Synthesis of New 2-Naphthyl Ethers and Their Protective Activities against DNA Damage Induced by Bleomycin-Iron

Abdel‐Wahab, Bakr F.; El-Ahl, Abdel-Aziz S.; Badria, Farid A.

doi:10.1248/cpb.57.1348

Cited by 38 publications

(15 citation statements)

References 31 publications

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“…After centrifugation, the extent of DNA damage was measured by increase in absorbance at 532 nm. [1819] The viability of the cells was determined by the microscopical examination[20] using a hemocytometer and using trypan blue stain (stains only the dead cells).…”

Section: Methodsmentioning

confidence: 99%

Antioxidant, cytotoxic, antitumor, and protective DNA damage metabolites from the red sea brown alga Sargassum sp

Ayyad¹,

Ezmirly²,

Basaif³

et al. 2011

Phcog Res

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Background:Macroalgae can be viewed as a potential antioxidant and anti-inflammatory sources owing to their capability of producing compounds for its protection from environmental factors such as heat, pollution, stress, oxygen concentration, and UV radiations.Objective:To isolate major compounds which are mainly responsible for the pharmacological activity of brown alga under investigation, Sargassum sp.Materials and Methods:Algal material was air dried, extracted with a mixture of organic solvents, and fractionated with different adsorbents. The structures of obtained pure compounds were elucidated with different spectroscopic techniques, and two pure materials were tested for protection of DNA from damage, antioxidant, antitumor, and cytotoxicity.Results:Four pure compounds were obtained, of which fucosterol (1) and fucoxanthin (4) were tested; it was found that fucoxanthin has strong antioxidant and cytotoxicity against breast cancer (MCF-7) with IC50 = 11.5 μg/ml.Conclusion:The naturally highly conjugated safe compound fucoxanthin could be used as antioxidant and as an antitumor compound.

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Section: Methodsmentioning

confidence: 99%

Antioxidant, cytotoxic, antitumor, and protective DNA damage metabolites from the red sea brown alga Sargassum sp

Ayyad¹,

Ezmirly²,

Basaif³

et al. 2011

Phcog Res

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“…Antioxidant behavior is determined using bleomycin‐dependent DNA damage assay (Section 2S.1 in Supporting Information) and erythrocyte hemolysis (Section 2S.2 in Supporting Information). Peroxyl radicals mediated erythrocyte hemolysis in this assay .…”

Section: Methodsmentioning

confidence: 99%

Structural studies and biological evaluation of Co (II), Ni (II) and Cu (II) complexes of carbohydrazone derived from ethyl acetoacetate in addition to crystallographic description of La (III) or Sm (III) catalytic activity abnormal product

Fetoh

Salah

El‐Reash

2018

Applied Organom Chemis

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New carbohydrazone ligand derived from the condensation of carbohydrazide and ethyl acetoacetate, diethyl 3,3′‐(carbonylbis (hydrazin‐2‐yl‐1‐ylidene))(3E,3′E)‐dibutyrate (H4EBC), and its divalent Co, Ni and Cu chelates have been isolated and characterized utilizing convenient methods. 1H‐NMR spectrum of H4EBC revealed the abundance of the enol isomer in solution, which was the opposite to what was shown by the solid IR. This was supported by comparing the theoretical IR of both keto and enol forms. In [Ni(H4EBC)Cl2(H2O)]·2H2O, H4EBC acts as a neutral NON tridentate ligand via the (C=O)carbonyl oxygen atom besides the two (C=N)azomethine nitrogen atoms, while in [Co(H4EBC)Cl2(2H2O)]·2H2O, H4EBC behaves as a neutral NN bidentate ligand through the two azomethine groups. Magnetic measurements inherent to their electronic spectra show that both Ni (II) and Co (II) chelates have octahedron coordination frameworks. On the other hand, the ligand behaves as a binegative tetradentate in [Cu2(H4EBC)Cl2]·H2O via the deprotonated (C=O)carbonyl groups of the ethyl acetoacetate framework and the two (C=N)azomethine groups. In the latter complex, the carbonyl group of the carbohydrazide moiety is converted to hydroxyl group. Cu (II) complex has a tetrahedral geometry according to ESR and electronic spectral data. The reaction of H4EBC with SmCl3·6H2O or LnCl3·7H2O gave single crystals of abnormal product (C16H16N4O4). The packing diagram of this crystal has a chain structure. The photoluminescence spectra of [Cu2(H4EBC)Cl2]·H2O, [Co(H4EBC)Cl2(H2O)2]·2H2O and [Ni(H4EBC)Cl2(H2O)]·2H2O display emission broad‐bands at 342, 321 and 337 nm, respectively. The microbial behavior of the synthesized moieties was investigated against various bacterial and fungal strains. [Cu2(H4EBC)Cl2]·H2O complex shows the same activity as ampicillin towards Escherichia coli and Staphylococcus aureus with inhibition zones of 26 and 22 mm, respectively. Antioxidant activity is determined using bleomycin‐dependent DNA damage assay besides erythrocyte hemolysis. Finally, in vitro cytotoxic activities against two different cell lines have been examined.

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“…To the reaction mixtures in a final volume of 1.0 mL, the following reagents at the final concentrations started were added: DNA (0.2 mg/mL), bleomycin sulfate (0.05 mg/mL), FeCl 3 (0.025 mM), magnesium chloride (5 mM), KH 2 PO 4 –KOH buffer pH 7.0 (30 mM), and ascorbic acid (0.24 mM) or the test fractions diluted in MeOH to give a concentration of (0.1 mg/mL). The reaction mixtures were incubated in a water bath at 37°C for 1 h. At the end of the incubation period, 0.1 mL of ethylene diamine tetraacetic acid (0.1 M) was added to stop the reaction (the iron–ethylene diamine tetraacetic acid complex is unreactive in the bleomycin assay) . DNA damage was assessed by adding 1 mL 1% (w/v) TBA and 1 mL of 25% (v/v) hydrochloric acid (HCL) following by heating in a water bath maintained at 80°C for 15 min.…”

Section: Methodsmentioning

confidence: 99%

One‐pot Synthesis of 1,2,3,4‐Tetrahydropyrimidin‐2(1H)‐thione Derivatives and their Biological Activity

Salem

Marzouk

Salem

et al. 2015

Journal of Heterocyclic Chem

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2‐Thioxo/oxo‐1,2,3,4‐tetrahydropyrimidine‐5‐carboxylate derivatives 2a, 2b, 2c, 2d were prepared by the reaction of ethyl acetoacetate and thiourea or urea with aldehydes using NH4Cl as a catalyst. Compounds 2a and 2c reacted with mono and bihalogenated compounds such as ethyl iodide, chloroacetonitrile, epichlorohydrin, acetyl chloride, ethyl bromoacetate, chloroacetic acid, chloroacetylchloride, and/or oxalyl chloride to afford compounds 3, 4a, 4b, 5, 6a, 6b, 7, 8, 9 and 10, respectively. Compounds 2a, 2c, and 7 were allowed to react with p‐fluorobenzaldehyde to yield the corresponding products 11a, 11b, and 12, respectively. Oxidation of 2a and 2c gave 2b, 13a, 13b, 14, 15, 16 dependent on the oxidizing agent used. Vilsmeiere‐Haack formylation of 2a and 2b with POCl3/DMF afforded 17a and 17b. Chlorination of 2b and 2d gave the chlorinated derivative 18a and 18b, which reacted with thiourea to give thioureidopyrimidine 19a and 19b. Reactions of 2a with hydrazine monohydrate, semicarbazide hydrochloride, and sodium hydroxide gave compounds 20, 21, 22, respectively. The cytotoxicity and in vitro anticancer evaluation of some prepared compounds have been assessed against two different human tumor cell lines including breast adenocarcinoma MCF‐7 and human hepatocellular carcinoma HepG2. Antimicrobial and antioxidant activities of some compounds were investigated. The newly synthesized compounds were characterized by IR, 1H‐NMR, 13C‐NMR, and mass spectral data.

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Synthesis of New 2-Naphthyl Ethers and Their Protective Activities against DNA Damage Induced by Bleomycin-Iron

Cited by 38 publications

References 31 publications

Antioxidant, cytotoxic, antitumor, and protective DNA damage metabolites from the red sea brown alga Sargassum sp

Antioxidant, cytotoxic, antitumor, and protective DNA damage metabolites from the red sea brown alga Sargassum sp

Structural studies and biological evaluation of Co (II), Ni (II) and Cu (II) complexes of carbohydrazone derived from ethyl acetoacetate in addition to crystallographic description of La (III) or Sm (III) catalytic activity abnormal product

One‐pot Synthesis of 1,2,3,4‐Tetrahydropyrimidin‐2(1H)‐thione Derivatives and their Biological Activity

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