PHOTOSENSITIZATION OF PYRIMIDINES BY 2‐METHYLNAPHTHOQUINONE IN WATER: A LASER FLASH PHOTOLYSIS STUDY

2‐Methylnaphthoquinone (MQ) has been excited in water with a 20 ns laser flash at 353 nm and the resultant transient species have been observed optically. Triplet‐state MQ (3MQ) decays on a sub‐microsecond time scale. It has been characterized in terms of its absorption spectrum and quantum yield. Rate constants have been measured for the decay of 3MQ in infinitely dilute solution, for self‐quenching by ground‐state MQ, and for reactions of 3MQ with oxygen, thymine, uracil, 6‐methyluracil, and orotic acid. The interaction of 3MQ with pyrimidines involves charge transfer to give the pyrimidine cation radical and the MQ : anion radical. These reactions are discussed in relation to the mechanism of pyrimidine photooxidation sensitized by MQ.

[1]  G. Catravas,et al.  Effects of WR 2721 on cyclic nucleotide levels and lysosomal enzyme activities. , 1982, International journal of radiation oncology, biology, physics.

[2]  R. Bensasson,et al.  Assignment of transient species observed on laser flash photolysis of p-benzoquinone and methylated p-benzoquinones in aqueous solution , 1980 .

[3]  R. S. Sinclair,et al.  QUANTUM YIELDS OF TRIPLET FORMATION OF SOME DERIVATIVES OF ANTHRAQUINONE , 1979 .

[4]  G. Smith The triplet-state charge-transfer reaction between p-nitroacetophenone and guanosine monophosphate: a possible mechanism for electron-affinic radiosensitization. , 1979, International journal of radiation biology and related studies in physics, chemistry, and medicine.

[5]  A. Kuboyama The Phosphorescence Spectra of 1,4-Naphthoquinone and Its Alkyl Derivatives in Solutions at 77 K , 1978 .

[6]  C. R. Goldschmidt,et al.  LASER INTENSITY AND THE COMPARATIVE METHOD FOR DETERMINATION OF TRIPLET QUANTUM YIELDS , 1978 .

[7]  H. Taber,et al.  NEAR ULTRAVIOLET INDUCTION OF GROWTH DELAY STUDIED IN A MENAQUINONE‐DEFICIENT MUTANT OF BACILLUS SUBTILIS , 1978, Photochemistry and photobiology.

[8]  J. Amesz,et al.  Purification and photochemical properties of reaction centers of Chromatium vinosum. Evidence for the photoreduction of a naphthoquinone. , 1977, Biochimica et biophysica acta.

[9]  J. Cadet,et al.  Radiation chemistry of nucleic acids: characterization of thymine hydroxy-hydroperoxides. , 1974, Biochemical and biophysical research communications.

[10]  E. Land,et al.  Optical and kinetic properties of semireduced plastoquinone and ubiquinone: electron acceptors in photosynthesis. , 1973, Biochimica et biophysica acta.

[11]  E. Hayon,et al.  One-electron redox reactions of free radicals in solution. Rate of electron transfer processes to quinones. , 1973, Biochimica et biophysica acta.

[12]  R. Willson,et al.  Semiquinone free radicals and oxygen. Pulse radiolysis study of one electron transfer equilibria , 1973 .

[13]  H. D. Roth,et al.  Cleavage of thymine dimers sensitized by quinones. Chemically induced dynamic nuclear polarization in radical ions. , 1972, Journal of the American Chemical Society.

[14]  G. Adams,et al.  Radical oxidation mechanisms in cellular radiosensitisation: electron transfer in the pulse radiolysis of aqueous nucleotide solutions. , 1972, Radiation Research.

[15]  F. Peterson,et al.  Nanosecond pulse radiolysis studies of aqueous thymine solutions. , 1971, The Journal of physical chemistry.

[16]  E. Land,et al.  Triplet-triplet extinction coefficients via energy transfer , 1971 .

[17]  F. Wilkinson,et al.  Photochemical reactions of duroquinone. Part 2.—Flash photolytic investigations , 1970 .

[18]  J. Eisinger,et al.  Triplet state of DNA. , 1967, The Journal of chemical physics.

[19]  M. Charlier,et al.  PHOTOSENSITIZED DIMERIZATION OF OROTIC ACID IN AQUEOUS SOLUTION , 1967 .

[20]  A. Lamola,et al.  Mechanisms of Photochemical Reactions in Solution. XXXIII. Intersystem Crossing Efficiencies , 1965 .

[21]  J. P. Keene PULSE RADIOLYSIS APPARATUS , 1964 .

[22]  M. Simon,et al.  The photodynamic reaction of methylene blue with deoxyribonucleic acid. , 1962, Journal of molecular biology.