Synthesis of 1,7-bis(carboxyalkylcarbamoyl)-m-carboranes as precursors of possible water-soluble preparations for boron-neutron-capture treatment of cancer

1996 ◽  
Vol 45 (11) ◽  
pp. 2661-2662
Author(s):  
V. A. Sergeev ◽  
N. I. Bekasova ◽  
E. A. Baryshnikova ◽  
M. Surikova ◽  
N. M. Mishina
Keyword(s):  
Neutron Capture ◽  
Water Soluble ◽  
Boron Neutron Capture

scholarly journals Aza-BODIPY: A New Vector for Enhanced Theranostic Boron Neutron Capture Therapy Applications

Cells ◽  
2020 ◽  
Vol 9 (9) ◽  
pp. 1953
Author(s):  
Ghadir Kalot ◽  
Amélie Godard ◽  
Benoît Busser ◽  
Jacques Pliquett ◽  
Mans Broekgaarden ◽  
...  
Keyword(s):  
Boron Neutron Capture Therapy ◽  
Neutron Capture ◽  
Ex Vivo ◽  
Chorioallantoic Membrane ◽  
Water Soluble ◽  
Neutron Capture Therapy ◽  
Breakdown Spectroscopy ◽  
Boron Neutron Capture ◽  
Tumor Area ◽  
Slow Neutrons

Boron neutron capture therapy (BNCT) is a radiotherapeutic modality based on the nuclear capture of slow neutrons by stable 10B atoms followed by charged particle emission that inducing extensive damage on a very localized level (<10 μm). To be efficient, a sufficient amount of 10B should accumulate in the tumor area while being almost cleared from the normal surroundings. A water-soluble aza-boron-dipyrromethene dyes (BODIPY) fluorophore was reported to strongly accumulate in the tumor area with high and BNCT compatible Tumor/Healthy Tissue ratios. The clinically used 10B-BSH (sodium borocaptate) was coupled to the water-soluble aza-BODIPY platform for enhanced 10B-BSH tumor vectorization. We demonstrated a strong uptake of the compound in tumor cells and determined its biodistribution in mice-bearing tumors. A model of chorioallantoic membrane-bearing glioblastoma xenograft was developed to evidence the BNCT potential of such compound, by subjecting it to slow neutrons. We demonstrated the tumor accumulation of the compound in real-time using optical imaging and ex vivo using elemental imaging based on laser-induced breakdown spectroscopy. The tumor growth was significantly reduced as compared to BNCT with 10B-BSH. Altogether, the fluorescent aza-BODIPY/10B-BSH compound is able to vectorize and image the 10B-BSH in the tumor area, increasing its theranostic potential for efficient approach of BNCT.

Carbaboranes – more than just phenyl mimetics

2015 ◽  
Vol 87 (2) ◽  
pp. 163-171 ◽  
Author(s):  
René Frank ◽  
Verena Ahrens ◽  
Solveig Boehnke ◽  
Sven Hofmann ◽  
Martin Kellert ◽  
...  
Keyword(s):  
Neutron Capture ◽  
Breast Tumour ◽  
Water Soluble ◽  
Propanoic Acid ◽  
Neutron Capture Therapy ◽  
Boron Clusters ◽  
Boron Neutron Capture ◽  
Modified Peptides ◽  
Highly Hydrophobic ◽  
Selective Accumulation

AbstractDicarba-closo-dodecaboranes(12) (C2B10H12, carbaboranes) are highly hydrophobic and stable icosahedral carbon-containing boron clusters. The cage framework of these clusters can be modified with a variety of substituents, both at the carbon and at the boron atoms. Substituted carbaboranes are of interest in medicine as boron neutron capture therapy (BNCT) agents or as pharmacophores. High and selective accumulation in tumour cells is an important requirement for a BNCT agent and is achieved by incorporating boron-rich, water-soluble carbaborane derivatives into breast tumour-selective modified neuropeptide Y, [F7, P34]-NPY. Preliminary studies showed that the receptor binding affinity and signal transduction of the boron-modified peptides were very well retained. Use of carbaboranes as pharmacophores was shown by replacement of Bpa32 (Bpa=benzoylphenylalanine) in the reduced-size NPY analogue [Pro30, Nle31, Bpa32, Leu34]-NPY 28–36 by ortho-carbaboranyl propanoic acid. The inclusion of the carbaborane derivative resulted in a short NPY agonist with an interesting hY2R/hY4R preference. This might be a promising approach in the field of anti-obesity drug development.

scholarly journals Water-Soluble closo-Docecaborate-Containing Pteroyl Derivatives Targeting Folate Receptor-Positive Tumors for Boron Neutron Capture Therapy

Cells ◽  
2020 ◽  
Vol 9 (7) ◽  
pp. 1615 ◽  
Author(s):  
Fumiko Nakagawa ◽  
Hidehisa Kawashima ◽  
Taiki Morita ◽  
Hiroyuki Nakamura
Keyword(s):  
Boron Neutron Capture Therapy ◽  
Neutron Capture ◽  
Human Cancer ◽  
Folate Receptor ◽  
Water Soluble ◽  
Cell Uptake ◽  
Neutron Capture Therapy ◽  
Human Cancer Cells ◽  
Boron Neutron Capture ◽  
Ic50 Values

Water-soluble pteroyl-closo-dodecaborate conjugates (PBCs 1–4), were developed as folate receptor (FRα) targeting boron carriers for boron neutron capture therapy (BNCT). PBCs 1–4 had adequately low cytotoxicity with IC50 values in the range of 1~3 mM toward selected human cancer cells, low enough to use as BNCT boron agents. PBCs 1–3 showed significant cell uptake by FRα positive cells, especially U87MG glioblastoma cells, although the accumulation of PBC 4 was low compared with PBCs 1–3 and L-4-boronophenylalanine (L-BPA). The cellular uptake of PBC 1 and PBC 3 by HeLa cells was arrested by increasing the concentration of folate in the medium, indicating that the major uptake mechanisms of PBC 1–3 are primarily through FRα receptor-mediated endocytosis.

A Novel Approach to the Syntheses of Functionalized, Water-Soluble Icosahedral Carboranyl Anions. Crystal Structure of Methyl N-[(Trimethylamineboryl)carbonyl]-L-tyrosinate: A Synthon for Novel Carboranylpeptides

2002 ◽  
Vol 67 (7) ◽  
pp. 1095-1108 ◽  
Author(s):  
Bernard F. Spielvogel ◽  
Geeta Rana ◽  
Kamesh Vyakaranam ◽  
Kurt Grelck ◽  
Kari E. Dicke ◽  
...  
Keyword(s):  
Crystal Structure ◽  
Boron Neutron Capture Therapy ◽  
Neutron Capture ◽  
Water Soluble ◽  
Neutron Capture Therapy ◽  
Boron Neutron Capture ◽  
Novel Approach ◽  
Peptide Precursor

New functionalized water-soluble carboranyl anions have been prepared from ortho-carborane through lithiation and subsequent derivatization. The reaction of Li2[1,2-C2B10H10] with Me3NBH2X produced the carboranylborane dianions, [1,2-(BH2X)-1,2-C2B10H10]2- (X = H (2a), CN (2b), COOMe (2c), COOH (2d)), while the reaction of [1-R-2-Li-C2B10H10]- with Me3NBH2X produced the monoanions [1-R-2-BH2X-C2B10H10]- (R = C6H5, X = H (2e), CN (2f), COOH (2h), COOCH3 (2g), CONHCH(CH2OH)COOMe (2i), CONHCH(CHMe2)COOMe (2j), CONHCH(4-CH2C6H4OH)- COOMe (2k); R = Me, X = H (2l), COOH (2m)). These water-soluble carboranylboranes have the potential of being effective hydrophilic boron neutron capture therapy (BNCT) agents. The crystal structure of the peptide precursor Me3NBH2CONHCH(4-CH2C6H4OH)COOMe (3b) which showed a special promise as a BNCT agent is also described.

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