Page last updated: 2024-12-06
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 Source | ID |
---|---|
PubMed CID | 150315 |
CHEMBL ID | 125582 |
SCHEMBL ID | 204496 |
MeSH ID | M0104412 |
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
Excerpt | Reference | Relevance |
---|---|---|
" 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
Bioavailability
Excerpt | Reference | Relevance |
---|---|---|
" 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
[information is derived through text-mining from research data collected from National Library of Medicine (NLM), extracted Dec-2023]
Bioassays (36)
Assay ID | Title | Year | Journal | Article |
---|---|---|---|---|
AID1419121 | Drug uptake in human A549 cells at 30 uM after 7 to 24 hrs under hypoxic condition by ICP-MS analysis | 2018 | Bioorganic & 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). |
AID1865527 | Ratio 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 | |||
AID1865521 | Ratio 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 | |||
AID1548556 | Cytotoxicity against mouse 3T3 cells assessed as cell viability incubated for 24 hrs by WST-1 assay (Rvb = 57 %) | 2020 | ACS 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. |
AID1865520 | Biodistribution 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 | |||
AID1548565 | Cytotoxicity 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 assay | 2020 | ACS 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. |
AID1548554 | Cytotoxicity against human U87MG cells assessed as cell viability at 100 uM incubated for 24 hrs by WST-1 assay (Rvb = 97 %) | 2020 | ACS 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. |
AID1419116 | Drug uptake in human A549 cells at 30 uM after 7 to 24 hrs under normoxic condition by ICP-MS analysis | 2018 | Bioorganic & 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). |
AID1866472 | Cytotoxicity against human fibroblasts assessed as reduction in cell viability at 0.01 to 3 mM measured after 72 hrs by MTT assay relative to control | 2022 | Bioorganic & medicinal chemistry, 04-01, Volume: 59 | Synthesis, equilibrium, and biological study of a C-7 glucose boronic acid derivative as a potential candidate for boron neutron capture therapy. |
AID1419125 | Substrate 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 analysis | 2018 | Bioorganic & 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). |
AID1865519 | Biodistribution 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 | |||
AID1865529 | Ratio 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 | |||
AID1419124 | Substrate 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 analysis | 2018 | Bioorganic & 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). |
AID1865523 | Ratio 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 | |||
AID1419114 | Cytotoxicity against human HeLaS3 cells assessed as reduction in cell viability up to 1600 uM after 16 hrs by MTT assay | 2018 | Bioorganic & 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). |
AID1865518 | Biodistribution 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 | |||
AID1865524 | Biodistribution in tumor of Wistar rat assessed as boron concentration at 300 mg/kg, ip measured after 6 hrs by quantitative neutron capture radiography analysis | |||
AID1548555 | Cytotoxicity against human LN229 cells assessed as cell viability at 100 uM incubated for 24 hrs by WST-1 assay (Rvb = 91 %) | 2020 | ACS 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. |
AID1419120 | Drug uptake in human HeLaS3 cells at 30 uM after 7 to 24 hrs under hypoxic condition by ICP-MS analysis | 2018 | Bioorganic & 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). |
AID1865522 | Ratio 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 | |||
AID1419123 | Substrate 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 analysis | 2018 | Bioorganic & 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). |
AID1419117 | Drug uptake in human HeLaS3 cells at 30 uM after 7 to 24 hrs under normoxic condition by ICP-MS analysis | 2018 | Bioorganic & 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). |
AID68925 | Actual boron concentration in media was determined by using direct current plasma atomic emission spectroscopy (DCP-AES) after 48 hr incubation | 1997 | Journal 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. |
AID1865468 | Effective permeability of the compound in pH 7.4 at 25 uM incubated for 4 hrs by PAMPA-BBB assay | |||
AID1865528 | Ratio 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 | |||
AID1865525 | Biodistribution in tumor of Wistar rat assessed as boron concentration at 600 mg/kg, ip measured after 6 hrs by quantitative neutron capture radiography analysis | |||
AID1419122 | Substrate 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 analysis | 2018 | Bioorganic & 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). |
AID1548563 | Ratio of drug uptake in human LN229 cells to drug uptake in mouse 3T3 cells measured at 1 hr | 2020 | ACS 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. |
AID1548567 | Effect on LAT-1 expression in human LN229 cells at 50 uM incubated for 2 hrs by Western blot analysis | 2020 | ACS 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. |
AID1419112 | Cytotoxicity against human A549 cells assessed as reduction in cell viability up to 1600 uM after 16 hrs by MTT assay | 2018 | Bioorganic & 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). |
AID1548566 | Effect on LAT-1 expression in human U87MG cells at 50 uM incubated for 2 hrs by Western blot analysis | 2020 | ACS 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. |
AID1548561 | Drug uptake in human LN229 cells at 50 uM incubated for 1 hr by ICP-MS analysis | 2020 | ACS 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. |
AID1865526 | Biodistribution in tumor of Wistar rat assessed as boron concentration at 1200 mg/kg, ip measured after 6 hrs by quantitative neutron capture radiography analysis | |||
AID1548568 | Downregulation of LAT-1 expression in mouse 3T3 cells at 50 uM incubated for 2 hrs by Western blot analysis | 2020 | ACS 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. |
AID68929 | In 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 incubation | 1997 | Journal 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. |
AID1548564 | Cytotoxicity 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 assay | 2020 | ACS 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)
Timeframe | Studies, This Drug (%) | All Drugs % |
---|---|---|
pre-1990 | 4 (1.90) | 18.7374 |
1990's | 67 (31.90) | 18.2507 |
2000's | 75 (35.71) | 29.6817 |
2010's | 50 (23.81) | 24.3611 |
2020's | 14 (6.67) | 2.80 |
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023] |
Study Types
Publication Type | This drug (%) | All Drugs (%) |
---|---|---|
Trials | 12 (5.24%) | 5.53% |
Reviews | 9 (3.93%) | 6.00% |
Case Studies | 7 (3.06%) | 4.05% |
Observational | 0 (0.00%) | 0.25% |
Other | 201 (87.77%) | 84.16% |
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023] |