Hydroperoxynaphthalimide Derivative‐mediated Oxidation of Heme Proteins on Photoirradiation: Horseradish Peroxidase

Yamamoto, Takahiro; Maeda, Yasushi; Matsugo, Seiichi; Kitano, Hiromi

doi:10.1111/j.1751-1097.1997.tb03139.x

Cited by 3 publications

(3 citation statements)

References 31 publications

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“…The photochemical mechanisms of damage by hydroperoxy-substituted naphthalene diimides have been explored using laser flash photolysis . Toward developing protein probes, the oxidation of the heme protein, horseradish peroxidase, mediated by UV excitation of these hydroperoxy-substituted naphthalimides, has also been demonstrated . From product analysis studies, tryptophan oxidation was observed, along with inhibition of horseradish peroxidase activity.…”

Section: Introductionmentioning

confidence: 99%

Reactivities of Carboxyalkyl-Substituted 1,4,5,8-Naphthalene Diimides in Aqueous Solution

et al. 2004

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A series of water-soluble 1,4,5,8-naphthalene diimide derivatives has been prepared and their redox and photophysical properties characterized. From laser flash photolysis studies, the triplet excited state of N,N'-bis[2-(N-pyridinium)ethyl]-1,4,5,8-naphthalene diimide (NDI-pyr) was found to undergo oxidative quenching with the electron donors DABCO, tyrosine, and tryptophan as expected from thermodynamics. Interestingly, the reactivities of naphthalene diimides (NDI) possessing alpha- and beta-carboxylic acid substituents (R = -CH2COO-, -C(CH3)2COO-, and -CH2CH2COO-) were strikingly different. In these compounds, the transient produced upon 355 nm excitation did not react with the electron donors. Instead, this transient reacted rapidly (k > 10(8)-10(9) M-1 s-1) with known electron acceptors, benzyl viologen and ferricyanide. The transient spectrum of the carboxyalkyl-substituted naphthalimides observed immediately after the laser pulse was nearly identical to the one-electron-reduced form of 1,4,5,8-naphthalene diimide (produced independently using the bis-pyridinium-substituted naphthaldiimide). From our studies, we conclude that the transient produced upon nanosecond laser flash photolysis of NDI-(CH2)nCOO- is the species produced upon intramolecular electron transfer from the carboxylate moiety to the singlet excited state of NDI. In separate experiments, we verified that the singlet excited state of NDI-pyr does, indeed, react intermolecularly with acetate, alanine, and glycine. The process is further substantiated using thermodynamic driving force calculations. The results offer new prospects of the efficient photochemical production of reactive carbon-centered radicals.

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Section: Introductionmentioning

confidence: 99%

Reactivities of Carboxyalkyl-Substituted 1,4,5,8-Naphthalene Diimides in Aqueous Solution

et al. 2004

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“…Upon photoexcitation, peptide chain cleavage was observed. The heme group was destroyed, and the formation of N -formylkynurenine following tryptophan oxidation was attributed to the photochemical formation of hydroxyl radical …”

Section: Introductionmentioning

confidence: 99%

“…The heme group was destroyed, and the formation of N-formylkynurenine following tryptophan oxidation was attributed to the photochemical formation of hydroxyl radical. 30 In this paper, we report the synthesis and characterization of three novel, water-soluble 1,8-naphthalimide compounds. The ground-and excited-state interactions of these compounds with amino acids and native proteins have been characterized to elucidate the mechanisms and targets for oxidative damage.…”

Section: Introductionmentioning

confidence: 99%

Photooxidation of Amino Acids and Proteins Mediated by Novel 1,8-Naphthalimide Derivatives

Abraham

Kelly

2003

J. Phys. Chem. B

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The ground- and excited-state interactions of N-(2-ethanoic acid)-1,8-naphthalimide (NI-ala), along with tryptophan and tyrosine-substituted 1,8-naphthalimide derivatives (NI-trp and NI-tyr), with amino acids and native proteins have been studied in aqueous buffered solution. The singlet excited state of NI-ala reacts with the aromatic amino acids, tryptophan, tyrosine, and histidine with a rate constant at or exceeding the diffusion-controlled limit. Reactivity with bovine serum albumin (BSA) and lysozyme was also demonstrated. However, in all cases, no long-lived redox products were observed from the singlet state quenching. The reactivity of the triplet excited state of NI-ala with the individual amino acids and proteins was studied using laser flash photolysis. Triplet-state reactivity was demonstrated with tryptophan and tyrosine, along with BSA and lysozyme proteins. In the case of tryptophan, tyrosine, and lysozyme, long-lived redox products were observed and quantified. Neutral tryptophan and tyrosyl radicals were observed by transient spectroscopy as quenching products. Upon photolysis of all three 1,8-naphthalimide derivatives, both cleavage and cross-linking of the lysozyme are observed. These studies have identified the potential oxidative targets in native proteins and demonstrated the utility of our naphthalimide derivatives to photomodify native proteins.

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Influence of the alkyl chain length on the fluorescence properties of N-alkyl-2,3-naphthalimides included in β-cyclodextrin

Ferreira¹,

Lemos²,

Wintgens³

et al. 1999

Spectrochimica Acta Part A: Molecular and Biomolecular Spectros

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Hydroperoxynaphthalimide Derivative‐mediated Oxidation of Heme Proteins on Photoirradiation: Horseradish Peroxidase

Cited by 3 publications

References 31 publications

Reactivities of Carboxyalkyl-Substituted 1,4,5,8-Naphthalene Diimides in Aqueous Solution

Reactivities of Carboxyalkyl-Substituted 1,4,5,8-Naphthalene Diimides in Aqueous Solution

Photooxidation of Amino Acids and Proteins Mediated by Novel 1,8-Naphthalimide Derivatives

Influence of the alkyl chain length on the fluorescence properties of N-alkyl-2,3-naphthalimides included in β-cyclodextrin

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