Synthesis and spermicidal activity of a putative nitric oxide-releasing derivative of nonoxynol-9

Objectives We report on the synthesis of a potential nitric oxide releasing derivative of nonoxynol-9 (N9). Methods This derivative was synthesised via AgNO3 mediated nitroxylation of a chloride derivative of a N9 which itself was synthesised by thionyl chloride mediated chlorination of N9. In an initial in vitro study the spermicidal efficacy of the nitric oxide derivative and the parent compound (N9) was examined using boar spermatozoa. Sperm motility and viability were examined. Results The data showed that nitroxylation of N9 did not disrupt spermicidal activity; both sperm motility and viability were comparable between N9 and its nitroxylated derivative. For both compounds, low doses (1–10 μg/mL) were sufficient to induce significant immobilization of sperm after 1 min, whereas concentrations of 10–100 μg/mL were required to achieve significant increase in membrane permeability. Conclusion The results show that a nitric oxide-releasing derivative of N9 retains the spermicidal activity of the parent compound and may have other beneficial effects associated with the release of NO.