PHOTOADDITION OF p‐AMINOBENZOIC ACID TO THYMINE AND THYMIDINE

Abstract

Abstract— Several studies in the literature have shown that DNA is damaged after UV irradiation in the presence of the sunscreen agent p‐aminobenzoic acid (PABA), both in vivo and in vitro. One type of damage has been shown to be the result of increased yields of pyrimidine cyclobutane dimer formation. However, it has been suggested that other types of lesions are produced as well. We have studied the photochemistry of the thymine‐PABA and thymidine‐PABA systems and report here the isolation and characterization of thymine‐PABA and thymidine‐PABA photoadducts. These products have been identified, respectively, as 5‐(2‐amino‐5‐carboxyphenyl)‐5,6‐dihydrothymine and isomeric forms of 5‐(2‐amino‐5‐carboxyphenyl)‐5,6‐dihydrothymidine. The quantum yields for the formation of these adducts in deaerated aqueous solutions at pH 7.0 have been determined to be 9.5 × 10–4 and 4.3 × 10–3 for the thymine and thymidine based adducts respectively. A pH profile for the thymine‐PABA system indicated a maximum quantum yield for adduct formation at pH 6.5, although it could be detected over the whole pH range studied (pH 3.5–11.0).