Organotin Dihalides Research Articles

Organotin Polymers as Antiviral Agents Including Inhibition of Zika and Vaccinia Viruses

The ability to inhibit two important viruses is described. Two groups of polymers exhibited ability to totally inhibit the Zika virus. These polymers are derived from organotin dihalides and camphoric acid and lamivudine. This is the initial report of complete inhibition of the Zika virus by simple drugs. The ability to inhibit vaccinia virus is also reported. The inhibition of the vaccinia virus is shown by a number of organotin drugs including those also derived from lamivudine and camphoric acid and additional drugs derived from 3-amino-1,2,4-triazole, dicumarol, 4,6-diaminopyridine, alpha-cyano-4-hydroxcinnamic acid, and a variety of organotin polyethers including water soluble polymers derived from poly(ethylene glycol). All the drugs described in these studies are rapidly (< 30 s) synthesized using commercially available reactants at room temperature employing the interfacial reaction system that is employed industrially so that scale up to kilograms is relatively straight forward.

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

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.

Synthesis and Structural and Initial Cancer Cell Line Characterization of Organotin Polyesters from Dipicolinic Acid

The interfacial polymerization is employed to produce high polymer poly(ester ethers) from the reaction of the salt of dipicolinic acid and various organotin dihalides. They are rapidly synthesized with yield increasing as the length of the organotin alkyl chain increases. Infrared spectroscopy shows the formation of new bands derived from the Sn–O and Sn–O(CO) linkages. IR also shows that the products exist as a combination of molecular geometries about the tin atom. MALDI MS shows formation of ion fragment clusters to five and six units in length. The products show good inhibition of a variety of cancer cell lines including two pancreatic cancer cell lines.

Synthesis and Preliminary Cancer Cell Line Results for the Product of Organotin Dihalides and Alpha-Cyano-4-Hydroxycinnamic Acid

High polymer poly(ester ethers) are rapidly synthesized in good yield employing the interfacial polycondensation reaction system. Infrared spectroscopy shows the formation of new bands derived from the Sn–O and Sn–O(CO) linkages. It also shows that the products exist as alternating Sn–O and Sn–O(CO) linkages. MALDI MS shows formation of ion fragment clusters several units in length. The products show reasonable inhibition of a variety of cancer cell lines including two pancreatic cancer cell lines.

Synthesis and Preliminary Anticancer Results for Polymers From the Reaction of Organotin Dihalides and Thiodiglycolic Acid

Organotin polyesters were synthesized in good to poor yield with yield and chain length generally decreasing as the alkyl chain on the organotin increases. MALDI MS, NMR, and IR data is consistent with the proposed repeat unit. MALDI MS ion fragment clusters to four repeat units are found. The IR shows the presence of a new band assigned to the formation of the Sn-O. With the exception of the dimethyltin polymer, all of the polymers exhibit good inhibition of a variety of cancer cell lines including two breast cancer, prostate, two pancreatic cancer and colon cancer cell lines.

Self-matrix activity of organotin polyether ester polymers containing alpha-cyano-4-hydroxycinnamic acid

Polymers derived from reacting organotin dihalides and the matrix alpha-cyano-4-hydroxycinnamic acid act as their own matrix agent when performing MALDI MS. Ion fragments containing two and more repeat units are formed. MALDI MS results for the dioctyltin product are reported using other combinations of additives. Addition of sodium sulfate, not a matrix agent, also gives ion fragment clusters containing two repeat units. Use of addition of only alpha-cyano-4-hydroxycinnamic acid, a widely used matrix, gives similar results to the use of the matrix-containing polymer itself as does the use of the matrix graphite. The advantage of graphite is that non-interfering ion fragment clusters are not produced. This is the initial report of the inclusion of alpha-cyano-4-hydroxycinnamic acid into a condensation polymer and the use of the polymer itself as a matrix material.

Synthesis of organotin poly(ether esters) from reaction with glycyrrhetinic acid and their preliminary activity against various cancer cell lines

Polyether esters are rapidly formed employing the interfacial condensation of organotin dihalides with glycyrrhetinic acid in high yield and oligomeric to polymeric chain length. Infrared spectroscopy shows the formation of tin–oxygen bonds. The products are a mixture of bridging and non-bridging structures about the tin atom. Proton NMR and MALDI MS results are consistent with the formation of the poly(ether esters). The dimethyltin, dibutyltin, and diphenyltin polymers exhibit good inhibition of the pancreatic and prostrate cell lines.

Synthesis and Characterization of Organotin Polyesters Derived from 3,5-Pyridinedicarboxylic Acid

Organotin polyesters were synthesized from the interfacial condensation of organotin dihalides and salts of 3,5-pyridinedicarboxylic acid. The polymers are synthesized in moderate to high yields and are moderate to high polymers. MALDI MS, IR spectral, and NMR spectral results are consistent with the proposed structure. The Sn–O stretching band is found at about 1,028 cm−1. Infrared spectra are consistent with majority of the products having a non-bridged structure about the tin. All of the polymers exhibit some inhibition of two pancreatic cancer cell lines. The dibutyltin and dicyclohexyltin products show sufficiently good inhibition of both cell lines as to merit further testing.

Synthesis, structural characterization, and ability to inhibit the growth of pancreatic cancer by organotin polymers containing chelidonic acid

In this study, organotin polyesters have been formed from the interfacial reaction between the disodium salt of chelidonic acid and a variety of organotin dihalides. Reactions occur rapidly within less than 15 seconds. Yields vary from moderate to high, and chain length varies from 30 to 800 repeat units. Infrared spectral analysis shows the presence of the Sn–O linkage and is consistent with the geometry about the tin being generally a mixture of tetrahedral or nonbridging and octahedral or bridging. The organotin polyesters exhibit reasonable inhibition of two pancreatic cancer cell lines.

Organotin Polyesters from 1,1′-Ferrocenedicarboxylic Acid

Organotin polyesters have been synthesized employing the classical interfacial polycondensation of organotin dihalides and the salt of 1,1′-ferrocenedicarboxylic acid. The products are oligomeric (DP = 5) to polymeric (DP = 220). The presence of new IR bands characteristic of formation of the Sn–O band are present. Ion fragments characteristic of the repeat unit and greater are found employing F MALDI MS.

Electrochemical preparation of some organotin compounds

Organotin dihalides R 2SnX 2 (X  Cl, Br, I) and their adducts with bidentate donor ligands have been prepared in high yield by the direct electrochemical reaction of metallic tin with alkyl or aryl halides in organic media at room temperature. Dimethyltin diiodide can be converted to tetramethyltin by reaction with methyl iodide at a cadmium anode. Electrochemical halide abstraction has been used to prepare R 6Sn 2 (R  Me, Ph) from the corresponding R 3Sn halide. The mechanism of these reactions is discussed.