Predicted multiple selected reaction monitoring to screen activated drug-mediated modifications on human serum albumin

Osaki, Fumio; Goto, Takaaki; Lee, Seon Hwa; Oe, Tomoyuki

doi:10.1016/j.ab.2013.12.016

Cited by 14 publications

(9 citation statements)

References 36 publications

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“…Moreover, a glucuronide acyl modification of different lysine residues of albumin was reported for diclofenac, ketoprofen, and acetaminophen. 54,55 In vitro prediction of an SNIUAA reaction on this basis is not yet feasible. …”

Section: Pathogenesismentioning

confidence: 99%

Approaches to the diagnosis and management of patients with a history of nonsteroidal anti-inflammatory drug–related urticaria and angioedema

Kowalski

Woessner

Sanak

2015

Journal of Allergy and Clinical Immunology

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Nonsteroidal anti-inflammatory drug (NSAID)-induced urticarial and angioedema reactions are among the most commonly encountered drug hypersensitivity reactions in clinical practice. Three major clinical phenotypes of NSAID-induced acute skin reactions manifesting with angioedema, urticaria, or both have been distinguished: NSAID-exacerbated cutaneous disease, nonsteroidal anti-inflammatory drug-induced urticaria/angioedema (NIUA), and single NSAID-induced urticaria and angioedema. In some patients clinical history alone might be sufficient to establish the diagnosis of a specific type of NSAID hypersensitivity, whereas in other cases oral provocation challenges are necessary to confirm the diagnosis. Moreover, classification of the type of cutaneous reaction is critical for proper management. For example, in patients with single NSAID-induced reactions, chemically nonrelated COX-1 inhibitors can be safely used. However, there is cross-reactivity between the NSAIDs in patients with NSAID-exacerbated cutaneous disease and NIUA, and thus only use of selective COX-2 inhibitors can replace the culprit drug if the chronic treatment is necessary, although aspirin desensitization will allow for chronic treatment with NSAIDs in some patients with NIUA. In this review we present a practical clinical approach to the patient with NSAID-induced urticaria and angioedema.

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Section: Pathogenesismentioning

confidence: 99%

Approaches to the diagnosis and management of patients with a history of nonsteroidal anti-inflammatory drug–related urticaria and angioedema

Kowalski

Woessner

Sanak

2015

Journal of Allergy and Clinical Immunology

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“…Quite a lot of information concerning molecular details of donor–acceptor pair can be had from non‐radiation energy transfer . Fluorescence resonance energy transfer (FRET) occurs when the emission spectrum of the donor overlaps the absorption spectrum of the acceptor.…”

Section: Resultsmentioning

confidence: 99%

“…Generally, the maximum distance is in the range of 1–10 nm. According to Fröster non‐radiation energy , energy transfer is related not only to the distance between the acceptor and donor, but also to the critical energy transfer distance (R 0 ) as follows:

normalE = {normalR}_{0}^{6} true/ ((), {normalR}_{0}^{6} + r^{6})

where R 0 is the critical transfer distance when the transfer efficiency is 50%, and r is the mean distance between the centers of the donor and acceptor diploes. Here the donor and acceptor are HSA (or BSA) and DiAmsar, respectively.…”

Section: Resultsmentioning

confidence: 99%

“…The most outstanding function of serum albumins is that they serve as depot proteins and transport proteins for many exogenous compounds . Serum albumins comprise three homologous helical domains (I–III), which are divided into A and B subdomains . These subdomains can accommodate various compounds, such as a large number of ligands .…”

Section: Introductionmentioning

confidence: 99%

“…Both HSA and BSA display approximately 80% sequence homology and a repeating pattern of disulfides. HSA only has one tryptophan (Trp 214) in subdomain IIA, whereas BSA has two tryptophan moieties (Trp 135 and Trp 214), located in subdomains IA and IIA, respectively . Many reports have shown that the intrinsic fluorescence of HSA and BSA appears at 350 and 345 nm, respectively, when excited at 295 nm.…”

Section: Introductionmentioning

confidence: 99%

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Investigations on the interactions of DiAmsar with serum albumins: Insights from spectroscopic and molecular docking techniques

et al. 2014

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Diamine-sarcophagine (DiAmsar) binding to human serum albumin (HSA) and bovine serum albumin (BSA) was investigated under simulative physiological conditions. Fluorescence spectra in combination with Fourier transform infrared (FT-IR), UV-visible (UV-vis) spectroscopy, cyclic voltammetry (CV), and molecular docking method were used in the present work. Experimental results revealed that DiAmsar had an ability to quench the HSA and BSA intrinsic fluorescence through a static quenching mechanism. The Stern-Volmer quenching rate constant (Ksv ) was calculated as 0.372 × 10(3) M(-1) and 0.640 × 10(3) M(-1) for HSA and BSA, respectively. Moreover, binding constants (Ka ), number of binding sites (n) at different temperatures, binding distance (r), and thermodynamic parameters (∆H°, ∆S°, and ∆G°) between DiAmsar and HSA (or BSA) were calculated. DiAmsar exhibited good binding propensity to HSA and BSA with relatively high binding constant values. The positive ∆H° and ∆S° values indicated that the hydrophobic interaction is main force in the binding of the DiAmsar to HSA (or BSA). Furthermore, molecular docking results revealed the possible binding site and the microenvironment around the bond.

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A hemoglobin adduct as a biomarker for the internal exposure to the rodent carcinogen furfuryl alcohol

et al. 2017

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Furfuryl alcohol is a common food contaminant, which is formed by acid- and heat-catalyzed degradation of fructose and glucose. Its carcinogenic effect in rodents originates most likely from sulfotransferase (SULT)-catalyzed conversion into the mutagenic sulfate ester 2-sulfoxymethylfuran. In this study, a protein adduct biomarker was sought for the medium-term internal exposure to furfuryl alcohol. A UPLC-MS/MS screening showed that the adduct N-((furan-2-yl)methyl)-Val (FFA-Val) at the N-terminus of hemoglobin is a valid target analyte. The Val cleavage by fluorescein isothiocyanate-mediated Edman degradation yielded 3-fluorescein-1-(furan-2-ylmethyl)-5-(propan-2-yl)-2-thioxoimidazolidin-4-one (FFA-Val-FTH), which was characterized by H andC NMR spectroscopy. An isotope-dilution method for the quantification of FFA-Val-FTH by UPLC-MS/MS was developed. It was used to study the adduct formation in furfuryl alcohol-treated FVB/N mice and the influence of ethanol and the alcohol dehydrogenase (ADH) inhibitor 4-methylpyrazole on the adduct levels. The administration of 400 mg/kg body weight furfuryl alcohol alone led to 12.5 and 36.7 pmol FFA-Val/g Hb in blood samples of male and female animals, respectively. The co-administration of 1.6 g ethanol/kg body weight increased FFA-Val levels by 1.4-fold in males and by 1.5-fold in females. The co-administration of 100 mg 4-methylpyrazole/kg body weight had a similar effect on the adduct levels. A high correlation was observed between adduct levels in hemoglobin and in hepatic DNA samples determined in the same animal experiment. This indicated that FFA-Val is a valid biomarker for the internal exposure to 2-sulfoxymethylfuran, which may be suitable to monitor furfuryl alcohol exposure also in humans.

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Predicted multiple selected reaction monitoring to screen activated drug-mediated modifications on human serum albumin

Cited by 14 publications

References 36 publications

Approaches to the diagnosis and management of patients with a history of nonsteroidal anti-inflammatory drug–related urticaria and angioedema

Approaches to the diagnosis and management of patients with a history of nonsteroidal anti-inflammatory drug–related urticaria and angioedema

Investigations on the interactions of DiAmsar with serum albumins: Insights from spectroscopic and molecular docking techniques

A hemoglobin adduct as a biomarker for the internal exposure to the rodent carcinogen furfuryl alcohol

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