L-p-Boronophenylalanine
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L-p-Boronophenylalanine is a boron-containing substrate for L-type amino acid transporters (LAT1 and LAT2). L-p-Boronophenylalanine enters tumor cells by competing with natural amino acids for LAT, selectively accumulating boron in cancer cells. L-p-Boronophenylalanine can be used in boron neutron capture therapy (BNCT). When boron-10 captures thermal neutrons, a nuclear reaction occurs, producing high-energy alpha particles and lithium nuclei, which kill cancer cells at close range with little damage to surrounding tissues. L-p-Boronophenylalanine can be used in cancer research, especially glioblastoma and anaplastic astrocytoma.
For research use only. We do not sell to patients.
- Purity: 99.79%
- CAS No.: 76410-58-7
- Formula: C9H12BNO4
- Molecular Weight:209.01
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Storage:Powder -20°C, 3 years , 4°C, 2 years ; In solvent -80°C, 6 months , -20°C, 1 month
Biological Activity
Boron neutron capture therapy (BNCT) is a selective cancer cell destruction therapy based on the nuclear capture and fission reaction that occurs when neutron beams are irradiated with boron. BNCT is based on the destructive properties of high-energy alpha particles and lithium nuclei produced by the fission reaction of neutron beams irradiating boron, and because the neutron beam irradiation range is limited (5-9 μm, equivalent to the diameter of a cell), BNCT can only destroy boron-containing cells. The effectiveness of radiotherapy can be assessed by measuring the level of L-p-Boronophenylalanine in the blood[1].
In whole blood samples, L-p-Boronophenylalanine can be reacted with the arylboronic acid derivative fluorescent reagent 4-iodobenzonitrile via Suzuki coupling reaction, achieving ultrasensitive detection (detection limit as low as 0.26 nM). The fluorescent cyanobiphenyl derivative formed by the reaction of L-p-Boronophenylalanine and 4-iodobenzonitrile has a maximum fluorescence of 335 nm under 290 nm excitation[1].
L-p-Boronophenylalanine (p-BPA) may form oligomers and other molecules in deuterated DMSO (DMSO-d6). The oligomerization may be due to the formation of an additional stereogenic center at the boron center through intermolecular chelation with the amino acid of another molecule of p-boronophenylalanine (-p-BPA)[2].
MedChemExpress (MCE) has not independently confirmed the accuracy of these methods. They are for reference only.
Chemical Information
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CAS No. 76410-58-7
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Appearance Solid
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Molecular Weight 209.01
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Formula C9H12BNO4
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Color White to off-white
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SMILES
O=C(O)[C@@H](N)CC1=CC=C(B(O)O)C=C1
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Synonyms
L-BPA
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Shipping
Room temperature in continental US; may vary elsewhere.
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Storage
Powder -20°C 3 years 4°C 2 years In solvent -80°C 6 months -20°C 1 month
Solvent & Solubility
DMSO : 10.94 mg/mL (52.34 mM; ultrasonic and adjust pH to 2 with 1 M HCl; Hygroscopic DMSO has a significant impact on the solubility of product, please use newly opened DMSO)
1 M HCl : 10 mg/mL (47.84 mM; ultrasonic and warming and adjust pH to 2 with 1 M HCl and heat to 60°C)
Please refer to the solubility information to select the appropriate solvent. Once prepared, please aliquot and store the solution to prevent product inactivation from repeated freeze-thaw cycles.
Storage method and period of stock solution: -80°C, 6 months; -20°C, 1 month. When stored at -80°C, please use it within 6 months. When stored at -20°C, please use it within 1 month.
Please refer to the solubility information to select the appropriate solvent. Once prepared, please aliquot and store the solution to prevent product inactivation from repeated freeze-thaw cycles.
Storage method and period of stock solution: -80°C, 6 months; -20°C, 1 month. When stored at -80°C, please use it within 6 months. When stored at -20°C, please use it within 1 month.
Concentration (start) × Volume (start) = Concentration (final) × Volume (final)
Purity & Documentation
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Data Sheet (272 KB)
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SDS (393 KB)
- English - EN (393 KB)
- Français - FR (393 KB)
- Deutsch - DE (393 KB)
- Norwegian - NO (393 KB)
- Español - ES (393 KB)
- Swedish - SV (393 KB)
- Italian - IT (393 KB)
- Korean - KR (393 KB)
- Portuguese - PT (393 KB)
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Handling Instructions (2659 KB)
References
Complete Stock Solution Preparation Table
Please refer to the solubility information to select the appropriate solvent. Once prepared, please aliquot and store the solution to prevent product inactivation from repeated freeze-thaw cycles.
Storage method and period of stock solution: -80°C, 6 months; -20°C, 1 month. When stored at -80°C, please use it within 6 months. When stored at -20°C, please use it within 1 month.
| Optional Solvent | Concentration Solvent Mass | 1 mg | 5 mg | 10 mg | 25 mg |
|---|---|---|---|---|---|
| 1 M HCl / DMSO | 1 mM | 4.7845 mL | 23.9223 mL | 47.8446 mL | 119.6115 mL |
| 5 mM | 0.9569 mL | 4.7845 mL | 9.5689 mL | 23.9223 mL | |
| 10 mM | 0.4784 mL | 2.3922 mL | 4.7845 mL | 11.9612 mL | |
| 15 mM | 0.3190 mL | 1.5948 mL | 3.1896 mL | 7.9741 mL | |
| 20 mM | 0.2392 mL | 1.1961 mL | 2.3922 mL | 5.9806 mL | |
| 25 mM | 0.1914 mL | 0.9569 mL | 1.9138 mL | 4.7845 mL | |
| 30 mM | 0.1595 mL | 0.7974 mL | 1.5948 mL | 3.9871 mL | |
| 40 mM | 0.1196 mL | 0.5981 mL | 1.1961 mL | 2.9903 mL | |
| DMSO | 50 mM | 0.0957 mL | 0.4784 mL | 0.9569 mL | 2.3922 mL |