Data Supplement
- Supplemental Data -
Supplemental Methods
Supplemental Fig. 1. ORTEP diagram with 50% probability of the asymmetric unit of 1a•Spraziquantel; restraints and constraints applied in the refinement of S-praziquantel
Supplemental Fig. 2. Electron density map Fo of S-praziquantel (contoured at the 2.02σ level)
Supplemental Fig. 3. Reciprocal h0l layer of a typical crystalline sponge crystal before soaking in C2/c. Absence of h=odd and l=odd reflexes is clearly visible.
Supplemental Fig. 4. Reciprocal h0l layer after soaking S-praziquantel into the crystalline sponge. Reflexes at h=2n and l=n (highlighted with orange arrows) clearly visible.
Supplemental Fig. 5. ORTEP diagram with 50% probability of the asymmetric unit of 1b•M1 praziquantel; restraints and constraints applied in the refinement of M1 praziquantel.
Supplemental Fig. 6. Electron density map Fo of M1 praziquantel (contoured at the 2.00σ level).
Supplemental Fig. 7. Reciprocal h0l layer after soaking S-trans-4'-hydroxy praziquantel into the crystalline sponge. Reflexes at h=2n and l=n (highlighted with orange arrows) visible.
Supplemental Fig. 8. ORTEP diagram with 50% probability of the asymmetric unit of 1b•M2 praziquantel; restraints and constraints applied in the refinement of M2 praziquantel.
Supplemental Fig. 9. Electron density map Fo of M2 praziquantel (contoured at the 3.70σ level).
Supplemental Fig. 10. Reciprocal h0l layer after soaking S-cis-4'-hydroxy praziquantel into the crystalline sponge. Reflexes at h=2n and l=n (highlighted with orange arrows) visible.
Supplemental Fig. 11. ORTEP diagram with 50% probability of the asymmetric unit of 1a•M3 praziquantel; restraints and constraints applied in the refinement of M3 praziquantel
Supplemental Fig. 12. Electron density map Fo of M3 praziquantel (contoured at the 3.33σ level)
Supplemental Fig. 13. Reciprocal h0l layer after soaking S-9-hydroxy praziquantel into the crystalline sponge. Reflexes at h=2n and l=n (highlighted with orange arrows) clearly visible.
Supplemental Fig. 14. ORTEP diagram with 50% probability of the asymmetric unit of 1a•M4 praziquantel; restraints and constraints applied in the refinement of M4 praziquantel.
Supplemental Fig. 15. Electron density map Fo of M4 praziquantel (contoured at the 2.11σ level)
Supplemental Fig. 16. Reciprocal h0l layer after soaking S-7-hydroxy S-praziquantel into the crystalline sponge. Reflexes at h=2n and l=n (highlighted with orange arrows) visible.
Supplemental Fig. 17. ORTEP diagram with 50% probability of the asymmetric unit of 1a•S-/R-M6 praziquantel; restraints and constraints applied in the refinement of S-/R-M6 praziquantel.
Supplemental Fig. 18. Electron density map Fo of S-M6 praziquantel (contoured at the 1.89σ level) and R-M6 praziquantel (contoured at the 2.78σ level).
Supplemental Fig. 19. Reciprocal h0l layer after soaking S-11b-hydroxy praziquantel and R11b-hydroxy praziquantel into the crystalline sponge. Absence of h=odd and l=odd reflexes is clearly visible.
Supplemental Fig. 20. ORTEP diagram with 50% probability of the asymmetric unit of 1a•RM6 praziquantel; restraints and constraints applied in the refinement of R-M6 praziquantel.
Supplemental Fig. 21. Electron density map Fo of R-M6 praziquantel (contoured at the 2.73σ level).
Supplemental Fig. 22. Reciprocal h0l layer after soaking R-11b-hydroxy praziquantel into the crystalline sponge. Reflexes at h=2n and l=n (highlighted with orange arrows) visible.
Supplemental Table 1. Mass spectral analysis of hydroxylated metabolites formed in vitro from S-praziquantel
Supplemental Fig. 23. Assigned 1 H NMR spectrum of S-9-hydroxy praziquantel (M3).
Supplemental Fig. 24. Edited heteronuclear single quantum coherence (HSQC) NMR spectrum of S-9-hydroxy praziquantel (M3). Red: CH/CH3, blue: CH2.
Supplemental Fig. 25. Edited homonuclear correlation spectroscopy (COSY) NMR spectrum of S-9-hydroxy praziquantel (M3).
Supplemental Fig. 26. Edited rotating frame Overhauser enhancement effect spectroscopy (ROESY) NMR spectrum of S-9-hydroxy praziquantel (M3).
Supplemental Fig. 27. Comparison of 1 H NMR spectra of praziquantel (PZQ), 9-hydroxy praziquantel (M3) and 11b-hydroxy praziquantel (M6) (1H NMR spectra of PZQ and M6 from Vendrell-Navarro et al., 2020)
Supplemental References