Science Advances

Supplementary Materials

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  • Scheme S1. General synthetic routes of α-amino boronic acid/ester derivatives with high enantiopurity.
  • Scheme S2. BAAs are converted from BAA/ester in quantitative yield.
  • Scheme S3. 18F-BAAs are radiosynthesized via one-step 18F-19F isotope exchange reaction.
  • Fig. S1. Radioactive HPLC chromatogram for the purification of Leu-BF3.
  • Fig. S2. The LC-HRMS spectrum of HPLC-purified Leu-BF3.
  • Fig. S3. 19F NMR spectrum of HPLC-purified Leu-BF3 (δ = −148.95 ppm).
  • Fig. S4. 1H NMR spectrum of HPLC-purified Leu-BF3.
  • Fig. S5. Radioactive HPLC chromatography of preparing Phe-BF3.
  • Fig. S6. The LC-HRMS spectrum of HPLC-purified Phe-BF3.
  • Fig. S7. 19F NMR spectrum of HPLC-purified Phe-BF3 (δ = −151.96 ppm).
  • Fig. S8. 1H NMR spectrum of HPLC-purified Phe-BF3.
  • Fig. S9. Radioactive HPLC chromatography of preparing Ala-BF3.
  • Fig. S10. The LC-HRMS spectrum of HPLC-purified Ala-BF3.
  • Fig. S11. 19F NMR spectrum of HPLC-purified Ala-BF3 (δ = −149.11 ppm).
  • Fig. S12. 1H NMR spectrum of HPLC-purified Ala-BF3.
  • Fig. S13. Radioactive HPLC chromatography of preparing Pro-BF3.
  • Fig. S14. The LC-HRMS spectrum of HPLC-purified Pro-BF3.
  • Fig. S15. 19F NMR spectrum of HPLC-purified Pro-BF3 (δ = −149.02 ppm).
  • Fig. S16. 1H NMR spectrum of HPLC-purified Pro-BF3.
  • Fig. S17. Radioactive HPLC chromatography of Sep-Pak purified Leu-BF3, Phe-BF3, Ala-BF3, and Pro-BF3, respectively (from top to bottom).
  • Fig. S18. In vitro stability assay of 18F-Leu-BF3.
  • Fig. S19. In vitro stability assay of 18F-Phe-BF3.
  • Fig. S20. In vitro stability assay of 18F-Ala-BF3.
  • Fig. S21. In vitro stability assay of 18F-Pro-BF3.
  • Fig. S22. LAT-1–AdiC alignment.
  • Fig. S23. Schematic representation of the binding site of LAT-1.
  • Fig. S24. Predicted structure of the LAT-1–Phe complex.
  • Fig. S25. Predicted structure of the LAT-1–Phe-BF3 complex.
  • Fig. S26. Predicted binding modes for LAT-1 ligands: Phe and Phe-BF3.
  • Fig. S27. Predicted structure of the LAT-1–Leu complex.
  • Fig. S28. Predicted structure of the LAT-1–Leu-BF3 complex.
  • Fig. S29. Predicted binding modes for LAT-1 ligands.
  • Fig. S30. The 18F-Leu-BF3 uptake in the presence of different concentrations of nonradioactive Leu-BF3.
  • Fig. S31. The 18F-Phe-BF3 uptake was measured at 0.3, 1, 3, 10, 30, 100, and 300 μM in PBS and plotted against the concentration of Phe-BF3.
  • Fig. S32. The 18F-Ala-BF3 uptake was measured at 1, 3, 10, 30, 100, 300, and 1000 μM in PBS and plotted against the concentration of Ala-BF3.
  • Fig. S33. The 18F-Pro-BF3 uptake was measured at 10, 30, 100, 400, 800, 1500, 2000, 3000, 6000, and 10,000 μM in PBS and plotted against the concentration of Pro-BF3.
  • Fig. S34. The biodistribution of 18F-Phe-BF3 with U87MG-bearing mice.
  • Fig. S35. 3D projection PET images of 18F-FDG (left) and 18F-Phe-BF3 (right) in mice bearing U87MG xenografts and inflammation (h, heart; t, tumor; i, inflammation; b, bladder; gb, gallbladder).
  • Fig. S36. Representative coronal 18F-FDG (left) and 18F-Phe-BF3 (right) PET images in mice bearing U87MG xenografts and inflammation (h, heart; t, tumor; i, inflammation; b, bladder; gb, gallbladder).
  • Fig. S37. 18F-Phe-BF3 is stable at in vivo conditions.
  • Table S1. A brief summary of 18F-AAs and proposed 18F-BAAs.
  • Table S2. Summary of the half-lives of BAAs.
  • Table S3. Structure of BAAs studied in this work and their counterpart AAs.
  • Table S4. Structure of AAs and their predicted ΔGbinding and Ki with LAT-1.

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