Reactive phosphate ester of the carcinogen 2-(N-hydroxy)acetamidofluorene

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Abstract
1. Reaction of 2-(N-acetoxy)-acetamidofluorene with orthophosphate buffer at pH7 yielded a large quantity of water-soluble fluorene derivatives, which showed absorption peaks at 303, 290 and 280nm. Tris buffer under similar conditions gave negligible reaction. 2. Hydrolysis of polar material with acid or alkaline phosphatases liberated equimolar amounts of inorganic phosphate and an ether-extractable fluorene derivative. On the basis of its u.v. spectrum, R(F) values after paper chromatography, solubility in alkali and colour with spray reagents, the derivative was characterized tentatively as 2-acetamido-5-hydroxyfluorene. 3. Polar material also contained a reactive fluorene derivative which gave characteristic reaction products with methionine and guanosine. The reactive derivative was characterized as a phosphate ester of 2-(N-hydroxy)-acetamidofluorene. 4. It is suggested that such reactive phosphate esters may also be some of the ultimate carcinogenic metabolites of carcinogenic aromatic hydroxamic acids.