Figure 1

Moieties of the N-acetylalaninate prodrug. The N-acetylalaninate prodrugs are hybrids of two esters. We previously demonstrated that the N-acetylalaninate moiety (A) is specifically hydrolyzed by OPH in prostate cell lines [24]. The GSH depleting ability of the quinone methide (QM) generating moiety (B) is well documented. Combining these two moieties creates an ester substrate that is specifically activated by OPH to generate a QM, which depletes GSH (see Figure 2).