BORONOPHENYLALANINE

Investigational

Details

Stereochemistry	ABSOLUTE
Molecular Formula	C9H12BNO4
Molecular Weight	209.007
Optical Activity	UNSPECIFIED
Defined Stereocenters	1 / 1
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

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

InChI

InChIKey=NFIVJOSXJDORSP-QMMMGPOBSA-N

InChI=1S/C9H12BNO4/c11-8(9(12)13)5-6-1-3-7(4-2-6)10(14)15/h1-4,8,14-15H,5,11H2,(H,12,13)/t8-/m0/s1

HIDE SMILES / InChI

Molecular Formula	C9H12BNO4
Molecular Weight	209.007
Charge	0
Count

Stereochemistry	ABSOLUTE
Additional Stereochemistry	No
Defined Stereocenters	1 / 1
E/Z Centers	0
Optical Activity	UNSPECIFIED

Approval Year

Targets

Primary Target	Pharmacology	Condition	Potency
tyrosine transport 2 Target ID: GO:0015828 Sources: https://www.ncbi.nlm.nih.gov/pubmed/24186331	Inhibitor 8297
phenylalanine transport 2 Target ID: GO:0015823 Sources: https://www.ncbi.nlm.nih.gov/pubmed/24186331	Inhibitor 8297

PubMed

Title	Date	PubMed
Imaging of fluorine and boron from fluorinated boronophenylalanine in the same cell at organelle resolution by correlative ion microscopy and confocal laser scanning microscopy.	2002 Aug	12171900
Cell cycle dependence of boron uptake from two boron compounds used for clinical neutron capture therapy.	2002 Dec 10	12359361
Improved treatment planning for boron neutron capture therapy for glioblastoma multiforme using fluorine-18 labeled boronophenylalanine and positron emission tomography.	2002 Oct	12408309
Mutagenic effect of borocaptate sodium and boronophenylalanine in neutron capture therapy.	2002 Oct 1	12243836
Prognostic and therapeutic indicator of fluoroboronophenylalanine positron emission tomography in patients with gliomas.	2003 Dec 1	14676111
Boron neutron capture therapy of brain tumors: clinical trials at the finnish facility using boronophenylalanine.	2003 Mar-Apr	12749708
The early successful treatment of glioblastoma patients with modified boron neutron capture therapy. Report of two cases.	2003 Nov	14686736
Synchrotron radiation-based experimental determination of the optimal energy for cell radiotoxicity enhancement following photoelectric effect on stable iodinated compounds.	2004 Aug 2	15266326
Accumulation of boron in human malignant glioma cells in vitro is cell type dependent.	2004 Jul	15332322
Boronated epidermal growth factor as a delivery agent for neutron capture therapy of EGF receptor positive gliomas.	2004 Nov	15308179
Radiobiology of BNCT mediated by GB-10 and GB-10+BPA in experimental oral cancer.	2004 Nov	15308172
The effect of dexamethasone on the uptake of p-boronophenylalanine in the rat brain and intracranial 9L gliosarcoma.	2004 Nov	15308168
MicroPET-based pharmacokinetic analysis of the radiolabeled boron compound [18F]FBPA-F in rats with F98 glioma.	2004 Nov	15308163
Modified boron neutron capture therapy for malignant gliomas performed using epithermal neutron and two boron compounds with different accumulation mechanisms: an efficacy study based on findings on neuroimages.	2005 Dec	16381186
Optimized 1H MRS and MRSI methods for the in vivo detection of boronophenylalanine.	2005 May	15844166
Therapeutic success of boron neutron capture therapy (BNCT) mediated by a chemically non-selective boron agent in an experimental model of oral cancer: a new paradigm in BNCT radiobiology.	2006 Aug	16881740
Impact of intra-arterial administration of boron compounds on dose-volume histograms in boron neutron capture therapy for recurrent head-and-neck tumors.	2006 Dec 1	17056200
Capillary electrophoresis-electrospray mass spectrometry and HR-ICP-MS for the detection and quantification of 10B-boronophenylalanine (10B-BPA) used in boron neutron capture therapy.	2006 Feb	16372182
Molecular targeting and treatment of EGFRvIII-positive gliomas using boronated monoclonal antibody L8A4.	2006 Jun 15	16778107
Early effects of boron neutron capture therapy on rat glioma models.	2007	18095138
Molecular targeting and treatment of an epidermal growth factor receptor-positive glioma using boronated cetuximab.	2007 Feb 15	17317838
Therapeutic effect of boron neutron capture therapy (BNCT) on field cancerized tissue: inhibition of DNA synthesis and lag in the development of second primary tumors in precancerous tissue around treated tumors in DMBA-induced carcinogenesis in the hamster cheek pouch oral cancer model.	2007 Mar	17137553
Effect of Boron Neutron Capture Therapy (BNCT) on normal liver regeneration: towards a novel therapy for liver metastases.	2007 Oct	17729164
Application of drug delivery system to boron neutron capture therapy for cancer.	2008 Apr	18426384
Comments to article: Henriksson R et al., Boron neutron capture therapy (BNCT) for glioblastoma multiforme: a phase II study evaluating a prolonged high-dose of boronophenylalanine (BPA) Radiother Oncol (2008).	2008 Aug	18617284
Boron neutron capture therapy (BNCT) for glioblastoma multiforme: a phase II study evaluating a prolonged high-dose of boronophenylalanine (BPA).	2008 Aug	18336940
An international dosimetry exchange for BNCT part II: computational dosimetry normalizations.	2008 Dec	19175101
Convection enhanced delivery of boronated EGF as a molecular targeting agent for neutron capture therapy of brain tumors.	2009 Dec	19588228
Role of p53 mutation in the effect of boron neutron capture therapy on oral squamous cell carcinoma.	2009 Dec 11	20003329
Boron neutron capture therapy for newly diagnosed glioblastoma.	2009 Jan	18957828
Boron neutron capture therapy of EGFR or EGFRvIII positive gliomas using either boronated monoclonal antibodies or epidermal growth factor as molecular targeting agents.	2009 Jul	19467880
Boron neutron capture therapy at the crossroads: challenges and opportunities.	2009 Jul	19467879
Synthesis and evaluation of a novel liposome containing BPA-peptide conjugate for BNCT.	2009 Jul	19446462
In vitro neutron irradiation of glioma and endothelial cultured cells.	2009 Jul	19410472
Calculations of dose distributions in the lungs of a rat model irradiated in the thermal column of the TRIGA reactor in Pavia.	2009 Jul	19406647
Selective uptake of p-boronophenylalanine by osteosarcoma cells for boron neutron capture therapy.	2009 Jul	19394838
Feasibility of boron neutron capture therapy for malignant spinal tumors.	2009 Jul	19376723
Boron neutron capture therapy (BNCT) inhibits tumor development from precancerous tissue: an experimental study that supports a potential new application of BNCT.	2009 Jul	19376711
Boronophenylalanine uptake in C6 glioma model is dramatically increased by L-DOPA preloading.	2009 Jul	19375337
Planned fractionated boron neutron capture therapy using epithermal neutrons for a patient with recurrent squamous cell carcinoma in the temporal bone: a case report.	2009 Mar	18767175
Insight into the mechanisms underlying tumor response to boron neutron capture therapy in the hamster cheek pouch oral cancer model.	2009 May	19141057
Metabolically stable bradykinin B2 receptor agonists enhance transvascular drug delivery into malignant brain tumors by increasing drug half-life.	2009 May 13	19439100
Aryl boronic acid inhibition of synthetic melanin polymerization.	2010 Aug 1	20594849
Boron neutron capture therapy induces apoptosis of glioma cells through Bcl-2/Bax.	2010 Dec 2	21122152
Early effect of boron neutron capture therapy mediated by boronophenylalanine (BPA-BNCT) on mast cells in premalignant tissue and tumors of the hamster cheek pouch.	2010 May	20308008

Patents

Substance Class	Chemical Created by `admin` on `Sat Dec 16 01:06:17 GMT 2023` Edited by `admin` on `Sat Dec 16 01:06:17 GMT 2023`
Record UNII	JSM63LV5MD
Record Status	`Validated (UNII)`
Record Version

Download

Name

Type

Language

BORONOPHENYLALANINE

Systematic Name

English

L-BPA

Common Name

English

4-BORONO-L-PHENYLALANINE

Systematic Name

English

BOROFALAN

Common Name

English

L-PHENYLALANINE, 4-BORONO-

Systematic Name

English

L-P-BORONOPHENYLALANINE

Common Name

English

Code System Code Type Description

CAS

76410-58-7