Boron Containing Pyrimidines, Nucleosides, and Oligonucleotides for Neutron Capture Therapy

Goudgaon, Ν. M.; El‐Kattan, G. Fulcrand; Schinazi, Raymond F.

doi:10.1080/15257779408013283

Cited by 57 publications

(28 citation statements)

References 44 publications

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“…The compounds containing 10 B isotope are used in the so‐called boron neutron‐capture therapy of cancer. Various boronic acids are used as boron‐carrying molecules for this purpose …”

Section: Introductionmentioning

confidence: 99%

Influence of fluorine substituents on the NMR properties of phenylboronic acids

Gierczyk

Kaźmierczak

Popenda

et al. 2014

Magnetic Reson in Chemistry

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The paper presents results of a systematic NMR studies on fluorinated phenylboronic acids. All possible derivatives were studied. The experimental (1)H, (13)C, (19)F, (11)B, and (17)O spectral data were compared with the results of theoretical calculations. The relation between the calculated natural bond orbital parameters and spectral data (chemical shifts and coupling constants) is discussed. The first examples of (10)B/(11)B isotopic effect on the (19)F spectra and (4)JFO scalar coupling in organic compounds are reported.

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“…The compounds containing 10 B isotope are used in the so‐called boron neutron‐capture therapy of cancer. Various boronic acids are used as boron‐carrying molecules for this purpose …”

Section: Introductionmentioning

confidence: 99%

Influence of fluorine substituents on the NMR properties of phenylboronic acids

Gierczyk

Kaźmierczak

Popenda

et al. 2014

Magnetic Reson in Chemistry

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“…The use of boron neutron capture therapy (19,20) for the treatment of malignant cancer has encouraged our laboratory to synthesize boron-containing nucleotides (21-23) and to investigate their incorporation into DNA (24,25). The boron modifications have been made either on the nucleobases (21) or phosphodiester backbone (21,22).…”

Section: Introductionmentioning

confidence: 99%

Boron-containing oligodeoxyribonucleotide 14mer duplexes: enzymatic synthesis and melting studies

Porter

Huang

et al. 1995

Nucl Acids Res

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We have purified to homogeneity a DNase from a Crithidia fasciculata crude mitochondrial lysate. The enzyme is present in two forms, either as a 32 kDa polypeptide or as a multimer containing the 32 kDa polypeptide in association with a 56 kDa polypeptide. Native molecular weight measurements indicate that these forms are a monomer and possibly an alpha 2 beta 2 tetramer, respectively. The monomeric and multimeric forms of the enzyme are similar in their catalytic activities. Both digest double-stranded DNA about twice as efficiently as single-stranded DNA. They introduce single-strand breaks into a supercoiled plasmid but do not efficiently make double-strand breaks. They degrade a linearized plasmid more efficiently than a nickel plasmid. Both enzymes degrade a 5'-32P-labeled double-stranded oligonucleotide to completion, with the 5'-terminal nucleotide ultimately being released as a 5'-mononucleotide. One difference between the monomeric and multimeric forms of the enzyme, demonstrated by a band shift assay, is that the multimeric form binds tightly to double-stranded DNA, possibly aggregating it.

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“…One of the first described compounds was the uracil derivative 56 (Figure 13) [78] which demonstrated unfavorable tumor:blood and brain:blood biodistribution ratios being in all studied times in favor to blood. After that some boronic acid-containing nucleosides, such as 57 (Figure 13), were prepared and studied as potential agents for BNCT; however, no studies with glioma were performed [79]. However, recently nucleoside 58, a boronic cyclic ester (a dioxaborolane derivative; Figure 13), was prepared and evaluated as cytotoxic agent against some tumoral cells [80,81] including U-118 MG glioblastoma cells [82].…”

Section: Boronic Acids and Their Estersmentioning

confidence: 99%

Medicinal Chemistry of Boron-Bearing Compounds for BNCT- Glioma Treatment: Current Challenges and Perspectives

Cerecetto¹,

Couto²

2019

Glioma - Contemporary Diagnostic and Therapeutic Approaches

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Since its first description, boron neutron capture therapy (BNCT) was a special type of radiotherapy for treatment of cancer and with focus mainly on glioma therapeutic. This procedure requires the selective accumulation of boron into the tumoral cells, and due to this requirement, different boron-enriched compounds have been designed and developed. Efforts to circumvent the selectivity-uptake challenge and other problems, such as solubility, stability, and toxicity, have been to driving force behind the medicinal chemistry field in boron-based compounds. In this regard, a wide diversity of medicinal chemistry hypothesis has been used to obtain new and efficient potential BNCT-glioma drugs. In this chapter, these ideas are analyzed focusing on their medicinal chemistry characteristics.

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Boron Containing Pyrimidines, Nucleosides, and Oligonucleotides for Neutron Capture Therapy

Cited by 57 publications

References 44 publications

Influence of fluorine substituents on the NMR properties of phenylboronic acids

Influence of fluorine substituents on the NMR properties of phenylboronic acids

Boron-containing oligodeoxyribonucleotide 14mer duplexes: enzymatic synthesis and melting studies

Medicinal Chemistry of Boron-Bearing Compounds for BNCT- Glioma Treatment: Current Challenges and Perspectives

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