ENZYMOLOGY AND MOLECULAR BIOLOGY OF CARBONYL METABOLISM 7 ADVANCES IN EXPERIMENTAL MEDICINE AND BIOLOGY EditorialBoard: NATHAN BACK,State UniversityofNew YorkatBuffalo IRUNR. COHEN, The Weizmann InstituteofScience DAVIDKRITCHEVSKY, WistarInstitute ABEL LAITHA,N. S. KlineInstitutefor PsychiatricResearch RODOLFO PAOLETTI,UniversityofMilan RecentVolumesinthisSeries Volume454 OXYGENTRANSPORTTOTISSUEXX EditedbyAntalG. Hudetzand DuaneF. Bruley Volume455 RHEUMADERM: CurrentIssuesin Rheumatologyand Dermatology EditedbyCarmelMalliaandJouni Uitto Volume456 RESOLVINGTHE ANTIBIOTIC PARADOX: Progressin Understanding DrugResistanceand DevelopmentofNew Antibiotics EditedbyBarryP. RosenandShahriarMobashery Volume457 DRUGRESISTANCE IN LEUKEMIA ANDLYMPHOMA III EditedbyG. J. L. Kaspers, R. Pieters,andA. J. P. Veerman Volume458 ANTIVIRALCHEMOTHERAPY5: New DirectionsforClinicalApplicationandResearch EditedbyJohn Mills, Paul A. 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ENZYMOLOGY AND MOLECULAR BIOLOGY OF CARBONYL METABOLISM 7 Edited by Henry Weiner Purdue University West Lafayette, Indiana Edmund Maser Philipps University of Marburg Marburg, Germany David W. Crabh Indiana University School of Medicine Indianapolis, Indiana and Ronald Lindahl University of South Dakota School of Medicine Vermillion, South Dakota Springer Science+Business Media, LLC Llbrary of Congress Catalog1ng-ln-Publ1cation Data International Symposlu. an Enzymology and Molecular Blology of Carbonyl Metaboli .. (9th, 1998 Vereelll, Italy) Enzymology and molecular biology of earbonyl metabolism 7 I edited by Henry Weiner ... [et a1.l. p. em. -- (Advances in experlmental ~ed1c1ne and biology ; v. 463) "Proeeedlngs of the Ninth International Sy"poslu, an Enzymology and Molecular Biology of Carbonyl Metabolism, held June 20-24, 1998, in Varallo Sesla, Vereelll, Italy." Ine ludes b I b 11 ograph I ca 1 referenees and Index. ISBN 978-1-4613-7146-5 ISBN 978-1-4615-4735-8 (eBook) DOI 10.1007/978-1-4615-4735-8 1. Aldehyde dehydrogenase Congresses. 2. Aleohol dehydrogenase Congresses. 3. Dehydrogenases Congresses. 4. Carbonyl reduetase Congresses. 5. Carbonyl eo.pounds--Metabollsm Congresses. I. Welner, Henry. II. Title. III. Series. OP603.A35I58 1999 572·.791--de21 99-14420 CIP Proceedings of the Ninth International Symposium on Enzymology and Molecular Biology of Carbonyl Metabolism, held June 20 - 24, 1998, in Varallo Sesia, Vercelli, Italy ISBN 978-1-4613-7146-5 © 1999 Springer Science+Business Media New York Originally published by Kluwer Academic / Plenum Publishers, New York in 1999 Softcover reprint ofthe hardcover Ist edition 1999 1098765432 A C.I.P. record for this book is available from the Library ofCongress. AII rights reserved No part ofthis book may be reproduced, stored in a retrieval system, or transmitted in any form or by any means, electronic, mechanical, photocopying, microfilming, recording, or otherwise, without written permission from the Publisher PREFACE Prior to the start ofthe eighth meeting, I had the good sense to ask Professor Rosa Angela Canuto of Turin, Italy if she would help me organize the ninth meeting. She quicklysuggestedthatbothsheand Dr. GuilianaMuzio,also ofTurin, helpplanthe meet ing. Eachofourpreviouseightmeetingswasauniqueexperiencefortheparticipants. The science was always outstanding and the presentations and discussions were excellent. By moving each meeting to a different partofthe world we were able to experience exciting foods and cultural aspects ofthe world in addition to the science. The ninth meeting was no exception. We met from June 18 to 22 in the small mountain city ofVarallo, Italy, the birth place ofDr. Canuto. Holding the scientific sessions in a several-hundred-year-old converted mansion and having an afternoon trip to either Lago Maggiore or Monte Rosa made some aspects ofthis meeting extremely memorable. An additional unique aspect of thesocialportion ofthemeetingwasourabilityto invitethetownspeople tosharewithus aconcertperformedinanoldchurch. Though the social and cultural aspects ofthe meeting were outstanding, the pur pose ofthe meeting was to exchange scientific information about the status ofthe three enzyme systems. Over 50 talksand 40 postersprovidedtheparticipantswith awide vari ety ofpresentations dealing with enzymology, molecular biology, and metabolic aspects ofthese carbonyl metabolizing oxido-reductases. Much new information was presented, including three-dimensional structures ofenzymes not previously reported, drug interac tions with the enzymes, and new aspects ofgene regulation along with sequence align ments, metabolism and enzyme mechanisms, to mention a few. In addition, there were serious discussions about developing standardized nomenclatures for the different en zyme families. Onbehalfofall the participants Iwantto thank Drs. Canuto and Muzio for organiz ing an outstanding meeting and providing us with a gastronomic and culturally exciting experience. We are not a society, hence we have no financial base to support these meet ings. Dr. Canuto found some local sponsors andtheir generosity helped make this an out standing affair. We especially wish to acknowledge the Sindaco del Comune di Varallo and Fondazione Cassa di Risparmio di Torino and sincerely thank them for helping to makeourninth meetingamemorableexperience. I want to thank all the participants for making this another outstanding meeting. I alsowanttothankmythreeco-editorsfor helpingmereviewall the manuscripts. v vi Preface Ourtenthmeetingwill beheld inTaos,New MexicofromJuly 1-5,2000. We invite ourfellow scientistsinterestedinthetopicofthemeetingtojoinus. Pleasewritemetore ceiveadditional infonnationaboutthe tenth meeting. HenryWeiner Scientific Organizer BiochemistryDepartment PurdueUniversity WestLafayette,Indiana47907-1153 CONTENTS Aldehyde Dehydrogenas~ 1. TheBigBookofAldehyde DehydrogenaseSequences: AnOverviewofthe ExtendedFamily . John Perozich,Hugh Nicholas,Ronald Lindahl,andJohn Hempel 2. Reaction-Chemistry-DirectedSequenceAlignmentofAldehydeDehydrogenases 9 Pritesh ShahandRegina Pietruszko 3. Three-DimensionalStructureofMitochondrialAldehydeDehydrogenase: Mechanistic Implications ....................................... 15 Thomas D. Hurley,Curtis G. Steinmetz,and Henry Weiner 4. AStructuralExplanationfortheRetinalSpecificityofClass 1ALDHEnzymes 27 Stanley A. Moore, HeatherM. Baker,Treena J. Blythe,Kathryn E. Kitson, TrevorM. Kitson, andEdwardN. Baker 5. StructureandFunctionofBetaineAldehydeDehydrogenase: AnEnzyme withintheMultienzymeAldehydeDehydrogenase System 39 Lars Hjelmqvist,MustafaEI-Ahmad, Kenth Johansson,Annika Norin, Ramaswamy S,andHans Jornvall 6. Evaluationofthe RolesoftheConservedResiduesofAldehyde Dehydrogenase 45 Thomas D. HurleyandHenry Weiner 7. AldehydeDehydrogenaseCatalyticMechanism: AProposal ............... 53 John Hempel,John Perozich,Toby Chapman,John Rose, Josette S. Boesch,Zhi-Jie Liu,Ronald Lindahl,andBi-Cheng Wang 8. InhibitionofHumanMitochondrialAldehydeDehydrogenasebyMetabolites ofDisulfiramand StructuralCharacterizationoftheEnzymeAdductby HPLC-TandemMass Spectrometry ............................... 61 Dennis C. Mays,Andy J. Tomlinson,Kenneth L. Johnson, Jennifer Lam, James J. Lipsky,andStephenNaylor vii vIII Contents 9. MechanismofInhibitionofRatLiverClass2ALDH by4-Hydroxynonenal .. 71 Stephen W. Luckey, Ronald B. Tjalkens,and Dennis R. Petersen 10. AldehydeInhibitorsofAldehydeDehydrogenases 79 Regina Pietruszko, Darryl P. Abriola,Gonzalo Izaguirre, Alexandra Kikonyogo, Marek Dryjanski,andWojciech Ambroziak 11. CovalentModificationofSheepLiverCytosolicAldehyde Dehydrogenaseby the OxidativeAdditionofColouredPhenoxazine,Phenothiazineand PhenazineDerivatives 89 Trevor M. Kitson, Kathryn E. Kitson, andGordon J. King 12. AThioesterAnalogueofanAminoAcetylenic AldehydeIsaSuicideInhibitor ofAldehyde Dehydrogenaseandan InducerofApoptosisinMouse LymphoidCellsOverexpressingthebcl2 Gene ..................... 97 Gerard Quash, Guy Fournet,Catherine Raffin, Jacqueline Chantepie, Yvonne Michal,Jacques Gore, and Uwe Reichert 13. Reactionbetween SheepLiverMitochondrial Aldep.yde Dehydrogenaseand a Chromogenic 'ReporterGroup'Reagent 107 Gordon 1. King, Gillian E. Norris, Kathryn E. Kitson, and Trevor M. Kitson 14. Activityofthe Human Aldehyde Dehydrogenase 2PromoterIsInfluenced by the BalancebetweenActivationbyHepatocyteNuclearFactor4and Repression byPerosixomeProliferatorActivatedReceptor 0,Chicken OvalbuminUpstreamPromoter-Transcription Factor, and ApolipoproteinRegulatoryProtein-l 115 Jane Pinaire,Wan-Yin Chou, Mark Stewart, Katrina Dipple, and David Crabb 15. <X.,f3-UnsaturatedAldehydes MediateInducibleExpressionofGlutathione s-Transferase inHepatomaCellsthrough Activationofthe Antioxidant Response Element(ARE) 123 Ronald B. Tjalkens, Stephen W. Luckey, David1. Kroll, and Dennis R. Petersen 16. EffectofArachidonicAcidAloneorwithProoxidantonAldehyde Dehydrogenases inHepatomaCells 133 Rosa A. Canuto, Margherita Ferro, Raffaella A. Salvo,Anna M. Bassi, Mario Terreno, Mario U. Dianzani, Ronald Lindahl, and Giuliana Muzio. 17. Prepubertal Regulationofthe Rat Dioxin-InducibleAldehyde Dehydrogenase (ALDH3) .................................................... 143 Panayiotis Stephanou,Periklis Pappas,Vasilis Vasiliou,and Marios Marselos 18. EffectsofTamoxifenandToremifeneonALDHI andALDH3 inHuman Retinal PigmentEpithelialCellsand Rat Liver 151 Periklis Pappas, Panayiotis Stephanou, Marianthi Sotiropoulou, Carol Murphy, Lotta Salminen, and Marios Marselos Contents Ix 19. NegativeRegulationofRatHepaticAldehydeDehydrogenase3by Glucocorticoids 159 Ronald Lindahl, Gong-Hua Xiao, K. CameronFalkner,and Russell A. Prough 20. ModulationofClass3AldehydeDehydrogenaseGeneExpression: An Eye OpeningExperience ........................................... 165 Maureen Burton,Richard Reisdorph, Russell Prough,and Ronald Lindahl 21. SusceptibilityofHepatomaCellstoLipidPeroxidationandAdaptationof ALDH3CActivitytoIron-InducedOxidativeStress 171 MargheritaFerro,Anna MariaBassi,Susanna Penco,Giuliana Muzio,and Rosa A. Canuto 22. TheLackofAHD4 InductionbyTCDD inCornealCellsMayInvolve Tissue-SpecificRegulatoryProteins .............................. 181 Vasilis VasiliouandTeyen Shiao 23. HumanCornealandLensAldehydeDehydrogenases: Localizationand Function(s)ofOcularALDHI andALDH3 Isozymes ................ 189 Gordon King, Lawrie Hirst,and Roger Holmes 24. TheRoleofRetinoidMetabolismbyAlcoholandAldehydeDehydrogenases inDifferentiationofCulturedNeuronalCells 199 Treena J. Blythe, MarkL. Grimes,andKathryn E. Kitson 25. MetabolismofRetinaldehydebyHumanLiverand Kidney " 205 Wojciech Ambroziak,Gonzalo Izaguirre,Darryl Abriola, Ming-Kai Chern, andR~ginaPietruszko 26. TheHuntfor aRetinal-Specific Aldehyde DehydrogenaseinSheepLiver. ... 213 Kathryn E. KitsonandTreenaJ. Blythe 27. CardiacMetabolismofEnals 223 Aruni Bhatnagar, SanjaySrivastava,Li-Fei Wang,Animesh Chandra, Naseem H. Ansari,andSatishK. Srivastava 28. OxidationofEthanoltoAcetaldehydeinBrainandthePossibleBehavioral Consequences 231 Sergey M. Zimatkin,Anton V. Liopo,andRichard A. Deitrich 29. CloningandExpressionofaeDNAEncodingaConstitutivelyExpressedRat LiverCytosolicAldehydeDehydrogenase. ........................ 237 Eva C. KathmannandJames J. Lipsky 30. TheRoles ofAcetaldehydeDehydrogenasesinSaccharomyces Cerevisiae 243 WayneTessier,Mark Dickinson,and MelvinMidgley x Contents 31. CharacterizationofanAldehydeDehydrogenaseGeneFragmentfrom Mung Bean(Vigna radiata)Usingthe Polymerase ChainReaction. ......... 249 Anatoley G. Ponomarev,Victoria V. Bubyakina,TatyanaD. Tatarinova, and SergeyM. Zelenin 32. Aldehyde DehydrogenaseGene Superfamily: The 1998Update 255 Thomas L. ZieglerandVasilis Vasiliou Alcohol Dehydrogenase 33. HumanAlcohol DehydrogenaseFamily: FunctionalClassification, Ethanol/RetinolMetabolism,andMedical Implications .............. 265 Shih-Jiun Yin,Chih-Li Han,An-I Lee, andChew-Wun Wu 34. Dynamicsin Alcohol DehydrogenaseElucidatedfrom Crystallographic Investigations 275 Ramaswamy S 35. StudiesonVariantsofAlcohol DehydrogenasesandItsDomains. .......... 285 Jawed Shafqat,Jan-Olov HMg, Lars Hjelmqvist,Udo Oppermann, Carlos Ibanez,andHans Jomvall 36. UncompetitiveInhibitorsofAlcohol Dehydrogenases 295 Bryce V. Plapp,Vijay K. Chadha,Kevin G. Leidal,HeeyeongCho, Michael Scholze,John F. Schindler,Kristine B. Berst,and Ramaswamy S 37. TandemMa~~SpectrometryofAlcoholDehydrogenaseandRelated Biomolecules 305 William J. Griffiths 38. FunctionofAlcoholDehydrogenaseandAldehydeDehydrogenaseGene FamiliesinRetinoid Signaling 311 Gregg Duester 39. PrimaryRoleofAlcohol DehydrogenasePathwayinAcuteEthanol-Induced ImpairmentofProteinKinaseC-Dependent SignalingSystem 321 Cinzia Domenicotti,Dimitri Paola,Antonella Vitali,Mariapaola Nitti, Damiano Cottalasso,Giuseppe Poli,Maria Adelaide Pronzato, and Umberto Maria Marinari 40. ClassIIAlcohol Dehydrogenase: ASuggestedFunctioninAldehyde Reduction 331 Jan-Olov HMg; Stefan Svensson,Patrik Stromberg,andMargareta Brandt 41. Zinc BindingCharacteristicsofthe Synthetic PeptideCorrespondingto the StructuralZinc SiteofHorseLiverAlcoholDehydrogenase 339 TomasBergman, Carina Palmberg,HansJomvall, David S. Auld,and BertL. Vallee