Mechanism and Kinetics of the Photocatalyzed Oxidation of p-Phenylenediamines by Peroxydisulfate in the Presence of Tri-2,2'-bipyridylylruthenium(II)

Nickel, Ulrich; Chen, Yao-Hong; Schneider, Siegfried; Silva, Maria Santos; Formosinho, Sebastião J.

doi:10.1021/j100062a026

Cited by 28 publications

(17 citation statements)

References 9 publications

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“…Photolysis of this metal complex is known to produce an excited state able to donate an electron to persulfate, resulting in cleavage of the O-O bond (16). The products are Ru(III), a potent one-electron oxidant (17)(18)(19), the sulfate radical, which should be a good hydrogen atom abstraction agent, and sulfate anion.…”

mentioning

confidence: 99%

Chemistry for the analysis of protein–protein interactions: Rapid and efficient cross-linking triggered by long wavelength light

Fancy

Kodadek

1999

Proc. Natl. Acad. Sci. U.S.A.

519

563

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Chemical cross-linking is a potentially useful technique for probing the architecture of multiprotein complexes. However, analyses using typical bifunctional cross-linkers often suffer from poor yields, and large-scale modification of nucleophilic side chains can result in artifactual results attributable to structural destabilization. We report here the de novo design and development of a type of protein cross-linking reaction that uses a photogenerated oxidant to mediate rapid and efficient cross-linking of associated proteins. The process involves brief photolysis of tris-bipyridylruthenium(II) dication with visible light in the presence of the electron acceptor ammonium persulfate and the proteins of interest. Very high yields of cross-linked products can be obtained with irradiation times of <1 second. This chemistry obviates many of the problems associated with standard cross-linking reagents.

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mentioning

confidence: 99%

Chemistry for the analysis of protein–protein interactions: Rapid and efficient cross-linking triggered by long wavelength light

Fancy

Kodadek

1999

Proc. Natl. Acad. Sci. U.S.A.

519

563

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“…Meanwhile, one of the hallmarks of visible light photocatalysis is the mild reaction condition and outstanding functional group tolerance which would provide some advantages over the current methods. It is well precedented that persulfate (S 2 O 8 2− ) is an effective oxidative quencher of Ru(bpy) 3 2+ *, 12 and the generated sulfate radical anion (SO 4 ˙ − ) is a reactive intermediate known to abstract activated hydrogen atoms and also be a strong oxidant. 13 Herein, we report a visible light enabled Friedel-Crafts amidoalkylation using persulfate at room temperature via the oxidative quenching cycle of Ru(bpy) 3 Cl 2 .…”

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confidence: 99%

Friedel–Crafts Amidoalkylation via Thermolysis and Oxidative Photocatalysis

et al. 2012

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Friedel-Crafts amidoalkylation was achieved by oxidation of dialkylamides using persulfate (S2O82−) in the presence of the visible light catalyst, Ru(bpy)3Cl2, at room temperature, via a reactive N-acyliminium intermediate. Alternatively, mild heating of the dialkylamides and persulfate afforded a metal and Lewis acid-free Friedel-Crafts amidoalkylation. Alcohols and electron–rich arenes served as effective nucleophiles, forming new C–O or C–C bonds. In general, photocatalysis provided higher yields and better selectivities.

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“…This is an aromatic amine of mineral origins of the family of aniline, used since 1863 by women as black hair dye for coloring hair, or adjuvant henna for tattoos in several countries in Africa and the Middle East. It is also widely used in industry for dyeing furs and textiles in the manufacture of household products, cosmetic agents, wheels, caoutchoucs, in the synthesis of plastics or as a photographic developer [13][14][15][16][17][18][19][20][21].…”

Section: Introductionmentioning

confidence: 99%

Chemical and Biological Analyses of the Role of the Poly- Para- Phenylenediamine in the Erythrocytes Resistance in Hypotonic Environment

Srhayri¹,

Naimi²,

Takky³

et al. 2016

J Membra Sci Technol

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potential scan rate of 200 mVs-1, two voltametric waves on the platen; which corresponds to two successive and reversible processes to a single electron, leading to the formation of a diamine [24].Moreover, the genotoxicity studies in vitro have shown that pPD, like several other aromatic amines which belong to the aniline family can react with DNA and cause breaks . Picardo et al. have shown that pPD at high concentrations and for long exposure time induced cell cycle block and toxicity, but at low concentrations (10 µg/mL)and for shorter periods exposure (30 min) increased keratinocyte proliferation [39]. Habti et al. [6] have shown that pPD at low concentrations (5µg/mL) and for 2h exposure time gives RBC temporary resistance to hemolysis in hypotonic blend, the mechanism remains unexplained till now [6]. The aim of our study is to contribute to elucidate the molecular mechanism responsible for this temporary resistance. Material and Methods Collection of human blood sampleBlood samples from volunteer donors, and healthy aged 25-35 years were collected in tubes of 7 mL containing EDTA. Blood donors were nonsmokers and had no history of allergic reaction to pPD or AbstractThe high chemical and biological reactivity of para-phenylenediamine (pPD) has been illustrated in several studies, including polymerization genotoxicity and oxidative stress at the level of the plasma membrane cells. However, its reactivity with red blood cells (RBC) was rarely explored.The aim of this study is to help expound the molecular actions of para-phenylenediamine in hypotonic environment of human red blood cells by conducting biological tests for the globular resistance and physicochemical cyclic voltammetry and UV-visible spectroscopy.Our results show that the para-phenylenediamine at low concentration gives red blood cells temporary resistance (30 min) against hemolysis in hypotonic environment with 4.5 g/L NaCl. Spectrometry results for UVvisible and cyclic voltammetry suggest that membrane stability is due to the presence of the polymer poly-paraphenylenediamine (poly-pPD).

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Mechanism and Kinetics of the Photocatalyzed Oxidation of p-Phenylenediamines by Peroxydisulfate in the Presence of Tri-2,2'-bipyridylylruthenium(II)

Cited by 28 publications

References 9 publications

Chemistry for the analysis of protein–protein interactions: Rapid and efficient cross-linking triggered by long wavelength light

Chemistry for the analysis of protein–protein interactions: Rapid and efficient cross-linking triggered by long wavelength light

Friedel–Crafts Amidoalkylation via Thermolysis and Oxidative Photocatalysis

Chemical and Biological Analyses of the Role of the Poly- Para- Phenylenediamine in the Erythrocytes Resistance in Hypotonic Environment

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