Mechanistic insights into the Michael addition of deoxyguanosine to catechol estrogen-3,4-quinones.

The reaction of catechol estrogen quinones with DNA to produce the depurinating adducts, 4-OHE 2(E 1)-1-N7Gua and 4-OHE 2(E 1)-1-N3Ade, has been linked to the initiation of breast and other human cancers. A better understanding into the mechanism of how these adducts are formed would be useful to studies aimed at correlating adduct formation to DNA damage. Possible reaction intermediates, produced as a result of Michael addition of deoxyguanosine (dG) to catechol estrogen-3,4-quninones, have been modeled using density functional theory to determine likely intermediates on the potential energy surface (PES) of this reaction.

Synthesis of a new fluorescent probe specific for catechols.

[reaction: see text] The synthesis of a new fluorescent probe, specific for the catechol moiety, has been conducted by preparation of alpha,alpha-dibromomalonamides containing an appropriate fluorophore. N,N'-Bis-anthracen-9-ylmethyl-2,2-dibromomalonamide reacted with various catechols in the presence of cesium carbonate to generate highly fluorescent derivatives.