A Spectroscopic Study of the Interaction of the Fluorescent Delta b-Carboline-3-carboxylic Acid N-methylamide with DNA Constituents: Nucleobases, Nucleosides and Nucleotides

Interaction between Delta *b-carboline-3-carboxylic acid N-methylamide, Delta *bCMAM, and nucleobases, nucleosides and nucleotides is studied in the ground state with UV-visible, 1H NMR and 31P NMR spectroscopies and in the first excited state, with steady-state and time-resolved fluorescence spectr...

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Bibliographic Details
Published in:Journal of fluorescence 2008-09, Vol.18 (5), p.961-972
Main Authors: Garcia-Zubiri, Inigo X, Burrows, Hugh D, de Melo, Joao S Seixas, Monteserin, Maria, Arroyo, Antonio, Tapia, Maria J
Format: Article
Language:English
Subjects:
Constants
Electronics
Fluorescence
Ground state
Nuclear magnetic resonance
Nucleosides
Nucleotides
Spectroscopy
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Summary:Interaction between Delta *b-carboline-3-carboxylic acid N-methylamide, Delta *bCMAM, and nucleobases, nucleosides and nucleotides is studied in the ground state with UV-visible, 1H NMR and 31P NMR spectroscopies and in the first excited state, with steady-state and time-resolved fluorescence spectroscopy. Job plots show a predominant 1:1 interaction in both electronic states. Association constants are estimated from changes in the absorption spectra, and show that the strongest interaction is produced with the nucleosides: 2'-deoxyadenosine (dAdo) and thymidine (Thd), and with the mononucleotides: 2'-deoxycytidine 5'- monophosphate (5'-dCMP) and uridine 5'- monophosphate (5'-UMP). These results are corroborated by the upfield shifts of two 1H NMR resonances of the Delta *bCMAM indole group. The 31P NMR resonance of nucleotides is shifted downfield, suggesting the presence of electrostatic or hydrogen bond interaction with Delta *bCMAM. In the first electronic singlet excited state, static and dynamic quenching of Delta *bCMAM emission is achieved upon addition of nucleobases, nucleosides and nucleotides. This has been analysed using Stern--Volmer kinetics.
ISSN:1053-0509
DOI:10.1007/s10895-008-0355-9