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5 Hydroperoxy 6

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Jean Bernard Ducep – One of the best experts on this subject based on the ideXlab platform.

  • evaluation of 5 and 6 fluoro derivatives of arachidonic acid and 5 8 14 eicosatrienoic acid as substrates and inhibitors of 5 lipoxygenase
    Biochemical Journal, 1991
    Co-Authors: Jeanfrancois Nave, D Jacobi, C Gaget, B Dulery, Jean Bernard Ducep
    Abstract:

    The 5– and 6-fluoro derivatives of arachidonic acid (5F-ETE and 6F-ETE) were evaluated as substrates of rat basophilic leukaemia cell (RBL-1) 5lipoxygenase. 5F-ETE was found to be a poor substrate and was converted into a single product, 5-oxoeicosa-6,8,11,14-tetraenoic acid (5-oxo-ETE). 6F-ETE was a good substrate and was mainly converted into 5Hydroperoxy6-fluoroeicosa-6,8,11,14-tetraenoic acid (5-OOH-6F-ETE) with concomitant formation of a small amount of 5-oxo-6-fluoroeicosa-6,8,11,14-tetraenoic acid (5-oxo-6F-ETE). However the formation of 5,12-dihydroxy-6-fluoroeicosa-6,8,10,14-tetraenoic acids, epimeric at C-12, was not observed. Eicosa-5(Z),8(Z),14(Z)-trienoic acid (ET), previously described as a good substrate of 5lipoxygenase, is oxidized mainly to 5Hydroperoxyeicosa-6,8,14-trienoic acid (5-OOH-ET), which does not serve as a substrate for the leukotriene A4 (LTA4) synthase activity of 5lipoxygenase [Nave, Dulery, Gaget & Ducep (1988) Prostaglandins 36, 385-398]. To allow a better estimation of the effect of fluorine substitution on the rate of oxidation of the 5,8-cis,cis-diene moiety by 5lipoxygenase, the 5– and 6-fluoro derivatives of ET were studied as substrates. Qualitatively, the metabolism of 5F-ET and 6F-ET was found to be similar to that observed for 5F-ETE and 6F-ETE. Quantitatively, 6F-ET proved to be a somewhat better substrate than ET, whereas 5F-ET was poorly metabolized. The relative ability of arachidonic acid, ET and the corresponding 5– and 6-fluoro derivatives to inhibit the 5lipoxygenase-catalysed oxidation of eicosa-5(Z),8(Z)-dienoic acid (ED) was also investigated. 6F-ETE and 5F-ETE were found to be effective and about equipotent inhibitors of 5lipoxygenase in the micromolar range. In view of their close structural similarity to arachidonic acid, these two inhibitors are expected to be important tools in the study of the 5lipoxygenase pathway in vivo.

  • Evaluation of 5– and 6-fluoro derivatives of arachidonic acid and 5,8,14-eicosatrienoic acid as substrates and inhibitors of 5-lipoxygenase.
    The Biochemical journal, 1991
    Co-Authors: J F Navé, C Gaget, D Jacobi, B Dulery, Jean Bernard Ducep
    Abstract:

    The 5– and 6-fluoro derivatives of arachidonic acid (5F-ETE and 6F-ETE) were evaluated as substrates of rat basophilic leukaemia cell (RBL-1) 5lipoxygenase. 5F-ETE was found to be a poor substrate and was converted into a single product, 5-oxoeicosa-6,8,11,14-tetraenoic acid (5-oxo-ETE). 6F-ETE was a good substrate and was mainly converted into 5Hydroperoxy6-fluoroeicosa-6,8,11,14-tetraenoic acid (5-OOH-6F-ETE) with concomitant formation of a small amount of 5-oxo-6-fluoroeicosa-6,8,11,14-tetraenoic acid (5-oxo-6F-ETE). However the formation of 5,12-dihydroxy-6-fluoroeicosa-6,8,10,14-tetraenoic acids, epimeric at C-12, was not observed. Eicosa-5(Z),8(Z),14(Z)-trienoic acid (ET), previously described as a good substrate of 5lipoxygenase, is oxidized mainly to 5Hydroperoxyeicosa-6,8,14-trienoic acid (5-OOH-ET), which does not serve as a substrate for the leukotriene A4 (LTA4) synthase activity of 5lipoxygenase [Navé, Dulery, Gaget & Ducep (1988) Prostaglandins 36, 385-398]. To allow a better estimation of the effect of fluorine substitution on the rate of oxidation of the 5,8-cis,cis-diene moiety by 5lipoxygenase, the 5– and 6-fluoro derivatives of ET were studied as substrates. Qualitatively, the metabolism of 5F-ET and 6F-ET was found to be similar to that observed for 5F-ETE and 6F-ETE. Quantitatively, 6F-ET proved to be a somewhat better substrate than ET, whereas 5F-ET was poorly metabolized. The relative ability of arachidonic acid, ET and the corresponding 5– and 6-fluoro derivatives to inhibit the 5lipoxygenase-catalysed oxidation of eicosa-5(Z),8(Z)-dienoic acid (ED) was also investigated. 6F-ETE and 5F-ETE were found to be effective and about equipotent inhibitors of 5lipoxygenase in the micromolar range. In view of their close structural similarity to arachidonic acid, these two inhibitors are expected to be important tools in the study of the 5lipoxygenase pathway in vivo.

B Dulery – One of the best experts on this subject based on the ideXlab platform.

  • evaluation of 5 and 6 fluoro derivatives of arachidonic acid and 5 8 14 eicosatrienoic acid as substrates and inhibitors of 5 lipoxygenase
    Biochemical Journal, 1991
    Co-Authors: Jeanfrancois Nave, D Jacobi, C Gaget, B Dulery, Jean Bernard Ducep
    Abstract:

    The 5– and 6-fluoro derivatives of arachidonic acid (5F-ETE and 6F-ETE) were evaluated as substrates of rat basophilic leukaemia cell (RBL-1) 5-lipoxygenase. 5F-ETE was found to be a poor substrate and was converted into a single product, 5-oxoeicosa-6,8,11,14-tetraenoic acid (5-oxo-ETE). 6F-ETE was a good substrate and was mainly converted into 5Hydroperoxy6-fluoroeicosa-6,8,11,14-tetraenoic acid (5-OOH-6F-ETE) with concomitant formation of a small amount of 5-oxo-6-fluoroeicosa-6,8,11,14-tetraenoic acid (5-oxo-6F-ETE). However the formation of 5,12-dihydroxy-6-fluoroeicosa-6,8,10,14-tetraenoic acids, epimeric at C-12, was not observed. Eicosa-5(Z),8(Z),14(Z)-trienoic acid (ET), previously described as a good substrate of 5-lipoxygenase, is oxidized mainly to 5Hydroperoxyeicosa-6,8,14-trienoic acid (5-OOH-ET), which does not serve as a substrate for the leukotriene A4 (LTA4) synthase activity of 5-lipoxygenase [Nave, Dulery, Gaget & Ducep (1988) Prostaglandins 36, 385-398]. To allow a better estimation of the effect of fluorine substitution on the rate of oxidation of the 5,8-cis,cis-diene moiety by 5-lipoxygenase, the 5– and 6-fluoro derivatives of ET were studied as substrates. Qualitatively, the metabolism of 5F-ET and 6F-ET was found to be similar to that observed for 5F-ETE and 6F-ETE. Quantitatively, 6F-ET proved to be a somewhat better substrate than ET, whereas 5F-ET was poorly metabolized. The relative ability of arachidonic acid, ET and the corresponding 5– and 6-fluoro derivatives to inhibit the 5-lipoxygenase-catalysed oxidation of eicosa-5(Z),8(Z)-dienoic acid (ED) was also investigated. 6F-ETE and 5F-ETE were found to be effective and about equipotent inhibitors of 5-lipoxygenase in the micromolar range. In view of their close structural similarity to arachidonic acid, these two inhibitors are expected to be important tools in the study of the 5-lipoxygenase pathway in vivo.

  • Evaluation of 5– and 6-fluoro derivatives of arachidonic acid and 5,8,14-eicosatrienoic acid as substrates and inhibitors of 5-lipoxygenase.
    The Biochemical journal, 1991
    Co-Authors: J F Navé, C Gaget, D Jacobi, B Dulery, Jean Bernard Ducep
    Abstract:

    The 5– and 6-fluoro derivatives of arachidonic acid (5F-ETE and 6F-ETE) were evaluated as substrates of rat basophilic leukaemia cell (RBL-1) 5-lipoxygenase. 5F-ETE was found to be a poor substrate and was converted into a single product, 5-oxoeicosa-6,8,11,14-tetraenoic acid (5-oxo-ETE). 6F-ETE was a good substrate and was mainly converted into 5Hydroperoxy6-fluoroeicosa-6,8,11,14-tetraenoic acid (5-OOH-6F-ETE) with concomitant formation of a small amount of 5-oxo-6-fluoroeicosa-6,8,11,14-tetraenoic acid (5-oxo-6F-ETE). However the formation of 5,12-dihydroxy-6-fluoroeicosa-6,8,10,14-tetraenoic acids, epimeric at C-12, was not observed. Eicosa-5(Z),8(Z),14(Z)-trienoic acid (ET), previously described as a good substrate of 5-lipoxygenase, is oxidized mainly to 5Hydroperoxyeicosa-6,8,14-trienoic acid (5-OOH-ET), which does not serve as a substrate for the leukotriene A4 (LTA4) synthase activity of 5-lipoxygenase [Navé, Dulery, Gaget & Ducep (1988) Prostaglandins 36, 385-398]. To allow a better estimation of the effect of fluorine substitution on the rate of oxidation of the 5,8-cis,cis-diene moiety by 5-lipoxygenase, the 5– and 6-fluoro derivatives of ET were studied as substrates. Qualitatively, the metabolism of 5F-ET and 6F-ET was found to be similar to that observed for 5F-ETE and 6F-ETE. Quantitatively, 6F-ET proved to be a somewhat better substrate than ET, whereas 5F-ET was poorly metabolized. The relative ability of arachidonic acid, ET and the corresponding 5– and 6-fluoro derivatives to inhibit the 5-lipoxygenase-catalysed oxidation of eicosa-5(Z),8(Z)-dienoic acid (ED) was also investigated. 6F-ETE and 5F-ETE were found to be effective and about equipotent inhibitors of 5-lipoxygenase in the micromolar range. In view of their close structural similarity to arachidonic acid, these two inhibitors are expected to be important tools in the study of the 5-lipoxygenase pathway in vivo.

C Gaget – One of the best experts on this subject based on the ideXlab platform.

  • evaluation of 5 and 6 fluoro derivatives of arachidonic acid and 5 8 14 eicosatrienoic acid as substrates and inhibitors of 5 lipoxygenase
    Biochemical Journal, 1991
    Co-Authors: Jeanfrancois Nave, D Jacobi, C Gaget, B Dulery, Jean Bernard Ducep
    Abstract:

    The 5– and 6-fluoro derivatives of arachidonic acid (5F-ETE and 6F-ETE) were evaluated as substrates of rat basophilic leukaemia cell (RBL-1) 5-lipoxygenase. 5F-ETE was found to be a poor substrate and was converted into a single product, 5-oxoeicosa-6,8,11,14-tetraenoic acid (5-oxo-ETE). 6F-ETE was a good substrate and was mainly converted into 5Hydroperoxy6-fluoroeicosa-6,8,11,14-tetraenoic acid (5-OOH-6F-ETE) with concomitant formation of a small amount of 5-oxo-6-fluoroeicosa-6,8,11,14-tetraenoic acid (5-oxo-6F-ETE). However the formation of 5,12-dihydroxy-6-fluoroeicosa-6,8,10,14-tetraenoic acids, epimeric at C-12, was not observed. Eicosa-5(Z),8(Z),14(Z)-trienoic acid (ET), previously described as a good substrate of 5-lipoxygenase, is oxidized mainly to 5Hydroperoxyeicosa-6,8,14-trienoic acid (5-OOH-ET), which does not serve as a substrate for the leukotriene A4 (LTA4) synthase activity of 5-lipoxygenase [Nave, Dulery, Gaget & Ducep (1988) Prostaglandins 36, 385-398]. To allow a better estimation of the effect of fluorine substitution on the rate of oxidation of the 5,8-cis,cis-diene moiety by 5-lipoxygenase, the 5– and 6-fluoro derivatives of ET were studied as substrates. Qualitatively, the metabolism of 5F-ET and 6F-ET was found to be similar to that observed for 5F-ETE and 6F-ETE. Quantitatively, 6F-ET proved to be a somewhat better substrate than ET, whereas 5F-ET was poorly metabolized. The relative ability of arachidonic acid, ET and the corresponding 5– and 6-fluoro derivatives to inhibit the 5-lipoxygenase-catalysed oxidation of eicosa-5(Z),8(Z)-dienoic acid (ED) was also investigated. 6F-ETE and 5F-ETE were found to be effective and about equipotent inhibitors of 5-lipoxygenase in the micromolar range. In view of their close structural similarity to arachidonic acid, these two inhibitors are expected to be important tools in the study of the 5-lipoxygenase pathway in vivo.

  • Evaluation of 5– and 6-fluoro derivatives of arachidonic acid and 5,8,14-eicosatrienoic acid as substrates and inhibitors of 5-lipoxygenase.
    The Biochemical journal, 1991
    Co-Authors: J F Navé, C Gaget, D Jacobi, B Dulery, Jean Bernard Ducep
    Abstract:

    The 5– and 6-fluoro derivatives of arachidonic acid (5F-ETE and 6F-ETE) were evaluated as substrates of rat basophilic leukaemia cell (RBL-1) 5-lipoxygenase. 5F-ETE was found to be a poor substrate and was converted into a single product, 5-oxoeicosa-6,8,11,14-tetraenoic acid (5-oxo-ETE). 6F-ETE was a good substrate and was mainly converted into 5Hydroperoxy6-fluoroeicosa-6,8,11,14-tetraenoic acid (5-OOH-6F-ETE) with concomitant formation of a small amount of 5-oxo-6-fluoroeicosa-6,8,11,14-tetraenoic acid (5-oxo-6F-ETE). However the formation of 5,12-dihydroxy-6-fluoroeicosa-6,8,10,14-tetraenoic acids, epimeric at C-12, was not observed. Eicosa-5(Z),8(Z),14(Z)-trienoic acid (ET), previously described as a good substrate of 5-lipoxygenase, is oxidized mainly to 5Hydroperoxyeicosa-6,8,14-trienoic acid (5-OOH-ET), which does not serve as a substrate for the leukotriene A4 (LTA4) synthase activity of 5-lipoxygenase [Navé, Dulery, Gaget & Ducep (1988) Prostaglandins 36, 385-398]. To allow a better estimation of the effect of fluorine substitution on the rate of oxidation of the 5,8-cis,cis-diene moiety by 5-lipoxygenase, the 5– and 6-fluoro derivatives of ET were studied as substrates. Qualitatively, the metabolism of 5F-ET and 6F-ET was found to be similar to that observed for 5F-ETE and 6F-ETE. Quantitatively, 6F-ET proved to be a somewhat better substrate than ET, whereas 5F-ET was poorly metabolized. The relative ability of arachidonic acid, ET and the corresponding 5– and 6-fluoro derivatives to inhibit the 5-lipoxygenase-catalysed oxidation of eicosa-5(Z),8(Z)-dienoic acid (ED) was also investigated. 6F-ETE and 5F-ETE were found to be effective and about equipotent inhibitors of 5-lipoxygenase in the micromolar range. In view of their close structural similarity to arachidonic acid, these two inhibitors are expected to be important tools in the study of the 5-lipoxygenase pathway in vivo.

D Jacobi – One of the best experts on this subject based on the ideXlab platform.

  • evaluation of 5 and 6 fluoro derivatives of arachidonic acid and 5 8 14 eicosatrienoic acid as substrates and inhibitors of 5 lipoxygenase
    Biochemical Journal, 1991
    Co-Authors: Jeanfrancois Nave, D Jacobi, C Gaget, B Dulery, Jean Bernard Ducep
    Abstract:

    The 5– and 6-fluoro derivatives of arachidonic acid (5F-ETE and 6F-ETE) were evaluated as substrates of rat basophilic leukaemia cell (RBL-1) 5-lipoxygenase. 5F-ETE was found to be a poor substrate and was converted into a single product, 5-oxoeicosa-6,8,11,14-tetraenoic acid (5-oxo-ETE). 6F-ETE was a good substrate and was mainly converted into 5Hydroperoxy6-fluoroeicosa-6,8,11,14-tetraenoic acid (5-OOH-6F-ETE) with concomitant formation of a small amount of 5-oxo-6-fluoroeicosa-6,8,11,14-tetraenoic acid (5-oxo-6F-ETE). However the formation of 5,12-dihydroxy-6-fluoroeicosa-6,8,10,14-tetraenoic acids, epimeric at C-12, was not observed. Eicosa-5(Z),8(Z),14(Z)-trienoic acid (ET), previously described as a good substrate of 5-lipoxygenase, is oxidized mainly to 5Hydroperoxyeicosa-6,8,14-trienoic acid (5-OOH-ET), which does not serve as a substrate for the leukotriene A4 (LTA4) synthase activity of 5-lipoxygenase [Nave, Dulery, Gaget & Ducep (1988) Prostaglandins 36, 385-398]. To allow a better estimation of the effect of fluorine substitution on the rate of oxidation of the 5,8-cis,cis-diene moiety by 5-lipoxygenase, the 5– and 6-fluoro derivatives of ET were studied as substrates. Qualitatively, the metabolism of 5F-ET and 6F-ET was found to be similar to that observed for 5F-ETE and 6F-ETE. Quantitatively, 6F-ET proved to be a somewhat better substrate than ET, whereas 5F-ET was poorly metabolized. The relative ability of arachidonic acid, ET and the corresponding 5– and 6-fluoro derivatives to inhibit the 5-lipoxygenase-catalysed oxidation of eicosa-5(Z),8(Z)-dienoic acid (ED) was also investigated. 6F-ETE and 5F-ETE were found to be effective and about equipotent inhibitors of 5-lipoxygenase in the micromolar range. In view of their close structural similarity to arachidonic acid, these two inhibitors are expected to be important tools in the study of the 5-lipoxygenase pathway in vivo.

  • Evaluation of 5– and 6-fluoro derivatives of arachidonic acid and 5,8,14-eicosatrienoic acid as substrates and inhibitors of 5-lipoxygenase.
    The Biochemical journal, 1991
    Co-Authors: J F Navé, C Gaget, D Jacobi, B Dulery, Jean Bernard Ducep
    Abstract:

    The 5– and 6-fluoro derivatives of arachidonic acid (5F-ETE and 6F-ETE) were evaluated as substrates of rat basophilic leukaemia cell (RBL-1) 5-lipoxygenase. 5F-ETE was found to be a poor substrate and was converted into a single product, 5-oxoeicosa-6,8,11,14-tetraenoic acid (5-oxo-ETE). 6F-ETE was a good substrate and was mainly converted into 5Hydroperoxy6-fluoroeicosa-6,8,11,14-tetraenoic acid (5-OOH-6F-ETE) with concomitant formation of a small amount of 5-oxo-6-fluoroeicosa-6,8,11,14-tetraenoic acid (5-oxo-6F-ETE). However the formation of 5,12-dihydroxy-6-fluoroeicosa-6,8,10,14-tetraenoic acids, epimeric at C-12, was not observed. Eicosa-5(Z),8(Z),14(Z)-trienoic acid (ET), previously described as a good substrate of 5-lipoxygenase, is oxidized mainly to 5Hydroperoxyeicosa-6,8,14-trienoic acid (5-OOH-ET), which does not serve as a substrate for the leukotriene A4 (LTA4) synthase activity of 5-lipoxygenase [Navé, Dulery, Gaget & Ducep (1988) Prostaglandins 36, 385-398]. To allow a better estimation of the effect of fluorine substitution on the rate of oxidation of the 5,8-cis,cis-diene moiety by 5-lipoxygenase, the 5– and 6-fluoro derivatives of ET were studied as substrates. Qualitatively, the metabolism of 5F-ET and 6F-ET was found to be similar to that observed for 5F-ETE and 6F-ETE. Quantitatively, 6F-ET proved to be a somewhat better substrate than ET, whereas 5F-ET was poorly metabolized. The relative ability of arachidonic acid, ET and the corresponding 5– and 6-fluoro derivatives to inhibit the 5-lipoxygenase-catalysed oxidation of eicosa-5(Z),8(Z)-dienoic acid (ED) was also investigated. 6F-ETE and 5F-ETE were found to be effective and about equipotent inhibitors of 5-lipoxygenase in the micromolar range. In view of their close structural similarity to arachidonic acid, these two inhibitors are expected to be important tools in the study of the 5-lipoxygenase pathway in vivo.

J F Navé – One of the best experts on this subject based on the ideXlab platform.

  • Evaluation of 5– and 6-fluoro derivatives of arachidonic acid and 5,8,14-eicosatrienoic acid as substrates and inhibitors of 5-lipoxygenase.
    The Biochemical journal, 1991
    Co-Authors: J F Navé, C Gaget, D Jacobi, B Dulery, Jean Bernard Ducep
    Abstract:

    The 5– and 6-fluoro derivatives of arachidonic acid (5F-ETE and 6F-ETE) were evaluated as substrates of rat basophilic leukaemia cell (RBL-1) 5-lipoxygenase. 5F-ETE was found to be a poor substrate and was converted into a single product, 5-oxoeicosa-6,8,11,14-tetraenoic acid (5-oxo-ETE). 6F-ETE was a good substrate and was mainly converted into 5Hydroperoxy6-fluoroeicosa-6,8,11,14-tetraenoic acid (5-OOH-6F-ETE) with concomitant formation of a small amount of 5-oxo-6-fluoroeicosa-6,8,11,14-tetraenoic acid (5-oxo-6F-ETE). However the formation of 5,12-dihydroxy-6-fluoroeicosa-6,8,10,14-tetraenoic acids, epimeric at C-12, was not observed. Eicosa-5(Z),8(Z),14(Z)-trienoic acid (ET), previously described as a good substrate of 5-lipoxygenase, is oxidized mainly to 5Hydroperoxyeicosa-6,8,14-trienoic acid (5-OOH-ET), which does not serve as a substrate for the leukotriene A4 (LTA4) synthase activity of 5-lipoxygenase [Navé, Dulery, Gaget & Ducep (1988) Prostaglandins 36, 385-398]. To allow a better estimation of the effect of fluorine substitution on the rate of oxidation of the 5,8-cis,cis-diene moiety by 5-lipoxygenase, the 5– and 6-fluoro derivatives of ET were studied as substrates. Qualitatively, the metabolism of 5F-ET and 6F-ET was found to be similar to that observed for 5F-ETE and 6F-ETE. Quantitatively, 6F-ET proved to be a somewhat better substrate than ET, whereas 5F-ET was poorly metabolized. The relative ability of arachidonic acid, ET and the corresponding 5– and 6-fluoro derivatives to inhibit the 5-lipoxygenase-catalysed oxidation of eicosa-5(Z),8(Z)-dienoic acid (ED) was also investigated. 6F-ETE and 5F-ETE were found to be effective and about equipotent inhibitors of 5-lipoxygenase in the micromolar range. In view of their close structural similarity to arachidonic acid, these two inhibitors are expected to be important tools in the study of the 5-lipoxygenase pathway in vivo.