Dye-conjugated complementary lipophilic nucleosides as useful probes to study association processes by fluorescence resonance energy transfer
EntityUAM. Departamento de Química Orgánica; UAM. Instituto de Investigación Avanzada en Ciencias Químicas (IAdChem)
PublisherRoyal Society of Chemistry
10.1039/c7ob01930kOrganic and Biomolecular Chemistry 15.36 (2017): 7558-75655
ISSN1477-0520 (print); 1477-0539 (online)
Funded byFunding from the European Research Council (ERC-Starting Grant 279548 PROGRAM-NANO) and MINECO (CTQ2014-57729-P) is gratefully acknowledged. E. F. would like to thank the Sharif University of Technology of Iran for financial support. D. S.M. would like to acknowledge Comunidad de Madrid for financial support through contract PEJ16/IND/AI-0849
ProjectGobierno de España. CTQ2014-57729-P; info:eu-repo/grantAgreement/EC/FP7/279548; Comunidad de Madrid. PEJ16/IND/AI-0849
SubjectsBinding energy; Aromatic compounds; Bins; Biomolecules; Chemical analysis; Chemical bonds; Chromophores; Emission spectroscopy; Energy transfer; Fluorescence spectroscopy; Organic polymers; Probes; Self assembly; Resonance; Supramolecular chemistry; Thermodynamics; Química
Rights© 2017 The Royal Society of Chemistry
Modern supramolecular chemistry relies on the combination of diverse analytical techniques that can provide complementary information on complex self-assembly landscapes. Among them, resonance energy transfer, monitored by fluorescence emission spectroscopy, arises as a sensitive and convenient phenomenon to report binding intermolecular interactions. The use of molecular probes labelled with suitable complementary energy-transfer pairs can provide valuable information about the thermodynamics, kinetics and self-sorting characteristics of a particular self-assembled system. The objective of this work is to generate a set of nucleoside FRET probes that can be reliably employed to prove and analyse quantitatively H-bonding interactions between complementary Watson-Crick pairs. We first describe the preparation of a set of lipophilic nucleosides that are linked to a π-conjugated functional fragment. The bases include guanosine and 2-aminoadenosine as purine heterocycles, and cytidine and uridine as complementary pyrimidine bases. The π-conjugated moiety comprises either a short phenylene-ethynylene oligomer, a bithiophene, or a BODIPY dye. We then demonstrate that the last two chromophores constitute an energy donor-acceptor couple and that donor emission quenching can be related to the ratio of molecules bound to the complementary acceptor pair. Hence, fluorescence spectroscopy in combination with resonance energy transfer, is shown here to be a useful tool to study and quantify the association and self-sorting events between complementary and non-complementary nucleosides in apolar aromatic solvents, where the binding strength is considerably high, and sensitive techniques that employ low concentrations are demanded
Google Scholar:Mayoral, M. J. - Camacho-García, J. - Magdalena-Estirado, E. - Blanco-Lomas, M. - Fadaei, E. - Montoro-García, C. - Serrano-Molina, D. - González-Rodríguez, D.
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