The primary structure of a lipoxygenase from the shoots of etiolated lentil seedlings derived from its cDNA

Hilbers, Martin P.; Rossi, Antonello; Finazzi‐Agrò, Alessandro; Veldink, Gerrit A.; Vliegenthart, Johannes F.G.

doi:10.1016/0005-2760(94)90275-5

Cited by 23 publications

(16 citation statements)

References 16 publications

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“…The correlation matrix shows that CMR and B 1-3 are independent vectors (CMR vs. B 1-3 ¼ 0.277). The most important single parameter is B [1][2][3] . Lipophilicity and electronic effects do not contribute to the biological activity (r ¼ 0.603).…”

Section: S 2-arylalkyl-substituted Anthracenones 68mentioning

confidence: 99%

“…2a,b They contain a ''non-heme'' iron per molecule in the active site as high-spin Fe(II) in the native state, and high-spin Fe(III) in the activated state. [3][4][5] The dioxygenation involves hydrogen abstraction, the first rate-limiting step, to produce a fatty acid radical, radical rearrangement to form a conjugated diene, and oxygen insertion to produce a fatty acid peroxyl radical intermediate before the release of lipid hydroperoxide (Fig. 2).…”

Section: Introduction a The Role Of Los (General Backgrmentioning

confidence: 99%

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Lipoxygenase inhibitors: A comparative QSAR study review and evaluation of new QSARs

Pontiki

Hadjipavlou‐Litina

2006

Medicinal Research Reviews

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This paper contains a quantitative structure activity relationship (QSAR) study for lipoxygenase (LO) inhibitors. It reveals that in almost all cases, the clog P parameter plays an important part in the QSARs (linear or bilinear model). In some cases the steric factors such as the overall molar refractivity (CMR) or the substituents molar refractivity (MR) (linear or parabola) are important. Electronic effects are comparatively unimportant. The study shows that log P as calculated from the Clog P program is suitable for this form of QSAR study.

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Section: S 2-arylalkyl-substituted Anthracenones 68mentioning

confidence: 99%

Section: Introduction a The Role Of Los (General Backgrmentioning

confidence: 99%

Lipoxygenase inhibitors: A comparative QSAR study review and evaluation of new QSARs

Pontiki

Hadjipavlou‐Litina

2006

Medicinal Research Reviews

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“…The synthesis of the arylacetic acids was accomplished according to the Knoevenangel condensation as indicated in Scheme (1). Since an E2 reaction was followed, the outcome of this appears to be controlled by the relative thermodynamic stability of the products, the most stable trans double bond being formed preferentially [26].…”

Section: Synthetic Methodologymentioning

confidence: 99%

“…Lipoxygenases are monomeric proteins that contain a "non-heme" iron per molecule in the active site as high-spin Fe(II) in the native state, and high-spin Fe(III) in the activated state [1][2][3]. They catalyze the incorporation of dioxygen into 1,4-cis,cis-pentadiene containing fatty acids (e.g., linoleic and arachidonic acids) to form hydroperoxides [4][5][6].…”

Section: Introductionmentioning

confidence: 99%

“…3-(1H-indol-5-yl)-2-phenylacrylamide1 H-NMR (DMSO-d 6 , CDCl 3 ): 6.76-7.55 (br, 10H), 7.94 (s, 1H), 8.06-8.26 (m, 3H) 13 C-NMR (DMSO-d 6 , CDCl 3 ): 106, 112, 117, 118, 120, 125, 128, 130, 131, 132, 134, 136, 138, 142, 143, 144, 171 MS m/e (%): 247 (13), 219 (13), 77(12).5ii . 2-N-hydroxy-3-(2-oxo-2H-chromen-7-yl)-2-phenylacrylamide1 H-NMR (DMSO-d 6 , CDCl 3 ): 6.35 (d, 1H), 7.08-7.37 (m, 10H), 7.66-7.68 (br, 1H), 12.3 (s, 1H).…”

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confidence: 99%

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Heterocyclic Aryl(Phenyl)Acetic Acid and Aryl Acetohydroxamic Acids as Antiinflammatory -Antioxidant Agents and Inhibitors of Lipoxygenase and Serine Proteases

Michaelidou¹,

Hadjipavlou‐Litina²,

Matsini

et al. 2007

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Taking into account that compounds bearing a thiazolyl, pyridyl and indolyl, moieties possess a wide spectrum of biological activities which is related to their capacity to transfer electrons and to scavenge reactive oxygen species (ROS), we synthesized some new heterocyclic aryl acetic acids and the corresponding acetohydroxamic acids and we explored their ability to inhibit soybean lipoxygenase, to present antioxidant and anti-inflammatory activities as well as to present serine proteases inhibition. The compounds were found to strongly inhibit lipid peroxidation and to decrease in vivo the carrageenin induced rat paw edema (28-56%). Compound 1i possesses the highest decrease 56%, in vivo. The tested derivatives presented interesting inhibitory activity on soybean lipoxygenase. Compound 5ii showed significant in vitro inhibition on trypsin (IC(50) 87 microM). The results are discussed in terms of structural and physicochemical characteristics of the compounds. The structures of the synthesized compounds were confirmed by spectral and elemental analysis. Their lipophilicity is experimentally determined by RPTLC method.

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Structure conservation in lipoxygenases: Structural analysis of soybean lipoxygenase-1 and modeling of human lipoxygenases

et al. 1996

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Lipoxygenases are a class of non-heme iron dioxygenases which catalyze the hydroperoxidation of fatty acids for the biosynthesis of leukotrienes and lipoxins. The structure of the 839-residue soybean lipoxygenase-1 was used as a template to model human 5-, 12-, and 15-lipoxygenases. A distance-based algorithm for placing side chains in a low homology environment (only the four iron ligands were fixed during side chain placement) was devised. Twenty-six of the 56 conserved lipoxygenase residues were grouped in four distinct regions of the enzyme. These regions were analyzed to discern whether the side chain interactions could be duplicated in the models or whether alternate conformers should be considered. The effects of site directed mutagenesis variants were rationalized using the models of the human lipoxygenases. In particular, variants which shifted positional specificity between 12and 15-lipoxygenase activity were analyzed. Analysis of active site residues produced a model which accounts for observed lipoxygenase positional specificity and stereospecificity.

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The primary structure of a lipoxygenase from the shoots of etiolated lentil seedlings derived from its cDNA

Cited by 23 publications

References 16 publications

Lipoxygenase inhibitors: A comparative QSAR study review and evaluation of new QSARs

Lipoxygenase inhibitors: A comparative QSAR study review and evaluation of new QSARs

Heterocyclic Aryl(Phenyl)Acetic Acid and Aryl Acetohydroxamic Acids as Antiinflammatory -Antioxidant Agents and Inhibitors of Lipoxygenase and Serine Proteases

Structure conservation in lipoxygenases: Structural analysis of soybean lipoxygenase-1 and modeling of human lipoxygenases

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