Lipoxygenase - A versatile biocatalyst for biotransformation of endobiotics and xenobiotics

Cellular and Molecular Life Sciences

Volumn 58, Issue 12-13, 2001, Pages 1805-1825

  Kulkarni, A P ^a  

^a UNIVERSITY OF SOUTH FLORIDA   (United States)

Author keywords

Carcinogen bioactivation; Co oxidation; Free radical; Glutathione conjugation; Lipoxygenase induction and inhibition; Reactive metabolite; Teratogen; Xenobiotic oxidation

Indexed keywords

1 [3 [5 (4 FLUOROPHENOXY) 2 FURYL] 1 METHYL 2 PROPYNYL] 1 HYDROXYUREA; 3 [3 TERT BUTYLTHIO 1 (4 CHLOROBENZYL) 5 ISOPROPYL 2 INDOLYL] 2,2 DIMETHYLPROPIONIC ACID; ALIMEMAZINE; CHLORPROMAZINE; FREE RADICAL; LINAZOLAST; LIPOXYGENASE; PHENOTHIAZINE DERIVATIVE; POLYUNSATURATED FATTY ACID; PROMAZINE; PROMETHAZINE; XENOBIOTIC AGENT;

CARCINOGENESIS; CHEMICAL ANALYSIS; CONJUGATION; DEALKYLATION; DESULFURIZATION; ELECTRON TRANSPORT; ENZYME ACTIVATION; ENZYME ACTIVITY; ENZYME INDUCTION; ENZYME INHIBITION; EPOXIDATION; HUMAN; HYDROXYLATION; INHIBITION KINETICS; MODULATION; NONHUMAN; OXIDATION; REVIEW; XENOBIOTIC METABOLISM;

MAMMALIA;

EID: 0035201922     PISSN: 1420682X     EISSN: None     Source Type: Journal    
DOI: 10.1007/PL00000820     Document Type: Review

References (191)

1. Lipoxygenases
2. Enzymology and physiology of reticulocyte lipoxygenase: Comparison with other lipoxygenases
3. Lipoxygenases and hydroperoxy/hydroxy-eicosatetraenoic acid formation
4. Arachidonic acid metabolism in airway epithelial cells
5. Lipoxygenase as a versatile biocatalyst
6. Lipoxygenase: Occurrence, functions, catalysis, and acquisition of substrate
7. The discovery of the leukotrienes
8. Mammalian lipoxygenases: Molecular structure and functions
9. The molecular biology of mammalian lipoxygenases and the quest for eicosanoid functions using lipoxygenase-deficient mice
10. The diversity of the lipoxygenase family: Many sequence data but little information on biological significance
11. Molecular cloning of a second human 15S-lipoxygenase and its murine homologue, an 8S-lipoxygenase
12. Expression of leukocyte-type 12-lipoxygenase and reticulocyte-type 15-lipoxygenase in rabbits
13. Insight into prostaglandin, leukotriene, and other eicosanoid functions using mice with targeted gene disruptions
14. 5-Lipoxygenase and leukotrienes: Transgenic mouse and nuclear targeting studies
15. The molecular biology and regulation of 5-lipoxygenase
16. The structure and function of lipoxygenase
17. Lipoxygenases: Structural principles and spectroscopy
18. Regio- and stereochemistry of the dioxygenation reaction catalyzed by (S)-type lipoxygenases or by the cyclooxygenase activity of prostaglandin H synthases
19. Leukotrienes and lipoxins: Structures, biosynthesis, and biological effects
20. The neutrophil and leukotrienes-role in health and disease
21. 12-(S)-HETE in cancer metastasis
22. 5-Lipoxygenase
23. The enzymology and pharmacology of 5-lipoxygenase and 5-lipoxygenase activating protein
24. The biology of lipoxygenase: Function, structure, and regulatory mechanisms
25. 5-Lipoxygenase: A target for antiinflammatory drugs revisited
26. Regulation of expression of the 5-lipoxygenase pathway
27. Arachidonate 12-lipoxygenase isozymes
28. 12-Lipoxygenase: Classification, possible therapeutic benefits from inhibition and inhibitors
29. Mammalian 15-lipoxygenases: Enzymatic properties and biological implications
30. Regulation of cellular 15-lipoxygenase activity on pretranslational, translational, and posttranslational levels
31. Probing the substrate alignment at the active site of 15-lipoxygenases by targeted substrate modification and site-directed mutagenesis: Evidence for an inverse substrate orientation
32. Identification of amino acid determinants of the positional specificity of mouse 8S-lipoxygenase and human 15S-lipoxygenase-2
33. Structural basis for the positional specificity of lipoxygenases
34. The arachidonate 12/15 lipoxygenases: A review of tissue expression and biologic function
35. Recent progress on the study of lipoxygenases-discovery of novel isozymes and molecular evolution
36. Cooxidation of acrylonitrile by soybean lipoxygenase and partially purified human lung lipoxygenase
37. Bioactivation of benzo(a)pyrene-7,8-dihydrodiol catalyzed by lipoxygenase purified from human term placenta and conceptal tissues
38. A simple and efficient method for hemoglobin removal from mammalian tissue cytosol by zinc sulfate and its application to the study of lipoxygenase
39. Intracellular compartmentalization of leukotrine biosynthesis
40. Linoleic acid peroxidation-the dominant lipid peroxidation process in low density lipoprotein and its relationship to chronic diseases
41. The oxidation of lipoproteins by monocytes-macrophages: Biochemical and biological mechanisms
42. Measurements of arachidonic acid metabolites derived from the lipoxygenase pathway by high-pressure liquid chromatography
43. Affinities of mammalian arachidonate lipoxygenases and cyclooxygenases for molecular oxygen as substrate
44. Dioxygenase and peroxidase activities of soybean lipoxygenase: Synergistic interaction between linoleic acid and hydrogen peroxide
45. Hydrogen peroxide: A potent activator of dioxygenase activity of soybean lipoxygenase
46. Hydroperoxidase activity of lipoxygenase: A potential pathway for xenobiotic metabolism in the presence of linoleic acid
47. Metabolic activation of aromatic amines by human pancreas
48. Triple primary cancers involving kidney, urinary bladder and liver in a dye worker
49. Benzidine mechanistic data and risk assessment: Species- and organ-specific metabolic activation
50. Co-oxidation of benzidine by renal medullary prostaglandin cyclooxygenase
51. Prostaglandin endoperoxide synthase: Structure and catalysis
52. Hydroperoxidase activity of lipoxygenase: Hydrogenperoxide-dependent oxidation of xenobiotics
53. Cytochrome P-450 as a microsomal peroxidase utilizing a lipid peroxide substrate
54. Bioactivation of xenobiotics by prostaglandin H synthase
55. Role of lipoxygenase in xenobiotic oxidation: Parathion metabolism catalyzed by highly purified soybean lipoxygenase
56. Arachidonic acid-dependent activation of benzo(a)pyrene to bind to protein with cytosolic and microsomal fractions from rat liver and lung
57. 1 in human lung
58. Coincubation of rat renal proximal tubules with hepatic subcellular fractions potentiates the effects of para-aminophenol
59. Studies of paracetamol/phenacetin toxicity: Isolation and characterization of p-aminophenol-glutathione conjugate
60. Lipoxygenase-mediated biotransformation of p-aminophenol in the presence of glutathione: Possible conjugate formation
61. Lipoxygenase-mediated N-demethylation of imipramine and related tricyclic antidepressants in the presence of hydrogen peroxide
62. Aldrin epoxidation: Catalytic potential of lipoxygenase coupled with linoleic acid oxidation
63. N-dealkylation of aminopyrine catalyzed by soybean lipoxygenase in the presence of hydrogen peroxide
64. Role of lipoxygenase in xenobiotic metabolism: Sulfoxidation of thiobenzamide by purified soybean lipoxygenase
65. Formation of free radical metabolites in the reaction between soybean lipoxygenase and its inhibitors: An ESR study
66. Peroxidase-like activity of lipoxygenase: Ddifferent substrate specificity of potato 5-lipoxygenase and soybean 15-lipoxygenase and particular affinity of vitamin E derivatives for the 5-lipoxygenase
67. Epoxidation of 7,8-dihydroxy-7,8 dihydrobenzo(a) pyrene via a hydroperoxide-dependent mechanism catalyzed by lipoxygenase
68. Soybean lipoxygenase-catalyzed oxidations by linoleic acid hydroperoxide: Different reducing substrates and dehydrogenation of phenidone and BW755C
69. Pseudoperoxidase activity of 5-lipoxygenase stimulated by potent benzofuranol and N-hydroxyurea inhibitors of the lipoxygenase reaction
70. Nitroxide metabolites from alkylhydroxylamines and N-hydroxyurea derivatives resulting from reductive inhibition of soybean lipoxygenase
71. Lipoxygenase-catalyzed oxidation of chlorpromazine by hydrogen peroxide at acidic pH
72. 2 system
73. Oxidation of aminopyrine by the hydroperoxidase activity of lipoxygenase: A new proposed mechanism of N-demethylation
74. Lipoxygenase-catalyzed oxidation of catecholamines
75. Co-oxidative metabolism of 4-aminobiphenyl by lipoxygenase from soybean and human term placenta
76. Hydroperoxide specificity of plant and human tissue lipoxygenase: An in vitro evaluation using N-demethylation of phenothiazines
77. Lipoxygenase-catalyzed epoxidation of benzo(a) pyrene-7,8-dihydrodiol
78. Metabolic fate of chemical mixtures. I. Shuttle oxidant effect of lipoxygenase-generated radical of chlorpromazine and related phenothiazines on the oxidation of benzidine and other xenobiotics
79. Hexanal phenyl hydrazone is a mechanism-based inactivator of soybean lipoxygenase-1
80. 2-[(4″-Hydroxy-3′-methoxy)-phenoxy]-4-(4″-hydroxy- 3″methoxy-phenyl)-8-hydroxy-6-oxo-3-oxabiclo[3.3.0]-7-octene: Unusual product of the soybean lipoxygenase-catalyzed oxygenation of curcumin
81. New minimal substrate structural requirements in the enzymatic peroxidation of alkenes with soybean lipoxygenase
82. Synergistic interaction between the probucol phenoxyl radical and ascorbic acid in inhibiting the oxidation of low density lipoprotein
83. Activation of 4-(methylnitrosamino)-1-(3-pyridyl)-1-butanone (NNK) in human lung microsomes by cytochrome P450, lipoxygenase and hydroperoxides
84. Inhibitors of lipoxygenase: A new class of cancer chemopreventive agents
85. Co-oxidation of NADH and NADPH by a mammalian 15-lipoxygenase: Inhibition of lipoxygenase activity at near-physiological NADH concentrations
86. One and two electron oxidation of reduced glutathione by peroxidases
87. Oxidation of glutathione to its thiyl free radical metabolite by prostaglandin H synthase: A potential endogenous substrate for the hydroperoxidase
88. Lipoxygenase mediated glutathione oxidation and superoxide generation
89. A novel mechanism of glutathione conjugation formation by lipoxygenase: A study with ethacrynic acid
90. Glutathione conjugation of ethacrynic acid by human term placental lipoxygenase
91. Pheomelanin production by the lipoxygenase-catalyzed oxidation of 5-S-cysteinyldopa and 5-S-cysteinyldopamine
92. Melanins from tetrahydroisoquinolines: Spectroscopic characteristics, scavenging activity and redox transfer properties
93. 2-catalyzed oxidation of dihydroxyindoles: Synthesis of melanin pigments and study of their antioxidant properties
94. Lipoxygenase: A new pathway for 2-aminofluorene bioactivation
95. Fatty acid-stimulated oxidation of methylazoxy-methanol by rat colonic mucosa
96. In vitro evidence for lipoxygenase-catalyzed bioactivation of phenytoin
97. Evidence for lipoxygenase-catalyzed bioactivation of phenytoin to a teratogenic reactive intermediate: In vitro studies using linoleic acid-dependent soybean lipoxygenase, and in vivo studies using pregnant CD-1 mice
98. Metabolism of cyclophosphamide by lipoxygenases
99. Hydroperoxidative oxidation of diethylstilbestrol by lipoxygenase
100. Hydroperoxidase activity of lipoxygenase: A kinetic study of isoproterenol oxidation
101. Reductive inactivation of soybean lipoxygenase 1 by catechols: A possible mechanism for regulation of lipoxygenase activity
102. Hydroperoxidase activity of lipoxygenase in the presence of cyclodextrins
103. Oxidation of oxyphenbutazone by sheep vesicular gland microsomes and lipoxygenase
104. Enzymes involved in the bioactivation of 4-(methylnitrosamino)-1-(3-pyridyl)-1-butanone in patas monkey lung and liver microsomes
105. Inhibition of lung tumorigenesis by NSAIDS: A working hypothesis
106. Co-oxidation of $-carotene catalysed by soybean and recombinant pea lipoxygenases
107. Co-oxidation of t-retinol acetate by human term placental lipoxygenase and soybean lipoxygenase
108. Purification and catalytic properties of chickpea lipoxygenases
109. 5,6-Epoxidation of all-trans-retinoic acid with soybean lipoxygenase-2 and lipoxygenase-3
110. Stereochemical studies of epoxides formed by lipoxygenase-catalyzed co-oxidation of retinol, β-ionone and 4-hydroxy-β-ionone
111. Induction of cytotoxicity and mutagenesis is facilitated by fatty acid hydroperoxidase activity in Chinese hamster lung fibroblast (V79 cells)
112. Fatty acid induced drug and carcinogen metabolism in rat and human colonic mucosa: A possible link to the association of high dietary fat intake and colonic carcinogenesis
113. Fatty acid-dependent benzo(a)pyrene oxidation in colonic mucosal microsomes: Evidence for a distinct metabolic pathway
114. Effect of aspirin and indomethacin on the formation of benzo(a)pyrene-induced pulmonary adenomas and DNA adducts in A/HeJ mice
115. NADPH-supported and arachidonic acid-supported metabolism of the enantiomers of trans-7,8-dihydrobenzo(a) pyrene-7,8-diol by human liver microsomal samples
116. Prostaglandin H synthase-dependent cooxidation of (±)-7,8-dihydroxy-7,8-dihydrobenzo[a]pyrene in hamster trachea and human bronchus explants
117. Detection of benzo(a)pyrene diol epoxide-DNA adducts in human placenta
118. 1 as detected in vitro in a simple fluorimetric assay
119. Inhibition of the metabolism of the mutagens occurring in food by arachidonic acid
120. 1-2,3-oxide: Evidence for its formation in rat liver in vivo and by human liver microsomes
121. 1 by lipoxygenases, prostaglandin H synthase and cytochrome P450 monooxygenase in guinea pig tissues
122. 1 epoxidation catalyzed by partially purified adult human liver lipoxygenase
123. 1 by lipoxygenase purified from human term placenta and intrauterine conceptal tissues
124. Roles of cyclooxygenase and lipoxygenases in ochratoxin A genotoxicity in human epithelial cells
125. The formation of styrene glutathione adduct catalyzed by prostaglandin H synthase: A possible new mechanism for the formation of glutathione conjugates
126. Styrene oxidation to styrene oxide coupled with arachidonic acid oxidation by soybean lipoxygenase
127. Metabolism of acrylonitrile to 2-cyanoethylene oxide in F-344 rat liver microsomes, lung microsomes and lung cells
128. A physiologically based dosimetry description of acrylonitrile and cyanoethylene oxide in the rat
129. N-demethylation of phenothiazines by lipoxygenase from soybean and human term placenta in the presence of hydrogen peroxide
130. Human term placental lipoxygenase-mediated N-demethylation of phenothiazines and pesticides in the presence of polyunsaturated fatty acids
131. Lipoxygenase-mediated hydrogen peroxide-dependent N-demethylation of N,N′-dimethylaniline and related compounds
132. Metabolism of aminopyrine and derivatives in man: In vivo study of monomorphic and polymorphic metabolic pathways
133. Soybean lipoxygenase-catalyzed demethylation of pesticides
134. Inhibition of soybean lipoxygenase by SKF 525-A and metyrapone
135. Denaturation of cytochrome P-450 by indomethacin and other non-steroidal anti-inflammatory drugs: Evidence for a surfactant mechanism and a selective effect of a D-chlorophenyl moiety
136. Aspirin-like drugs inhibit arachidonic acid metabolism via lipoxygenase and cyclooxygenase in rat neutrophils from carrageenan exudates
137. Indomethacin increases the formation of lipoxygenase products in calcium ionophore stimulated human neutrophils
138. Indomethacin inhibits arachidonic acid metabolism via lipoxygenase and cyclo-oxygenase in hamster isolated lungs
139. Potential use of lipoxygenase inhibitors for cancer chemoprevention
140. Pharmacological aspects of 5-lipoxygenase inhibition
141. 5-Lipoxygenase inhibitors and their anti-inflammatory activities
142. Biosynthesis inhibitors for leukotrienes in bronchial asthma
143. 15-Lipoxygenase and its inhibition: A novel therapeutic target for vascular disease
144. A selective inhibitor of arachidonate 5-lipoxygenase scavenging peroxide activator
145. (Carboxyalkyl) benzyl propargyl ethers as selective inhibitors of leukocyte-type 12-lipoxygenases
146. Generation and recycling of radicals from phenolic antioxidants
147. The role of prostaglandin H synthase-mediated metabolism in the induction of oxidative DNA damage by BHA metabolites
148. A kinetic study of the one-electron oxidation of Trolox C by the hydroperoxidase activity of lipoxygenase
149. Resveratrol is a potent inhibitor of dioxygenase activity of lipoxygenase
150. Inactivation of lipoxygenase by inhibitors in the presence of 15-hydroperoxyeicosatetraenoic acid
151. Inhibition of soybean lipoxygenase 1 by N-alkylhydroxylamines
152. N-(4-chlorophenyl)-N-hydroxy-N′-(3-chlorophenyl) urea, a general reducing agent for 5-, 12-, and 15-lipoxygenases and a substrate for their pseudoperoxidase activities
153. Inhibition of soybean lipoxygenase-1 by a diaryl-N-hydroxyurea by reduction of the ferric enzyme
154. Inhibition of mammalian 5-lipoxygenase by aromatic disulfides
155. Inhibition of soybean lipoxygenase-1 by n-alcohols and n-alkylthiols
156. Effect of naturally occurring flavonoids and biflavonoids on epidermal cyclooxygenase and lipoxygenase from guinea pigs
157. Inhibition of cyclooxygenase/lipoxygenase from human platelets by polyhydroxylated/methoxylated flavonoids isolated from medicinal plants
158. Renal oxygenases: Differential contribution to vasoconstriction induced by ET-1 and ANG II
159. Human renal lipoxygenase
160. Mechanism of phosgene-induced lung toxicity: Role of arachidonate mediators
161. 15-Lipoxygenase induction as an index of oxidative stress and atherogenesis
162. Systemic activation of 15-lipoxygenase in heart, lung, and vascular tissues by hypercholesterolemia: Relationship to lipoprotein oxidation and atherogenesis
163. Activation of 12- and 15-lipoxygenase in the cardiopulmonary system by hemorrhagic events
164. The role of cyclooxygenase and lipoxygenase mediators in oxidant-induced lung injury
165. Nedocromil sodium prevents the release of 15-hydroxyeicosatetraenoic acid from human epithelial cells exposed to toluene diisocyanate in vitro
166. Acrolein stimulates eicosanoid release from bovine airway epithelial cells
167. Assay of liver cytosol lipoxygenase by differential pulse polarography
168. Liver lipoxygenase arachidonic acid metabolites in streptozotocin-induced diabetes in rats
169. Streptozotocin-induced diabetes is associated with increased renal lipoxygenase activity
170. Inhibition of two-stage skin carcinogenesis as well as complete skin carcinogenesis by oral administration of TMK688, a potent lipoxygenase inhibitor
171. Activity and protein distribution of 12-lipoxygenase in HEL cells: Induction of membrane-association by phorbol ester TPA, modulation of activity by glutathione and 13-HPOD, and Ca2+-dependent translocation to membranes
172. Induction of 12-lipoxygenase expression by phorbol 12-myristate 13-acetate in human epidermoid carcinoma A431 cells
173. Uptake, production and metabolism of cysteinyl leukotrienes in the isolated perfused rat liver
174. Production of Chemotactic activity for polymorphonuclear leukocytes by cultured rat hepatocytes exposed to ethanol
175. Endotoxin-induced lung injury in rats: Role of eicosanoids
176. Increased 5-lipoxygenase metabolism in the lungs of human subjects exposed to ozone
177. Phorbol ester induction of 8-lipoxygenase in inbred SENCAR (SSIN) but not C57/BL/6J mice correlated with hyperplasia, edema, and oxidant generation but not ornithine decarboxylase induction
178. Influence of N-phenyllinoleamide from toxic oil samples on the lipoxygenase metabolism of exogenous arachidonic acid in mouse peritoneal macrophages
179. On the induction of 5-lipoxygenase expression and activity in HL-60 cells: Effects of vitamin-D3, retinoic acid, DMSO and TGF-beta
180. Regulation of 5-lipoxygenase activity by the glutathione status in human polymorphonuclear leukocytes
181. Involvement of glutathione peroxidase activity in the stimulation of 5-lipoxygenase activity by glutathione-depleting agents in human polymorphonuclear' leukocytes
182. 4 in the immune system
183. Indomethacin increases the formation of lipoxygenase products in calcium ionophore stimulated human neutrophils
184. 5-Lipoxygenase upregulation by dexamethasone in human mast cells
185. Dexamethasone increases expression of 5-lipoxygenase and its activating protein in human monocytes and THP-1 Cells
186. Regulation of 12-lipoxygenase in rat intestinal epithelial cells during differentiation and apoptosis induced by sodium butyrate
187. Expression of 5-lipoxygenase by human colorectal carcinoma Caco-2 cells during butyrate-induced cell proliferation
188. Inhibition of 12-o-tetradecanoyl-phorbol-13-acetate-caused tumor promotion in 7,12-dimethylbenz(a)anthracene-initiated Sencar mouse skin by a polyphenolic fraction isolated from green tea
189. Influence of esculetin on incidence, proliferation, and cell kinetics of mammary carcinomas induced by 7,12-dimethylbenz(a)-anthracene in rats on high and low-fat diets
190. Comparative effects of piroxicam and esculetin on incidence, proliferation, and cell kinetics of mammary carcinomas induced by 7,12-dimethylbenz(a)-anthracene in rats on high and low fat diet
191. Lipoxygenases in rat embryo tissues