Racemic warfarin

Manufactured by Merck Group

Sourced in United States, Germany

Racemic warfarin is a chemical compound used as a laboratory standard for analytical testing and research purposes. It serves as a reference material for the identification and quantification of warfarin in various samples.

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Warfarin (83 citations)

20 protocols using racemic warfarin

Analytical Evaluation of Mycotoxins

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Beauvericin (BEA) was purchased from Cfm Oskar Tropitzsch GmbH (Marktredwitz, Germany). Cyclopiazonic acid (CPA), sterigmatocystin (STC), human serum albumin (HSA), racemic warfarin, racemic naproxen, and S-camptothecin were obtained from Merck (Darmstadt, Germany). Other reagents applied were of analytical or HPLC grade.

Fliszár-Nyúl E., Faisal Z., Skaper R., Lemli B., Bayartsetseg B., Hetényi C., Gömbös P., Szabó A, & Poór M. (2022). Interaction of the Emerging Mycotoxins Beauvericin, Cyclopiazonic Acid, and Sterigmatocystin with Human Serum Albumin. Biomolecules, 12(8), 1106.

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Warfarin Binding in Physiological Buffer

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Racemic warfarin, bilirubin, biliverdin, hemin, and human serum albumin (Product No.: A1653) were purchased from Merck (Darmstadt, Germany). Methyl orange was from Reanal (Budapest, Hungary), while HPLC-grade acetonitrile and methanol were obtained from VWR (Budapest, Hungary). To mimic extracellular physiological conditions, measurements were performed in phosphate-buffered saline (PBS, pH 7.4).

Lemli B., Lomozová Z., Huber T., Lukács A, & Poór M. (2022). Effects of Heme Site (FA1) Ligands Bilirubin, Biliverdin, Hemin, and Methyl Orange on the Albumin Binding of Site I Marker Warfarin: Complex Allosteric Interactions. International Journal of Molecular Sciences, 23(22), 14007.

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Enzymatic Inhibitor Binding Kinetics

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All reagents were analytical or HPLC grade. Inhibitors MI-432, MI-463, MI-482 and MI-1900 were synthesized as it has been reported [21] (link). Human serum albumin (HSA), racemic warfarin, CypExpress™ 3A4 Cytochrome P450 human kit, testosterone, 6β-hydroxytestosterone and ketoconazole were purchased from Merck (Darmstadt, Germany). To mimic extracellular physiological conditions, fluorescence spectroscopic measurements were performed in phosphate-buffered saline (PBS; 8.00 g/L NaCl, 0.20 g/L KCl, 1.81 g/L Na₂HPO₄ x 2 H₂O, 0.24 g/L KH₂PO₄; pH 7.4).

Pászti-Gere E., Szentkirályi A., Fedor Z., Nagy G., Szimrók Z., Pászti Z., Pászti A., Pilgram O., Steinmetzer T., Bodnárová S., Fliszár-Nyúl E, & Poór M. (2021). In vitro interaction of potential antiviral TMPRSS2 inhibitors with human serum albumin and cytochrome P 450 isoenzymes. Biomedicine & Pharmacotherapy, 146, 112513.

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Evaluation of Furin Inhibitor MI-1851

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The furin inhibitor MI-1851 was available from the previous studies [16] (link), its chemical structure is demonstrated in
Fig. 1. Human serum albumin (HSA), racemic warfarin, racemic naproxen, CypExpress™ 3A4 Cytochrome P450 human kit, ketoconazole, testosterone and 6β-hydroxytestosterone were purchased from Merck (Darmstadt, Germany).Fig. 1

Chemical structure of the furin inhibitor MI-1851.

Fig. 1

Pászti-Gere E., Szentkirályi-Tóth A., Szabó P., Steinmetzer T., Fliszár-Nyúl E, & Poór M. (2022). In vitro characterization of the furin inhibitor MI-1851: Albumin binding, interaction with cytochrome P450 enzymes and cytotoxicity. Biomedicine & Pharmacotherapy, 151, 113124.

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Protein-Ligand Binding Interactions Study

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Alternariol (AOH) was obtained from Cfm Oskar Tropitzsch (Marktredwitz, Germany). Racemic warfarin (WAR), naproxen (NAP), human serum albumin (HSA), bovine serum albumin (BSA), porcine serum albumin (PSA), rat serum albumin (RSA), glimepiride (GLIM), furosemide (FUR), bilirubin (BIL), phenylbutazone (PBut), indomethacin (IME), racemic ibuprofen (IBU) and S-camptothecin (CPT) were purchased from Sigma-Aldrich (Budapest, Hungary). Ethinylestradiol (EE) was purchased from Serva (Budapest, Hungary). Spectroscopic grade ethanol (96%), as well as HPLC-grade acetonitrile and methanol were obtained from VWR (Budapest, Hungary). Stock solutions of AOH (5000 μM), bilirubin (500 μM), methyl orange (2000 μM), and glimepiride (2000 μM) were prepared in spectroscopic grade dimethyl sulfoxide (DMSO; Fluka, Bucharest, Romania). Stock solutions of indomethacin and ethinylestradiol (both 2000 μM), as well as ibuprofen, furosemide, phenylbutazone, and naproxen (each 2500 μM) were prepared in ethanol (96%, spectroscopic grade). The applied amounts of organic solvents did not affect significantly the fluorescence measurements (tested in each spectroscopic model). All stock solutions were stored at −20 °C, and protected from light.

Fliszár-Nyúl E., Lemli B., Kunsági-Máté S., Dellafiora L., Dall’Asta C., Cruciani G., Pethő G, & Poór M. (2019). Interaction of Mycotoxin Alternariol with Serum Albumin. International Journal of Molecular Sciences, 20(9), 2352.

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Warfarin Drug Interaction Evaluation

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Racemic warfarin, 7-hydroxywarfarin, ketoconazole, sulfaphenazole, and piperine were purchased from Sigma Aldrich, St. Louis MO, USA. Naproxen was supplied from Hikma pharmaceuticals, Amman, Jordan. All organic solvents (acetonitrile, ethylacetate and methanol) were purchased from Fisher Scientific, Pittsburgh, PA, USA. Acetic acid was obtained from Scharlau, Spain. Phosphate buffer and potassium monobasic and dibasic were obtained from Sigma-Aldrich (St. Louis MO, USA) provided.

Zayed A., Babaresh W.M., Darweesh R.S., El-Elimat T, & Hawamdeh S.S. (2020). Piperine Alters the Pharmacokinetics and Anticoagulation of Warfarin in Rats. Journal of Experimental Pharmacology, 12, 169-179.

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Glycogen Purification and Characterization

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The HSA (essentially fatty acid free, ≥ 96% pure), Con A (type V, lyophilized powder, highly purified), glycogen (bovine liver type IX, total glucose ≥ 85 %, dry basis), racemic warfarin (purity ≥ 98%), 4-methylumbellipheryl α-D-mannopyranoside (MUM, purity ≥ 96%) and 4-methylumbellipheryl α-D-galactopyranoside (MUGA, purity ≥ 98%) were purchased from Sigma-Aldrich (St. Louis, MO, USA). Nucleosil Si-300 silica (7 μm particle diameter, 300 Å pore size) was obtained from Macherey Nagel (Duren, Germany). All other chemicals were of the purest grades available. Vivaspin 6 ultrafiltration tubes (30 kDa cutoff; Sartorius, Gottingen, Germany) were used for purification of the oxidized glycogen. All buffers and aqueous solutions were prepared using water from a Nanopure system (Barnstead, Dubuque, IA, USA). Buffers were filtered using 0.20 μm GNWP nylon membranes from Fisher Scientific (Pittsburgh, PA, USA) and were degassed by sonication under vacuum for at least 30 min prior to use.

Vargas-Badilla J., Poddar S., Azaria S., Zhang C, & Hage D.S. (2019). Optimization of Protein Entrapment in Affinity Microcolumns using Hydrazide-Activated Silica and Glycogen as a Capping Agent. Journal of chromatography. B, Analytical technologies in the biomedical and life sciences, 1121, 1-8.

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Purification and Characterization of HSA

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The polyclonal anti-HSA antibodies (goat, affinity-purified polyclonal antibodies, product 2080–01) were purchased from VWR (Radnor, PA, USA). The polyclonal anti-HSA goat serum (product A1151), protein G Sepharose 4B fast flow (recombinant protein expressed in E. coli), immunoglobulin G (IgG; goat, ≥ 95% pure), HSA (essentially fatty acid free, ≥ 96%), glycogen (from bovine liver, ≥ 85% glucose), oxalic dihydrazide (> 99%), acetohexamide (99%), glibenclamide (≥ 99%), and racemic warfarin (≥ 98%) were purchased from Sigma-Aldrich (St. Louis, MO, USA). The Nucleosil Si-300 and Si-1000 silica (7 µm, particle diameter; pore size, 300 or 1000 Å, respectively) were acquired from Macherey-Nagel (Duren, Germany). All buffers and aqueous solutions were prepared using water from a Milli-Q Advantage 10 A Water system and were filtered using 0.2 µm nylon membranes (EMD Millipore Corporation, Billerica, MA, USA).

Rodriguez E.L., Poddar S., Choksi M, & Hage D.S. (2019). Development of an On-line Immunoextraction/Entrapment System for Protein Capture and Use in Drug Binding Studies by High-Performance Affinity Chromatography. Journal of chromatography. B, Analytical technologies in the biomedical and life sciences, 1136, 121812.

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Warfarin Binding to Human Serum Albumin

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The racemic warfarin (≥ 98% pure) and HSA (Cohn fraction V, essentially fatty acid-free, ≥ 96%) were acquired from Sigma (St. Louis, MO, USA). Nucleosil Si-300 (300 Å pore size and 7 μm particle diameter) was purchased from Macherey Nagel (Dűren, Germany). The pH 7.4, 0.067 M potassium phosphate buffer was prepared using water from a Milli-Q system (EMD Millipore Sigma, Burlington, MA) and filtered using 0.22 μm GNWP nylon membrane filters acquired from Fisher Scientific (Pittsburgh, PA, USA). The reagents for the micro bicinchoninic acid (BCA) protein assay were purchased from Pierce (Rockford, IL, USA).

Iftekhar S., Li Z., Tao P., Poddar S, & Hage D.S. (2022). Analysis of the Binding of Warfarin to Glyoxal- and Methylglyoxal-Modified Human Serum Albumin by Ultrafast Affinity Extraction. Journal of chromatography. B, Analytical technologies in the biomedical and life sciences, 1211, 123500.

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Binding Affinity of Chrysin Metabolites

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Chrysin, racemic warfarin, naproxen, ochratoxin A, human serum albumin (HSA), and bovine serum albumin (BSA) were purchased from Sigma-Aldrich (Waltham, MA, USA). Chyrsin-7-sulfate (C7S) was synthetized based on a method described regarding the sulfation of baicalein [44 (link)]. Chrysin-7-glucuronide (C7G) was obtained from Carbosynth (Compton, Berkshire, UK). Chrysin and its metabolites were dissolved in dimethyl sulfoxide (DMSO; Reanal, Budapest, Hungary, spectroscopic grade), and stock solutions (2000 μM each) were stored and protected from light at −20 °C.

Mohos V., Fliszár-Nyúl E., Schilli G., Hetényi C., Lemli B., Kunsági-Máté S., Bognár B, & Poór M. (2018). Interaction of Chrysin and Its Main Conjugated Metabolites Chrysin-7-Sulfate and Chrysin-7-Glucuronide with Serum Albumin. International Journal of Molecular Sciences, 19(12), 4073.

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