Synthesis and antiproliferative activity of novel methylselenocarbamates

Romano, Beatriz; Font, Marı́a; Encı́o, Ignacio; Palop, Juan Antonio; Sanmartín, Carmen

doi:10.1016/j.ejmech.2014.06.076

Cited by 17 publications

(7 citation statements)

References 41 publications

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“…In addition to these classical precursors, our group has been synthesizing during the last decade several methylseleno derivatives [ 18 , 19 , 20 , 21 , 22 ]. These compounds exhibited significant anticancer activity compared to other alkyl derivatives against a broad spectrum of cancer cells both in vitro and in vivo.…”

Section: Introductionmentioning

confidence: 99%

Novel Methylselenoesters as Antiproliferative Agents

et al. 2017

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Selenium (Se) compounds are potential therapeutic agents in cancer. Importantly, the biological effects of Se compounds are exerted by their metabolites, with methylselenol (CH3SeH) being one of the key executors. In this study, we developed a new series of methylselenoesters with different scaffolds aiming to modulate the release of CH3SeH. The fifteen compounds follow Lipinski’s Rule of Five and with exception of compounds 1 and 14, present better drug-likeness values than the positive control methylseleninic acid. The compounds were evaluated to determine their radical scavenging activity. Compound 11 reduced both DPPH and ABTS radicals. The cytotoxicity of the compounds was evaluated in a panel of five cancer cell lines (prostate, colon and lung carcinoma, mammary adenocarcinoma and chronic myelogenous leukemia) and two non-malignant (lung and mammary epithelial) cell lines. Ten compounds had GI50 values below 10 μM at 72 h in four cancer cell lines. Compounds 5 and 15 were chosen for further characterization of their mechanism of action in the mammary adenocarcinoma cell line due to their similarity with methylseleninic acid. Both compounds induced G2/M arrest whereas cell death was partially executed by caspases. The reduction and metabolism were also investigated, and both compounds were shown to be substrates for redox active enzyme thioredoxin reductase.

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Section: Introductionmentioning

confidence: 99%

Novel Methylselenoesters as Antiproliferative Agents

et al. 2017

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“…They have also demonstrated higher radical scavenging efficiency than the corresponding S and Se compounds. 41,42 Organotellurium compounds have been much less explored in biology unlike the compounds of its lower congeners (S and Se), even though tellurium exhibit various similar properties of sulfur and selenium [43][44][45][46] which may be due to the fact that tellurium was considered non-essential biological trace element, commercial non-availability of a wide variety of organotellurium compounds as starting materials and some misconception that they are air sensitive, foul smelling and even toxic. A few reasons among enhanced interest currently in the biological chemistry of organotellurium compounds are the availability of modern analytical techniques ( 125 Te Fourier transform nuclear magnetic resonance, FT-NMR; atomic absorption spectroscopy, AAS; and inductively coupled plasma-atomic emission spectrometry, ICP-AES) to study and understand the solution behavior of Te containing systems, such an option does not exist for sulfur compounds, the secondary interactions (Te … X where X = O, Cl, Br, I or M) arises from the hypervalent nature of Te, thus increases the stability of organotellurium compounds and higher redox activity of the tellurium.…”

Section: Introductionmentioning

confidence: 99%

“…Recently reported that the organoselenium and tellurium compounds which contain the secondary interactions between chalcogen atom and other heteroatoms [TeX, X = N, O, S, Cl, Br, I] through internal chelation play an important role in the catalytic antioxidant activity. [48][49][50] There are numerous synthetic and natural chiral organoselenium compounds [20][21][22][23][24][25][26][43][44][45][46] but there has not been studied antioxidant properties of chiral organotellurium compounds containing peptide and carbamate functionalities.…”

Section: Introductionmentioning

confidence: 99%

Synthesis, Characterization andin vitroAntioxidant Activity of New ChiralN-boc Organotellurium Compounds, (CH₃)₃OC(O)NHCH(R)C(O)NHCH₂-CH₂Te-C₆H₄-4-OCH₃, Containing Carbamate and Peptide Groups

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Panchangam

Bhanu

et al. 2016

Journal of the Brazilian Chemical Society

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Synthesis, characterization and antioxidant activity of a new series of chiral N-boc oraganotellurium compounds, (CH 3 ) 3 OC(O)NHCH(R)C(O)NHCH 2 CH 2 Te-C 6 H 4 -4-OCH 3 , containing carbamate and peptide groups have been reported in this paper. These chiral peptides were synthesized in good to excellent yields, via acid-amine coupling reaction of N-boc L-amino acids with 2-(4-methoxyphenyltelluro) ethylamine in presence of dicyclohexyl carbodimide (DCC) at room temperature. The elemental analyses, Fourier transform infrared (FTIR), 1 H and 13 C { 1 H} nuclear magnetic resonance (NMR) spectra and mass spectra were characteristic. Specific optical rotation (SOR) was also determined. In vitro antioxidant activity of these multi-functional compounds in methanol has been evaluated against 2,2-diphenyl-1-picrylhydrazyl (DPPH) radicals with 2,6-di-tert-butyl-4-methylphenol (BHT) as a standard reference compound. The IC 50 (inhibitory concentration 50) values of these chiral peptides revealed significant inhibition against DPPH radicals and found to be effective antioxidants.

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“…21 Moreover, some diselenides have been designed as potential therapeutic agents mimicking the peroxidase activity of selenium based glutathione peroxidases. 22 Taking into account our previous experience in selenocyanate and diselenide chemistry [23][24][25] and the fact that we have recently reported some carbamates as potential antiproliferative drugs, 26 we decided to further extend our research by synthesising thirty new hybrid compounds in which selenocyanate or diselenide and carbamate moieties were combined. In these compounds the carbamate function, a group commonly found in antitumour active http compounds [27][28][29][30][31][32] acts as a link between the central and ending scaffolds, thus enabling their chemical accessibility and increasing polarity in this area as compared to our previously described structures.…”

Section: Introductionmentioning

confidence: 99%