N(4)-[B-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan)methyl]-2′-deoxycytidine as a potential boron delivery agent with respect to glioblastoma

Uram, Łukasz; Nizioł, Joanna; Maj, Piotr; Sobich, Justyna; Rode, Wojciech; Ruman, Tomasz

doi:10.1016/j.biopha.2017.08.134

Cited by 5 publications

(7 citation statements)

References 31 publications

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“…The DMSO concentration was adjusted to 0.4% in all samples, which had no significant effect on treated cell lines. Following a 24 h incubation, an NR assay was performed as described before [32].…”

Section: Methodsmentioning

confidence: 99%

Mixed-Generation PAMAM G3-G0 Megamer as a Drug Delivery System for Nimesulide: Antitumor Activity of the Conjugate Against Human Squamous Carcinoma and Glioblastoma Cells

Zaręba

Sareło

Kopaczyńska

et al. 2019

IJMS

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Polyhydroxylated dendrimer was synthesized from poly(amidoamine) (PAMAM) dendrimer generation 3 by addition of glycidol (G3gl). G3gl megamer was further modified by binding PAMAM G0 dendrimers by activation of G3gl with p-nitrophenylchloroformate, followed by the addition of excess PAMAM G0 and purification using dialysis. The maximum G0 binding capacity of G3gl was 12 in the case when G0 was equipped with two covalently attached nimesulide equivalents. Nimesulide (N) was converted into N-(p-nitrophenyl) carbonate derivative and fully characterized using X-ray crystallography and spectral methods. Nimesulide was then attached to G0 via a urea bond to yield G02N. The mixed generation G3gl–G02N megamer was characterized using 1H NMR spectroscopy, and its molecular weight was estimated to be 22.4 kDa. The AFM image of G3gl–G02N deposited on mica demonstrated aggregation of nimesulide-covered megamer. The height of the deposited megamer was 8.5 nm. The megameric conjugate with nimesulide was tested in vitro on three human cell lines: squamous cell carcinoma (SCC-15) and glioblastoma (U-118 MG) overexpressing cyclooxygenase-2 (COX-2), and normal skin fibroblasts (BJ). The conjugate efficiently penetrated into all cells and was more cytotoxic against SCC-15 than against BJ. Moreover, the conjugate produced a strong and selective antiproliferative effect on both cancer cell lines (IC50 < 7.5 µM).

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Section: Methodsmentioning

confidence: 99%

Mixed-Generation PAMAM G3-G0 Megamer as a Drug Delivery System for Nimesulide: Antitumor Activity of the Conjugate Against Human Squamous Carcinoma and Glioblastoma Cells

Zaręba

Sareło

Kopaczyńska

et al. 2019

IJMS

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“…In fact, because of the negatively charged phosphate group, they may be entrapped in cancerous cells 9 . Compound 30 (Figure 5) (N(4)‐[B‐(4,4,5,5‐tetramethyl‐1,3,2‐dioxaborolan) methyl]‐2′‐deoxycytidine), appears to be a potential candidate for the 10 B delivery agent to be used in BNCT for glioblastoma multiforme (GBM) 30 showed low toxicity against both cancer (C85, SCC‐15) and healthy (BJ) cell lines, in particular resulting three times more inhibiting cancer cell development 28 …”

Section: Debut Of the New Boron Agent Developed For Bnctmentioning

confidence: 99%

“…9 Compound 30 (Figure 5) (N( 4)-[B-(4,4,5,5-tetramethyl-1,3,2dioxaborolan) methyl]-2′-deoxycytidine), appears to be a potential candidate for the 10 B delivery agent to be used in BNCT for glioblastoma multiforme (GBM) 30 showed low toxicity against both cancer (C85, SCC-15) and healthy (BJ) cell lines, in particular resulting three times more inhibiting cancer cell development. 28 Some groups have investigated 3-carboranyl thymidine analogs that showed limited toxicity, selective tumor accumulation with high rate of phosphorylation into the corresponding nucleotide. 68 In Figure 5, 31 is a representative selection of single boron bearing nucleoside is shown.…”

Section: Boronated Nucleosidesmentioning

confidence: 99%

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Next generation of boron neutron capture therapy (BNCT) agents for cancer treatment

Coghi

Hosmane

et al. 2023

Medicinal Research Reviews

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Boron neutron capture therapy (BNCT) is one of the most promising treatments among neutron capture therapies due to its long‐term clinical application and unequivocally obtained success during clinical trials. Boron drug and neutron play an equivalent crucial role in BNCT. Nevertheless, current clinically used l‐boronophenylalanine (BPA) and sodium borocaptate (BSH) suffer from large uptake dose and low blood to tumor selectivity, and that initiated overwhelm screening of next generation of BNCT agents. Various boron agents, such as small molecules and macro/nano‐vehicles, have been explored with better success. In this featured article, different types of agents are rationally analyzed and compared, and the feasible targets are shared to present a perspective view for the future of BNCT in cancer treatment. This review aims at summarizing the current knowledge of a variety of boron compounds, reported recently, for the application of BCNT.

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“…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]. Additionally, the ability of ester 58 to be incorporated into cellular DNA and its selectivity for tumoral cells become its potential usefulness tool in glioma BNCT.…”

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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N(4)-[B-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan)methyl]-2′-deoxycytidine as a potential boron delivery agent with respect to glioblastoma

Cited by 5 publications

References 31 publications

Mixed-Generation PAMAM G3-G0 Megamer as a Drug Delivery System for Nimesulide: Antitumor Activity of the Conjugate Against Human Squamous Carcinoma and Glioblastoma Cells

Mixed-Generation PAMAM G3-G0 Megamer as a Drug Delivery System for Nimesulide: Antitumor Activity of the Conjugate Against Human Squamous Carcinoma and Glioblastoma Cells

Next generation of boron neutron capture therapy (BNCT) agents for cancer treatment

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

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