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PHOTO‐CIDNP AS A TOOL FOR THE STUDY OF THE REACTIVITY OF PHOTOSENSITIZING DRUGS: THE FUROCOUMARINS
Author(s) -
Marko J.,
Vermeersch G.,
FebvayGarot N.,
LablacheCombier A.,
Moron J.,
Bisagni E.
Publication year - 1988
Publication title -
photochemistry and photobiology
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.818
H-Index - 131
eISSN - 1751-1097
pISSN - 0031-8655
DOI - 10.1111/j.1751-1097.1988.tb02690.x
Subject(s) - cidnp , chemistry , furocoumarin , bifunctional , furocoumarins , photochemistry , reactivity (psychology) , moiety , stereochemistry , organic chemistry , radical , biochemistry , medicine , dna , alternative medicine , pathology , catalysis
— Several monofunctional and bifunctional furocoumarin derivatives were studied by means of the photo‐CIDNP technique. Nuclear spin polarizations were observed on some of these derivatives when irradiated in acetonitrile solutions. The likely occurrence of both semi‐reduced and semi‐oxidized species of the FC in the reaction scheme is discussed. When N‐acetyltyrosine was added to the solution, CIDNP effects were observed on both reactants. They arose from a highly reversible pathway, as no photoproduct was polarized. On the FC part, the stronger effects were always observed on the 3,4 pyrone double bond suggesting that it must possess the highest spin density in the reaction intermediate. According to previous studies, the latter should be the FC anion or neutral radical. For the amino‐acid moiety, the intensity of the polarizations was strongly dependent on the nature of the FC. This allowed the classification of the FC into three groups (zero, weak and strong intensities). As compared with their photobiological reactivity, this classification seemed to be related to the usual mono‐ and bifunctional distinction. This is the second example showing that photo‐CIDNP could be used as a preliminary test for the study of the photosensitizing drug properties.