Ch3

Distamycin A

FIGURE 6.4 Three-centred hydrogen bonds in the distamycin A-DNA interaction.

initial expectations, the protonated guanidine or amidine groups do not bind directly to DNA phosphate groups, but line the floor of the minor groove.

The synthesis of analogues of distamycin A by increasing the number of N-methylpyrrole-2-carboxamide units or replacement of some pyrrole nucleus by an imidazole, and also by preparation of hybrid structures with intercalating or alkylating portions, has led, in some instances, to much enhanced cyto-toxicity.5 Two of the most promising compounds in this area are tallimustine and brostallicin (PNU-166196).

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