Synthesis and cytotoxicity of some biurets against human breast cancer T47D cell line

Fouladdel, Shamileh; Khalaj, Ali; Adibpour, Neda; Azizi, Ebrahim

doi:10.1016/j.bmcl.2010.07.137

Cited by 14 publications

(9 citation statements)

References 17 publications

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“…The selected internal standard (1-([[3-(1,3-benzothiazol-2-ylsulfanyl) propyl] carbamoyl]amino) -N-phenylformamide is another biuret derivative (4) which is well separated from endogenous compound and PEQB. As could be seen from the chromatogram of rat blank plasma (Figure 2) there was no remarkable interference of endogenous compounds with PEQB and the internal standard.…”

Section: Resultsmentioning

confidence: 99%

“…1-(2-Phenylethyl)-5-(quinaldin-4-yl biuret and 1-([[3-(1,3-benzothiazol-2-ylsulfanyl)propyl]carbamoyl]amino)-N-phenylformamide used as internal standards were synthesized as previously reported (4), and further purified by preparative thick layer chromatography using silica gel (60 HF254-366) as stationary phase and a mixture of chloroform-ethyl acetate (3:1) as a mobile phase, and recrystallization. For recrystallization, the sample was first dissolved in a minimum amount of warm ethyl acetate, and then recrystallized with cooling the mixture and adding n-hexane portion by portion up to complete precipitation of the biuret compounds .Methanol and acetonitrile were of chromatography grade and purchased from Merck (Germany).…”

Section: Methodsmentioning

confidence: 99%

“…Recently, synthesis and cytotoxicity of N,N`-diphenyl, N-phenyl-N`-alkylphenyl, and N,N`-bisalkylphenyl biurets and analogous compounds by replacing one phenyl group with 2-ethylquinoline-4-yl,benzo[d]thiazol-2-ylthio and (1-phenyl-1H-tetrazol-5-yl) thio moieties against T47D breast cancer cell line have been described. It has been shown that 1-(2-phenylethyl)-5-(quinaldin-4-yl) biuret (Figure 1) is the most cytotoxic biuret derivative on T47D cells (4). An in silico study by Adibpour et al indicated that biuret derivatives could inhibit pteridine reductase 1 of different strains of leishmania and could be considered as potential antileishmaniasis agents (5).…”

Section: Introductionmentioning

confidence: 99%

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Development and Validation of a High-Performance Liquid Chromatography Method With UV Detection for Determination of 1-(2-phenylethyl)-5- (quinaldin-4-yl) Biuret in Rat Plasma

Adibpour

Ahmadnasr

Khodayar

et al. 2013

Jundishapur J Nat Pharm Prod

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Background:Recently, biuret derivatives have been reported as showing moderate to good cytotoxic effect against certain cancer cell lines. In this study, a high-performance liquid chromatography method was developed for determination of 1-(2-phenylethyl)-5-(quinaldin-4-yl) biuret (PEQB) in rat plasma to use in future studies on this compound and related derivatives. Objectives: In this study, we describe a simple and sensitive high-performance liquid chromatography method with UV detection for determination of 1-(2-phenylethyl)-6-(quinaldin-4-yl) biuret (PEQB) in rat plasma. Materials and Methods: Separations were performed on a Nucleosil-100 CN HPLC column (125 × 4.0 mm) (5 µm), using a mixture of acetonitrile: methanol: potassium dihydrogen phosphate buffer (0.05 M, pH 3.5) (10:10:80) as mobile phase delivered at a flow rate of 1 mL/ minute. Detection of PEQB and internal standard (1-([[3-(1,3-benzothiazol-2-ylsulfanyl)propyl]carbamoyl]amino)-N-phenylformamide) was performed at 235 nm and ambient temperature. Plasma samples (200 µL) were prepared by addition of 40 µL internal standard (100 µg/ mL), and 400 µL acetonitrile. After vortex mixing and centrifugation at 10000 g, 50 µL of the clear supernatant was directly injected onto the chromatography column. Calibration curves were constructed by fitting the peak area ratio of the biuret to internal standard against concentration of biuret to a power model using generalized least squares nonlinear regression method. Results: Under the above chromatography condition, biuret compound (PEQB) and the internal standard were detected at 4.5 and 13.5 minutes, respectively. Limit of quantitation of the PEQB was 0.1 µg/mL. Accuracy of the method over the concentration range of 0.1-100 µg/mL was between 88-109%. Inter-and intraday precisions were 4-19% and 6-8%, respectively. A good relationship in the form of a power model was found for two separate concentration ranges of 0.1-1 and 2.5-100 µg/mL (R 2 > 0.99). Conclusions:The presented simple HPLC method is sufficiently accurate, precise and sensitive for the quantitation of 1-(2-phenylethyl)-5-(quinaldin-4-yl) biuret in rat plasma.

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Section: Resultsmentioning

confidence: 99%

Section: Methodsmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

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Development and Validation of a High-Performance Liquid Chromatography Method With UV Detection for Determination of 1-(2-phenylethyl)-5- (quinaldin-4-yl) Biuret in Rat Plasma

Adibpour

Ahmadnasr

Khodayar

et al. 2013

Jundishapur J Nat Pharm Prod

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“…Cell viability was determined by the colorimetric assay with MTT 11 . Briefly, fibroblast cells grown in 96‐well plates to 75% confluency were incubated with 25–500 μ m Pep‐1, 2–5 μ m elastin and its related complexes in RPMI medium for one hour.…”

Section: Methodsmentioning

confidence: 99%

A peptide carrier for the delivery of elastin into fibroblast cells

et al. 2012

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Background Transmembrane delivery of active peptides and proteins, including skin delivery of cosmeceutical proteins such as collagen and elastin, has been a challenging issue. Amphipathic cell‐penetrating peptides (CPPs) have been proposed as carrier peptides to mediate cellular uptake of proteins without covalent binding. Materials and methods In this study, we have used a short peptide, Pep‐1, as our CPP to transport elastin into fibroblast cells. Different ratios of Pep‐1/elastin complexes were produced by using a fixed amount of elastin and different molar ratio of Pep‐1. The ability of transduction into cells was determined by fluorescence microscopy. The characteristics of Pep‐1/elastin complexes were monitored using scanning electron microscopy and photon correlation spectroscopy. Results No cellular toxicity was observed in cells treated with Pep‐1/elastin complex. Finally, we determined a Pep‐1 : elastin ratio of 10 : 1 as the most effective ratio in cellular delivery of elastin. Conclusion Pep‐1 mediated fast and effective delivery of elastin as a cosmetic protein into fibroblast cells in the treatment of skin‐aging symptoms.

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“…Both methods have been used, for example for the preparation of glycosyl biurets [296,297] or potentially pharmacologically active compounds. [298] Another method of biuret preparation involves reaction between nitrobiuret and amines at elevated temperatures. [299] Triurets are typically synthesized by reacting suitable urea derivatives with phosgene or related reagents.…”

Section: Synthesis Of Biurets and Triuretsmentioning

confidence: 99%