7-Methylguanosine monophosphate analogues with 5′-(1,2,3-triazoyl) moiety: Synthesis and evaluation as the inhibitors of cNIIIB nucleotidase

Kozarski, Mateusz; Kubacka, Dorota; Wojtczak, Błażej A.; Kasprzyk, Renata; Baranowski, Marek R.; Kowalska, Joanna

doi:10.1016/j.bmc.2017.11.032

Cited by 9 publications

(16 citation statements)

References 32 publications

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“…[32,66,67] Previously,w es howed the application of an (6)FAM-labeled m 7 GDPa nalogue in an MST experiment to determine the K AS values of some weak eIF4E ligands. [33] We furtherfound some versatility in the nucleobase-pyrene quenching interactions, which can also be applied for developing fluorescent methods for studies on Gand Cnucleotide-binding proteins.…”

Section: Discussionmentioning

confidence: 99%

“…The other probesc ould be applied in techniques requiring low sensitivity to changes in the local environment, such as fluorescentp olarization (FP) or microscalet hermophoresis (MST). [33] The fluorescencei ntensity changes upon probe cleavage can differ from changes occurring upon binding by an on-enzymaticp rotein. Therefore, we also determined Q b factorsb y measuring fluorescencei ntensity changes upon binding with saturating concentrationso fe IF4E ( Figure 2).…”

Section: Initial Spectroscopic Characterization Of the Probesmentioning

confidence: 99%

“…[26][27][28] Other methods of exploring eIF4E cap-binding site include surface plasmon resonance (SPR)-based assays, [29] fluorescence-polarization assays, [30,31] and microscale thermophoresis. [32,33] Methods to examine DcpS activity,i nhibition, and ligand binding [34] include radioactivea ssays, [20,35] HPLC assays, [36] tsFQT, [37] application of covalently bindingp robes, [38] and fluorescent probes. [39] DcpS bindingh as also been studied by terbiumbased TR-FRETm ethods using the non-nucleotide fluorescent DcpS inhibitor Atto-DAQ.…”

Section: Introductionmentioning

confidence: 99%

“…Time‐synchronized fluorescence quenching titration (tsFQT) and isothermal titration calorimetry (ITC) are considered standard methods for determining association constants for cap analogue‐eIF4E complexes . Other methods of exploring eIF4E cap‐binding site include surface plasmon resonance (SPR)‐based assays, fluorescence‐polarization assays, and microscale thermophoresis . Methods to examine DcpS activity, inhibition, and ligand binding include radioactive assays, HPLC assays, tsFQT, application of covalently binding probes, and fluorescent probes .…”

Section: Introductionmentioning

confidence: 99%

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Fluorescent Turn‐On Probes for the Development of Binding and Hydrolytic Activity Assays for mRNA Cap‐Recognizing Proteins

Kasprzyk

Starek

Ciechanowicz

et al. 2019

Chemistry A European J

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The m 7 Gc ap is au nique nucleotide structure at the 5'-end of all eukaryotic mRNAs. The cap specificallyinteracts with numerous cellular proteins and participates in biological processes that are essential for cell growth and function. To provide small molecularp robest os tudy important cap-recognizing proteins, we synthesized m 7 Gn ucleotides labeled with fluorescent tags via the terminal phosph(on)ate group and studied how their emission properties changed upon protein binding or enzymaticc leavage. Only the pyrene-labeled compounds behaved as sensitive turn-on probes. Ap yrene-labeled m 7 GTP analogue showed up to eightfold enhanced fluorescencee mission upon binding to eukaryotic translation initiation factor 4E (eIF4E) and over 30-folde nhancementu pon cleavageb yd ecapping scavenger (DcpS) enzyme. These observations serveda st he basis for developing binding-and hydrolytic-activity assays. The assay utility was validated with previously characterizedl ibraries of eIF4E ligands and DcpS inhibitors. The DcpS assay was also appliedtostudy hydrolytic activity and inhibition of endogenous enzyme in cytoplasmic extracts from HeLa and HEK cells.

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Section: Discussionmentioning

confidence: 99%

Section: Initial Spectroscopic Characterization Of the Probesmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

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Fluorescent Turn‐On Probes for the Development of Binding and Hydrolytic Activity Assays for mRNA Cap‐Recognizing Proteins

Kasprzyk

Starek

Ciechanowicz

et al. 2019

Chemistry A European J

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“…Kozarski et al 156 reported a set of 7-methylguanosine phosphate substances bearing a 1,2,3-triazole ring at the position 5 as promising inhibitors of human cNIIIB. Among the four prepared analogues, compound 131 (Fig.…”

Section: Miscellaneous Activitiesmentioning

confidence: 99%

1,2,3-Triazole-containing hybrids as leads in medicinal chemistry: A recent overview

Bozorov

Zhao

Aisa

2019

Bioorganic & Medicinal Chemistry

614

289

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A B S T R A C TThe 1,2,3-triazole ring is a major pharmacophore system among nitrogen-containing heterocycles. These fivemembered heterocyclic motifs with three nitrogen heteroatoms can be prepared easily using 'click' chemistry with copper-or ruthenium-catalysed azide-alkyne cycloaddition reactions. Recently, the 'linker' property of 1,2,3-triazoles was demonstrated, and a novel class of 1,2,3-triazole-containing hybrids and conjugates was synthesised and evaluated as lead compounds for diverse biological targets. These lead compounds have been demonstrated as anticancer, antimicrobial, anti-tubercular, antiviral, antidiabetic, antimalarial, anti-leishmanial, and neuroprotective agents. The present review summarises advances in lead compounds of 1,2,3-triazolecontaining hybrids, conjugates, and their related heterocycles in medicinal chemistry published in 2018. This review will be useful to scientists in research fields of organic synthesis, medicinal chemistry, phytochemistry, and pharmacology. Chemistry: synthesis and properties of the 1,2,3-triazolesThe general synthetic route of 1,2,3-triazoles using click chemistry is described in Scheme 1A. The most popular route to 1,2,3-triazoles is Cu(I)-catalysed Huisgen 1,3-dipolar cycloaddition, which is the https://doi.

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Synthesis of Triazole‐Containing Furanosyl Nucleoside Analogues and Their Phosphate, Phosphoramidate or Phoshonate Derivatives as Potential Sugar Diphosphate or Nucleotide Mimetics

et al. 2020

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The synthesis of stable and potentially bioactive xylofuranosyl nucleoside analogues and potential sugar diphosphate or nucleotide mimetics comprising a 1,2,3‐triazole moiety is reported. 3′‐O‐Methyl‐branched N‐benzyltriazole isonucleosides were accessed in 5–7 steps and 42–54 % overall yields using a Cu(I)‐catalyzed cycloaddition of 3‐O‐propargyl‐1,2‐O‐isopropylidene‐α‐D‐xylofuranose with benzyl azide as key step. Related isonucleotides were obtained by 5‐O‐phosphorylation of acetonide‐protected 3‐O‐propargyl xylofuranose and further “click” cycloaddition or by Staudinger‐phosphite reaction of a 5‐azido N‐benzyltriazole isonucleoside. Hydroxy‐, amino‐ or bromomethyl triazole 5′‐isonucleosides were synthesized by thermal cycloaddition of 5‐azido 3‐O‐benzyl/dodecyl xylofuranoses with propargyl alcohol, propargylamine or propargyl bromide. Better yields (82–85 %) were obtained when using propargyl alcohol and a high 1,4‐regioselectivity was attained with propargyl bromide. Further O/N‐phosphorylation or Arbuzov reaction led to (triazolyl)methyl phosphates, phosphoramidates or phosphonates. The latter were converted into uracil nucleoside 5′‐(triazolyl)methyl phosphonates as prospective nucleoside diphosphate mimetics.

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7-Methylguanosine monophosphate analogues with 5′-(1,2,3-triazoyl) moiety: Synthesis and evaluation as the inhibitors of cNIIIB nucleotidase

Cited by 9 publications

References 32 publications

Fluorescent Turn‐On Probes for the Development of Binding and Hydrolytic Activity Assays for mRNA Cap‐Recognizing Proteins

Fluorescent Turn‐On Probes for the Development of Binding and Hydrolytic Activity Assays for mRNA Cap‐Recognizing Proteins

1,2,3-Triazole-containing hybrids as leads in medicinal chemistry: A recent overview

Synthesis of Triazole‐Containing Furanosyl Nucleoside Analogues and Their Phosphate, Phosphoramidate or Phoshonate Derivatives as Potential Sugar Diphosphate or Nucleotide Mimetics

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