Synthesis, characterization, antitumor activity and safety testing of novel polyphosphoesters bearing anthracene-derived aminophosphonate units

Kraicheva, I.; Vodenicharova, Elitsa; Shenkov, S.; Tashev, E.; Tosheva, T.; Tsacheva, Ivelina; Kril, A.; Topashka-Ancheva, Margarita; Georgieva, A. I.; Илиев, Иван; Vladov, Ivelin; Gerasimova, Ts.; Troev, K.

doi:10.1016/j.bmc.2013.12.001

Cited by 14 publications

(17 citation statements)

References 27 publications

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“…The results from this and our previous study [18] reveal similarity of the cytotoxic activities of copolymers 1 and 2 in human breast cancer cells and animal mammary carcinoma cells, and underline the significance of the EAC model for studies on the antitumour activity of different compounds. In addition, similar subcellular distribution pointing to a similar mode of biological activity has been established.…”

Section: Fluorescent Studiesmentioning

confidence: 88%

“…The content of the aminophosphonate units in the studied copolymers is 43% and 13% degree of polymerization for polymers 1 and 2, respectively. [18] Cells and culture conditions…”

Section: Tested Substancesmentioning

confidence: 99%

“…[18] Poly(oxyethylene H-phosphonate)s were synthesized via a polytransesterification reaction of dimethyl H-phosphonate and poly(ethylene glycol)s (PEGs) with an average molecular weight of 600 Da (PEG 600) and 200 Da (PEG 200). Copolymers 1 and 2 were prepared from poly(oxyethylene H-phosphonate)s obtained on the basis of PEG 600 and PEG 200, respectively.…”

Section: Tested Substancesmentioning

confidence: 99%

“…[18] Both compounds showed high antiproliferative activity against human cell lines from ductal carcinoma of the breast (MCF-7 and MDA-MB-231), with low and high metastatic potential, respectively. [18] In this study, in vitro cultures of Ehrlich ascites carcinoma (EAC) cells were used to confirm the antineoplastic effect of these polymers on mammary adenocarcinoma cells. The EAC is a transplantable, poorly differentiated, rapidly growing tumour with very aggressive behaviour, derived from spontaneous mouse mammary adenocarcinoma and hence growing in solid and ascitic forms.…”

Section: Introductionmentioning

confidence: 99%

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In vitroantitumour activity, safety testing and subcellular distribution of two poly[oxyethylene(aminophosphonate-co-H-phosphonate)]s in Ehrlich ascites carcinoma and BALB/c 3T3 cell culture systems

Georgieva

Iliev

Topashka-Ancheva

et al. 2015

Biotechnology & Biotechnological Equipment

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Two polyphosphoesters containing anthracene-derived aminophosphonate and hydrophilic Hphosphonate repeating units, poly[oxyethylene(aminophosphonate-co-H-phosphonate)]s (1 and 2), were tested for the in vitro antitumour activity on cell cultures derived from ascitic form of Ehrlich mammary adenocarcinoma by 3-(4,5-dimethylthiazol-2-yl)-2,5-diphenyltetrazolium bromide (MTT)-dye reduction assay. The in vitro safety testing of the copolymers was performed by BALB/c 3T3 neutral red uptake assay. A study on their uptake and subcellular distribution in nontumourigenic and tumour cells was performed by means of fluorescence microscopy. Both copolymers showed significant antitumour activity towards Ehrlich ascites carcinoma (EAC) cells. However, the in vitro safety testing revealed significant toxicity of polymer 2 to BALB/c 3T3 mouse embryo cells. In contrast, polymer 1 showed complete absence of cytotoxicity to BALB/c 3T3 cells. The fluorescent studies showed that the substances were diffusely distributed in the cytoplasm in both cell culture systems. As opposed to BALB/c 3T3 cells, in EAC cells, intense fluorescent signal was observed in the nuclei and in the perinuclear region. The tested polyphosphoesters are expected to act under physiological conditions as prodrugs of aminophosphonates.

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Section: Fluorescent Studiesmentioning

confidence: 88%

“…The content of the aminophosphonate units in the studied copolymers is 43% and 13% degree of polymerization for polymers 1 and 2, respectively. [18] Cells and culture conditions…”

Section: Tested Substancesmentioning

confidence: 99%

Section: Tested Substancesmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

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In vitroantitumour activity, safety testing and subcellular distribution of two poly[oxyethylene(aminophosphonate-co-H-phosphonate)]s in Ehrlich ascites carcinoma and BALB/c 3T3 cell culture systems

Georgieva

Iliev

Topashka-Ancheva

et al. 2015

Biotechnology & Biotechnological Equipment

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“…They play a vital role in antibody generation . Recently, α‐amino phosphonates are proved to posses potent biological activities, such as selective inhibitors of tyrosine kinase, cytotoxic to cancer cells,,, antibacterial, antifungal, antitumor and antiproliferative agents, enzyme inhibitors, [15,16] antiviral, and plant growth regulators …”

Section: Introductionmentioning

confidence: 99%

Synthesis of Novel α‐Aminophosphonate Derivatives, Biological Evaluation as Potent Antiproliferative Agents and Molecular Docking

Deshmukh

Kharat²,

Yadav

et al. 2018

ChemistrySelect

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A series of novel fluorine containing α‐aminophosphonate derivatives (4 a–4 q) were synthesized in excellent yield and high purity. All these novel Fluorinated α‐aminophosphonate compounds were screened for antiproliferative and apoptosis activity on human non small cell lung carcinoma cells (A549) and human skin melanoma cells (SK‐MEL‐2). Compounds 4 a, 4 b, 4 c, 4 f, 4 i, 4 j and 4 m were found to be more active antiproliferative agent against A549 and SK‐MEL‐2 cells with IC50 value 0.22 to 1.25 μM. Molecular docking study related to binding affinity and binding mode analysis showed that synthesized compounds had potential to inhibit human Topoisomerase IIa enzyme system. Flow cytometric study showed some of these derivatives also induced cell apoptosis and arrest cell cycle at G1 and at G2/M phase. Overall, this study provides future perspective of lead candidate for the future anticancer drug discovery initiatives.

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Recent Advances in H-Phosphonate Chemistry. Part 1. H-Phosphonate Esters: Synthesis and Basic Reactions

Sobkowski

Kraszewski

Stawiński

2014

Topics in Current Chemistry

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This review covers recent progress in the preparation of H-phosphonate mono- and diesters, basic studies on mechanistic and stereochemical aspects of this class of phosphorus compounds, and their fundamental chemistry in terms of transformation of P-H bonds into P-heteroatom bonds. Selected recent applications of H-phosphonate derivatives in basic organic phosphorus chemistry and in the synthesis of biologically important phosphorus compounds are also discussed.

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Synthesis, characterization, antitumor activity and safety testing of novel polyphosphoesters bearing anthracene-derived aminophosphonate units

Cited by 14 publications

References 27 publications

In vitroantitumour activity, safety testing and subcellular distribution of two poly[oxyethylene(aminophosphonate-co-H-phosphonate)]s in Ehrlich ascites carcinoma and BALB/c 3T3 cell culture systems

In vitroantitumour activity, safety testing and subcellular distribution of two poly[oxyethylene(aminophosphonate-co-H-phosphonate)]s in Ehrlich ascites carcinoma and BALB/c 3T3 cell culture systems

Synthesis of Novel α‐Aminophosphonate Derivatives, Biological Evaluation as Potent Antiproliferative Agents and Molecular Docking

Recent Advances in H-Phosphonate Chemistry. Part 1. H-Phosphonate Esters: Synthesis and Basic Reactions

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