L-p-Boronophenylalanine  (Synonyms: L-BPA)

L-p-Boronophenylalanine is a boron-containing substrate for L-type amino acid transporters (L_AT1 and L_AT2). 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^[1][2].

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.

209.01

C₉H₁₂BNO₄

76410-58-7

Solid

White to off-white

O=C(O)[C@@H](N)CC1=CC=C(B(O)O)C=C1

Room temperature in continental US; may vary elsewhere.

* 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.

• [1]. Fukuda T, et al. 4-Iodobenzonitrile as a fluorogenic derivatization reagent for chromatographic analysis of L-p-boronophenylalanine in whole blood samples using Suzuki coupling reaction. Anal Chim Acta. 2024 Jul 18;1313:342700.  [Content Brief]

  [2]. Shull Brian K, et al. Evidence for spontaneous, reversible paracyclophane formation. Aprotic solution structure of the boron neutron capture therapy drug, Lp-boronophenylalanine. Journal of the Chemical Society, Perkin Transactions 2 3 (2000): 557-561.