Esterase-Like Activity of Human Serum Albumin II: Reaction with N-trans-Cinnamoylimidazoles

Ohta, Nobuhiro; Kurono, Yukihisa; Ikeda, Ken

doi:10.1002/jps.2600720416

Cited by 28 publications

(9 citation statements)

References 14 publications

(4 reference statements)

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“…dmd.aspetjournals.org long-and short-chain fatty acid esters (Wolfbeis and Gürakar, 1987). Among previous studies, the most relevant example of albumincatalyzed metabolism to this study is that of N-trans-cinnamoyl imidazoles (Ohta et al, 1983). It appears that this interaction involves fast acylation of albumin to form cinnamoyl albumin, followed by a slow deacylation of cinnamoyl albumin.…”

Section: Discussionmentioning

confidence: 94%

“…Considering the fact that a delamanid analog without the nitro group was not metabolized by HSA (data not shown), an electron-withdrawing nitro group of delamanid is suggested to be important for the propensity toward ring scission by albumin. Ohta et al (1983) proposed that acylation by albumin occurs at a reactive residue of the R site (Tyr-411), which corresponds to Sudlow's Site II (Sudlow et al, 1976;Ozeki et al, 1980;Salvi et al, 1997). The nucleophilic character of Tyr-411 for the esterase-like activity toward p-nitrophenyl esters suggested that nucleophilic attack by albumin on the substrate results in an acylated albumin derivative that is then deacylated by a general acid or base catalysis (Sakurai et al, 2004).…”

Section: Discussionmentioning

confidence: 99%

“…Albumin, the most abundant protein in plasma (Theodore, 1996), displays pseudo-enzymatic properties and has been found to catalyze the hydrolysis of numerous compounds, such as cinnamoyl imidazole (Ohta et al, 1983), p-nitrophenyl esters (Means and Bender, 1975;Kurono et al, 1979;Watanabe et al, 2000;Sakurai et al, 2004;Lockridge et al, 2008), olmesartan medoxomil (Ma et al, 2005), carbaryl (Sogorb et al, 2004), aspirin (Rainsford et al, 1980;Liyasova et al, 2010), organophosphate insecticides (Sultatos et al, 1984), and Fig. 8.…”

Section: Discussionmentioning

confidence: 99%

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Metabolic Mechanism of Delamanid, a New Anti-Tuberculosis Drug, in Human Plasma

et al. 2015

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The metabolism of delamanid (OPC-67683, Deltyba), a novel treatment of multidrug-resistant tuberculosis, was investigated in vitro using plasma and purified protein preparations from humans and animals. Delamanid was rapidly degraded by incubation in the plasma of all species tested at 37°C, with half-life values (hours) of 0.64 (human), 0.84 (dog), 0.87 (rabbit), 1.90 (mouse), and 3.54 (rat). A major metabolite, (R)-2-amino-4,5-dihydrooxazole derivative (M1), was formed in the plasma by cleavage of the 6-nitro-2,3-dihydroimidazo(2,1-b)oxazole moiety of delamanid. The rate of M1 formation increased with temperature (0237°C) and pH (6.028.0). Delamanid was not converted to M1 in plasma filtrate, with a molecular mass cutoff of 30 kDa, suggesting that bioconversion is mediated by plasma proteins of higher molecular weight. When delamanid was incubated in plasma protein fractions separated by gel filtration chromatography, M1 was observed in the fraction consisting of albumin, g-globulin, and a 1 -acid glycoprotein. In pure preparations of these proteins, only human serum albumin (HSA) metabolized delamanid to M1. The formation of M1 followed Michaelis-Menten kinetics in both human plasma and the HSA solution, with similar K m values: 67.8 mM in plasma and 51.5 mM in HSA. The maximum velocity and intrinsic clearance values for M1 were also comparable in plasma and HSA. These results strongly suggest that albumin is predominantly responsible for metabolizing delamanid to M1. We propose that delamanid degradation by albumin begins with a nucleophilic attack of amino acid residues on the electron-poor carbon at the 5 position of nitro-dihydroimidazooxazole, followed by cleavage of the imidazooxazole moiety to form M1.

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Section: Discussionmentioning

confidence: 94%

Section: Discussionmentioning

confidence: 99%

Section: Discussionmentioning

confidence: 99%

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Metabolic Mechanism of Delamanid, a New Anti-Tuberculosis Drug, in Human Plasma

et al. 2015

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“…Commentary: The investigators were able to unravel an interesting reaction involving metabolism of delamanid through albumin to form M1. Several reports on albumin-catalyzed reactions exist, but they mostly involve simple hydrolytic reactions such as ester hydrolysis, as is the case with N-transcinnamoylimidazoles (Ohta et al, 1983). The mechanism of formation of M1 is not straightforward, and multiple steps, which are not yet fully characterized, are assumed to be involved.…”

Section: Referencesmentioning

confidence: 99%

Biotransformation and bioactivation reactions – 2015 literature highlights

Baillie

Dalvie

Rietjens

et al. 2016

Drug Metabolism Reviews

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Since 1972, Drug Metabolism Reviews has been recognized as one of the principal resources for researchers in pharmacological, pharmaceutical and toxicological fields to keep abreast of advances in drug metabolism science in academia and the pharmaceutical industry. With a distinguished list of authors and editors, the journal covers topics ranging from relatively mature fields, such as cytochrome P450 enzymes, to a variety of emerging fields. We hope to continue this tradition with the current compendium of mini-reviews that highlight novel biotransformation processes that were published during the past year. Each review begins with a summary of the article followed by our comments on novel aspects of the research and their biological implications. This collection of highlights is not intended to be exhaustive, but rather to be illustrative of recent research that provides new insights or approaches that advance the field of drug metabolism. Abbreviations NAPQI N-acetyl-p-benzoquinoneimine ALDH aldehyde dehydrogenase AO aldehyde oxidase AKR aldo-keto reductase CES carboxylesterase CSB cystathionine β-synthase CSE cystathionine γ-lyase P450 cytochrome P450 DHPO 2,3-dihydropyridin-4-one ESI electrospray FMO flavin monooxygenase GSH glutathione GSSG glutathione disulfide ICPMS inductively coupled plasma mass spectrometry i.p. intraperitoneal MDR multidrug-resistant NNAL 4-(methylnitrosamino)-1-(3-pyridyl)-1-butanol NNK 4-(methylnitrosamino)-1-(3-pyridyl)-1-butanone oaTOF orthogonal acceleration time-of-flight PBK physiologically based kinetic PCP pentachlorophenol SDR short-chain dehydrogenase/reductase SULT sulfotransferase TB tuberculosis.

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“…One particularly interesting property of albumin is its catalytic abilities toward various organic molecules. Studies have shown that albumin can catalyze the following reactions: hydrolysis of esters (esterase-like activities: Tildon and Ogilvie, 1972;Means and Bender, 1975;Kurono et al, 1992), hydrolysis of amides (protease-like activities: Ohta et al, 1983), chiral inversion of thalidomide (Reist et al, 1998), cyanide detoxification (Jarabak and Westley, 1986), decomposition of a Meisenheimer complex (Taylor and Vatz, 1973;Taylor et al, 1975), proton transfer reaction (Kikuchi et al, 1996;Hollfelder et al, 1996), ␤-elimination (Klein and Reymond, 1998), methylation of naphthol (Cavazza and Zandomeneghi, 1993), sorbic acid-thiol reaction (Wedzicha and Zeb, 1991), stereoselective reactions such as asymmetric Weitz-Scheffer epoxidation (Colonna et al, 1987), asymmetric periodate oxidation of sulfides (Colonna et al, 1986), and Diels-Alder reactions (Colonna et al, 1988). All of the above reactions were studied under aqueous solutions.…”

Section: Introductionmentioning

confidence: 99%

Biocatalysis of isomerization of 1,2‐benzisoxazole by bovine serum albumin in an organic solvent

Liu

Lemma-Gray

2001

Biotech & Bioengineering

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The catalytic properties of bovine serum albumin (BSA) have been studied rather extensively. The protein has shown catalytic activities toward a variety of reactions in aqueous media. However, there appears to be no reports of reactions catalyzed exclusively in organic media. In this study, we report the catalytic property of BSA on the isomerization of 1,2-benzisoxazole in an organic solvent. Kinetics were performed using a continuous flow system in a spectrophotometer at 330 nm. The catalysis showed a Michaelis-Menten behavior with an estimated catalytic efficiency (k(cat)/K(M)) of 8.77 M(-1)S(-1). The influence of water content and inhibitors was also studied. The activity of BSA in acetonitrile is approximately 20% of that in water under similar conditions. Inhibition studies show that the active site may be the pyridoxal binding site involving Lys-220.

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Esterase-Like Activity of Human Serum Albumin II: Reaction with N-trans-Cinnamoylimidazoles

Cited by 28 publications

References 14 publications

Metabolic Mechanism of Delamanid, a New Anti-Tuberculosis Drug, in Human Plasma

Metabolic Mechanism of Delamanid, a New Anti-Tuberculosis Drug, in Human Plasma

Biotransformation and bioactivation reactions – 2015 literature highlights

Biocatalysis of isomerization of 1,2‐benzisoxazole by bovine serum albumin in an organic solvent

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