Silicon-Mediated Inactivation of Diamine Oxidase

The design, synthesis, and biologic evaluation of potential silicon-containing inhibitors of diamine oxidases (siladiaminopropane1, silaputrescine2, and sila analogs of cadaverine3, 4,and5) are described. All compounds have been prepared independently. The common feature in the reported syntheses is the way chosen to introduce the amine group relative to silicon: the Gabriel-type approach to obtaining aminomethyl- and aminopropylsilanes and the Mitsunobu-type approach to obtaining aminoethylsilanes. Among the synthesized silane diamines, compounds1and3have been found to be time-dependent inhibitors of diamine oxidases prepared from hog kidney and rat small intestine. These results extend and generalize the concept of silicon-based inactivation of amine oxidases.