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Ivo Piantanida, v. zn. sur. IRB-a Ocjenitelji: Dr. sc. Marina Cindri, red. prof. PMF-a Dr. sc. Ivo Piantanida, v. zn. sur. IRB-a Dr. sc. Ivana Weygand-uraaevi, red. prof. PMF-a Rad prihvaen: 2009. ABSTRACT University of Zagreb Faculty of Science Doctoral Thesis Department of Chemistry SYNTHESIS OF UREA-PHENANTHRIDINIUM derivatives AND THEIR INTERACTIONS WITH NUCLEIC ACIDS IN AQUEOUS MEDIA MARIJANA RADI STOJKOVI Laboratory of Supramolecular and Nucleoside Chemistry Division of Organic Chemistry and Biochemistry Ruer Boakovi Institute, Zagreb, Bijeni ka 54, Croatia In the scope of this thesis new compounds, urea-phenanthridinium derivatives 3-12, and their precursors, 1-2 were prepared and characterized spectroscopicaly. Interactions of 6-8 with nucleotides and compounds 3, 6-8 and 10-12 with double stranded polynucleotides were studied in aqueous media by fluorimetric, UV-Vis and CD titrations, and by melting temperature measurements. Determined pK values of phenanthridine analogues, 3, 6-8 are probably related to the length of the aliphatic linker connecting two urea-phenanthridinium subunits and therefore to the efficiency of intramolecular interactions between those subunits. Such presumption was based on differences in molar extinction coefficients of urea-phenanthridinium derivatives 3, 6-8, their fluorescence intensities and pK values. Values of stability constants of 6-8 nucleotide complexes (log Ks = 2  3) were almost the same indicating the predominance of aromatic interactions 6 8  nucleotide complexes. The comparable binding affinity of compounds 3, 6-8 and 10-12 was obtained in fluorimetric titration experiments (pH = 5, pH = 7) towards most of the studied polynucleotides (log Ks = 5  6). Exceptions were stability constants of 6 and 7 poly G poly C complexes. Such finding could be explained by agglomeration of 6 and 7 inside the polynucleotide hydrophobic grooves and most likely by the recognition of G-C basepairs by bis-urea linkers of 6 and 7. Addition of poly G poly C to 3, 8 and 10-12 solutions resulted in efficient fluorescence quenching of their fluorescence. This observation presume strong aromatic stacking interactions of fluorophore with polynucleotide and therefore support intercalation of these compounds into double stranded RNA. In comparison to other studied compounds, addition of poly A poly U to 3, 8 and 12 solutions resulted in good thermal stabilisation of double helices. Those results observed in melting temperature measurements as well as specific CD effects (weak positive induced CD band in the region between ( = 300 and 350 nm) suggested intercalation as a dominant binding mode to ds-RNA. The thermal stabilisation effect of 6 on the ds-DNA and significant decrease of CD spectra of all studied polynucleotides, indicated that dominant interactions of 6 are formed within ds-DNA minor groove. (115 pages, 44 figures, 8 schemes, 14 tables, 84 references, original in Croatian) Thesis is deposed at Central Chemical Library, Horvatovac 102A, Zagreb and at the Chemical Library of Ruer Boakovi Institute Keywords: urea / (bis)phenantridines / intercalators / groove agglomeration / polynucleotides / selectivity of binding / fluorescence selectivity / hydrogen bonds Supervisor: Dr. Ivo Piantanida, Scientific Assistant, Rudjer Boakovi Institute Reviewers: Dr. Marina Cindri, Professor, Faculty of Science Dr. Ivo Piantanida, Scientific Assistant, Rudjer Boakovi Institute Dr. Ivana Weygand-uraaevi, Professor, Faculty of Science Thesis accepted: 2009. 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seriesInputBinUpperTrayRESDLLUniresDLLHPPreAnalysisFalseMSPreAnalysisFalseHPReportSymmetricMarginsFalseHPMinimizeMarginsTrueHPAlignMarginsForMDTrueDuplexNONEHPPrintPreviewFalseHPOverSprayOptionAutomaticHPOverSpray100HPBorderLessPhotoFalseHPBorderLessAutoFitFalseHPCustomBorderlessTrueHPOutputOrderReverseTrueJobUITruePaperSizeLETTEROrientationPORTRAITHPPaperSizeDuplexConstraintsINDEX_CARD_3X5HPDocPropResourceDatahpzhl43a.cabHPNUseDiffFirstPageChoiceTrueHPMediaTypeDuplexConstraintsHP_PHOTO_GREETING_CARDSHPDryTimeOptionAutomaticHPDryTime0HPInkVolumeOptionAutomaticHPInkVolumeNormalHPPrintInGrayScaleFalsePrintQualityNormalPrintQualityGroupPQGroup_2HPJobAccountingHPJOBACCT_JOBACNT_TIMESTAMPHPColorModeCOLOR_MODEHPPDLTypePDL_PCL3HPPJLEncoding8bitEncodingHPXMLFileUsedhpf69403.xmlHPPosterPrintingFalseHPPosterPrintingOptionPOSTER_2HPMediaTypeTreeviewPopupTrueColorModeColor24TextAsBlackFalseMediaTypeAUTOMATICResolution600dpiPQDPIInstalledHPMirrorPrintFalseHPAutoDuplexScalingTrueHPPrintOnBothSidesManuallyFalseHPManualDuplexDialogItemsInstructionID_01_FACEUP-NOROTATEHPManualDuplexPageRotateUserRotateHPManualFeedOrientationFACEUPHPSpeedMechFastDraftHPOutputBinOrientationFACEUPHPManualDuplexDialogModelModalHPManualDuplexPageOrderOddPagesFirstHPMapManualFeedToTray1FalseHPSendPJLUsageCmdLNNAME_COUSPSAlignmentFileHPZ3A43aPSServicesOptionHPServiceFileNameEndHPCleaningFilesDataHP_Clean_TestPageHPConsumerCustomPaperHPCustomHPColorSelectionForHPAEnabledHPSmartDuplexSinglePageJobTrueHPBornOnDateHPBODHPInputColorSpaceCOLORSMARTJobUINetworkTrueHPDriverDataDriverDataHPICCProfileNamesRGB_0Color_0Space_0Profile_1icmHPDisplayPrintingHelpRegPathHPCustomSizeCommandTRUEHPSendPreloadCommandTRUEESPRITSupportedTrueHPUseAutoDuplexUnitFalseHPHideManualFeedTrueHPRESDLLNameHPFRS43aHPRedEyeReductionOnHPDigitalImagingHPHomePrintingHPSmartFocusOnHPContrastOffHPDigitalFlashOffHPSharpnessOffHPSmoothingOffHPJpegPngPassthroughTrueHPReverseBandOrderForEvenPagesReverseBandOrderHalftoneHT_PATSIZE_DEFAULTHPQuietPrintingFalseHPHTDLLNameHPFIG43aHPMHDLLNameHPFIE43aHPHPAFilterTrueHPIntentPERCEPTUALHPInstalledPrintCartridgesTRICOLOR_BLACKHPAdvancedColorSettingTrueHPICCPrinterFamily5700_6500HPCRDCommandTrueHPSendUnitMeasureCommandTRUEHPPaperSizeTreeviewPopupMetricPIUPHdA4 4 [none] [none]4P d?ADMINISTRATOR44dMicrosoft Office WordWINWORD.EXEC:\Program Files\Microsoft Office\OFFICE11\WINWORD.EXEAuto HP DeskJet 6940 series on%C 4dXXA4DINU"x PU]x SMTJh HP DeskJet 6940 seriesInputBinUpperTrayRESDLLUniresDLLHPPreAnalysisFalseMSPreAnalysisFalseHPReportSymmetricMarginsFalseHPMinimizeMarginsTrueHPAlignMarginsForMDTrueDuplexNONEHPPrintPreviewFalseHPOverSprayOptionAutomaticHPOverSpray100HPBorderLessPhotoFalseHPBorderLessAutoFitFalseHPCustomBorderlessTrueHPOutputOrderReverseTrueJobUITruePaperSizeLETTEROrientationPORTRAITHPPaperSizeDuplexConstraintsINDEX_CARD_3X5HPDocPropResourceDatahpzhl43a.cabHPNUseDiffFirstPageChoiceTrueHPMediaTypeDuplexConstraintsHP_PHOTO_GREETING_CARDSHPDryTimeOptionAutomaticHPDryTime0HPInkVolumeOptionAutomaticHPInkVolumeNormalHPPrintInGrayScaleFalsePrintQualityNormalPrintQualityGroupPQGroup_2HPJobAccountingHPJOBACCT_JOBACNT_TIMESTAMPHPColorModeCOLOR_MODEHPPDLTypePDL_PCL3HPPJLEncoding8bitEncodingHPXMLFileUsedhpf69403.xmlHPPosterPrintingFalseHPPosterPrintingOptionPOSTER_2HPMediaTypeTreeviewPopupTrueColorModeColor24TextAsBlackFalseMediaTypeAUTOMATICResolution600dpiPQDPIInstalledHPMirrorPrintFalseHPAutoDuplexScalingTrueHPPrintOnBothSidesManuallyFalseHPManualDuplexDialogItemsInstructionID_01_FACEUP-NOROTATEHPManualDuplexPageRotateUserRotateHPManualFeedOrientationFACEUPHPSpeedMechFastDraftHPOutputBinOrientationFACEUPHPManualDuplexDialogModelModalHPManualDuplexPageOrderOddPagesFirstHPMapManualFeedToTray1FalseHPSendPJLUsageCmdLNNAME_COUSPSAlignmentFileHPZ3A43aPSServicesOptionHPServiceFileNameEndHPCleaningFilesDataHP_Clean_TestPageHPConsumerCustomPaperHPCustomHPColorSelectionForHPAEnabledHPSmartDuplexSinglePageJobTrueHPBornOnDateHPBODHPInputColorSpaceCOLORSMARTJobUINetworkTrueHPDriverDataDriverDataHPICCProfileNamesRGB_0Color_0Space_0Profile_1icmHPDisplayPrintingHelpRegPathHPCustomSizeCommandTRUEHPSendPreloadCommandTRUEESPRITSupportedTrueHPUseAutoDuplexUnitFalseHPHideManualFeedTrueHPRESDLLNameHPFRS43aHPRedEyeReductionOnHPDigitalImagingHPHomePrintingHPSmartFocusOnHPContrastOffHPDigitalFlashOffHPSharpnessOffHPSmoothingOffHPJpegPngPassthroughTrueHPReverseBandOrderForEvenPagesReverseBandOrderHalftoneHT_PATSIZE_DEFAULTHPQuietPrintingFalseHPHTDLLNameHPFIG43aHPMHDLLNameHPFIE43aHPHPAFilterTrueHPIntentPERCEPTUALHPInstalledPrintCartridgesTRICOLOR_BLACKHPAdvancedColorSettingTrueHPICCPrinterFamily5700_6500HPCRDCommandTrueHPSendUnitMeasureCommandTRUEHPPaperSizeTreeviewPopupMetricPIUPHdA4 4 [none] [none]4P d?ADMINISTRATOR44dMicrosoft Office WordWINWORD.EXEC:\Program Files\Microsoft Office\OFFICE11\WINWORD.EXE 3 3!% 3 3 vvvvvvvvvvvvvI3PP P PP @PP4@PP P"P&P(P*P,P.P0P2P4P:PnUnknownGz Times New Roman5Symbol3& z Arial7&  Verdana"1hꦏf +\+\!4d332qHP?Q2!Ovaj je magistarski rad izraen uPreferred CustomerMarijana Radi Stojkovi$      Oh+'0   DP p |  $Ovaj je magistarski rad izraen uPreferred Customer Normal.dotMarijana Radi Stojkovi3Microsoft Office Word@vA@?@ABCDEFGHIJKLMNOPQRSTUVWYZ[\]^_`abcdefghijklmnopqrstuvwxyz{|}~Root Entry Fcq1TableXWordDocument@SummaryInformation(DocumentSummaryInformation8CompObjs  F!Microsoft Office Wordov dokument MSWordDocWord.Document.89q