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Chemical Compound Review

Dasuansu     3-prop-2- enylsulfanyldisulfanylprop-1- ene

Synonyms: allitridi, Allitridin, allitridum, CHEMBL123040, CCRIS 3251, ...
 
 
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Disease relevance of CCRIS 3251

 

High impact information on CCRIS 3251

  • Cotreatment with thiol antioxidants decreased the ARE activity and Nrf2 protein level induced by DATS [5].
  • Three major mitogen-activated protein kinases (MAPKs)--extracellular signal-regulated protein kinase, c-Jun N-terminal kinase, and p38--were activated by DATS treatment [5].
  • Treatment of mice with DADS and DATS, which are potent inhibitors of BP-induced forestomach tumorigenesis, resulted in a statistically significant increase (2.4- and 1.5-fold, respectively) in forestomach NQO activity [1].
  • DATS treatment (10 microM) did not alter MRC-5 cell growth [6].
  • Exposure to 1 microM DATS for 24 hours significantly induced apoptosis, as indicated by increased DNA fragmentation [6].
 

Biological context of CCRIS 3251

  • To better understand the signaling events involved in the upregulation of detoxifying enzymes by DATS, ARE activity and Nrf2 protein levels were examined after transient transfection of HepG2 cells with mutant Nrf2, cotreatment with antioxidants, and pretreatment with protein kinase inhibitors [5].
  • Both immediate early gene (ie1) transcription and IEA (IE(1)72 and IE(2)86) expression was suppressed by allitridin, but not by GCV in a single HCMV cycle format [3].
  • According to the results of cell viability assay, 50 or 100 microM DATS significantly decreased the cell viability as compared with the control (P < 0.05) in dose and time dependent relations [7].
  • Phenomena of cell number loss, shape deformation and lysis were observed after treatment with 100 microM DATS for 24 h [7].
  • Cell cycle studies showed that J5 cells were significantly arrested in G2/M phase as the cells were treated with 100 microM DADS, 10, 50 or 100 microM DATS for 24 h (P < 0.05) [7].
 

Anatomical context of CCRIS 3251

  • GO, DADS and DATS treatment significantly increased the glutathione (GSH) content (48-84%) in red blood cells (P < 0.05) [4].
  • This preventive effect of DADS and DATS was confirmed when liver microsomes were used, and further verified by 32P post-labeling analysis [8].
  • Analysis of B[a]P metabolites revealed that the level of 7,8-diol formed was significantly reduced in the DADS and DATS treated microsomes as compared to the control [9].
  • DADS-treated HT-29 cells and both DATS-treated cell lines exhibit inverse correlation between p-H3 positivity and compound concentration due to higher apoptotic rate [10].
 

Associations of CCRIS 3251 with other chemical compounds

  • The modulation of garlic oil (GO) and three allyl compounds, diallyl sulfide (DAS), diallyl disulfide (DADS) and diallyl trisulfide (DATS), on the antioxidation system in rat livers and red blood cells was examined [4].
  • This study was aimed to investigate the effect of allitridin (diallyl trisulfide, a compound from A. sativum extraction) on the replication of HCMV and the expression of viral immediate-early genes [3].
 

Gene context of CCRIS 3251

  • According to the Western blot analysis, DATS decreased cyclin-dependent kinase (Cdks)-Cdk7 (i.e. Cdc2 activate kinase) protein levels in J5 cells but increased cyclin B1 protein level [7].
  • Immunoblot results indicated that the B[a]P inducible CYP1A2 protein was suppressed by 100-1,000 microM of DADS and 10-100 microM of DATS, but CYP1A1 and 1B1 were not detectable in any microsomes [9].
  • The modulation potency to cyclin B1 and Cdk7 protein levels increased with increasing in DATS concentration and culture time [7].
  • The effects of allitridin on the expression of transcription factors T-bet and GATA-3 in mice infected by murine cytomegalovirus [11].
  • DADS and DATS inhibited the B[a]P-induced ethoxyresorufin O-deethylase (EROD) activity, a marker enzyme for CYP1, by 30-90% and 70-95% at 100-1,000 microM concentration, respectively [9].
 

Analytical, diagnostic and therapeutic context of CCRIS 3251

  • DATS (10 microM) caused a marked and progressive increase in intracellular Ca2+ in A549 cells during the first four hours after treatment [6].
  • Twenty mice were allocated randomly into an allitridin-treated group (n = 10) and a placebo control group (n = 10) [11].
  • Allyl sulfides such as diallyl sulfide (DAS), diallyl disulfide (DADS), and diallyl trisulfide (DATS), typical flavor components of Allium vegetables, have been shown to inhibit benzo[a]pyrene (B[a]P)-induced carcinogenesis in animal models [9].

References

  1. Differential induction of NAD(P)H:quinone oxidoreductase by anti-carcinogenic organosulfides from garlic. Singh, S.V., Pan, S.S., Srivastava, S.K., Xia, H., Hu, X., Zaren, H.A., Orchard, J.L. Biochem. Biophys. Res. Commun. (1998) [Pubmed]
  2. Experimental study on the prevention and treatment of murine cytomegalovirus hepatitis by using allitridin. Liu, Z.F., Fang, F., Dong, Y.S., Li, G., Zhen, H. Antiviral Res. (2004) [Pubmed]
  3. Experimental study on the action of allitridin against human cytomegalovirus in vitro: Inhibitory effects on immediate-early genes. Zhen, H., Fang, F., Ye, D.Y., Shu, S.N., Zhou, Y.F., Dong, Y.S., Nie, X.C., Li, G. Antiviral Res. (2006) [Pubmed]
  4. Effects of organosulfur compounds from garlic oil on the antioxidation system in rat liver and red blood cells. Wu, C.C., Sheen, L.Y., Chen, H.W., Tsai, S.J., Lii, C.K. Food Chem. Toxicol. (2001) [Pubmed]
  5. Induction of detoxifying enzymes by garlic organosulfur compounds through transcription factor Nrf2: effect of chemical structure and stress signals. Chen, C., Pung, D., Leong, V., Hebbar, V., Shen, G., Nair, S., Li, W., Kong, A.N. Free Radic. Biol. Med. (2004) [Pubmed]
  6. Allyl sulfides from garlic suppress the in vitro proliferation of human A549 lung tumor cells. Sakamoto, K., Lawson, L.D., Milner, J.A. Nutrition and cancer. (1997) [Pubmed]
  7. Differential effects of allyl sulfides from garlic essential oil on cell cycle regulation in human liver tumor cells. Wu, C.C., Chung, J.G., Tsai, S.J., Yang, J.H., Sheen, L.Y. Food Chem. Toxicol. (2004) [Pubmed]
  8. Prevention of chemical carcinogen DNA binding and inhibition of nuclear RNA polymerase activity by organosulfur compounds as the possible mechanisms for their anticancer initiation and proliferation effects. Yu, F.L., Bender, W., Fang, Q., Ludeke, A., Welch, B. Cancer Detect. Prev. (2003) [Pubmed]
  9. Modulation of cytochrome P4501-mediated bioactivation of benzo[a]pyrene by volatile allyl sulfides in human hepatoma cells. Chun, H.S., Kim, H.J., Choi, E.H. Biosci. Biotechnol. Biochem. (2001) [Pubmed]
  10. Garlic-derived organosulfides induce cytotoxicity, apoptosis, cell cycle arrest and oxidative stress in human colon carcinoma cell lines. Jakubíková, J., Sedlák, J. Neoplasma (2006) [Pubmed]
  11. The effects of allitridin on the expression of transcription factors T-bet and GATA-3 in mice infected by murine cytomegalovirus. Yi, X., Feng, F., Xiang, Z., Ge, L. Journal of medicinal food. (2005) [Pubmed]
 
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