Page last updated: 2024-11-06

4-boronophenylalanine

Description Research Excerpts Clinical Trials Roles Classes Pathways Study Profile Bioassays Related Drugs Related Conditions Protein Interactions Research Growth

Description

4-boronophenylalanine: neutron absorbing (10)B-cpd used in thermal neutron capturetherapy of malignant melanoma; RN given refers to (L)-isomer; structure given in first source [Medical Subject Headings (MeSH), National Library of Medicine, extracted Dec-2023]

Cross-References

ID SourceID
PubMed CID150315
CHEMBL ID125582
SCHEMBL ID204496
MeSH IDM0104412

Synonyms (47)

Synonym
para-boronophenylalanine
para-borono-l-phenylalanine
l-phenylalanine, 4-borono-
10b-bpa
4-boronophenylalanine
76410-58-7
4-borono-l-phenylalanine
CHEMBL125582
l-para-boronophenylalanine
(2s)-2-amino-3-(4-boronophenyl)propanoic acid
A843586
A838693
(2s)-2-azanyl-3-[4-(dihydroxyboranyl)phenyl]propanoic acid
p-boronophenylalanine
jsm63lv5md ,
unii-jsm63lv5md
(s)-(4-boronic acid)-phenylalanine
l-4-boronophenylalanine
l-4-phenylalanineboronic acid
(s)-2-amino-3-(4-boronophenyl)propanoic acid
l-phe[b(oh)2]
4-(2-amino-2-carboxyethyl)benzeneboronic acid
(s)-4-borono-l-phenylalanine
(2s)-2-amino-3-[4-(dihydroxyboranyl)phenyl]propanoic acid
AKOS022172460
SCHEMBL204496
l-p-boronophenylalanine
borofalan
DTXSID70227242
NFIVJOSXJDORSP-QMMMGPOBSA-N
(s)-4-boronophenylalanine
(2s)-2-amino-3-[4-(dihydroxyboryl)phenyl]propanoic acid
4-(dihydroxyboryl)phenylalanine
AC-30249
J-514524
J-513654
4-borono-l-phenylalanine, >=95.0% (hplc)
DS-6558
7n8 ,
(s)-2-amino-3-(4-boronophenyl)propanoicacid
CS-0128618
Q27281677
l-4-(2-amino-2-carboxyethyl)benzeneboronic acid
W18622
4-dihydroxyboryl-l-phenylalanine
HY-W087830
PD063256

Research Excerpts

Toxicity

ExcerptReferenceRelevance
" In the acute toxicity test of 10B-BPA, LD50 values of acidic 10B-BPA for intraperitoneal and subcutaneous injections were 640 mg/kg for male and 710 mg/kg for female rats, and more than 1,000 mg/kg for male and female rats, respectively."( Acute and subacute toxicity of 10B-paraboronophenylalanine.
Fujiwara, H; Kuno, T; Saito, N; Sakaue, M; Shuntoh, H; Tanaka, C; Taniyama, K,
)
0.13
" In conclusion, a lack of toxic effects of L-(10)BPA was demonstrated, nevertheless accompanied by cellular stress phenomena (e."( Blood-brain barrier (BBB) toxicity and permeability assessment after L-(4-¹⁰Boronophenyl)alanine, a conventional B-containing drug for boron neutron capture therapy, using an in vitro BBB model.
Bernocchi, G; Coccini, T; Nion, S; Roda, E, 2014
)
0.4

Pharmacokinetics

ExcerptReferenceRelevance
" The validity of this model was demonstrated by successfully predicting the average pharmacokinetic response for a cohort of patients who were administered BPA-F using an infusion schedule different from those used to derive the parameters of the model."( A pharmacokinetic model for the concentration of 10B in blood after boronophenylalanine-fructose administration in humans.
Busse, PM; Kiger, WS; Palmer, MR; Riley, KJ; Zamenhof, RG, 2001
)
0.31
"This paper describes results to-date from a human pharmacokinetic study which began recruitment in December 2007."( A cancer research UK pharmacokinetic study of BPA-mannitol in patients with high grade glioma to optimise uptake parameters for clinical trials of BNCT.
Boddy, A; Braithwaite, R; Chester, M; Chopra, A; Croswell, G; Cruickshank, GS; Detta, A; Doran, J; Elliot, M; Ford, S; Ghani, Z; Graham, N; Green, S; Halbert, G; Hardie, J; James, ND; Lockyer, N; Ngoga, D; Sheehan, TM; Steinfeldt, H; Sugar, R; Vickerman, J; Wojnecki, C, 2009
)
0.35
" Ten animals were scanned for approximately 3 h to estimate the uptake of (18)F radioactivity with respect to time for the pharmacokinetic analysis."( Pharmacokinetic analysis and uptake of 18F-FBPA-Fr after ultrasound-induced blood-brain barrier disruption for potential enhancement of boron delivery for neutron capture therapy.
Chang, CW; Chang, WY; Chen, JC; Li, JJ; Wang, HE; Yang, FY, 2014
)
0.4
" Furthermore, the K1/k2 pharmacokinetic ratio after intravenous injection of (18)F-FBPA-Fr with BBB-D was significantly higher than that after intravenous injection without BBB-D."( Pharmacokinetic analysis and uptake of 18F-FBPA-Fr after ultrasound-induced blood-brain barrier disruption for potential enhancement of boron delivery for neutron capture therapy.
Chang, CW; Chang, WY; Chen, JC; Li, JJ; Wang, HE; Yang, FY, 2014
)
0.4

Bioavailability

ExcerptReferenceRelevance
" The bioavailability of BPA in rats was improved with oral administration of the BPA-alpha-CD, G1-alpha-CD, and G2-alpha-CD complexes."( Improved bioavailability of para-boronophenylalanine by cyclodextrin complexation.
Hatanaka, H; Komada, F; Mishima, Y; Okumura, K, 1993
)
0.29

Dosage Studied

ExcerptRelevanceReference
" Cell survival dose-response curves, for cells preincubated in the presence or absence of p-boronophenylalanine."( Neutron irradiation of human melanoma cells.
Allen, BJ; Brown, K; Ichihashi, M; Mishima, Y; Mountford, MH; Parsons, P,
)
0.13
"5 micrograms/g) after oral dosing with BPA."( Response of rat skin to boron neutron capture therapy with p-boronophenylalanine or borocaptate sodium.
Coderre, JA; Hopewell, JW; Micca, PL; Morris, GM; Rezvani, M, 1994
)
0.29
"This study was undertaken to develop an oral dosage form for para-boronophenylalanine (BPA) plus cyclodextrin (CD) for use in the thermal neutron capture therapy for malignant melanoma."( Improved bioavailability of para-boronophenylalanine by cyclodextrin complexation.
Hatanaka, H; Komada, F; Mishima, Y; Okumura, K, 1993
)
0.29
" Substantial genotoxic potential of alpha and lithium particles generated inside or near the malignant cell by the BNC reaction was observed in a dose-response manner as measured by the frequency of micronucleated binucleated melanoma cells and by the number of micronuclei (MN) per binucleated cell."( Evaluation of the genotoxic effects of the boron neutron capture reaction in human melanoma cells using the cytokinesis block micronucleus assay.
Cassapo, R; Castro, M; Chaveca, T; Fernandes, AP; Gonçalves, IC; Oliveira, NG; Rodrigues, AS; Rueff, J; Toscano-Rico, JM, 2001
)
0.31
" Improvement in drug delivery and the development of the best dosing paradigms for both boronophenylalanine (BPA) and sodium borocaptate (BSH) are of major importance and these still have not been optimized."( Boron neutron capture therapy at the crossroads: challenges and opportunities.
Barth, RF, 2009
)
0.35
" Initially, the l-DOPA dosing paradigm was evaluated."( Effects of l-DOPA pre-loading on the uptake of boronophenylalanine using the F98 glioma and B16 melanoma models.
Barth, RF; Chandra, S; Haider, SA; Huo, T; Kabalka, GW; Shaikh, AL; Yang, W, 2014
)
0.4
" For the (10)B(n, α)(7)Li reaction, linear dose-response relations for dicentrics with coefficients α = 0."( The effectiveness of the high-LET radiations from the boron neutron capture [10B(n,α) 7Li] reaction determined for induction of chromosome aberrations and apoptosis in lymphocytes of human blood samples.
Canella, L; Kudejova, P; Röhrmoser, A; Schmid, E; Schmid, TE; Wagner, FM, 2015
)
0.42
" The combined dosimetric and radiobiological model includes an analytical formulation that accounts for the type of neutron source, the tissue- or cancer-specific dose-response characteristics, and the microdistribution of boron."( Mechanistic Modeling of the Relative Biological Effectiveness of Boron Neutron Capture Therapy.
Jevremovic, T; Moffitt, G; Stewart, RD; Streitmatter, SW, 2020
)
0.56
[information is derived through text-mining from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Bioassays (36)

Assay IDTitleYearJournalArticle
AID1419121Drug uptake in human A549 cells at 30 uM after 7 to 24 hrs under hypoxic condition by ICP-MS analysis2018Bioorganic & medicinal chemistry, 12-01, Volume: 26, Issue:22
Design and synthesis of boron containing monosaccharides by the hydroboration of d-glucal for use in boron neutron capture therapy (BNCT).
AID1865527Ratio of boron concentration in tumor to blood of Wistar rat assessed as boron concentration at 300 mg/kg, ip measured after 6 hrs by quantitative neutron capture radiography analysis
AID1865521Ratio of boron concentration in brain to blood of Wistar rat assessed as boron concentration at 300 mg/kg, ip measured after 6 hrs by quantitative neutron capture radiography analysis
AID1548556Cytotoxicity against mouse 3T3 cells assessed as cell viability incubated for 24 hrs by WST-1 assay (Rvb = 57 %)2020ACS medicinal chemistry letters, Apr-09, Volume: 11, Issue:4
Boron Accumulation in Brain Tumor Cells through Boc-Protected Tryptophan as a Carrier for Boron Neutron Capture Therapy.
AID1865520Biodistribution in brain gray matter of Wistar rat assessed as boron concentration at 1200 mg/kg, ip measured after 6 hrs by quantitative neutron capture radiography analysis
AID1548565Cytotoxicity against human LN229 cells assessed as cell viability at 50 uM incubated for 1 hr followed by neutron irradiation for 3 mins by WST-1 assay2020ACS medicinal chemistry letters, Apr-09, Volume: 11, Issue:4
Boron Accumulation in Brain Tumor Cells through Boc-Protected Tryptophan as a Carrier for Boron Neutron Capture Therapy.
AID1548554Cytotoxicity against human U87MG cells assessed as cell viability at 100 uM incubated for 24 hrs by WST-1 assay (Rvb = 97 %)2020ACS medicinal chemistry letters, Apr-09, Volume: 11, Issue:4
Boron Accumulation in Brain Tumor Cells through Boc-Protected Tryptophan as a Carrier for Boron Neutron Capture Therapy.
AID1419116Drug uptake in human A549 cells at 30 uM after 7 to 24 hrs under normoxic condition by ICP-MS analysis2018Bioorganic & medicinal chemistry, 12-01, Volume: 26, Issue:22
Design and synthesis of boron containing monosaccharides by the hydroboration of d-glucal for use in boron neutron capture therapy (BNCT).
AID1866472Cytotoxicity against human fibroblasts assessed as reduction in cell viability at 0.01 to 3 mM measured after 72 hrs by MTT assay relative to control2022Bioorganic & medicinal chemistry, 04-01, Volume: 59Synthesis, equilibrium, and biological study of a C-7 glucose boronic acid derivative as a potential candidate for boron neutron capture therapy.
AID1419125Substrate activity at GLUT1 in human HeLaS3 cells assessed as cellular uptake at 30 uM after 7 hrs in presence of GLUT1 inhibitor WZB-117 under hypoxic condition by ICP-MS analysis2018Bioorganic & medicinal chemistry, 12-01, Volume: 26, Issue:22
Design and synthesis of boron containing monosaccharides by the hydroboration of d-glucal for use in boron neutron capture therapy (BNCT).
AID1865519Biodistribution in brain gray matter of Wistar rat assessed as boron concentration at 600 mg/kg, ip measured after 6 hrs by quantitative neutron capture radiography analysis
AID1865529Ratio of boron concentration in tumor to blood of Wistar rat assessed as boron concentration at 1200 mg/kg, ip measured after 6 hrs by quantitative neutron capture radiography analysis
AID1419124Substrate activity at GLUT1 in human HeLaS3 cells assessed as cellular uptake at 30 uM after 7 hrs in presence of GLUT1 inhibitor WZB-117 under normoxic condition by ICP-MS analysis2018Bioorganic & medicinal chemistry, 12-01, Volume: 26, Issue:22
Design and synthesis of boron containing monosaccharides by the hydroboration of d-glucal for use in boron neutron capture therapy (BNCT).
AID1865523Ratio of boron concentration in brain to blood of Wistar rat assessed as boron concentration at 1200 mg/kg, ip measured after 6 hrs by quantitative neutron capture radiography analysis
AID1419114Cytotoxicity against human HeLaS3 cells assessed as reduction in cell viability up to 1600 uM after 16 hrs by MTT assay2018Bioorganic & medicinal chemistry, 12-01, Volume: 26, Issue:22
Design and synthesis of boron containing monosaccharides by the hydroboration of d-glucal for use in boron neutron capture therapy (BNCT).
AID1865518Biodistribution in brain gray matter of Wistar rat assessed as boron concentration at 300 mg/kg, ip measured after 6 hrs by quantitative neutron capture radiography analysis
AID1865524Biodistribution in tumor of Wistar rat assessed as boron concentration at 300 mg/kg, ip measured after 6 hrs by quantitative neutron capture radiography analysis
AID1548555Cytotoxicity against human LN229 cells assessed as cell viability at 100 uM incubated for 24 hrs by WST-1 assay (Rvb = 91 %)2020ACS medicinal chemistry letters, Apr-09, Volume: 11, Issue:4
Boron Accumulation in Brain Tumor Cells through Boc-Protected Tryptophan as a Carrier for Boron Neutron Capture Therapy.
AID1419120Drug uptake in human HeLaS3 cells at 30 uM after 7 to 24 hrs under hypoxic condition by ICP-MS analysis2018Bioorganic & medicinal chemistry, 12-01, Volume: 26, Issue:22
Design and synthesis of boron containing monosaccharides by the hydroboration of d-glucal for use in boron neutron capture therapy (BNCT).
AID1865522Ratio of boron concentration in brain to blood of Wistar rat assessed as boron concentration at 600 mg/kg, ip measured after 6 hrs by quantitative neutron capture radiography analysis
AID1419123Substrate activity at GLUT1 in human HeLaS3 cells assessed as cellular uptake at 30 uM after 7 hrs in presence of 100 mM D-glucose under hypoxic condition by ICP-MS analysis2018Bioorganic & medicinal chemistry, 12-01, Volume: 26, Issue:22
Design and synthesis of boron containing monosaccharides by the hydroboration of d-glucal for use in boron neutron capture therapy (BNCT).
AID1419117Drug uptake in human HeLaS3 cells at 30 uM after 7 to 24 hrs under normoxic condition by ICP-MS analysis2018Bioorganic & medicinal chemistry, 12-01, Volume: 26, Issue:22
Design and synthesis of boron containing monosaccharides by the hydroboration of d-glucal for use in boron neutron capture therapy (BNCT).
AID68925Actual boron concentration in media was determined by using direct current plasma atomic emission spectroscopy (DCP-AES) after 48 hr incubation1997Journal of medicinal chemistry, Nov-21, Volume: 40, Issue:24
Boron-containing polyamines as DNA targeting agents for neutron capture therapy of brain tumors: synthesis and biological evaluation.
AID1865468Effective permeability of the compound in pH 7.4 at 25 uM incubated for 4 hrs by PAMPA-BBB assay
AID1865528Ratio of boron concentration in tumor to blood of Wistar rat assessed as boron concentration at 600 mg/kg, ip measured after 6 hrs by quantitative neutron capture radiography analysis
AID1865525Biodistribution in tumor of Wistar rat assessed as boron concentration at 600 mg/kg, ip measured after 6 hrs by quantitative neutron capture radiography analysis
AID1419122Substrate activity at GLUT1 in human HeLaS3 cells assessed as cellular uptake at 30 uM after 7 hrs in presence of 100 mM D-glucose under normoxic condition by ICP-MS analysis2018Bioorganic & medicinal chemistry, 12-01, Volume: 26, Issue:22
Design and synthesis of boron containing monosaccharides by the hydroboration of d-glucal for use in boron neutron capture therapy (BNCT).
AID1548563Ratio of drug uptake in human LN229 cells to drug uptake in mouse 3T3 cells measured at 1 hr2020ACS medicinal chemistry letters, Apr-09, Volume: 11, Issue:4
Boron Accumulation in Brain Tumor Cells through Boc-Protected Tryptophan as a Carrier for Boron Neutron Capture Therapy.
AID1548567Effect on LAT-1 expression in human LN229 cells at 50 uM incubated for 2 hrs by Western blot analysis2020ACS medicinal chemistry letters, Apr-09, Volume: 11, Issue:4
Boron Accumulation in Brain Tumor Cells through Boc-Protected Tryptophan as a Carrier for Boron Neutron Capture Therapy.
AID1419112Cytotoxicity against human A549 cells assessed as reduction in cell viability up to 1600 uM after 16 hrs by MTT assay2018Bioorganic & medicinal chemistry, 12-01, Volume: 26, Issue:22
Design and synthesis of boron containing monosaccharides by the hydroboration of d-glucal for use in boron neutron capture therapy (BNCT).
AID1548566Effect on LAT-1 expression in human U87MG cells at 50 uM incubated for 2 hrs by Western blot analysis2020ACS medicinal chemistry letters, Apr-09, Volume: 11, Issue:4
Boron Accumulation in Brain Tumor Cells through Boc-Protected Tryptophan as a Carrier for Boron Neutron Capture Therapy.
AID1548561Drug uptake in human LN229 cells at 50 uM incubated for 1 hr by ICP-MS analysis2020ACS medicinal chemistry letters, Apr-09, Volume: 11, Issue:4
Boron Accumulation in Brain Tumor Cells through Boc-Protected Tryptophan as a Carrier for Boron Neutron Capture Therapy.
AID1865526Biodistribution in tumor of Wistar rat assessed as boron concentration at 1200 mg/kg, ip measured after 6 hrs by quantitative neutron capture radiography analysis
AID1548568Downregulation of LAT-1 expression in mouse 3T3 cells at 50 uM incubated for 2 hrs by Western blot analysis2020ACS medicinal chemistry letters, Apr-09, Volume: 11, Issue:4
Boron Accumulation in Brain Tumor Cells through Boc-Protected Tryptophan as a Carrier for Boron Neutron Capture Therapy.
AID68929In vitro uptake of compound by F98 glioma cells was determined by measuring cellular boron content using direct current plasma atomic emission spectroscopy (DCP-AES) after 48 hr incubation1997Journal of medicinal chemistry, Nov-21, Volume: 40, Issue:24
Boron-containing polyamines as DNA targeting agents for neutron capture therapy of brain tumors: synthesis and biological evaluation.
AID1548564Cytotoxicity against human U87MG cells assessed as cell viability at 50 uM incubated for 1 hr followed by neutron irradiation for 3 mins by WST-1 assay2020ACS medicinal chemistry letters, Apr-09, Volume: 11, Issue:4
Boron Accumulation in Brain Tumor Cells through Boc-Protected Tryptophan as a Carrier for Boron Neutron Capture Therapy.
[information is prepared from bioassay data collected from National Library of Medicine (NLM), extracted Dec-2023]

Research

Studies (210)

TimeframeStudies, This Drug (%)All Drugs %
pre-19904 (1.90)18.7374
1990's67 (31.90)18.2507
2000's75 (35.71)29.6817
2010's50 (23.81)24.3611
2020's14 (6.67)2.80
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Study Types

Publication TypeThis drug (%)All Drugs (%)
Trials12 (5.24%)5.53%
Reviews9 (3.93%)6.00%
Case Studies7 (3.06%)4.05%
Observational0 (0.00%)0.25%
Other201 (87.77%)84.16%
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]