Table 4. Benznidazole-derived metabolites.
Metabolites were identified by accurate mass and presence in the sample, but absence in the control incubations.
| Retention time (min) | Structure | Metabolite number1 | [M+H]+ | Ionisation state | WT lysate | NTROE Lys B | Control | TcAKR |
|---|---|---|---|---|---|---|---|---|
| 3.1 | Benznidazole | NA | 261.10 | 1 | NA | NA | NA | NA |
| 1.59 | Hydroxylamine or hydroxy derivative 1 or 2 | 11 or 19 | 247.11 | 1 | Y | Y | N | N |
| 1.8 | Amino derivative of benznidazole | 1 | 231.12 | 1 | Y | Y | N | N |
| 1.49/1.59 | Dihydroxy-dihydro derivative | 3 | 265.13 | 1 | Y | Y | N | N |
| 1.59 | N-benzyl-2-guanidinoacetamide | 5 | 207.13 | 1 | N | Y | N | N |
| 1.3 | 2-Amino-N-benzylacetamide | 22 | 165.10 | 1 | Y | Y | N | N |
| 1.74 | Amino derivative + glutathione (isomer 1) | 7 or 8 | 536.19 | 1 | Y | Y | N | N |
| 268.56 | 2 | Y | Y | N | N | |||
| 1.83 | Amino derivative + glutathione (isomer 2) | 7 or 8 | 536.19 | 1 | Y | Y | N | N |
| 268.56 | 2 | Y | Y | N | N | |||
| 1.55/1.64 | Amino derivative + glutathione + H2O | 4 | 554.20 | 1 | Y | Y | N | N |
| 277.60 | 2 | Y | Y | N | N | |||
| 1.76/1.93/2.31 | Amino derivative + cysteine | 9 | 350.13 | 1 | Y | Y | NN | NN |
| 1.34 | Amino derivative + ovothiol A | 12 or 14 | 430.17 | 1 | Y | Y | N | N |
| 215.58 | 2 | Y | Y | N | N | |||
| 3.8 | Possible benznidazole adduct | 26 | 385.18 | 1 | Y | Y | N | N |
| 1.63 | Possible benznidazole adduct | 28 | 368.12 | 1 | N | Y | N | N |
| 3.64/3.8 | Possible benznidazole adduct | NA | 614.35 | 1 | Y | Y | N | N |
| 2.13 | Possible benznidazole metabolite | NA | 204.05 | 1 | Y | Y | N | N |
Abbreviations: NA, not applicable.
1
The metabolite numbers refer to the metabolite list in Trochine et al. [10].