Non-canonical Cyclic Nucleotides PDF
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Handbook of Experimental Pharmacology 238 Roland Seifert E ditor Non- canonical Cyclic Nucleotides Handbook of Experimental Pharmacology Volume 238 Editor-in-Chief J.E.Barrett,Philadelphia EditorialBoard V.Flockerzi,Homburg M.A.Frohman,StonyBrook,NY P.Geppetti,Florence F.B.Hofmann,Mu¨nchen M.C.Michel,Mainz C.P.Page,London W.Rosenthal,Berlin K.Wang,Beijing More information about this series at http://www.springer.com/series/164 Roland Seifert Editor Non-canonical Cyclic Nucleotides Editor RolandSeifert InstituteofPharmacology HannoverMedicalSchool Hannover,Germany ISSN0171-2004 ISSN1865-0325 (electronic) HandbookofExperimentalPharmacology ISBN978-3-319-52671-3 ISBN978-3-319-52673-7 (eBook) DOI10.1007/978-3-319-52673-7 LibraryofCongressControlNumber:2017940389 #SpringerInternationalPublishingAG2017 Thisworkissubjecttocopyright.AllrightsarereservedbythePublisher,whetherthewholeorpartof the material is concerned, specifically the rights of translation, reprinting, reuse of illustrations, recitation, broadcasting, reproduction on microfilms or in any other physical way, and transmission or information storage and retrieval, electronic adaptation, computer software, or by similar or dissimilarmethodologynowknownorhereafterdeveloped. The use of general descriptive names, registered names, trademarks, service marks, etc. in this publicationdoesnotimply,evenintheabsenceofaspecificstatement,thatsuchnamesareexempt fromtherelevantprotectivelawsandregulationsandthereforefreeforgeneraluse. Thepublisher,theauthorsandtheeditorsaresafetoassumethattheadviceandinformationinthis book are believed to be true and accurate at the date of publication. Neither the publisher nor the authors or the editors give a warranty, express or implied, with respect to the material contained hereinor for anyerrors oromissionsthat may havebeenmade. Thepublisher remainsneutralwith regardtojurisdictionalclaimsinpublishedmapsandinstitutionalaffiliations. Printedonacid-freepaper ThisSpringerimprintispublishedbySpringerNature TheregisteredcompanyisSpringerInternationalPublishingAG Theregisteredcompanyaddressis:Gewerbestrasse11,6330Cham,Switzerland Preface Ingeneral,thepurposeoftheseriesHandbookofExperimentalPharmacologyisto criticallyreviewandsummarizethestate-of-the-artofawell-establishedscientific field. For this volume, this situation is quite different: Here, experts from various disciplines discuss a young field. The development of the area was impeded by previous methodological difficulties that have been overcome only recently. Accordingly, the book also discusses scientific gaps in our knowledge and aims tofosterfurtherresearch.IamthankfultotheEditorsoftheHandbookofExperi- mentalPharmacologyforgivingmetheopportunitytoputtogetherthisbook. The book is about cyclic nucleotides (cNMPs). cAMP and cGMP are firmly established second messenger molecules with broad pharmacotherapeutic implications. These two cNMPs are also designated as canonical cNMPs. cAMP and cGMP have several relatives that are designated as noncanonical cNMPs. A majorfocusofthisbookistodiscussthecyclicpyrimidinenucleotidescCMPand cUMP with respect to their endogenous and bacterial generators, effectors, biological functions, and elimination. The chapters cover both conceptual and methodological aspects. Most importantly, the recent development of the field was strongly enhanced by new analytical methods for cNMP detection and the synthesisofcNMPanalogsthatcanbeusedasexperimentaltools. InadditiontocCMPandcUMP,thisbookcoverscNMPsrelatedtocGMP,i.e., cIMP,8-nitro-cGMP,andthecyclicdinucleotidecGAMP.Hence,thisvolumeisa logicalcontinuationofVolume191oftheHandbookofExperimentalPharmacol- ogy(2009) edited by H.H.Schmidt,F. Hofmann,andJ.P.Stasch, entitledcGMP: Generators, Effectors and Therapeutic Implications. Lastly, the present volume covers 20,30-cNMPs. The major difference between 20,30-cNMPs and the cNMPs mentioned above (cAMP, cGMP, cCMP, cUMP, cIMP, and 8-nitro-cGMP) is the nature of the phosphodiester bond (30,50 in the latter compounds). However, this apparentlysmallchemicaldifferencehasmajorconsequencesforbiologicaleffects. As is expected from a young field, currently, there is not yet an established pharmacotherapeutic application. More systematic basic research in multiple biological systems is required. Nonetheless, it is beginning to emerge that each cNMP plays a unique functional role that could be exploited therapeutically. One particularly prominent case is the cUMP generated by Pseudomonas aeruginosa v vi Preface toxinExoY.TargetingcUMPmaybeanapproachtotreatinfectionwiththisGram- negative bacterium, a major problem in hospitalized patients and patients with cysticfibrosis. Iamveryindebtedtoalltheauthorswhopreparedtheirchapterssocarefullyand implemented all my suggestions for revision. All authors of this book have made substantial experimental, methodological, and/or conceptual contributions to the fieldandpresentpersonalbutbalancedviewsonspecificaspects. IalsowouldliketothanktheeditorialteamfromSpringerfortheirdedicationto completepublicationofthebook. Aswithmanymultiauthorbooks,ittookmoretimetocompleteallchaptersthan originallyplanned,amajorreasonbeingthatseveralauthorswishedtoincludevery recently published peer-reviewed data into their chapters. After completion of several chapters, some new and important findings were published. Specifically, the natural compound thymoquinone was identified as a pharmacological tool to manipulate cIMP levels [Detremmerie et al. (2016) J Pharmacol Exp Ther 358:558].Moreover,crystalstructures ofHCN channel2incomplexwith nonca- nonicalcNMPshavebeenresolved[Ngetal.(2016)Structure24:1629].Thesedata highlight that even in a small field, scientific progress can be so fast that it is difficultforamultiauthorbooktobeatthecuttingedge. Ihopethatthis bookoffers asuitableplatform for both cNMPaficionados and newcomers to conduct productive research in this exciting area. If the field develops, perhaps, in 20 years, another volume on the topic is warranted in the HandbookofExperimentalPharmacology. Hannover,Germany RolandSeifert September2016 Contents PartI 30,50-cCMPand30,50-cUMPasSecondMessengers cCMPandcUMPAcrosstheTreeofLife:FromcCMPandcUMP GeneratorstocCMP-andcUMP-RegulatedCellFunctions. . . . . . . . . . 3 RolandSeifert cCMPandcUMPinApoptosis:ConceptsandMethods. . . . . . . . . . . . . 25 SabineWolter,FanniDittmar,andRolandSeifert MammalianNucleotidylCyclasesandTheirNucleotide BindingSites. . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 49 StefanDove ThePseudomonasaeruginosaExoenzymeY:APromiscuous NucleotidylCyclaseEdemaFactorandVirulenceDeterminant. . . . . . . 67 K.AdamMorrow,DaraW.Frank,RonBalczon,andTroyStevens CyclicNucleotideMonophosphatesinPlantsandPlantSignaling. . . . . 87 ClaudiusMarondedze,AloysiusWong,LudivineThomas,HelenIrving, andChrisGehring cAMP-DependentProteinKinaseandcGMP-DependentProtein KinaseasCyclicNucleotideEffectors. . . . . . . . . . . . . . . . . . . . . . . . . . 105 RobinLorenz,DanielaBertinetti,andFriedrichW.Herberg RegulationofHCNIonChannelsbyNon-canonicalCyclicNucleotides. . . 123 BryanVanSchouwenandGiuseppeMelacini InteractionofEpacwithNon-canonicalCyclicNucleotides. . . . . . . . . . 135 HolgerRehmann IdentificationofcCMPandcUMPSubstrateProteinsandCross TalkBetweencNMPs. . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 149 JensSchlossmannandStefanieWolfertstetter InactivationofNon-canonicalCyclicNucleotides:Hydrolysis andTransport. . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 169 ErichH.SchneiderandRolandSeifert vii viii Contents PartII 30,50-cIMP,8-nitro-cGMP,20,30-cNMPsandCyclic DinucleotidesasSignalingMolecules 30,50-cIMPasPotentialSecondMessengerintheVascularWall. . . . . . 209 SusanW.S.Leung,YuanshengGao,andPaulM.Vanhoutte DiscoveryandRolesof20,30-cAMPinBiologicalSystems. . . . . . . . . . . . 229 EdwinK.Jackson 8-Nitro-cGMP:ANovelProtein-ReactivecNMPandItsEmerging RolesinAutophagy. . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 253 HirokazuArimotoandDaikiTakahashi CyclicDinucleotidesintheScopeoftheMammalianImmune System. . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 269 ArunK.Mankan,MartinaMüller,GregorWitte,andVeitHornung PartIII Methods/ToolsforcNMPResearch MassSpectrometricAnalysisofNon-canonicalCyclicNucleotides. . . . 293 HeikeBa¨hreandVolkhardKaever MedicinalChemistryoftheNoncanonicalCyclicNucleotidescCMP andcUMP. . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 307 FrankSchwede,AndreasRentsch,andHans-GottfriedGenieser HolisticMethodsfortheAnalysisofcNMPEffects. . . . . . . . . . . . . . . . 339 ManuelGrundmannandEviKostenis TheChemistryoftheNoncanonicalCyclicDinucleotide2030-cGAMP andItsAnalogs. . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 359 FrankSchwede,Hans-GottfriedGenieser,andAndreasRentsch Index. . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 385 cCMP and cUMP Across the Tree of Life: From cCMP and cUMP Generators to cCMP- and cUMP-Regulated Cell Functions Roland Seifert Contents 1 Introduction................................................................................... 4 2 OverviewofcAMPandcGMPSignaling................................................... 8 3 cCMPandcUMPGenerators................................................................ 9 3.1 InitialProblemsandRevitalizationoftheField....................................... 9 3.2 SolubleGuanylylCyclase.............................................................. 10 3.3 SolubleAdenylylCyclase.............................................................. 12 4 OccurrenceofcCMPandcUMPinBiologicalSystems.................................... 13 5 cCMP-andcUMP-RegulatedCellFunctions............................................... 17 6 ConclusionsandFuturePerspectives........................................................ 19 References........................................................................................ 20 Abstract The cyclic purine nucleotides cAMP and cGMP are well-established second messenger molecules that are generated by distinct nucleotidyl cyclases (NCs) andregulatenumerouscellfunctionsviaspecificeffectormolecules.Incontrast, the existence of the cyclic pyrimidine nucleotides cCMP and cUMP has been controversialformanyyears.Thedevelopmentofhighlyspecificandsensitive massspectrometrymethodshasenabledtheunequivocaldetectionandquantita- tionofcCMPandcUMPinbiologicalsystems.ThesecNMPsoccurbroadlyin numerousmammaliancelllinesandprimarycells.cCMPhasalsobeendetected in mouse organs, and both cCMP and cUMP occur in various developmental stages of the zebrafish Danio rerio. So far, the soluble guanylyl cyclase (sGC) and soluble adenylyl cyclase (sAC) have been identified as cCMP and cUMP generators.DissociationsintheexpressionpatternsofsACandsGCrelativeto R.Seifert(*) InstituteofPharmacology,HannoverMedicalSchool,Carl-Neuberg-Str.1,30625Hannover, Germany e-mail:[email protected] #SpringerInternationalPublishingAG2016 3 R.Seifert(ed.),Non-canonicalCyclicNucleotides, HandbookofExperimentalPharmacology238,DOI10.1007/164_2016_5005
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