Synthesis of new N-arylamino(2-furyl)methylphosphonic acid diesters, and in vitro evaluation of their cytotoxicity against esophageal cancer cells

Klimczak, Anna; Kuropatwa, Agnieszka; Lewkowski, J.; Szemraj, Janusz

doi:10.1007/s00044-012-0065-3

Cited by 19 publications

(25 citation statements)

References 24 publications

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“…Both tobacco and alcohol consumption increase the risk of EC (1). Nowadays, a variety of methods exist to examine EC and more is known about the disease, however, further research is necessary in order to take effective steps to prevent and treat it (5). EC treatment choice is dependent on the developmental stage of the disease.…”

Section: Introductionmentioning

confidence: 99%

Expression of MMP9, SERPINE1 and miR-134 as prognostic factors in esophageal cancer

et al. 2016

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Abstract. Esophageal cancer (EC) is a malignant tumor with a typically poor prognosis for patients. It is well known that certain microRNA (miRNA/miR) genes can regulate other genes responsible for carcinogenesis. In the present study, a group of these genes (miR-21, miR-134, miR-205 and miR-495) and genes connected with cancer-related pathways (MET, MMP9, PDGFA and SERPINE1) were chosen for analysis in order to find a potential correlation between their expression and the clinicopathological factors of EC. Esophageal tumors and adjacent non-cancerous tissue specimens were collected from a total of 63 patients and embedded in paraffin. Commercial arrays were used on KYSE-30, KYSE-150 and KYSE-270 EC cell lines in order to find genes of different expression profiles compared with those acquired from the control Het-1A cell line. Quantitative polymerase chain reaction was used on formalin-fixed, paraffin-embedded samples in order to analyze the expression of the genes chosen in the earlier step. The results were analyzed by the Kruskal-Wallis and Mann-Whitney U tests, Spearman's rank correlation coefficient, Kaplan-Meier methods and the long-rank test. Only miR-495 was not expressed in the analyzed samples. The expression of MMP9 and SERPINE1 was significantly coefficient with age range (P=0.011 and P=0.044, respectively) according to the Kruskal-Wallis test. The Spearman's rank-order correlation measurement showed that there was a coefficient correlation between age and miR-134 expression. The same measurement demonstrated a correlation between age range and MMP9 expression. The expression of miR-134 and MMP9 were also found to be correlated. In all cases, a value of P<0.049 was recorded. Overall, the present study demonstrated that MMP9, SERPINE1 and miR-134 were the most prognostic genes in Caucasian patients with EC.

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Section: Introductionmentioning

confidence: 99%

Expression of MMP9, SERPINE1 and miR-134 as prognostic factors in esophageal cancer

et al. 2016

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“…19 In the present paper, we report cytotoxicities of new aminophosphonates 2b-d and aminophosphonic acids 3a-c toward these cells and, on the basis of these and previous 19 results, we present preliminary conclusions on the structure versus activity relationship of this group of compounds.…”

Section: Introductionmentioning

confidence: 89%

“…19 Schiff bases 1a-e were synthesized following the previously published 19,27,28 procedures and their identity was confirmed by melting point measurement and/or the 1 H NMR spectroscopy and comparing the obtained data with literature reports. 17,19,20,[29][30][31][32] (2-Furyl)-N-arylaminomethylphosphonic acid esters (2b-d) were prepared based on the previously published procedures, 19,27,28 from a Schiff base 1b-c by the aza-Pudovik reaction. Reactions of Schiff bases 1b-c with phosphites were carried out in acetonitrile with a catalytic amount (two drops) of trifluoroacetic acid.…”

Section: Chemistrymentioning

confidence: 99%

“…As dimethyl (2-furyl)-N-(2-methoxyphenyl)-aminomethylphosphonate (2a) demonstrated the promising cytotoxic properties, 19 we performed investigations in order to verify, if the compound 2a is able to induce apoptosis of the studied cells. …”

Section: Introductionmentioning

confidence: 99%

“…15 They show interesting impact on higher plants, 16,17 they also show a high cytotoxicity toward some cancers . 13 Recently, the synthesis of several furan moiety-bearing aminophosphonates and their strong action on leukemia 18 and squamous esophageal cancer 19 cell lines were reported.…”

Section: Introductionmentioning

confidence: 99%

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Dimethyl (2-Furyl)-N-(2-Methoxyphenyl)Aminomethylphosphonate Induces Apoptosis in Esophageal Squamous Cancer Cells. Structure Versus Activity of its Selected Analogs

Klimczak

Matusiak

Lewkowski

et al. 2015

Phosphorus, Sulfur, and Silicon and the Related Elements

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Cytotoxicities of several new aminophosphonic compounds bearing 2-furyl moiety 2b-d and 3a-c on KYSE 30, 150, and 270 esophageal cancer cell lines are reported here. The qualitative study on correlations between the structure and cytotoxic activity of furan-deriving aminophosphonates has been performed. Dimethyl (2-furyl)-N-(2-methoxyphenyl)aminomethylphosphonate (2a), which has been previously shown to have the interesting values of cytotoxicity on these esophageal cancer cell lines was tested and found to induce apoptosis. The analyses of correlations between apoptosis, necrosis, and viability were also performed.

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Synthesis, Characterization and Evaluation of Cytotoxic Activities of Novel Aziridinyl Phosphonic Acid Derivatives

Khan

Ulusan

Banerjee

et al. 2019

Chemistry & Biodiversity

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New aziridine 2‐phosphonic acids were prepared by monohydrolysis of the aziridine 2‐phosphonates that were obtained by the modified Gabriel−Cromwell reaction of vinyl phosphonate or α‐tosylvinyl phosphonate with a primary amine or a chiral amine. The cellular cytotoxicity of these compounds was tested against the HCT‐116 colorectal cancer cell lines and the CCD‐18Co normal colon fibroblast lines using the MTT assay. Three of the synthesized phosphonic acid derivatives 2e (ethyl hydrogen {(2S)‐1‐[(1S)‐1‐(naphthalen‐2‐yl)ethyl]aziridin‐2‐yl}phosphonate), 2h (ethyl hydrogen (1‐benzylaziridin‐2‐yl)phosphonate), and 2i (ethyl hydrogen (1‐cyclohexylaziridin‐2‐yl)phosphonate) showed higher cytotoxicity than the reference cancer treatment agent etoposide. Cell death was through a robust induction of apoptosis even more effectively than etoposide, a well‐known apoptosis inducing agent.

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Synthesis of new N-arylamino(2-furyl)methylphosphonic acid diesters, and in vitro evaluation of their cytotoxicity against esophageal cancer cells

Cited by 19 publications

References 24 publications

Expression of MMP9, SERPINE1 and miR-134 as prognostic factors in esophageal cancer

Expression of MMP9, SERPINE1 and miR-134 as prognostic factors in esophageal cancer

Dimethyl (2-Furyl)-N-(2-Methoxyphenyl)Aminomethylphosphonate Induces Apoptosis in Esophageal Squamous Cancer Cells. Structure Versus Activity of its Selected Analogs

Synthesis, Characterization and Evaluation of Cytotoxic Activities of Novel Aziridinyl Phosphonic Acid Derivatives

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