Adenosine-mediated photoreaction of 4,5',8-trimethylpsoralen with alcohols

Photochem Photobiol. 1993 Aug;58(2):164-8. doi: 10.1111/j.1751-1097.1993.tb09543.x.

Abstract

Irradiation of thin films consisting of 4,5',8-trimethylpsoralen (TMP), adenosine and small amounts of alcohols led to TMP-alcohol photoadducts in addition to TMP-adenosine photoadducts. Four TMP-ethanol and two TMP-methanol adducts have been separated and characterized. Covalent bonds were formed between the 4-carbon of TMP and the alpha-carbon to the hydroxy group in the alcohols. The TMP-alcohol photoadducts were formed only in the TMP film containing small amounts of alcohol and adenosine. Furthermore, no photoadduct of TMP and ribose was detected upon photolysis of a TMP-ribose film, suggesting that the adenine moiety plays a specific role in the reaction. The interaction of adenosine with psoralens in a dry film may be related to the DNA sequence selectivity observed for the photoreaction of psoralens with DNA.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Adenosine / chemistry*
  • Adenosine / radiation effects
  • Chromatography, High Pressure Liquid
  • Ethanol / chemistry*
  • Ethanol / radiation effects
  • Photolysis*
  • Spectrophotometry, Ultraviolet
  • Spectrum Analysis
  • Trioxsalen / chemistry*
  • Trioxsalen / radiation effects

Substances

  • Ethanol
  • Adenosine
  • Trioxsalen