Synthesis,Structural Characterization,and Initial Evaluation as Anticancer Drugs of Dibutyltin Polyamines Derived from Various 4,6-Diaminopyrimidines

A number of diaminopyrimidines have been incorporated into dibutyltin polyamines with molecular weights ranging from 3.5 × 10⁴ to 3.7 × 10⁶ and product yields from 47 to 88%. Infrared spectroscopy is consistent with the inclusion of the diaminopyridines into the polymer backbone with the IR spectroscopy showing the formation of the Sn–N bond as well as the presence of bands from both reactants being present in the polymer. F MALDI MS is also consistent with the products being polymeric and containing units from both the dibutyltin and pyrimidine reactants. The products exhibit good inhibition of cancer cell lines including those derived from human lung, bone, breast, prostrate, and colon cancers. Inhibition occurs within the same concentration range, and lower than that of the most widely employed chemotherapeutic drug, cisplatin.     

Preliminary Results for the Inhibition of Pancreatic Cancer Cells by Organotin Polymers

Pancreatic cancer kills nearly all patients within 3–6 months after detection. There is no effective chemotherapy for it. We have found a number of organotin polymers that are effective at inhibiting pancreatic cancer cell lines with Chemotherapeutic Index values greater than two with some to values of 50.     

Synthesis,Structural Characterization,and Ability to Inhibit Cancer Growth of a Series of Organotin Poly(ethylene glycols)

A series of organotin poly(ethylene glycols) were synthesized including the first water soluble organotin polymers. These products are all polymeric with weight average molecular weights about 10⁵. Infrared spectroscopy shows the presence of moieties from both reactants and the formation of the Sn–O linkage. F MALDI MS shows the presence of up to over a hundred units and by isotopic abundance the presence of one, two, and three tin-containing ion fragments. The polymers inhibit the growth of cancer cell lines from bone, prostate, colon, breast, and lung cancers. In a number of instances chemotherapeutic index values of two and greater are found consistent with these polymers being more active against cancer cells than non-cancerous healthy cells. Thus, some of these polymers show good promise as a new family of anticancer drugs including the water-soluble organotin-containing polymers.     

Synthesis, Structural Characterization, and Preliminary Biological Characterization of Organotin Polyethers Derived from Hydroquinone and Substituted Hydroquinones

A variety of dibutyltin polyethers have been synthesized employing the interfacial polymerization technique. The products are polymers with degrees of polymerization ranging from 60 to 390. Infrared spectral and mass spectral results are consistent with the proposed structure. The products show good inhibition of a variety of cancer cells including those associated with bone, breast, prostrate, and lung cancers. Some also show good viral inhibition of the HSV-1 (herpes simplex) and Vaccina (small pox) viruses with those derived from electron rich hydroquinone derivative being most active. Hydroquinone-derived polymers containing electron withdrawing groups exhibit inhibition of a variety of gram positive and gram negative bacteria.     

Synthesis of Organotin Polyamine Ethers Containing Acyclovir and their Preliminary Anticancer and Antiviral Activity

Organotin polyamine ethers containing acyclovir in their backbone were synthesized in moderate to high yield employing the aqueous interfacial polycondensation system. The products are high molecular weight polymers. Infrared spectroscopy of the products shows new bands characteristic of the formation of Sn–N and Sn–O bonds consistent with the proposed structure. MALDI-TOF MS below 2000 Da shows the presence of organotin and acyclovir units containing these two moieties. The products show moderate inhibition of a number of cancer cell lines and exhibit the ability to inhibit a number of viruses, particularly the herpes simplex virus-1 and varicella zoster virus that are responsible for herpes, chicken pox and shingles.     

Synthesis and Preliminary Cancer Activity of Chelidonic Acid Polyesters Containing the Triphenylarsenic,Triphenylantimony, and Triphenylbismuth Moiety

Polyesters derived from the interfacial reaction of the salt of chelidonic acid and triphenylarsenic dibromide, triphenylantimony dichloride, and triphenylbismuth dichloride are formed in moderate yield using commercially available reactants. IR data shows new bands characteristic of the formation of the M-O bond. MALDI MS shows formation of ion fragment clusters to two units. The polymers were tested for their ability to inhibit prostate, colon, breast (two cell lines), and pancreatic (two cell lines) cancer cells. All polymers showed ability to inhibit some of the cancer cell lines. The arsenic polymer exhibits good inhibition of the AsPC-1 pancreatic cell line. All three polymers inhibit the estrogen independent 7233 cell line to a much greater extent compared to inhibition of the 7259 estrogen positive receptor cell line. The arsenic and bismuth polymers also exhibit decent inhibition of the other cancer cell lines while the antimony polymer shows only decent inhibition of the 3465 prostate cell line.     

Synthesis and Characterization of Urea Nitrate and Nitrourea

Urea nitrate (UN) has not found use as a legitimate explosive but is commonly used as an improvised explosive. The dehydration product of UN is nitrourea (NU). Visually both UN and NU are white solids that both melt around 160 °C. Other properties differ markedly as might be expected from an inorganic salt (UN) and an organic molecular compound (NU). An extensive physical characterization of NU and UN is reported. Two reported routes to the NU product are compared and a decomposition mechanism of UN proposed.