4428-14-2Relevant articles and documents
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)
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
The biothiol-triggered organotrisulfide-based self-immolative fluorogenic donors of hydrogen sulfide enable lysosomal trafficking
Mahato, Sulendar K.,Bhattacherjee, Debojit,Bhabak, Krishna P.
supporting information, p. 7769 - 7772 (2020/07/27)
Biothiol-reactive organotrisulfide-based self-immolative fluorogenic donors of H2S are rationally designed for the efficient monitoring of intracellular and lysosomal trafficking of H2S with a concomitant turn-on fluorescence. The non-toxic nature of the donors with a sustained release of H2S will certainly be helpful for their biomedical applications in the future.
Novel and efficient methods for the synthesis of symmetrical trisulfides
Kertmen, Ahmet,Lach, Slawomir,Rachon, Janusz,Witt, Dariusz
experimental part, p. 1459 - 1462 (2009/12/08)
We have developed convenient methods for the synthesis of symmetrical trisulfides under mild conditions in very good yields. The described methods are based on the straightforward preparation of (5,5-dimethyl-2-thioxo-1,3,2- dioxaphosphorin-2-yl)disulfany
