Structure of Adriamycin showing its covalent and
noncovalent bonding array to, respectively, the c-strand and the
n-strand of DNA. Rings B–D are intercalated into duplex DNA from the
minor groove, and drug-DNA association, whether covalent or
noncovalent, is mediated through guanine N2 amino groups on either
strand. The covalent methylene linkage between Adriamycin-N3′ and
c-strand guanine N2 derives from formaldehyde.