Free Radicals and Antioxidant Protocols

475 Pages·2010·11.17 MB·English

by  Deepti S. Vikram

M M B TM
ETHODS IN OLECULAR IOLOGY
SeriesEditor
JohnM.Walker
SchoolofLifeSciences
UniversityofHertfordshire
Hatfield,Hertfordshire,AL109AB,UK
Forothertitlespublishedinthisseries,goto
www.springer.com/series/7651
Free Radicals and Antioxidant
Protocols
Second Edition
Editedby
Rao M. Uppu
SouthernUniversityandA&MCollege,BatonRouge,LA,USA
Subramanyam N. Murthy
TulaneUniversitySchoolofMedicine,NewOrleans,LA,USA
William A. Pryor
LouisianaStateUniversity,BatonRouge,LA,USA
Narasimham L. Parinandi
TheOhioStateUniversityMedicalCenter,Columbus,OH,USA
Editors
RaoM.Uppu SubramanyamN.Murthy
DepartmentofEnvironmental DepartmentofMedicine
ToxicologyandtheHealth andPharmacology
ResearchCenter TulaneUniversity
SouthernUniversityandA&M SchoolofMedicine
College 1430TulaneAve.
108FisherHall NewOrleans,LA70112
JamesL.HuntStreet USA
BatonRouge,LA70813 [email protected]
USA
rao [email protected]
NarasimhamL.Parinandi
DepartmentofInternalMedicine
WilliamA.Pryor
andtheDavisHeart&
DepartmentofChemistry
LungResearchInstitute
LouisianaStateUniversity
OhioStateUniversity
BatonRouge,LA70808 473West12thAve.
USA Columbus,OH43210
[email protected] USA
[email protected]
ISSN1064-3745 e-ISSN1940-6029
ISBN978-1-58829-710-5 e-ISBN978-1-60327-029-8
DOI10.1007/978-1-60327-029-8
LibraryofCongressControlNumber:2009940921
©HumanaPress,apartofSpringerScience+BusinessMedia,LLC2010
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Preface
Reactive oxygen and nitrogen species (RONs) affect normal physiological processes and
pathological conditions. In spite of the development of analytical and technological
advancements in the detection and determination of RONs, there is a growing demand
to achieve more rapid and accurate detection and determination of RONs and also of
redox stress. In order to satisfy such a demand, we chose to prepare this current volume
which comprises 27 chapters contributed by world-renowned experts on the state-of-
the-art analytical and technological aspects of the detection and determination of RONs,
and oxidative, nitrative, nitrosative, and redox stresses in biological systems, in vitro and
invivo.
There is a need to establish biomarkers for the oxidative stress-induced genetic dam-
age in cellular and animal models. This need is addressed herein by offering protocols
for (1) the generation of stable oxidative stress-resistant phenotypes of Chinese hamsters
fibroblasts,(2)invivodetectionandmeasurementoffreeradicalsandoxygen,(3)invivo
determination of tissue and DNA damage as a result of radical exposure, and (4) in vivo
and in vitro monitoring of footprints of free-radical and antioxidant reactions. In the sec-
tionsdedicatedtotheanalysisofantioxidantsandtheirmetabolites,wedescribemethods
for the analysis of phenolic acids and flavonoids, eugenol antioxidants, and the recycling
ofascorbicandlipoicacids.Wealsoreportoncellularreductivecapacity,determinationof
glutathione, mitochondrial transmembrane potential, and cytotoxicity in cardiomyocytes
underRONsstresses.
Lipids are at the epicenter of oxidative stress. However, the analysis of lipid perox-
idation, either in vitro or in vivo, is still complex, and novel methods and technologies
are always in great demand to accurately analyze the peroxidized lipids. This volume
presentstherecentadvancesinthesoft(electrospray)ionizationmassspectrometry(MS)
of phospholipid hydroperoxides for cellular and tissue oxidative lipidomics, the simulta-
neous analysis of multiple lipid oxidation products in vivo by LC-MS, and protocols for
enzyme immunoassay of isoprostanes and chemiluminescence determination of nitrite in
plasma.Wealsodiscussthepreparation,purification,andcharacterizationoflipoxygenase-
catalyzed phosphatidylinositol peroxides, and the biology and chemistry of oxidized low-
densitylipoprotein.
Genetransferhasbecomeausefultherapeuticstrategyinthetreatmentofcertaindis-
eases/disorders.Alongthoselines,thecurrentvolumedescribestechniquesforgenether-
apy involving endothelial nitric oxide synthase delivery to the lung in pulmonary hyper-
tensionandthetechniquesfordeliveryoftheextracellularsuperoxidedismutase(ecSOD)
gene for erectile dysfunction therapy. Drug delivery to the target areas has been identi-
fiedasapreferredtherapeuticapproachtotreatcertaindiseases,andthispharmacological
strategyisbeingactivelyexploredtocombatcertainoxidativestress-mediateddiseases.In
viewofthat,thisvolumedescribesthepreparationofdrug-loadedpolymericnanoparticles
andevaluationoftheantioxidantactivityagainstlipidperoxidation,design,synthesis,and
actionofantiatherogenicantioxidants,synthesisandcharacterizationofpolymernanocar-
riers for the targeted delivery of therapeutic enzymes in vitro, nanoparticle and iron
v
vi Preface
chelators as a potential novel Alzheimer therapy, and a simple method for effective and
safe removal of membrane cholesterol from lipid rafts in endothelial cells with implica-
tionsintheoxidant-mediatedlipidsignaling.
Molecular oxygen is the key life-supporting species in aerobes, and methods for the
accurate measurement of oxygen levels in the biological systems are just emerging. For
that,electronparamagneticresonancespectroscopy(EPR)appearstobeanovelanalytical
techniqueofchoice,andthecurrentvolumepresentsthemethodsofEPRimagingoffree
radicals and oxygen in vivo and the EPR spectroscopic determination of tissue oxygen in
vivowiththeaidofoxygen-sensitiveparamagneticlithiumphthalocyanineparticles.
Thisbookwouldnothavebeenpossiblewithoutthecontributionofchaptersbysev-
eralexpertsinthefieldofoxidativestress,andtherefore,theeditorsdeemitadistinctpriv-
ilege to gratefully acknowledge every individual author of the chapters that has made this
book a reality. We thank Drs. Achuthan Raghavamenon, Michelle Fletcher Claville, and
Deidra Atkins-Ball for help in editing and organizing the chapters. The patience shown
by Professor Walker and the team of Humana Press is beyond words and cannot be ade-
quately articulated. The editors express profound gratitude to Professor John Walker for
the confidence shown and consider it an honor that he gave us this assignment. We also
thank the following organizations and universities for financial support and use of insti-
tutional facilities: Departments of Chemistry and Environmental Toxicology, Southern
University and A&MCollege,Baton Rouge,LA; Departments ofMedicine and Pharma-
cology,TulaneUniversitySchoolofMedicine,NewOrleans,LA;DepartmentofInternal
Medicine and the Davis Heart and Lung Research Institute, The Ohio State University
MedicalCollege,Columbus,OH;NationalInstitutesofHealth,Bethesda,MD;National
Science Foundation, Washington, DC; and US Department of Education, Washington,
DC. Finally, we would be remiss if we did not express our heartfelt appreciation to our
familiesfortheirunparalleledsupport.
RaoM.Uppu
SubramanyamN.Murthy
WilliamA.Pryor
NarasimhamL.Parinandi
Contents
Preface . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . v
Contributors . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . xi
SECTION I REACTIVE OXYGEN AND NITROGEN SPECIES . . . . . . . . . 1
1. InVivoImagingofFreeRadicalsandOxygen . . . . . . . . . . . . . . . . . . . 3
DeeptiS.Vikram,BrianK.Rivera,andPeriannanKuppusamy
2. In Vivo Measurement of Tissue Oxygen Using Electron Paramagnetic
Resonance Spectroscopy with Oxygen-Sensitive Paramagnetic Particle,
LithiumPhthalocyanine . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 29
F.Hyodo,S.Matsumoto,E.Hyodo,A.Matsumoto,K.Matsumoto,
andM.C.Krishna
3. MeasurementofPlasmaNitritebyChemiluminescence . . . . . . . . . . . . . . 41
EnikaNagababuandJosephM.Rifkind
4. DeterminationofGlutathione,MitochondrialTransmembranePotential,
andCytotoxicityinH9c2CardiomyoblastsExposedtoReactiveOxygen
andNitrogenSpecies . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 51
K.Sathishkumar,XueliGao,AchuthanC.Raghavamenon,
SubramanyamN.Murthy,PhilipJ.Kadowitz,andRaoM.Uppu
SECTION II NATURAL AND SYNTHETICANTIOXIDANTS . . . . . . . . . . 63
5. PhenolicAcidsandFlavonoids:OccurrenceandAnalyticalMethods . . . . . . . . 65
ConstantineD.Stalikas
6. Design,Synthesis,andActionofAntiatherogenicAntioxidants . . . . . . . . . . 91
OsamuCynshi,KunioTamura,andEtsuoNiki
7. Preparation of Drug-Loaded Polymeric Nanoparticles and Evaluation
oftheAntioxidantActivityAgainstLipidPeroxidation . . . . . . . . . . . . . . . 109
AdrianaR.Pohlmann,ScheilaRezendeSchaffazick,
TaˆniaB.Creczynski-Pasa,andSı´lviaS.Guterres
8. NanoparticleandIronChelatorsasaPotentialNovelAlzheimerTherapy . . . . . 123
GangLiu,PingMen,GeorgePerry,andMarkA.Smith
9. SynthesisandCharacterizationofPolymerNanocarriersfortheTargeted
DeliveryofTherapeuticEnzymes . . . . . . . . . . . . . . . . . . . . . . . . . 145
EricSimone,ThomasDziubla,VladimirShuvaev,
andVladimirR.Muzykantov
10. AssessmentofAntioxidantActivityofEugenolInVitroandInVivo. . . . . . . . 165
EnikaNagababu,JosephM.Rifkind,SesikeranBoindala,
andLakshmaiahNakka
vii
viii Contents
SECTION III CELLULAROXIDATIVE STRESS . . . . . . . . . . . . . . . . . 181
11. The Generation of Stable Oxidative Stress-Resistant Phenotypes in
ChineseHamsterFibroblastsChronicallyExposedtoHydrogenPeroxide
orHyperoxia . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 183
DouglasR.SpitzandShannonJ.Sullivan
12. A Simple Method for Effective and Safe Removal of Membrane
CholesterolfromLipidRaftsinVascularEndothelialCells:Implications
inOxidant-MediatedLipidSignaling . . . . . . . . . . . . . . . . . . . . . . . . 201
MichelleA.Kline,E.S.O’ConnorButler,AdamHinzey,SeanSliman,
SainathR.Kotha,ClayB.Marsh,RaoM.Uppu,andNarasimham
L.Parinandi
13. Superoxide Dismutase – A Target for Gene Therapeutic Approach to
ReduceOxidativeStressinErectileDysfunction . . . . . . . . . . . . . . . . . . 213
W.Deng,T.J.Bivalacqua,H.C.Champion,W.J.Hellstrom,
SubramanyamN.Murthy,andPhilipJ.Kadowitz
14. Assessing the Reductive Capacity of Cells by Measuring
theRecyclingofAscorbicandLipoicAcids. . . . . . . . . . . . . . . . . . . . . 229
JamesM.May
15. Biomarkers of Oxidative Stress: Methods and Measures of Oxidative
DNADamage(COMETAssay)andTelomereShortening . . . . . . . . . . . . 245
MuthuswamyBalasubramanyam,AntonysunilAdaikalakoteswari,
ZaheerSameermahmood,andViswanathanMohan
16. Simultaneous Analysis of Expression of Multiple Redox-Sensitive
and Apoptotic Genes in Hypothalamic Neurons Exposed
toCholesterolSecoaldehyde . . . . . . . . . . . . . . . . . . . . . . . . . . . . 263
K.Sathishkumar,AchuthanC.Raghavamenon,Karunakaran
Ganeshkumar,RameshwariTelaprolu,NarasimhamL.Parinandi,
andRaoM.Uppu
17. Redox Homeostasis and Cellular Stress Response in Aging
andNeurodegeneration . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 285
VittorioCalabrese,CarolinCornelius,CesareMancuso,Riccardo
Lentile,A.M.GiuffridaStella,andD.AllanButterfield
18. Gene Therapy Techniques for the Delivery of Endothelial Nitric Oxide
SynthasetotheLungforPulmonaryHypertension . . . . . . . . . . . . . . . . 309
W.Deng,T.J.Bivalacqua,H.C.Champion,W.J.Hellstrom,
SubramanyamN.Murthy,andPhilipJ.Kadowitz
SECTION IV DNAOXIDATION,OXIDATIVE LIPIDOMICS, AND BIOMARKERS 323
19. A General Method for Quantifying Sequence Effects
onNucleobaseOxidationinDNA . . . . . . . . . . . . . . . . . . . . . . . . . 325
YelenaMargolinandPeterC.Dedon
Contents ix
(cid:2)
20. Analysis of Urinary 8-oxo-7,8-dihydro-2-deoxyguanosine by Liquid
Chromatography–TandemMassSpectrometry . . . . . . . . . . . . . . . . . . . 341
MarkD.Evans,RajinderSingh,VilasMistry,PeterB.Farmer,
andMarcusS.Cooke
21. Oxidative Lipidomics of Apoptosis: Quantitative Assessment of
PhospholipidHydroperoxidesinCellsandTissues . . . . . . . . . . . . . . . . . 353
VladimirA.Tyurin,YuliaY.Tyurina,VladimirB.Ritov,Andriy
Lysytsya,AndrewA.Amoscato,PatrickM.Kochanek,RonaldHamilton,
StevenT.DeKosky,JoelS.Greenberger,Hu¨lyaBayir,andValerianE.Kagan
22. SimultaneousAnalysisofMultipleLipidOxidationProductsInVivoby
LiquidChromatographic-MassSpectrometry(LC-MS) . . . . . . . . . . . . . . 375
HuiyongYin,ToddDavis,andNedA.Porter
23. Lipoxygenase-Catalyzed Phospholipid Peroxidation: Preparation,
Purification,andCharacterizationofPhosphatidylinositolPeroxides . . . . . . . . 387
E.SusanO’ConnorButler,JessicaN.Mazerik,JasonP.Cruff,
ShariqI.Sherwani,BarbaraK.Weis,ClayB.Marsh,
AchuthanC.Raghavamenon,RaoM.Uppu,HaraldH.O.Schmid,
andNarasimhamL.Parinandi
24. OxidizedLow-DensityLipoprotein . . . . . . . . . . . . . . . . . . . . . . . . 403
SampathParthasarathy,AchuthanRaghavamenon,MahdiOmar
Garelnabi,andNaliniSantanam
25. Detection and Localization of Markers of Oxidative Stress by In Situ
Methods:ApplicationintheStudyofAlzheimerDisease . . . . . . . . . . . . . . 419
PaulaI.Moreira,LawrenceM.Sayre,XiongweiZhu,Akihiko
Nunomura,MarkA.Smith,andGeorgePerry
26. EnzymeImmunoassayofIsoprostanes . . . . . . . . . . . . . . . . . . . . . . . 435
DenisM.CallewaertandCharlesSloan
27. ApplicationofMembraneExtractionwithSorbentInterfaceforBreathAnalysis. . 451
VictorMa,HeatherLord,MelissaMorley,andJanuszPawliszyn
SubjectIndex . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 469
Contributors
ANTONYSUNIL ADAIKALAKOTESWARI • Department of Cell and Molecular Biology,
Madras Diabetes Research Foundation & Dr. Mohan’s Diabetes Specialties, Gopalapu-
ram,Chennai,India
ANDREW A. AMOSCATO • Department Pathology, University of Pittsburgh, Pittsburgh,
PA,USA
MUTHUSWAMY BALASUBRAMANYAM • Department of Cell and Molecular Biology,
Madras Diabetes Research Foundation & Dr Mohan’s Diabetes Specialties Centre,
Gopalapuram,Chennai,India
HU¨LYA BAYIR • Center for Free Radical and Antioxidant Health, Departments of Envi-
ronmental&OccupationalHealthandCriticalCareMedicine,UniversityofPittsburgh,
Pittsburgh,PA,USA
T.J. BIVALACQUA • Department of Pharmacology, Tulane University Health Sciences
Center, New Orleans, LA, USA. Present address: Department of Urology, Johns Hopkins
Hospital,Baltimore,MD,USA
SESIKERAN BOINDALA • National Institute of Nutrition, Indian Council of Medical
Research,Jamai-Osmania,Hyderabad,India
ALLAN BUTTERFIELD • DepartmentofChemistry,Sanders-BrownCenteronAgingand
CenterofMembraneSciences,UniversityofKentucky,Lexington,Kentucky,USA
E.S. O’CONNOR BUTLER • Division of Pulmonary, Allergy, Critical Care, and Sleep
Medicine, Department of Internal Medicine, The Ohio State University Medical Center,
Columbus,OH,USA
VITTORIO CALABRESE • Department of Chemistry, Biochemistry & Molecular Biology
Section,FacultyofMedicine,UniversityofCatania,Catania,Italy
DENIS M. CALLEWAERT • DepartmentofChemistryandCenterforBiomedicalResearch,
OaklandUniversity,Rochester,MI,USA
CAROLIN CORNELIUS • Department of Chemistry, Biochemistry and Molecular Biology
Section,FacultyofMedicine,UniversityofCatania,Catania,Italy
H.C. CHAMPION • DepartmentofMedicineUniversity,Pittsburg,PA,USA
MARCUS S. COOKE • Radiation&OxidativeStressGroup,DepartmentofGenetics,Uni-
versityofLeicester,Leicester,UK
TAˆNIA B. CRECZYNSKI-PASA • DepartamentodeCieˆnciasFarmaceˆuticas,Universidade
FederaldeSantaCatarina,UFSC,PortoAlegre,Brazil
xi