2179-60-4Relevant articles and documents
The cytotoxicity of garlic-related disulphides and thiosulfonates in WHCO1 oesophageal cancer cells is dependent on S-thiolation and not production of ROS
Smith, Muneerah,Hunter, Roger,Stellenboom, Nashia,Kusza, Daniel A.,Parker, M. Iqbal,Hammouda, Ahmed N.H.,Jackson, Graham,Kaschula, Catherine H.
, p. 1439 - 1449 (2016/05/09)
Background Garlic has been used for centuries in folk medicine for its health promoting and cancer preventative properties. The bioactive principles in crushed garlic are allyl sulphur compounds which are proposed to chemically react through (i) protein S-thiolation and (ii) production of ROS. Methods A collection of R-propyl disulphide and R-thiosulfonate compounds were synthesised to probe the importance of thiolysis and ROS generation in the cytotoxicity of garlic-related compounds in WHCO1 oesophageal cancer cells. Results A significant correlation (R2 = 0.78, Fcrit (7,1) α = 0.005) was found between the cytotoxicity IC50 and the leaving group pKa of the R-propyl disulphides and thiosulfonates, supporting a mechanism that relies on the thermodynamics of a mixed disulphide exchange reaction. Disulphide (1) and thiosulfonate (11) were further evaluated mechanistically and found to induce G2/M cell-cycle arrest and apoptosis, inhibit cell proliferation, and generate ROS. When the ROS produced by 1 and 11 were quenched with Trolox, ascorbic acid or N-acetyl cysteine (NAC), only NAC was found to counter the cytotoxicity of both compounds. However, NAC was found to chemically react with 11 through mixed disulphide formation, providing an explanation for this apparent inhibitory result. Conclusion Cellular S-thiolation by garlic related disulphides appears to be the cause of cytotoxicity in WHCO1 cells. Generation of ROS appears to only play a secondary role. General significance Our findings do not support ROS production causing the cytotoxicity of garlic-related disulphides in WHCO1 cells. Importantly, it was found that the popular ROS inhibitor NAC interferes with the assay.
Phosphine-catalyzed disulfide metathesis
Caraballo, Remi,Rahm, Martin,Vongvilai, Pornrapee,Brinck, Tore,Ramstroem, Olof
scheme or table, p. 6603 - 6605 (2009/04/20)
The reaction between disulfides and phosphines generates a reversible disulfide metathesis process. The Royal Society of Chemistry 2008.
Process for the production of isosolanone and solanone, intermediates useful in said process and organoleptic uses of said intermediates
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, (2008/06/13)
Described is a novel genus of compounds defined according to the structure: STR1 wherein Z represents hydrogen, MgX and the moiety having the structure: STR2 and X represents chlor, bromo, or iodo; as well as 5-isopropyl-8-methyl-5,8-nonadien-2-one; uses of same as intermediates in a process for producing isosolanone and solanone; and organoleptic uses of 5-isopropyl-8-methyl-5,8-nonadien-2-one and 2,6-dimethyl-5-methylene-1-hepten-4-ol. The novel process of our invention involved the steps of: (i) formation of the compound having the structure: STR3 by means of reacting 3-methyl-2-methylenebutanal with the compound having the structure: STR4 (ii) acid hydrolysis of the resulting compound in order to form 2,6-dimethyl-5-methylene-1-heptene-4-ol; (iii) reaction of 2,6-dimethyl-5-methylene-1-hepten-4-ol with methyl aceto acetate in order to form 2,6-dimethyl-5-methylene-1-hepten-4-yl aceto acetate or, directly, 5-isopropyl-8-methyl-5,8-nonadiene-2-one; (iv) reacting 2,6-dimethyl-5-methylene-1-hepten-4-yl aceto acetate in the presence of an appropriate catalyst to form the 5-isopropyl-8-methyl-5,8-nonadiene-2-one; and (v) isomerizing the 5-isopropyl-8-methyl-5,8-nonadien-2-one in order to form a mixture of solanone and the isosolanone or 5-isopropyl-8-methyl-5,8-nonadiene-2-one.
NEW SIMPLE SYNTHESIS OF UNSYMMETRICAL DISULFIDE
Gupta, D.
, p. 31 - 36 (2007/10/02)
Unsymmetrical disulfides from the co-photolysis of mixtures of symmetrical alkyl disulfides is reported.Rates have been obtained for 35 combinations of C2 to C10 alkyl disulfides and their isomers.An equilibrium is attained after relatively short irradiation periods in cyclohexane.
Equilibrium Studies in Photolysis of Liquid Disulphide Mixtures
Gupta, Dinesh
, p. 328 - 330 (2007/10/02)
The photolysis of liquid disulphide mixtures, viz dimethyl-diethyl, dimethyl-dipropyl and diethyl-dipropyl disulphides, has been carried out and the initial rates and equilibrium constants have been determined.
Reaction of thiyl radicals. XIII. Photochemically induced exchange reactions of liquid alkyl disulfides
Gupta, Dinesh,Knight, Arthur R.
, p. 1350 - 1354 (2007/10/02)
The liquid phase photolysis of some 35 liquid alkyl disulfide mixtures has been studied.The corresponding unsymmetrical disulfide is the only significant product of the reaction and the system attains a photo-equilibrium state at longer exposure times.Product formation is completely eliminated by the addition of nitric oxide.Quantum yields have been redetermined for the methyl disulfide- ethyl disulfide system using four different light sources.Initial rates have been measured for each of the 35 combinations and have been shown to be a function of total molecular weight of the disulfide mixture and to be strongly influenced by steric factors.These effects are most pronounced for mixtures wherein the exchange reaction between thiyl radical and a symmetrical disulfide is important as indicated by quantum yields above unity.Combinations of isodisulfides give rise to anomalously high rates.
