Sulfur mustards poly

Bi- and poly-thioethers with aliphatic backbones are produced by attack of RS on the appropriate haloalkane. This is the method of choice for RS(CH2)raSR (R = Me or Ph),26 MeC(CH2SR)3,27,28 MeS(CH2)raS(CH2)raSMe (n = 2 or 3) and MeS(CH2)raS(CH2) S(CH2) SMe.28,29 [Caution Some of these syntheses involve sulfur mustard derivatives as intermediates - these are very powerful vesicants and should be handled only with extreme care.] The other tridentates RS(CH2)3S(CH2)3SR (R = Et, Pr or Ph) may be obtained from nucleophilic attack by RS on the ditosylate TsO(CH2)3S(CH2)3OTs.30 Tetra-dentate thioethers involving o-phenylene interdonor linkages are also known.31 More recently the preparation and coordination chemistry of the silicon-apex derivative MeSi(CH2SMe)3 has been described.32... 

Rosenthal, D.S., Simhulan-Rosenthal, C.M., Iyer, S., Smith, W.J., Ray, R., Smulson, M.E. (2000). Calmodulin, poly(ADP-ribose)polymerase and p53 are targets for modulating the effects of sulfur mustard. J. Appl. Toxicol. 20 (Suppl. 1) S43-9. 

Debiak, M., Kehe, K., Burkle, A. (2008). Role of poly(ADP-ribose) polymerase in sulfur mustard toxicity. Toxicology (June 18, Epub ahead of print) doi 10.1016/j.tox.2008.06.002. 

Hinshaw, D.B., Lodhi, I.J., Hurley, L.L., Atkins, K.B., Dabrowska, M.I. (1999). Activation of poly [ADP-ribose] polymerase in endothelial cells and keratinocytes role in an in vitro model of sulfur mustard-mediated vesication. Toxicol. Appl. Pharmacol. 156 17-29. 

Bhat, K.R., Benton, B.J., Ray, R. (2006). Poly (ADP-rihose) polymerase (PARP) is essential for sulfur mustard-induced DNA damage repair, hut has no role in DNA ligase activation. J. Appl. Toxicol. 26 452-7. 

Kehe, K., Raithel, K., Kreppel, H., Jochum, M., Worek, F., Thiermann, H. (2007). Inhibition of poly(ADP-rihose) polymerase (PARP) influences the mode of sulfur mustard (SM)-induced cell death in HaCaT cells. Arch. Toxicol. 82 461-70. 

Meier, H.L. (1996). The time-dependent effect of 2,2 -dichlor-odiethyl sulfide (sulfur mustard, HD, l,l -thiobis [2-chloro-ethane]) on the lymphocyte viability and the kinetics of protection by poly(ADP-ribose) polymerase inhibitors. Cell. Biol. Toxicol. 12 147-53. 

Meier, H.L., Millard, C.B. (1998). Alterations in human lymphocyte DNA caused by sulfur mustard can be mitigated by selective inhibitors of poly(ADP-ribose) polymerase. Biochim. Biophys. Acta 1404 367-76. 

Meier, H.L., Millard, C., Moser, J. (2000). Poly(ADP-ribose) polymerase inhibitors regulate the mechanism of sulfur mustard-initiated cell death in human lymphocytes. J. Appl. Toxicol 20 S93-100. 

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