Structure of 8-[4'-(3''-nitrobenzamido) benzamido]naphthalene-1,3,6-trisulfonate (NF-033), and molecular basis of its cellular toxicity

Abstract

The title compound is one of a large number of compounds related to the drug suramin which have been found to have anti-HIV properties. However, its toxicity to uninfected cells is high. We crystallized the compound, determined its structure, and investigated the molecular basis for its high toxicity. The crystals are monoclinic, C2/c, a = 28.614(1), b = 10.031(0), c = 24.051(1) Å, β = 98.36(2)°, Z = 8, convergence at R = 0.066 for 4264 reflections with I > 2σ(I). The oxygen atoms of one of the sulfonate groups are disordered, as are several water molecules. Stereochemical comparisons with a segment of B-DNA have yielded a plausible explanation for the molecule's toxicity. Key words: crystal structure, cellular toxicity, stereochemistry, NF-033.