Endogenous Toxins: Targets for Disease Treatment and Prevention

967 Pages·2009·8.819 MB·English

EndogenousToxins
Editedby
PeterJ.O’Brienand
W.RobertBruce
FurtherReading
Geacintov,N.E.,Broyde,S.(eds.) Meyers,R.A.(ed.)
TheChemicalBiologyofDNA Cancer
Damage FromMechanismstoTherapeutic
Approaches
2010
2007
ISBN:978–3–527–32295–4
ISBN:978-3-527-31768-4
Ku¨lpmann,W.R.(ed.)
Du¨bel,S.(ed.)
ClinicalToxicological Analysis
HandbookofTherapeutic
Procedures,Results,Interpretation
Antibodies
2009
ISBN:978–3–527–31890–2 2007
ISBN:978-3-527-31453-9
Knasmu¨ller,S.,DeMarini,D.M.,Johnson,
I.,Gerha¨user,C.(eds.) Brigelius-Flohe´,R.,Joost,H.-G.(eds.)
ChemopreventionofCancer NutritionalGenomics
andDNA DamagebyDietary ImpactonHealthandDisease
Factors
2006
ISBN:978–3–527–31294–8
2008
ISBN:978–3–527–32058–5
Endogenous Toxins
Diet, Genetics, Disease and Treatment
Edited by
Peter J. O’Brien and W. Robert Bruce
VOLUMEI
Endogenous Toxins
Diet, Genetics, Disease and Treatment
Edited by
Peter J. O’Brien and W. Robert Bruce
VOLUMEII
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ISBN:978-3-527-32363-0
TheAuthors
Albano, Emanuele Austin, Rick Baynes, John Beisswenger, Paul Benov, Ludmil Bilodeau, Marc
Bruce, Robert Cani, Patrice Chan, Tom S. Corpet, Denis Danpure, Christopher Dedon, Peter
Delzenne, Nathalie Doorn, Jonathan Eyssen, Gail Frizzell, Norma Giacca, Adria Gieseg, Steven
Hayase, Fumitaka Henderson, Jeffrey Herrmann, WolfgangHui, Kelvin Hyogo, HideyukuJ Jaeschke, Hartmut
Kim, Hyun-Jung Klassen, Lyn Kong, Tony Labandeira-García, JoséMartin, Lisa Mathews, Jason
Monestier, Marc Newmark, Harold O’Brien, Peter Obeid, Rima Pamplona, Reinald Rao, R. K.
Sharer, Daniel Shiraldi, Michael Siraki, Arno Strazzullo, PasqualeSurh, Young-Joon Tazuma, Susuma
Templeton, Douglas Thiele, Geoff Thompson, Henry Vangala, Mani Wright, Jim Yamagishi, Sho-ichi
VII
Contents
VOLUMEI
Preface XXXI
ListofContributors XXXIII
Abbreviations XLIII
PartOne EndogenousToxinsAssociatedwithExcessiveSugar,Fat,Meat,
orAlcoholConsumption 1
Sub-Part ChemistryandBiochemistry 3
1 EndogenousDNADamage 5
ErinG.PrestwichandPeterC.Dedon
1.1 Introduction 5
1.2 OxidativelyDamagedDNA 8
1.2.1 BaseOxidation 9
1.2.2 TandemLesions:MultipleProductsDerivedfromaSingleOxidation
Event 12
1.2.3 BaseNitration 13
1.2.4 Halogenation 14
1.2.5 2-DeoxyriboseOxidation 14
1.3 DNAAlkylationbyEndogenousElectrophiles 15
1.3.1 LipidPeroxidation-DerivedAdducts 17
1.3.2 Malondialdehyde-LikeAdducts 21
1.3.3 DNAGlycation 22
1.3.4 Estrogen-DerivedDNAAdducts 24
1.4 DNAandRNADeamination 25
1.4.1 HydrolyticDeamination 26
1.4.2 NitrosativeChemistryandInflammation 26
1.4.3 EnzymaticDeamination 27
EndogenousToxins.Diet,Genetics,DiseaseandTreatment.
EditedbyPeterJ.O’BrienandW.RobertBruce
Copyright2010WILEY-VCHVerlagGmbH&Co.KGaA,Weinheim
ISBN:978-3-527-32363-0
VIII Contents
1.5 Summary 28
References 28
2 ModificationofCysteineResiduesinProteinbyEndogenousOxidants
andElectrophiles 43
NormaFrizzellandJohnW.Baynes
2.1 Introduction 43
2.2 AutoxidationofCysteine 44
2.3 Glutathione 44
2.3.1 Glutathionylation 45
2.3.2 GlutathioneasanElectrophileTrap 45
2.4 Lipoxidation 46
2.4.1 Glyceraldehyde-3-PhosphateDehydrogenase(GAPDH) 47
2.4.2 Albumin 48
2.4.3 Actin 48
2.4.4 QuantitativeAnalysis 49
2.5 MaillardReactionsofCysteine 50
2.5.1 Transglycosylation 50
2.5.2 Carboxyalkylation 51
2.6 Succination 53
2.6.1 DiscoveryandMetabolicOriginofS-(2-Succinyl)cysteine(2SC) 53
2.6.2 2SCinSkeletalMuscleinDiabetes 55
2.6.3 2SCinAdiposeTissueinDiabetes 55
2.6.4 OverviewonSuccinationofProtein 57
2.7 Conclusion 57
Acknowledgment 58
References 58
3 EndogenousMacromoleculeRadicals 65
ArnoG.SirakiandMarilynEhrenshaft
3.1 Introduction 65
3.2 WhatisaFreeRadical? 66
3.2.1 SuperoxideAnion 67
3.2.2 SingletOxygen 68
3.2.3 HydrogenPeroxide 68
3.2.4 PeroxynitriteandCarbonateRadicals 69
3.2.5 Nitrogen-BasedRadicals 70
3.2.6 HypochlorousAcid 71
3.2.7 ThiylRadicals 72
3.2.8 LipidPeroxidation 73
3.2.9 Summary 73
3.3 FreeRadicalsasInitiatorsofMacromoleculeDamage 74
3.4 MacromoleculeRadicalFormationInducedbySmallMoleculeFree
Radicals 78
Contents IX
3.5 ExamplesandPotentialApplicationofImmuno-SpinTrapping(IST)
fortheDetectionofMacromoleculeRadicals 80
3.5.1 Superoxide-InducedMacromoleculeRadicals 80
3.5.2 SingletOxygen–InducedMacromoleculeRadicals 81
3.5.3 HydroxylRadical–InducedMacromoleculeRadicals 82
3.5.4 Peroxynitrite,NitrogenDioxideRadicals,andNitricOxide 83
3.5.5 CarbonateRadicals 84
3.5.6 HOCl-InducedMacromoleculeRadicals 85
3.5.7 ThiylRadical–InducedMacromoleculeRadicals 86
3.5.8 MyeloperoxidaseProteinRadicalDetection 87
3.5.9 HemeProteinRadicals–AUniqueExceptionofSubstrate-Induced
ProteinRadicalFormation 88
3.5.10 ExampleofInvivoDetectionofMacromoleculeRadicalsUsing
IST 89
3.5.11 FutureDirections 91
3.6 ImmunologicalDetectionofOxidizedTryptophanResiduesin
Proteins 92
References 92
4 Alcohol-DerivedBioadducts 103
GeoffreyM.ThieleandLynellW.Klassen
4.1 Introduction 103
4.2 TheGenerationofReactiveMetabolites 104
4.3 EthanolMetabolitesReactwithProteins 106
4.4 AcetaldehydeAdducts 107
4.4.1 FormationandTypesofAdducts 107
4.4.2 BiologicalDetectionand/orSignificance 109
4.5 Malondialdehyde 111
4.5.1 FormationandTypesofAdducts 111
4.5.2 BiologicalDetectionand/orSignificance 113
4.6 Malondialdehyde–Acetaldehyde(MAA)Adducts 114
4.6.1 FormationandTypesofAdducts 114
4.6.2 BiologicalDetectionand/orSignificance 114
4.7 4-Hydroxyalkenals 116
4.7.1 FormationandTypesofAdducts 116
4.7.2 BiologicalDetectionand/orSignificance 116
4.8 FreeRadical–DerivedAdducts 117
4.8.1 FormationandDetectionofAdducts 117
4.8.2 BiologicalDetectionand/orSignificance 117
4.9 5-Deoxy-D-xylulose-1-phosphate(DXP) 118
4.10 Acetaldehyde–GlucoseAmadoriProductAdduct 119
4.11 ImmuneResponsestoProteinsModifiedwithAlcohol
Metabolites 119
4.12 TheRoleofAlcohol-DerivedBioadductsinAlcohol-RelatedTissue
Injury 121
X Contents
4.13 FutureDirections 123
Acknowledgments 124
References 124
5 IronfromMeatProducesEndogenousProcarcinogenicPeroxides 133
DenisE.Corpet,Fran¸coiseGue´raud,andPeterJ.O’Brien
5.1 Introduction 133
5.2 ToxicEffectsofIron:MolecularMechanisms 134
5.2.1 Fe-/Cu-CatalyzedFentonChemistry 135
5.2.2 Fe-/Cu-CatalyzedOxidationofProteins 135
5.2.3 Fe-/Cu-CatalyzedProteinCarbonylation 136
5.2.4 Fe-/Cu-CatalyzedAdvancedGlycationEndProducts(AGEs)
Formation 136
5.2.5 Fe-/Cu-CatalyzedLipidPeroxidationandAdvancedLipoxidationEnd
Products(ALEs) 138
5.2.6 Fe-/Cu-CatalyzedOxidationofNucleicAcids 138
5.2.7 RoleofLysosomalFe/CuinOxidativeStressCytotoxicity 139
5.2.8 RoleofROSandIroninCellularRedoxSignalingthatCouldCause
CellTransformation 140
5.3 ProcarcinogenicEffectsofIron:InvitroStudies 140
5.3.1 IroninFood 140
5.3.2 IroninCellCulture 141
5.4 ProcarcinogenicEffectsofIronintheGut 141
5.4.1 FreeRadicalsinGutLumen 141
5.4.2 HeminEffectintheColonofRats 141
5.4.3 Iron-InducedLipidPeroxidationProducts 142
5.4.4 EffectofHemeIrononExperimentalCarcinogenesis 142
5.4.5 CarcinogenesisPrevention 142
5.5 ProcarcinogenicEffectsofIronInsidetheBody 143
5.5.1 IronConcentrationisTightlyLimitedinBodyFluids 143
5.5.2 IronOverloadCausesSevereDiseases 143
5.5.3 ColorectalCancerandIronOverload 144
5.6 GeneralConclusion 144
References 144
Sub-Part MolecularToxicologyMechanismsofDietaryEndogenousToxins 151
6 ShortChainSugarsasEndogenousToxins 153
LudmilT.Benov
6.1 DefinitionandProperties 153
6.2 ShortChainSugarsandReactiveOxygenSpecies 154
6.3 Dicarbonyls 156
6.4 DirectReactionswithBiomolecules 156
6.5 ShortChainSugarsandTheirSources 157
6.5.1 TriosesandTriosephosphates 157