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. 2015 Jan 29;58(5):2091–2113. doi: 10.1021/jm5019093

Figure 4.

Figure 4

Labile adducts between p-hydroxyarylsulfonamides (6) and GSH detected by qualitative UPLC–MS. (A) Simplified scheme of adduct formation between biological thiols and chemotype 6. (B) UPLC–MS analyses of compound 6a mixed with GSH in HTS buffer. 6a was treated with GSH after varying lengths of incubation in HTS buffer (5, 15, 30 min). After 5 min, reaction aliquots were analyzed by UPLC–MS. Trace (iv) shows the same sample from trace (i) analyzed 15 min later. (C). Summary of experiments described in (B) performed with compounds 6a–6e. All test compounds initially formed the expected adducts (6a′–6e′). A common breakdown product 6″ was detected for all five sulfonamides tested (rt = 3.28 min, m/z = 446). See Supporting Information, Figures S5, S7, and S11, for additional stability studies with chemotype 6. a = compound incubated in HTS buffer for 5 min, then GSH added, then analyzed by UPLC-MS 5 min later; b = same sample from a, but analyzed by UPLC-MS 15 min later.