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Chemical Compound Review

CCRIS 3331     [(2S)-1-decanoyloxy-3- hydroxy-propan-2-yl]...

Synonyms: CHEBI:18155, KST-1A7303, LS-59369, CTK5B1625, AR-1A3298, ...
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Disease relevance of CCRIS 3331


High impact information on CCRIS 3331

  • A single application of 10 mumol sn-1,2-didecanoylglycerol, a model sn-1,2-diacylglycerol and complete tumor promoter, induced ornithine decarboxylase to an extent similar to that of 2 nmol TPA [1].
  • sn-1,2-Didecanoylglycerol, a synthetic lipid second messenger and model diacylglycerol, was evaluated as a complete skin tumor promoter in CD-1 mice [4].
  • A marked effect of the acyl chain length, 3-10 carbons, of symmetric sn-1,2-diacylglycerols was observed on their ability to mimic the effect of 4 beta-phorbol 12 beta-myristate 13 alpha-acetate (PMA). sn-1,2-Dipropanoylglycerol did not mimic the effects of PMA, but sn-1,2-didecanoylglycerol potently mimicked PMA action [5].
  • By combining the above sandwich ELISA technique with the monomolecular film technique, it was possible for the first time to measure the enzymatic activity of HGL on 1,2-didecanoyl-sn-glycerol (dicaprin) monolayers as well as to determine the corresponding interfacial excess of the enzyme [6].
  • By use of directing binding studies with a nondegradable anionic substrate analogue and monomolecular surface film kinetics on 1,2-didecanoyl-sn-glycerol 3-sulfate, it is shown that the aggregation process is controlled by the ionization state of the side chains of the amino acid residues at positions 6 and 17 [7].

Biological context of CCRIS 3331


Gene context of CCRIS 3331


  1. Differential down-regulation of epidermal protein kinase C by 12-O-tetradecanoylphorbol-13-acetate and diacylglycerol: association with epidermal hyperplasia and tumor promotion. Hansen, L.A., Monteiro-Riviere, N.A., Smart, R.C. Cancer Res. (1990) [Pubmed]
  2. Genetic alterations cooperate with v-Ha-ras to accelerate multistage carcinogenesis in TG.AC transgenic mouse skin. Owens, D.M., Spalding, J.W., Tennant, R.W., Smart, R.C. Cancer Res. (1995) [Pubmed]
  3. Comparison of the effect of sn-1,2-didecanoylglycerol and 12-O-tetradecanoylphorbol-13-acetate on cutaneous morphology, inflammation and tumor promotion in CD-1 mice. Smart, R.C., Huang, M.T., Monteiro-Riviere, N.A., Wong, C.Q., Mills, K.J., Conney, A.H. Carcinogenesis (1988) [Pubmed]
  4. Synthetic lipid second messenger sn-1,2-didecanoylglycerol: a complete tumor promoter in mouse skin. Smart, R.C., Mills, K.J., Hansen, L.A., Conney, A.H. Cancer Res. (1989) [Pubmed]
  5. Structural requirements for diacylglycerols to mimic tumor-promoting phobol diester action on the epidermal growth factor receptor. Davis, R.J., Ganong, B.R., Bell, R.M., Czech, M.P. J. Biol. Chem. (1985) [Pubmed]
  6. Interfacial binding of human gastric lipase to lipid monolayers, measured with an ELISA. Aoubala, M., Ivanova, M., Douchet, I., De Caro, A., Verger, R. Biochemistry (1995) [Pubmed]
  7. Interaction of pancreatic phospholipases A2 and semisynthetic mutants with anionic substrates and substrate analogues. de Haas, G.H., van Scharrenburg, G.J., Slotboom, A.J. Biochemistry (1987) [Pubmed]
  8. Decanoyl lysophosphatidic acid induces platelet aggregation through an extracellular action. Evidence against a second messenger role for lysophosphatidic acid. Watson, S.P., McConnell, R.T., Lapetina, E.G. Biochem. J. (1985) [Pubmed]
  9. Phorbol ester-mediated suppression of cytochrome P450 Cyp1a-1 induction in murine skin: involvement of protein kinase C. Reiners, J.J., Cantu, A.R., Schöller, A. Biochem. Biophys. Res. Commun. (1992) [Pubmed]
  10. Inactivation of pancreatic and gastric lipases by tetrahydrolipstatin and alkyl-dithio-5-(2-nitrobenzoic acid). A kinetic study with 1,2-didecanoyl-sn-glycerol monolayers. Ransac, S., Gargouri, Y., Moreau, H., Verger, R. Eur. J. Biochem. (1991) [Pubmed]
  11. Mechanism of action of milk lipoprotein lipase at substrate interfaces: effects of apolipoproteins. Jackson, R.L., Pattus, F., de Haas, G. Biochemistry (1980) [Pubmed]
  12. Incorporation of synthetic 1,2-diacylglycerol into platelet phosphatidylinositol is increased by cyclic AMP. Lapetina, E.G. FEBS Lett. (1986) [Pubmed]
  13. Intracellular production of reactive oxygen species in human neutrophils following activation by the soluble stimuli FMLP, dioctanoylglycerol and ionomycin. Follin, P., Johansson, A., Dahlgren, C. Cell Biochem. Funct. (1991) [Pubmed]
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