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

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Abstract

Interaction between β-carboline-3-carboxylic acid N-methylamide, βCMAM, 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 βCMAM indole group. The 31P NMR resonance of nucleotides is shifted downfield, suggesting the presence of electrostatic or hydrogen bond interaction with βCMAM. In the first electronic singlet excited state, static and dynamic quenching of βCMAM emission is achieved upon addition of nucleobases, nucleosides and nucleotides. This has been analysed using Stern–Volmer kinetics.

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Acknowledgment

Financial support from Spanish Junta de Castilla y León and European Union (Bu29/04) and Acción Integrada Hispano-Portuguesa (HP2003-0077, Acçcão E/405) is gratefully acknowledged. We are indebted to Dr. Virginia Diez and Dr. Jacinto José Delgado for their valuable help with NMR experiments.

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Authors and Affiliations

  1. Departamento de Química, Universidad de Burgos, Plaza Misael Bañuelos s/n, Burgos, 09001, Spain

    Iñigo X. García-Zubiri, María Monteserín, Antonio Arroyo & María J. Tapia

  2. Departamento de Química, Universidade de Coimbra, 3004-535, Coimbra, Portugal

    Hugh D. Burrows & Joao S. Seixas de Melo

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  1. Iñigo X. García-Zubiri
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  2. Hugh D. Burrows
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  3. Joao S. Seixas de Melo
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  4. María Monteserín
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  5. Antonio Arroyo
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  6. María J. Tapia
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Correspondence to Hugh D. Burrows or María J. Tapia.

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García-Zubiri, I.X., Burrows, H.D., Seixas de Melo, J.S. et al. A Spectroscopic Study of the Interaction of the Fluorescent β-Carboline-3-carboxylic Acid N-methylamide with DNA Constituents: Nucleobases, Nucleosides and Nucleotides. J Fluoresc 18, 961–972 (2008). https://doi.org/10.1007/s10895-008-0355-9

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  • DOI: https://doi.org/10.1007/s10895-008-0355-9

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