The world's first wiki where authorship really matters (Nature Genetics, 2008). Due credit and reputation for authors. Imagine a global collaborative knowledge base for original thoughts. Search thousands of articles and collaborate with scientists around the globe.

wikigene or wiki gene protein drug chemical gene disease author authorship tracking collaborative publishing evolutionary knowledge reputation system wiki2.0 global collaboration genes proteins drugs chemicals diseases compound
Hoffmann, R. A wiki for the life sciences where authorship matters. Nature Genetics (2008)
Chemical Compound Review

Biallyl     hexa-1,5-diene

Synonyms: Diallyl, CHEMBL31747, ACMC-1AXER, AG-G-10813, ANW-33202, ...
Welcome! If you are familiar with the subject of this article, you can contribute to this open access knowledge base by deleting incorrect information, restructuring or completely rewriting any text. Read more.

Disease relevance of HEXADIENE


High impact information on HEXADIENE

  • Primary hepatocytes from pyrazole-injected rats with high levels of CYP2E1 showed an increase in GSH levels as well as GCLC and GCLM mRNAs compared with saline controls, and this was prevented by diallyl sulfide [6].
  • Catalase and diallyl sulfide prevented basal and AA-induced messenger RNA (mRNA) levels of GCLC and the modulatory subunit of GCL (GCLM) [6].
  • Metabolism of carcinogenic nitrosamines by rat nasal mucosa and the effect of diallyl sulfide [7].
  • Checkpoint kinase 1 regulates diallyl trisulfide-induced mitotic arrest in human prostate cancer cells [8].
  • The lack of a role of checkpoint kinase 2 in diallyl trisulfide-induced phosphorylation of Cdc25C or G(2)-M phase cell cycle arrest was confirmed using HCT-15 cells stably transfected with phosphorylation-deficient mutant (T68A mutant) of checkpoint kinase 2 [8].

Chemical compound and disease context of HEXADIENE


Biological context of HEXADIENE

  • The diallyl trisulfide-induced Ser(216) phosphorylation of Cdc25C as well as mitotic arrest were significantly attenuated by knockdown of check-point kinase 1 protein in both PC-3 and DU145 cells [8].
  • On the other hand, depletion of checkpoint kinase 2 protein did not have any appreciable effect on G(2) or M phase arrest or Cdc25C phosphorylation caused by diallyl trisulfide [8].
  • We attribute this activity to hydrophobic intermolecular interactions of the diallyl side chains of the acyclic bacteriocin 5 that assist realization of the correct conformation at the receptor active site [13].
  • Lahav, Milstein, and co-workers reported that the complex [(bpy)Rh(hd)](+)PF(6)(-) (bpy = substituted bipyridine ligand, hd = 1,5-hexadiene) shows catalytic activity in the hydrogenation of acetone (Töllner, K. et al. Science 1997, 278, 2100) [14].
  • Salicylate potentiated AA-induced lipid peroxidation in the E47 cells, a reaction blocked by diallyl sulfide [15].

Anatomical context of HEXADIENE


Associations of HEXADIENE with other chemical compounds


Gene context of HEXADIENE


Analytical, diagnostic and therapeutic context of HEXADIENE


  1. c-Jun NH(2)-terminal kinase signaling axis regulates diallyl trisulfide-induced generation of reactive oxygen species and cell cycle arrest in human prostate cancer cells. Antosiewicz, J., Herman-Antosiewicz, A., Marynowski, S.W., Singh, S.V. Cancer Res. (2006) [Pubmed]
  2. Diallyl trisulfide suppresses the proliferation and induces apoptosis of human colon cancer cells through oxidative modification of beta-tubulin. Hosono, T., Fukao, T., Ogihara, J., Ito, Y., Shiba, H., Seki, T., Ariga, T. J. Biol. Chem. (2005) [Pubmed]
  3. A proteomic investigation into a human gastric cancer cell line BGC823 treated with diallyl trisulfide. Li, N., Guo, R., Li, W., Shao, J., Li, S., Zhao, K., Chen, X., Xu, N., Liu, S., Lu, Y. Carcinogenesis (2006) [Pubmed]
  4. Garlic extract and two diallyl sulphides inhibit methicillin-resistant Staphylococcus aureus infection in BALB/cA mice. Tsao, S.M., Hsu, C.C., Yin, M.C. J. Antimicrob. Chemother. (2003) [Pubmed]
  5. In vitro activity of garlic oil and four diallyl sulphides against antibiotic-resistant Pseudomonas aeruginosa and Klebsiella pneumoniae. Tsao, S., Yin , M. J. Antimicrob. Chemother. (2001) [Pubmed]
  6. Cytochrome P450 2E1 responsiveness in the promoter of glutamate-cysteine ligase catalytic subunit. Nieto, N., Marí, M., Cederbaum, A.I. Hepatology (2003) [Pubmed]
  7. Metabolism of carcinogenic nitrosamines by rat nasal mucosa and the effect of diallyl sulfide. Hong, J.Y., Smith, T., Lee, M.J., Li, W.S., Ma, B.L., Ning, S.M., Brady, J.F., Thomas, P.E., Yang, C.S. Cancer Res. (1991) [Pubmed]
  8. Checkpoint kinase 1 regulates diallyl trisulfide-induced mitotic arrest in human prostate cancer cells. Herman-Antosiewicz, A., Singh, S.V. J. Biol. Chem. (2005) [Pubmed]
  9. Organosulfur compounds of garlic modulate mutagenesis, metabolism, and DNA binding of aflatoxin B1. Tadi, P.P., Teel, R.W., Lau, B.H. Nutrition and cancer. (1991) [Pubmed]
  10. Effects of the garlic compounds diallyl sulphide and diallyl disulphide on arylamine N-acetyltransferase activity in Klebsiella pneumoniae. Chen, G.W., Chung, J.G., Ho, H.C., Lin, J.G. Journal of applied toxicology : JAT. (1999) [Pubmed]
  11. 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]
  12. Investigation of the role of oxidative stress in amiodarone-induced pulmonary toxicity in the hamster. Leeder, R.G., Brien, J.F., Massey, T.E. Can. J. Physiol. Pharmacol. (1994) [Pubmed]
  13. Antimicrobial leucocin analogues with a disulfide bridge replaced by a carbocycle or by noncovalent interactions of allyl glycine residues. Derksen, D.J., Stymiest, J.L., Vederas, J.C. J. Am. Chem. Soc. (2006) [Pubmed]
  14. Catalytic reduction of acetone by [(bpy)Rh]+: a theoretical mechanistic investigation and insight into cooperativity effects in this system. Iron, M.A., Sundermann, A., Martin, J.M. J. Am. Chem. Soc. (2003) [Pubmed]
  15. Sodium salicylate increases CYP2E1 levels and enhances arachidonic acid toxicity in HepG2 cells and cultured rat hepatocytes. Wu, D., Cederbaum, A.I. Mol. Pharmacol. (2001) [Pubmed]
  16. Cadmium induced mitochondrial injury and apoptosis in vero cells: Protective effect of diallyl tetrasufide from garlic. Murugavel, P., Pari, L., Sitasawad, S.L., Kumar, S., Kumar, S. Int. J. Biochem. Cell Biol. (2007) [Pubmed]
  17. PD 115,199: an antagonist ligand for adenosine A2 receptors. Bruns, R.F., Fergus, J.H., Badger, E.W., Bristol, J.A., Santay, L.A., Hays, S.J. Naunyn Schmiedebergs Arch. Pharmacol. (1987) [Pubmed]
  18. Inhibition of CYP2E1 reverses CD4+ T-cell alterations in trichloroethylene-treated MRL+/+ mice. Griffin, J.M., Gilbert, K.M., Pumford, N.R. Toxicol. Sci. (2000) [Pubmed]
  19. Diallyl Trisulfide Inhibits Angiogenic Features of Human Umbilical Vein Endothelial Cells by Causing Akt Inactivation and Down-Regulation of VEGF and VEGF-R2. Xiao, D., Li, M., Herman-Antosiewicz, A., Antosiewicz, J., Xiao, H., Lew, K.L., Zeng, Y., Marynowski, S.W., Singh, S.V. Nutrition and cancer. (2006) [Pubmed]
  20. Diallyl trisulfide inhibits tumor necrosis factor-alpha expression in inflammed mucosa of ulcerative colitis. Bai, A.P., Ouyang, Q., Hu, R.W. Dig. Dis. Sci. (2005) [Pubmed]
  21. Conformation-dependent state selectivity in O-O cleavage of ONOONO: an "inorganic cope rearrangement" helps explain the observed negative activation energy in the oxidation of nitric oxide by dioxygen. Olson, L.P., Kuwata, K.T., Bartberger, M.D., Houk, K.N. J. Am. Chem. Soc. (2002) [Pubmed]
  22. Bioactive S-alk(en)yl cysteine sulfoxide metabolites in the genus Allium: the chemistry of potential therapeutic agents. Rose, P., Whiteman, M., Moore, P.K., Zhu, Y.Z. Natural product reports. (2005) [Pubmed]
  23. Chemoprotective effects of capsaicin and diallyl sulfide against mutagenesis or tumorigenesis by vinyl carbamate and N-nitrosodimethylamine. Surh, Y.J., Lee, R.C., Park, K.K., Mayne, S.T., Liem, A., Miller, J.A. Carcinogenesis (1995) [Pubmed]
  24. Inhibition of benzoyl peroxide-mediated tumor promotion in 7,12-dimethylbenz(a)anthracene-initiated skin of Sencar mice by antioxidants nordihydroguaiaretic acid and diallyl sulfide. Athar, M., Raza, H., Bickers, D.R., Mukhtar, H. J. Invest. Dermatol. (1990) [Pubmed]
  25. Diallyl trisulfide-induced apoptosis in human prostate cancer cells involves c-Jun N-terminal kinase and extracellular-signal regulated kinase-mediated phosphorylation of Bcl-2. Xiao, D., Choi, S., Johnson, D.E., Vogel, V.G., Johnson, C.S., Trump, D.L., Lee, Y.J., Singh, S.V. Oncogene (2004) [Pubmed]
  26. Diallyl Trisulfide Suppresses Growth of PC-3 Human Prostate Cancer Xenograft In vivo in Association with Bax and Bak Induction. Xiao, D., Lew, K.L., Kim, Y.A., Zeng, Y., Hahm, E.R., Dhir, R., Singh, S.V. Clin. Cancer Res. (2006) [Pubmed]
  27. Induction of the multidrug resistance-associated protein family of transporters by chemical activators of receptor-mediated pathways in mouse liver. Maher, J.M., Cheng, X., Slitt, A.L., Dieter, M.Z., Klaassen, C.D. Drug Metab. Dispos. (2005) [Pubmed]
  28. Decrease of hepatic catalase level by treatment with diallyl sulfide and garlic homogenates in rats and mice. Chen, L., Hong, J.Y., So, E., Hussin, A.H., Cheng, W.F., Yang, C.S. J. Biochem. Mol. Toxicol. (1999) [Pubmed]
  29. Balancing dynamic and nondynamic correlation for diradical and aromatic transition states: a renormalized coupled-cluster study of the cope rearrangement of 1,5-hexadiene. McGuire, M.J., Piecuch, P. J. Am. Chem. Soc. (2005) [Pubmed]
  30. Influence of vinyl monomers and temperature on immobilization of cellulose 3,5-dimethylphenylcarbamate onto silica gel as chiral stationary phases for high-performance liquid chromatography. Chen, X.M., Yamamoto, C., Okamoto, Y. Journal of chromatography. A. (2006) [Pubmed]
  31. Enhanced diallyl trisulfide has in vitro synergy with amphotericin B against Cryptococcus neoformans. Shen, J., Davis, L.E., Wallace, J.M., Cai, Y., Lawson, L.D. Planta Med. (1996) [Pubmed]
  32. Chemoprevention of chemically induced skin tumor development by diallyl sulfide and diallyl disulfide. Dwivedi, C., Rohlfs, S., Jarvis, D., Engineer, F.N. Pharm. Res. (1992) [Pubmed]
  33. Immunochemical comparison of 3'-hydroxyacetanilide and acetaminophen binding in mouse liver. Salminen, W.F., Roberts, S.M., Pumford, N.R., Hinson, J.A. Drug Metab. Dispos. (1998) [Pubmed]
WikiGenes - Universities