Gluthione transferases and gamma-glutamyl transpeptidases

00 401mie_0121828069.jpg......Page 1
01 fm.pdf......Page 2
02 preface.pdf......Page 3
03 toc.pdf......Page 4
04 contributors.pdf......Page 7
Introduction......Page 11
References......Page 17
Human Alpha Class Glutathione S-Transferases: Genetic Polymorphism, Expression, and Susceptibility to Disease......Page 19
Introduction......Page 21
Expression......Page 22
Genetic Polymorphism......Page 26
Susceptibility to Cancer......Page 31
Response to Chemotherapy......Page 33
Cardiovascular and Other Diseases......Page 34
Immunochemistry......Page 35
"GST-alpha" in Blood Plasma and Serum......Page 36
Isoenzyme-Specific Substrates......Page 37
Genetic Polymorphisms......Page 39
Concluding Remarks......Page 41
Acknowledgments......Page 44
 GSH-affinity chromatography (all steps at 4deg)......Page 45
References......Page 46
Regulation of GST-P Gene Expression During Hepatocarcinogenesis......Page 53
Introduction......Page 54
Transactivation of GSTP Gene during Chemical Hepatocarcinogenesis......Page 58
Identification of Control Element for Tumor-Specific Expression of  GSTP Gene......Page 59
Nrf2/MafK Binds to the GPE1 Element of GST-P Gene......Page 60
Nrf2 Strongly Activates GPE1 Enhancer Element......Page 63
Nrf2 and MafK Bind to GPE1 in Preneoplastic Liver Lesions and Hepatoma Cells......Page 64
Conclusion and Discussion......Page 67
References......Page 69
Human Glutathione Transferase Zeta......Page 73
Introduction......Page 74
Discovery of GSTZ......Page 75
Maleylacetoacetate Isomerase Activity......Page 76
Xenobiotic alpha-Haloacid Substrates......Page 78
Mechanism-Based Inactivation of GSTZ by alpha-Haloacids......Page 79
GSTZ Polymorphic Variants......Page 81
Crystallographic Analysis of GSTZ......Page 84
GSTZ-/- Mouse Strains......Page 85
References......Page 86
Further Reading......Page 89
Introduction......Page 90
Discovery of the Omega Class GSTs......Page 91
Gsto Genes in Mice......Page 92
Omega Class GST Sequences......Page 95
The Crystal Structure of the Omega Class GSTs......Page 97
Tissue and Cellular Distribution of Omega Class GSTs......Page 99
Purification of GSTO1-1......Page 100
Expression and Purification of GSTO2-2......Page 101
Determination of Enzymatic Activity......Page 102
Dehydroascorbate Reductase......Page 103
Monomethylarsonate Reductase......Page 104
Genetic Polymorphism in Omega Class GSTs......Page 105
Interaction with Cytokine Release Inhibitory Drugs......Page 106
Acknowledgments......Page 107
References......Page 108
Further Reading......Page 111
Introduction......Page 112
Glutathione Transferases......Page 130
GST P......Page 132
Targeting Strategy......Page 135
GST P and Tumorigenesis......Page 137
GST P, Drug Metabolism, and Toxicity......Page 139
GST P, Oxidative Stress, and Cellular Signaling......Page 140
Novel Antitumor Agents Exploiting GST P Overexpression......Page 142
References......Page 143
Introduction......Page 150
Liver Microsome Preparation......Page 151
Enzyme Purification......Page 152
Preparation of MGST1 for Electrospray Mass Spectrometry......Page 153
Heterologous Expression and Purification from Bacterial Membranes......Page 154
Glutathione Transferase......Page 155
Meisenheimer Complex Formation......Page 156
Activation of MGST1 by N-Ethylmaleimide......Page 157
References......Page 158
Introduction......Page 161
MGST1, FLAP, and LTC4 Synthase......Page 162
The MAPEG Proteins and Glutathione......Page 164
Cloning of Human MPGES1......Page 165
Purification of Solubilized Human MPGES1......Page 166
Prostaglandin E2 Synthase Activity Assay with PGH2......Page 167
Prostaglandi n E2 Synthase Activity Assay with PGG2......Page 168
Gradient Centrifugation......Page 169
The PGES Activity of MPGES1......Page 170
Quaternary Structure Results......Page 171
References......Page 172
Two-Dimensional Crystallization and Electron Crystallography of MAPEG Proteins......Page 176
Introduction......Page 177
2-D Crystallization......Page 178
Properties of 2-D Crystals of MAPEG Proteins......Page 179
References......Page 182
Introduction......Page 184
Purification of Plant GSTs and Component Subunits......Page 186
Assay of Phi and Tau Class GSTs......Page 188
Extraction of Plant GSTs......Page 189
HPLC-Based Assays......Page 190
Preparation of Fatty Acid Hydroperoxides......Page 191
GPOX Activity of Theta GSTs......Page 192
Assay of Lambda Class GSTs......Page 193
Assay of Zeta Class GSTs......Page 194
Cloning and Expression of HDO and FAH......Page 195
Assay of MAAI Activity......Page 196
Notes......Page 197
References......Page 198
Introduction......Page 202
The Four Glutathione Transferase Families......Page 203
The Metazoan-Specific Glutathione Transferases......Page 204
Mammalian Orthologs and Paralogs......Page 207
Identifying Cytoplasmic Glutathione Transferase Homologs......Page 209
Mitochondrial Glutathione Transferases......Page 210
Microsomal Glutathione Transferases......Page 212
Thioredoxin and Glutathione Transferase Progenitors......Page 215
Conclusion......Page 217
References......Page 218
Drosophila Glutathione S-Transferases......Page 221
Biochemical Function of GST......Page 222
Genetic Repertoire of Glutathione S-Transferases in Drosophilamelanogaster......Page 224
Purification of GSTs from the Organism and Cell Lines......Page 226
Synthetic Gene Method......Page 227
Advantages and Limitations......Page 228
CDNB Plating Procedure......Page 229
Chimeric GSTs......Page 230
Background......Page 231
Transgenic Techniques for Drosophila gsts......Page 234
PB as a Model Chemical Inducer of Drosophila gsts......Page 235
Isolation of Total Fly RNAs by Guanidine Hydrochloride-CsCl Gradient Centrifugation......Page 236
Investigation of Translational Regulation by Polysome Pattern Analysis......Page 237
Concluding Remarks and the Way Ahead......Page 238
References......Page 239
Introduction......Page 244
Nomenclature......Page 245
Delta Class GSTs......Page 246
Epsilon Class GSTs......Page 248
Theta Class GSTs......Page 249
Structure of Cytosolic GSTs......Page 250
Microsomal GSTs......Page 251
Functions of Mosquito GSTs......Page 252
GSTs and Insecticide Resistance......Page 253
GSTs as Protectors against Oxidative Stress......Page 254
Regulation of Mosquito GST Expression......Page 255
References......Page 256
Functions of Parasite GSTs......Page 260
Biochemical Properties of PfGST......Page 262
Tertiary and Quaternary Structure of PfGST......Page 264
PfGST and Drug Resistance......Page 265
The Potential of PfGST as Drug Target......Page 267
References......Page 270
Background......Page 273
Choice of Expressed Form of the Recombinant Protein......Page 274
Construction of a GST M2-2 Expression Library......Page 275
Construction of a Partially Codon-Randomized cDNA Library Encoding Human GST M2-2......Page 276
Small-Scale Expression and Activity Screening......Page 278
Large-Scale Expression and Purification......Page 279
High-Level Expression Clones......Page 280
General Comments......Page 281
References......Page 282
Human Glutathione Transferase A3-3 Active as Steroid Double-Bond Isomerase......Page 285
Biosynthesis of Steroid Hormones......Page 286
Discovery of the Isomerase Activity of Certain Glutathione Transferases......Page 287
GSTA3 Gene......Page 288
Splice Variants of GSTA3......Page 289
Cloning Procedure I......Page 291
Using the pKK-D Plasmid......Page 292
Steroid Substrates......Page 293
Possible Reaction Mechanism......Page 294
Other Mammalian GSTs with High Sequence Similarity to Human GST A3-3......Page 295
References......Page 296
Introduction......Page 299
The Genes......Page 300
The Proteins......Page 301
Resolution of GST Subunits by HPLC......Page 302
Expression of the M3solM5 GST Subclass......Page 303
Questions To Be Resolved......Page 305
References......Page 307
Introduction......Page 309
GSH and GST in Cell Signaling......Page 310
GSTpi as a Drug Target......Page 314
TLK286 (Telcyta)......Page 316
PABA-NO......Page 320
Modulation of Glutathione and Glutathionylation......Page 322
References......Page 325
Modification of N-Acetyltransferases and Glutathione S-Transferases by Coffee Components: Possible Relevance for Cancer Risk......Page 330
Introduction: Xenobiotic Metabolism and Cancer......Page 331
Xenobiotic Metabolism and Chemoprevention......Page 332
Coffee and Cancer: Epidemiology......Page 333
General Principles and Chemoprotection by Whole Coffee......Page 334
Chemoprotection by Polyphenols......Page 335
Summary of Chemoprotectants in Coffee......Page 338
NAT......Page 339
GST......Page 340
Glutathione, gamma-Glutamylcysteine Synthetase, and GGT......Page 341
Interpretation of Time Course and Dose Requirement of the Modifications of GST and NAT in Ligh t of Chemoprevention by Human Coffee Consumption......Page 343
Effects of K/C on UDP-Glucuronosyltransferase and Other Parameters......Page 344
Animals......Page 345
Humans......Page 346
GST......Page 347
Effects of Melanoidins, N-Methylpyridinium Ion, and Fiber on GSTs......Page 349
Summary and Conclusions......Page 350
References......Page 351
Introduction......Page 365
Rat GST 5-5......Page 366
Conjugation of Ethylene Dihalides......Page 367
Haloforms (trihalomethanes)......Page 368
Enzyme Selectivity and Kinetic Mechanism......Page 369
Genotoxicity of GSH-haloalkane Conjugates......Page 372
References......Page 373
Introduction......Page 377
Materials and Methods......Page 378
Random Peptide Library Displayed on Phage......Page 379
Identification of Cloned Peptides by DNA Sequencing......Page 381
Database Analysis......Page 383
Construction of GST M2-2 and GST A1-1 into pSTC HA Tagged Expression Vector......Page 384
Discussion......Page 386
References......Page 389
Fosfomycin Resistance Proteins: A Nexus of Glutathione Transferases and Epoxide Hydrolases in a Metalloenzyme Superfamily......Page 391
Introduction......Page 392
Genomically Encoded FosA from Pseudomonas aeruginosa (FosAPA)......Page 394
Genomically Encoded FosB from Bacillus subtilis (FosBBS)......Page 395
Genomically Encoded FosB from Staphylococcus aureus (FosBSA)......Page 396
Genomically Encoded FosX from Listeria monocytogenes (FosXLM)......Page 397
Assay of FosA and FosB by Fluorescence-Detected HPLC......Page 398
Assay of FosX by Gas Chromatography/Mass Spectrometry......Page 399
Assay of FosA, FosB, and FosX by 31P-NMR Spectroscopy......Page 401
References......Page 402
Introduction......Page 404
Formation......Page 406
Metabolism of HNE......Page 408
Disposition of GSH Conjugates......Page 410
Measurement of GS-HNE Transport and HNE Levels......Page 411
Transport Measurement......Page 412
Chromatographic Analysis of HNE and Its Metabolites......Page 413
Spectrophotometric Methods for HNE Determination......Page 414
HNE-Mediated Signaling Processes......Page 415
Concentration-Dependent Effect of 4-HNE......Page 417
Catalytic Activity of Various GSTs for HNE......Page 418
Overexpression of alpha-Class GSTs Protects Against Stress-Induced Apoptosis......Page 420
Oxidative Stress-Induced Apoptosis Can Be Blocked by Limiting HNE Formation......Page 421
Induction of GST and RLPI76, an Early Response to Stress......Page 422
Stress Preconditioning Confers Resistance to Apoptosis by UVA and Oxidative Stress......Page 423
Inhibition of GS-HNE Transport Sensitizes Stress-Preconditioned Cells to Stress-Induced Apoptosis......Page 424
Depletion of HNE by GSTA4-4 in HLE-B3 and CCL-75 Cells Leads to Transformation......Page 425
Depletion of HNE by GSTA4-4 in HLE-B3 Causes Profound Changes in the Expression of Genes......Page 426
References......Page 427
Further Reading......Page 432
gamma-Glutamyltranspeptidase and Glutathione Metabolism......Page 433
Biosynthesis of gamma-Glutamyltranspeptidase......Page 434
Tissue-Specific Expression of gamma-Glutamyltranspeptidase......Page 435
Induction of Hepatic gamma-Glutamyltranspeptidase......Page 437
gamma-Glutamyltranspeptidase Gene Structure......Page 439
Multiple Promoters and Hepatic Expression of gamma-Glutamyltranspeptidase......Page 440
Transcription Factors Involved in gamma-Glutamyltranspeptidase Expression......Page 441
Human gamma-Glutamyltranspeptidase Gene and Its Expression......Page 442
gamma-Glutamyltranspeptidase-Related Gene Products......Page 443
References......Page 444
Further Reading......Page 450
gamma-Glutamyltranspeptidase: Disulfide Bridges, Propeptide Cleavage, and Activation in the Endoplasmic Reticulum......Page 451
gammaGT Synthesis and Processing......Page 452
gammaGT Isoforms and Their Potential Function......Page 453
Identification of Disulfide Bridges in gammaGT......Page 455
gammaGT Enzymatic Activity Correlates with Propeptide Cleavage......Page 458
gammaGT Propeptide Cleavage Occurs within the ER......Page 463
Disulfide Bridges in gammaGT and Functional Implications......Page 467
gammaGT and the Ntn Family of Hydrolases......Page 469
gammaGT Cleavage and Activation in the ER......Page 470
References......Page 471
Gamma-Glutamyl Transpeptidase Substrate Specificity and Catalytic Mechanism......Page 475
Donor and Acceptor Substrate Affinities and Potential Amino Acid Interactions......Page 476
Structure-Based GGT Inhibitors......Page 478
Kinetic Analysis of Diastereomeric Inhibitor Specificity......Page 479
Acyl-Enzyme Intermediate......Page 480
Acylation Step of Transpeptidation Reaction......Page 482
Deacylation Step of the Transpeptidation Reaction......Page 484
Unified Mechanism of GGT-Mediated Transpeptidation......Page 485
Kinetic Analysis of Diastereomeric Inhibitors......Page 486
Pre-Steady State Kinetics......Page 488
Linear Free-Energy Relationship (LFER) Analysis-Hammett Plot......Page 489
Linear Free-Energy Relationship (LFER) Analysis-Broslashnsted Plot......Page 490
References......Page 491
Further Reading......Page 493
Glutathione (GSH): Biological functions and metabolism......Page 494
Roles of GGT in gamma-Glutamyl Cycle and Metabolism of GSH S Conjugates......Page 496
Expression Pattern and Gene Structures of GGT......Page 497
Increased Expression of GGT during Oxidative Stress......Page 498
GGT Activity Assay......Page 499
Reagents......Page 500
GGT mRNA Assay......Page 501
Reagents......Page 502
Reagents......Page 504
References......Page 505
Introduction......Page 510
Soluble and Cell-Membrane-Bound Enzyme......Page 511
Histochemical and Cytochemical Demonstration of GGT Activity......Page 512
Detection of LPO in Tissue Sections......Page 513
Detection of LPO in Isolated Cells......Page 514
GGT-Dependent Production of Reactive Oxygen Species (ROS)......Page 515
Fluorimetric Determination of Hydrogen Peroxide Production......Page 516
Determination of Cell Surface Protein Thiols by Western blot......Page 518
Cytochemical Visualization of Cell Surface Protein Thiols......Page 519
Assay of Thiol Redox Status in Individual Proteins by Mal-PEG......Page 520
GGT-Induced Protein S-Cysteyl-Glycylation......Page 522
Concluding Remarks......Page 524
References......Page 525
Further Reading......Page 527
x subject index.pdf......Page 528
xx author index.pdf......Page 540
xxx mie index.pdf......Page 586
B7CV2-4J0R5GP-6-1.pdf......Page 0
Mu Class......Page 113
Sigma Class......Page 114
Delta Class......Page 115
Tertiary Structures......Page 117
Intersubunit Interaction at Either End of the Twofold Axis......Page 120
Substrate Specificity......Page 122
Conclusion......Page 124
References......Page 125
Further Reading......Page 128