7‐(β‐<scp>D</scp>‐Ribofuranosyl)guanine and its Analogues Modified in the Sugar Portion: Synthesis and Antiglioma Properties

Wawrzyniak, Dariusz; Framski, Grzegorz; Januszczyk, Piotr; Ostrowski, Tomasz; Baraniak, Dagmara; Jahnz‐Wechmann, Zofia; Fogt, Joanna; Manikowski, Andrzej; Baranowski, Daniel; Rolle, Katarzyna; Boryski, Jerzy

doi:10.1002/slct.202003393

Cited by 3 publications

(1 citation statement)

References 40 publications

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“…Many modifications, included replacing of purine with triazole-thione as in (E) [ 14 ] and changing the acyclic chains by sugar moiety like glucose in (F), have been exemplified and reviewed [ 12 , 15 , 16 ]. …”

Section: Introductionmentioning

confidence: 99%

Synthesis of novel seco-acyclo-N-diazolyl-thione nucleosides analogous derived from acetic acid: characterization, complex formation with ions Pb(II), Hg(II) and antibacterial activity

Chehrouri

Othman

2021

J IRAN CHEM SOC

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Graphic abstract Three diazoles namely 5-methyl-1,3,4-oxadiazole -2(3H)-thione, 5-methyl-1,3,4-thiadiazol-2(3H)-thione and 4-amino-5-methyl-2H-1,2,4-triazole-3-thiol were synthesized from acetic acid or ethyl acetate. Seco-acyclo-N-nucleoside analogous was synthesized by condensation of 1,3-benzylidine-glyceryl-2-tosylate with the three diazoles. Structural proof was based upon IR, 1 H-NMR, 13 C-NMR spectroscopy and MS measurements. The tendency to form complex between 1,3,4-oxadiazole and 1,3,4-thiadiazoles and Pb(II) and Hg(II) ions was achieved, and their structures were assigned by observing some changes in physical properties such as, MP, coloration, R f (TLC), IR and UV spectroscopy. Most compounds were tested in vitro against Gram-positive and Gram-negative bacteria and showed variable activity. Hg 2+ complexes of oxadiazole and thiadiazole derivatives exhibited appreciable antibacterial effect at lower MIC, compatible to the reference vancomycin. Similarly, oxadiazole-nucleoside exhibited high effect on Gram-positive bacteria. Supplementary Information The online version contains supplementary material available at 10.1007/s13738-021-02358-x.

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Section: Introductionmentioning

confidence: 99%

Synthesis of novel seco-acyclo-N-diazolyl-thione nucleosides analogous derived from acetic acid: characterization, complex formation with ions Pb(II), Hg(II) and antibacterial activity

Chehrouri

Othman

2021

J IRAN CHEM SOC

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7-(β-d-Ribofuranosyl)-3-methylguanine: Synthesis from guanine and comparative multinuclear NMR studies

Baranowski

Boryski

Ostrowski

2022

Journal of Molecular Structure

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COXIBs and 2,5-dimethylcelecoxib counteract the hyperactivated Wnt/β-catenin pathway and COX-2/PGE2/EP4 signaling in glioblastoma cells

et al. 2021

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Background Glioblastoma (GBM) is the deadliest and the most common primary brain tumor in adults. The invasiveness and proliferation of GBM cells can be decreased through the inhibition of Wnt/β-catenin pathway. In this regard, celecoxib is a promising agent, but other COXIBs and 2,5-dimethylcelecoxib (2,5-DMC) await elucidation. Thus, the aim of this study was to analyze the impact of celecoxib, 2,5-DMC, etori-, rofe-, and valdecoxib on GBM cell viability and the activity of Wnt/β-catenin pathway. In addition, the combination of the compounds with temozolomide (TMZ) was also evaluated. Cell cycle distribution and apoptosis, MGMT methylation level, COX-2 and PGE2 EP4 protein levels were also determined in order to better understand the molecular mechanisms exerted by these compounds and to find out which of them can serve best in GBM therapy. Methods Celecoxib, 2,5-DMC, etori-, rofe- and valdecoxib were evaluated using three commercially available and two patient-derived GBM cell lines. Cell viability was analyzed using MTT assay, whereas alterations in MGMT methylation level were determined using MS-HRM method. The impact of COXIBs, in the presence and absence of TMZ, on Wnt pathway was measured on the basis of the expression of β-catenin target genes. Cell cycle distribution and apoptosis analysis were performed using flow cytometry. COX-2 and PGE2 EP4 receptor expression were evaluated using Western blot analysis. Results Wnt/β-catenin pathway was attenuated by COXIBs and 2,5-DMC irrespective of the COX-2 expression profile of the treated cells, their MGMT methylation status, or radio/chemoresistance. Celecoxib and 2,5-DMC were the most cytotoxic. Cell cycle distribution was altered, and apoptosis was induced after the treatment with celecoxib, 2,5-DMC, etori- and valdecoxib in T98G cell line. COXIBs and 2,5-DMC did not influence MGMT methylation status, but inhibited COX-2/PGE2/EP4 pathway. Conclusions Not only celecoxib, but also 2,5-DMC, etori-, rofe- and valdecoxib should be further investigated as potential good anti-GBM therapeutics.

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7‐(β‐D‐Ribofuranosyl)guanine and its Analogues Modified in the Sugar Portion: Synthesis and Antiglioma Properties

Cited by 3 publications

References 40 publications

Synthesis of novel seco-acyclo-N-diazolyl-thione nucleosides analogous derived from acetic acid: characterization, complex formation with ions Pb(II), Hg(II) and antibacterial activity

Synthesis of novel seco-acyclo-N-diazolyl-thione nucleosides analogous derived from acetic acid: characterization, complex formation with ions Pb(II), Hg(II) and antibacterial activity

7-(β-d-Ribofuranosyl)-3-methylguanine: Synthesis from guanine and comparative multinuclear NMR studies

COXIBs and 2,5-dimethylcelecoxib counteract the hyperactivated Wnt/β-catenin pathway and COX-2/PGE2/EP4 signaling in glioblastoma cells

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