Polycyclic Aromatic Hydrocarbon Quinones as Redox and Electrophilic Chemicals Contaminated in the Atmosphere

Kumagai, Yoshito

doi:10.1248/jhs.55.887

Cited by 18 publications

(7 citation statements)

References 28 publications

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“…As a result of the two-electron reduction reaction, hydrogen peroxide (H 2 O 2 ) and 9,10-PQ •-are formed (Fig. 3) (Taguchi et al, 2007(Taguchi et al, , 2008Kumagai, 2009). Overall, it is postulated that ROS such as O 2…”

Section: Figmentioning

confidence: 99%

“…DEP and 9,10-PQ enhance allergic airway infl ammation in mice (Takano et al, 1997;Hiyoshi et al, 2005b) and 9,10-PQ exposure causes recruitment of inflammatory cells to the murine airways (Hiyoshi et al, 2005a), suggesting that 9,10-PQ is a key molecule in ambient air to increase health risks through oxidative stress. 9,10-PQ and NQs, which are electron acceptors, can generate ROS through redox cycling (Kumagai et al, 1997;Kumagai, 2009). The NQs, but not 9,10-PQ, have electrophilic carbon and readily react with nucleophiles such as thiol groups on proteins to yield protein adducts involved in modulation of cellular signals and protein functions (Kumagai et al, 2012).…”

Section: Introductionmentioning

confidence: 99%

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Chemical toxicology of reactive species in the atmosphere: two decades of progress in an electron acceptor and an electrophile

2016

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Air pollutants such as diesel exhaust particles (DEP) are thought to cause pulmonary diseases such as asthma as a result of oxidative stress. While DEP contain a large number of polycyclic aromatic hydrocarbons, we have focused on 9,10-phenanthrenequinone (9,10-PQ) and 1,2-naphthoquinone (1,2-NQ) because of their chemical properties based on their oxidative and chemical modification capabilities. We have found that 9,10-PQ interacts with electron donors such as NADPH (in the presence of enzymes) and dithiols, resulting in generation of excess reactive oxygen species (ROS) through redox cycling. We have also shown that 1,2-NQ is able to modify protein thiols, leading to protein adducts associated with activation of redox signal transduction pathways at lower concentrations and toxicity at higher concentrations. In this review, we briefly introduce our findings from the last two decades.

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Section: Figmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

Chemical toxicology of reactive species in the atmosphere: two decades of progress in an electron acceptor and an electrophile

2016

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“…[13] They have been identified as major contributors to air pollution. [2,14] Their toxicity is higher than that of naphthalene, [15] which is one of the most abundant PAHs in the atmosphere. [16,17] 1,4-naphthoquinone (1,4-NQ, see Figure 1) is the major structural component of vitamin K, [18] and has been found to strongly inhibit cancer cell growth.…”

Section: Introductionmentioning

confidence: 99%

“…They can also form through reaction of naphthalene with OH and NO 3 radicals, [10–12] and by photolysis of other species [13] . They have been identified as major contributors to air pollution [2,14] . Their toxicity is higher than that of naphthalene, [15] which is one of the most abundant PAHs in the atmosphere [16,17] …”

Section: Introductionmentioning

confidence: 99%

Structural Changes Induced by Quinones: High‐Resolution Microwave Study of 1,4‐Naphthoquinone

et al. 2020

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1,4-Naphthoquinone (1,4-NQ) is an important product of naphthalene oxidation, and it appears as a motif in many biologically active compounds. We have investigated the structure of 1,4-NQ using chirped-pulse Fourier transform microwave spectroscopy and quantum chemistry calculations. The rotational spectra of the parent species, and its 13 C and 18 O isotopologues were observed in natural abundance, and their spectroscopic parameters were obtained. This allowed the determination of the substitution r s , mass-weighted r m and semi-experimental r e SE structures of 1,4-NQ. The obtained structural parameters show that the quinone moiety mainly changes the structure of the benzene ring where it is inserted, modifying the CÀ C bonds to having predominantly single or double bond character. Furthermore, the molecular electrostatic surface potential reveals that the quinone ring becomes electron deficient while the benzene ring remains a nucleophile. The most electrophilic areas are the hydrogens attached to the double bond in the quinone ring. Knowledge of the nucleophilic and electrophilic areas in 1,4-NQ will help understanding its behaviour interacting with other molecules and guide modifications to tune its properties.

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“…As an example, we shall mention a series of antitumor antibi otics, as well as the commonly used analgetic paraceta mol, whose main metabolite is highly toxic N acetyl 1,4 benzoquinone monoimine [1]. One of the main causes of the toxicity of quinone compounds is their capability of reacting with the S-H groups of sulfur containing biosubstances (cysteine, glutathione, and other compounds acting as bioantioxidants [2]), which results in their irreversible binding ("desulfurization" of body), giving rise to serious diseases [3][4][5][6][7][8][9]. For this rea son, the reactions of quinone compounds with thiols attract biochemists' interest.…”

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Mechanism of the reaction between N,N′-diphenyl-1,4-benzoquinone diimine and thiophenol in n-propanol

2015

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We studied the kinetics of the reaction between N,N' diphenyl 1,4 benzoquinone diimine and thiophenol in n propanol at 343 K and compared the results with the same data for the chlorobenzene medium. The replacement of chlorobenzene with n propyl alcohol increases the reaction rate by one order of magnitude. The order of the reaction with respect to thiophenol was determined to be 1.0 in both solvents, and the order of the reaction with respect to quinone diimine decreases from 1.5 to 1.2 on passing from chlo robenzene to n propanol. In contrast to the reaction in chlorobenzene, where the radical chain mechanism is realized, the reaction in n propanol simultaneously proceeds via a radical chain channel and a heterolytic channel. In the absence of an initiator and at equal reactant concentrations of ~10 -4 mol/L, the reaction rates in both pathways are commensurable. The chain reaction is characterized by short chains whose length is a few units. Chain generation in the absence of an initiator occurs by the direct bimolecular reaction between the reactants, whose rate constant in n propanol is one order of magnitude higher than that in chloroben zene, which is explained by the high polarity of the transition state in this endothermic homolytic reaction. The reaction mechanism was proposed, and, for this mechanism, the rate constants of elementary steps were determined.

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Polycyclic Aromatic Hydrocarbon Quinones as Redox and Electrophilic Chemicals Contaminated in the Atmosphere

Cited by 18 publications

References 28 publications

Chemical toxicology of reactive species in the atmosphere: two decades of progress in an electron acceptor and an electrophile

Chemical toxicology of reactive species in the atmosphere: two decades of progress in an electron acceptor and an electrophile

Structural Changes Induced by Quinones: High‐Resolution Microwave Study of 1,4‐Naphthoquinone

Mechanism of the reaction between N,N′-diphenyl-1,4-benzoquinone diimine and thiophenol in n-propanol

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