Reactions of excited states of phenoxazin-3-one dyes with amino acids.

Abstract:

:The interaction with amino acids of the excited states of the N-oxide resazurin and its deoxygenation product resorufin, has been studied in aqueous solution at pH 7.5. Steady-state and time-resolved studies show that the fluorescence is quenched by amino acids. Complexation of the dyes in the ground state with aromatic amino acids was also observed. The singlet quenching is attributed to electron transfer from the amino acids to the excited dye based on the dependence of the bimolecular rate constants with the ionization potential of quenchers. Flash photolysis experiments allowed determination of the quenching rate constants for the triplet deactivation of dyes by several amino acids, as well as the characterization of the transients formed in the process. These data show that the triplet is also deactivated by an electron transfer process. However, the deactivation of the N-oxide dye by tryptophan can be described by a hydrogen atom transfer. The protolytic dissociation constants of the dye radical ions are reported. The irradiation of rezasurin in the presence of amino acids leads to deoxygenation of the dye to give resorufin. This process involves the triplet excited state of resazurin and is efficient only in the presence of amino acids containing the -SH group.

journal_name

Photochem Photobiol

authors

Villegas ML,Bertolotti SG,Previtali CM,Encinas MV

doi

10.1562/2004-10-12-RA-342

subject

Has Abstract

pub_date

2005-07-01 00:00:00

pages

884-90

issue

4

eissn

0031-8655

issn

1751-1097

pii

2004-10-12-RA-342

journal_volume

81

pub_type

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