determined using infrared and mass spectroscopy. Further characterization involved determination of solubility, degree of polymerization and electrical conductivity. The biological potential of the products was tested against selected microorganisms and Balb/3T3 cell lines. One of the products showed activity in the 0.2mug/ml range, one hundredth of that of similar compounds. Germination experiments using the PGH incorporated polymers were performed on sawgrass and cattail seeds as well as selected vegetable seeds and compared to a control. Sawgrass germination, typically in the 0--2% range were increased to about 60% through the treatment with kinetin-containing polymers.