Steady-state and time-resolved studies of the fluorescence of four aromatic unconjugated pterins (pterin (Ptr), 6-(hydroxymethyl)pterin (Hmp), 6-methylpterin (Mep), and 6,7-dimethylpterin (Dmp)) in aqueous solutions in the presence of different nucleotides (2′-deoxyguanosine 5′- monophosphate (dGMP), 2′-deoxyadenosine 5′-monophosphate (dAMP), and 2′-deoxycytosine 5′-monophosphate (dCMP)) have been performed using the single-photon counting technique. The singlet excited states of acid forms of pterins are deactivated by purine nucleotides (dGMP and dAMP) via a combination of dynamic and static processes. The efficiency of the dynamic quenching is high, independently of the nature of the purine base of the nucleotide and of the chemical structure of the substituents linked to the pterin moiety. Analysis of the static quenching indicates that ground-state association between pterins and purine nucleotides takes place, but the formation of the corresponding complexes is significant only at relatively high reactant concentrations. The quenching of the fluorescence of acid forms of pterin derivatives by dCMP, a pyrimidine nucleotide, is slightly less efficient than the quenching by purine nucleotides and is purely dynamic. In alkaline media, the fluorescence quenching is much less efficient than in acidic media, the deactivation by purine nucleotides being purely dynamic, whereas quenching by dCMP is negligible. Possible mechanisms for the quenching of fluorescence of pterin derivatives by the different nucleotides are discussed. © 2009 American Chemical Society.
Documento: | Artículo |
Título: | Quenching of the fluorescence of aromatic pterins by deoxynucleotides |
Autor: | Petroselli, G.; Dántola, M.L.; Cabrerizo, F.M.; Lorente, C.; Braun, A.M.; Oliveros, E.; Thomas, A.H. |
Filiación: | Instituto de Investigaciones Fisicoquímicas Teoricas y Aplicadas (INIFTA), Departamento de Química, Universidad Nacional de la Plata, CCT la Plata-CONICET, Boulevard 113 y 64, 1900 La Plata, Argentina Departamento de Química Orgánica, Facultad de Ciencias Exactas y Naturales, Universidad de Buenos Aires, Pabellón 2, 3p, 1428 Buenos Aires, Argentina Lehrstuhl für Umweltmesstechnik, Engler-Bunte Institut, Universität Karlsruhe, D-76128 Karlsruhe, Germany Laboratoire des IMRCP, UMR CNRS 5623, Université de Toulouse (Paul Sabatier), 118, route de Narbonne, F-31062 Toulouse cédex 9, France |
Palabras clave: | Acidic medias; Alkaline medias; Aqueous solutions; Chemical structures; Deoxyadenosine; Dynamic quenching; Fluorescence quenching; Ground-state; Monophosphate; Purine nucleotides; Quenching of the fluorescences; Reactant concentrations; Single-photon counting; Singlet excited state; Static quenching; Time-resolved studies; Acids; Aromatic compounds; Fluorescence; Methanol; Nucleic acids; Nucleotides; Quenching; 2' deoxy 5' adenosine monophosphate; 2'-deoxy-5'-adenosine monophosphate; 2'-deoxyguanosine 5'-phosphate; deoxyadenosine phosphate; deoxycytidine phosphate; deoxyguanosine phosphate; deoxyribonucleotide; pterin derivative; water; deoxyribonucleotide; pterin derivative; article; chemical structure; chemistry; fluorescence; kinetics; pH; spectrofluorometry; thermodynamics; Deoxyadenine Nucleotides; Deoxycytidine Monophosphate; Deoxyguanine Nucleotides; Deoxyribonucleotides; Fluorescence; Hydrogen-Ion Concentration; Kinetics; Molecular Structure; Pterins; Spectrometry, Fluorescence; Thermodynamics; Water; Deoxyadenine Nucleotides; Deoxycytidine Monophosphate; Deoxyguanine Nucleotides; Deoxyribonucleotides; Fluorescence; Hydrogen-Ion Concentration; Kinetics; Molecular Structure; Pterins; Spectrometry, Fluorescence; Thermodynamics; Water |
Año: | 2009 |
Volumen: | 113 |
Número: | 9 |
Página de inicio: | 1794 |
Página de fin: | 1799 |
DOI: | http://dx.doi.org/10.1021/jp8101496 |
Título revista: | Journal of Physical Chemistry A |
Título revista abreviado: | J Phys Chem A |
ISSN: | 10895639 |
CODEN: | JPCAF |
CAS: | deoxyadenosine phosphate, 653-63-4; deoxycytidine phosphate, 1032-65-1; deoxyguanosine phosphate, 902-04-5; pterin derivative, 948-60-7; water, 7732-18-5; 2'-deoxy-5'-adenosine monophosphate, 653-63-4; 2'-deoxyguanosine 5'-phosphate, 902-04-5; Deoxyadenine Nucleotides; Deoxycytidine Monophosphate, 1032-65-1; Deoxyguanine Nucleotides; Deoxyribonucleotides; Pterins; Water, 7732-18-5; 2'-deoxy-5'-adenosine monophosphate; 2'-deoxyguanosine 5'-phosphate; Deoxyadenine Nucleotides; Deoxycytidine Monophosphate; Deoxyguanine Nucleotides; Deoxyribonucleotides; Pterins; Water |
Registro: | https://bibliotecadigital.exactas.uba.ar/collection/paper/document/paper_10895639_v113_n9_p1794_Petroselli |