7764-29-6Relevant articles and documents
Reactions of hexamethylditin and trimethyltin sulfide with N-thio-derivatives of phthalimide
Shcherbakov, V. I.,Grigor'eva, I. K.
, p. 2025 - 2028 (1993)
The initial formation of organotin derivatives with Sn-S-N bonds in heterolytic reactions of hexamethylditin or trimethyltin sulfide with N-(chlorothio)phthalimide is suggested.Subsequent interaction of these compounds with sulfenyl chloride affords N,N'-thio- or N,N'-dithiobisphthalimide.Homolytic reaction of hexamethylditin with N,N'-dithiobisphthalimide also occurs via an organotin intermediate, which, in the absence of a nucleophilic reagent, eliminates sulfur and converts into N-trimethylstannylphthalimide. - Key words: hexamethylditin; trimethyltin sulfide; N-(chlorothio)phthalimide; N,N'-dithiobisphthalimide; reactivity.
H2S-Donating trisulfide linkers confer unexpected biological behaviour to poly(ethylene glycol)-cholesteryl conjugates
Davis, Thomas P.,Ercole, Francesca,Li, Yuhuan,Quinn, John F.,Whittaker, Michael R.
, p. 3896 - 3907 (2020/05/18)
Inspired by the properties of the naturally occurring H2S donor, diallyl trisulfide (DATS, extracted from garlic), the biological behaviour of trisulfide-bearing PEG-conjugates was explored. Specifically, three conjugates comprising an mPEG tail and a cholesteryl head were investigated: conjugates bridged by a trisulfide linker (T), a disulfide linker (D) or a carbamate linker (C), and a fourth comprising two mPEG tails bridged by a trisulfide linker (P). H2S testing using both a fluorescent chemical probe in HEK293 cells and an amperometric sensor to monitor release in suspended cells, demonstrated the ability of the trisulfide conjugates,TandP, to release H2S in the presence of cellular thiols. Cytotoxicity and cyto-protective capacity on HEK293 cells showed thatTwas the best tolerated of the conjugates studied, and remarkably more so thanDorC. Moreover, it was noted that application ofTconferred a protective effect to the cells, effectively abolishing the toxicity associated with co-administeredC. The interaction of conjugates and combinations thereof with the cell membrane of HEK cells, as well as ROS generation were also investigated. It was found thatCcaused significant membrane perturbation, correlating with high losses in cell viability and pronounced generation of ROS, especially in the mitochondria.T, however, did not disturb the membrane and was able to mitigate the generation of ROS, especially in the mitochondria. The interplay of the cholesteryl group and H2S donation for conferring cytoprotective effects was clearly demonstrated asPdid not display the same beneficial characteristics asT
Design, synthesis and biological evaluation of novel podophyllotoxin derivatives bearing 4β-disulfide/trisulfide bond as cytotoxic agents
Zhu, Shi-Jun,Ying, Hua-Zhou,Wu, Yan,Qiu, Ni,Liu, Tao,Yang, Bo,Dong, Xiao-Wu,Hu, Yong-Zhou
, p. 103172 - 103183 (2015/12/23)
A novel series of C-4β-disulfide/trisulfide-containing podophyllotoxin derivatives were designed, synthesized, and biologically evaluated for their cytotoxic activities against human cancer cell lines, including KB (Mouth Epidermal Carcinoma Cells) and KB/VCR (Vincristine-resistant Mouth Epidermal Carcinoma Cells). Most of these compounds exhibited promising moderate to good cytotoxic activities. In particular, some of them displayed even superior activities to that of etoposide, especially for KB/VCR cell lines, indicating that introduction of the disulfide/trisulfide moiety would be beneficial for overcoming the multi-drug resistant limitation of etoposide. Moreover, the metabolic evaluation of the most promising compound was further performed to reveal that disulfide bond can be stable in human plasma over 8 hours, indicating good potential of these compounds for in vivo anti-cancer activities.
