Pyrroloquinolinone methylderivatives, furocoumarin analogues: interaction with biomolecules and computer-aided studies.
Farmaco
; 49(10): 615-23, 1994 Oct.
Article
en En
| MEDLINE
| ID: mdl-7826467
ABSTRACT
Pyrroloquinolinones, furocoumarin analogues, contain a divinilbenzene moiety, suggesting possible photoreactivity. Quantum mechanics calculations indicate that the pyrrole-side double bond exhibits strong photoreactivity, while the pyridone-side double bond is only poorly photoreactive. Intercalation models obtained by molecular mechanics calculations suggest that, in the cis-syn intercalation arrangement, the pyridone-side double bond is well aligned with the nearby thymine, supporting possible C4-cycloaddition with the 5,6 double bond of thymine, while the pyrrole-side double bond assumes an unfavourable position for photobinding. These data suggest that photoreaction between the pyridone-side and thymine double bonds may takes place, although with very low yield. Experimental evidence concerning DNA-photobinding exhibited by 2,6-dimethyl-9-methoxy-4H-pyrroloquinolinone (Compound I) confirms theoretical predictions. The formation of C4-cycloadducts between the pyridone side double bond and thymine also takes place with very low yield. Compound I shows marked BSA photobinding, suggesting that pyrroloquinolinones may photoreact with proteins. The three pyrroloquinolinones examined show high yields of singlet oxygen generation, suggesting that photobiological effects may be obtained through this photodynamic pathway, rather than through DNA photobinding.
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Bases de datos:
MEDLINE
Asunto principal:
Fotoquimioterapia
/
Furocumarinas
/
ADN
/
Fármacos Fotosensibilizantes
/
Quinolonas
Tipo de estudio:
Prognostic_studies
Idioma:
En
Revista:
Farmaco
Asunto de la revista:
FARMACOLOGIA
/
QUIMICA
Año:
1994
Tipo del documento:
Article
País de afiliación:
Italia