The sequence specificity of photobinding to DNA of two tetrahydrobenzo
psoralen derivatives has been investigated by testing the photoreactiv
ity toward a number of self-complementary oligonucleotides. The thermo
dynamic constant for noncovalent binding to each DNA sequence was eval
uated. The extent of photoreactivity was greatly dependent upon base c
omposition. The two tetracyclic compounds show similar behavior in com
parison to other bifunctional derivatives. Their overall rate constant
s were greatly enhanced in comparison to classical psoralens. However,
their high efficiency of covalent binding is counterbalanced by low a
ffinity for noncovalent interaction with DNA.