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  • 1
    Article
    Article
    Sorafenib hepatobiliary disposition: mechanisms of hepatic uptake and disposition of generated metabolites
    2013
    ISSN: 0090-9556 
    Details
    Language: English
    In: Drug metabolism and disposition, 2013-06, Vol.41 (6), p.1179-1186
    Description: Sorafenib is an orally active tyrosine kinase inhibitor used in the treatment of renal and hepatocellular carcinoma. This study was designed to establish whether transport proteins are involved in the hepatic uptake of sorafenib and to determine the extent of biliary excretion of sorafenib and its metabolites in human hepatocytes. Initial uptake was assessed in freshly isolated, suspended human hepatocytes in the presence of inhibitors and modulators. [(14)C]Sorafenib (1 µM) uptake at 4°C was reduced by about 61-63% of the uptake at 37°C, suggesting a high degree of passive diffusion. Hepatocyte uptake of [(14)C]sorafenib was not Na(+) dependent or influenced by the organic anion transporter 2 inhibitor ketoprofen. However, initial [(14)C]sorafenib hepatocyte uptake was reduced by 46 and 30% compared with control values in the presence of the organic anion transporting polypeptide inhibitor rifamycin SV and the organic cation transporter (OCT) inhibitor decynium 22, respectively. [(14)C]Sorafenib (0.5-5 µM) uptake was significantly higher in hOCT1-transfected Chinese hamster ovary cells compared with mock cells, and inhibited by the general OCT inhibitor, 1-methyl-4-phenylpryidinium. OCT1-mediated uptake was saturable with a Michaelis-Menten constant of 3.80 ± 2.53 µM and a V(max) of 116 ± 42 pmol/mg/min. The biliary excretion index and in vitro biliary clearance of sorafenib (1 µM) in sandwich-cultured human hepatocytes were low (∼11% and 11 ml/min/kg, respectively). Results suggest that sorafenib uptake in human hepatocytes occurs via passive diffusion, by OCT1, and by organic anion transporting polypeptide(s). Sorafenib undergoes modest biliary excretion, predominantly as a glucuronide conjugate(s).
    Subject(s): Adult ; Animals ; Cells, Cultured ; CHO Cells ; Cricetinae ; Cricetulus ; Female ; Hepatocytes - drug effects ; Hepatocytes - metabolism ; Humans ; Male ; Middle Aged ; Niacinamide - analogs & derivatives ; Niacinamide - metabolism ; Niacinamide - pharmacology ; Phenylurea Compounds - metabolism ; Phenylurea Compounds - pharmacology ; Protein Kinase Inhibitors - metabolism ; Protein Kinase Inhibitors - pharmacology
    ISSN: 0090-9556
    E-ISSN: 1521-009X
    DOI: 10.1124/dmd.112.048181
    Source: Alma/SFX Local Collection
    URL: https://www.ncbi.nlm.nih.gov/pubmed/23482500$$D View this record in MEDLINE/PubMed
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  • 2
    Article
    Article
    Human milk oligosaccharides are minimally digested in vitro
    2000
    ISSN: 0022-3166 
    Details
    Language: English
    In: The Journal of nutrition, 2000, Vol.130 (12), p.3014-3020
    Description: In examining the functional aspects of human milk oligosaccharides (HMO), it is not known whether they are digested during the passage through the infant's gastrointestinal tract. HMO were prepared from individual milk samples (n = 6) and separated into neutral and acidic compounds by chromatography. These oligosaccharide fractions were studied for their digestibility by human salivary amylase, porcine pancreatic amylase and brush border membrane vesicles (BBMV) isolated from porcine small intestine; we also examined the effect of low pH on these structures. The characterization of HMO and their digestion products was performed by high-pH anion-exchange chromatography with pulsed amperometric detection (HPAEC-PAD) as well as TLC. It was shown that neither salivary amylase nor pancreatic amylase cleaved HMO. Only after a 2-h incubation with BBMV were slight modifications of the HMO observed. HPAEC-PAD analysis revealed two new components within the neutral oligosaccharide fractions; these were characterized by mass spectrometric analysis as lacto-N:-triose and galactose. Only lacto-N:-triose was present within digestion assays of oligosaccharides, which did not contain fucosyl or N:-acetylneuraminic acid residues. These results suggest that 〈5% of the HMO are digested in the intestinal tract. Hence, HMO may play a role as prebiotics or as factors influencing the local immune system of the intestine in breast-fed infants.
    Subject(s): Amylases - analysis ; Biological and medical sciences ; Breast milk ; Brush border membrane ; Chromatography, High Pressure Liquid ; Digestion ; Digestive system ; Digestive System - metabolism ; Enzymes ; Feces - chemistry ; Female ; Fundamental and applied biological sciences. Psychology ; Galactose - analysis ; Humans ; Hydrogen-Ion Concentration ; In Vitro Techniques ; Lactation ; Mass Spectrometry ; Metabolism ; Microvilli - metabolism ; Milk ; Milk, Human - chemistry ; Milk, Human - enzymology ; Milk, Human - metabolism ; Mother. Fetoplacental unit. Mammary gland. Milk ; Oligosaccharides ; Oligosaccharides - chemistry ; Oligosaccharides - metabolism ; Physiological aspects ; Pregnancy. Parturition. Lactation ; Research ; Time Factors ; Trisaccharides - analysis ; Urinalysis ; Vertebrates: reproduction
    ISSN: 0022-3166
    E-ISSN: 1541-6100
    DOI: 10.1093/jn/130.12.3014
    Source: Alma/SFX Local Collection
    URL: http://pascal-francis.inist.fr/vibad/index.php?action=getRecordDetail&idt=1037370$$DView record in Pascal Francis
    URL: https://www.ncbi.nlm.nih.gov/pubmed/11110861$$D View this record in MEDLINE/PubMed
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  • 3
    Article
    Article
    Inhaled Agonists of Soluble Guanylate Cyclase Induce Selective Pulmonary Vasodilation
    2007
    ISSN: 1073-449X 
    Details
    Language: English
    In: American journal of respiratory and critical care medicine, 2007-12-01, Vol.176 (11), p.1138-1145
    Description: Nitric oxide-independent agonists of soluble guanylate cyclase (sGC) have been developed. We tested whether inhalation of novel dry-powder microparticle formulations containing sGC stimulators (BAY 41-2272, BAY 41-8543) or an sGC activator (BAY 58-2667) would produce selective pulmonary vasodilation in lambs with acute pulmonary hypertension. We also evaluated the combined administration of BAY 41-8543 microparticles and inhaled nitric oxide (iNO). Finally, we examined whether inhaling BAY 58-2667 microparticles would produce pulmonary vasodilation when the response to iNO is impaired. In awake, spontaneously breathing lambs instrumented with vascular catheters and a tracheostomy tube, U-46619 was infused intravenously to increase mean pulmonary arterial pressure to 35 mm Hg. Inhalation of microparticles composed of either BAY 41-2272, BAY 41-8543, or BAY 58-2667 and excipients (dipalmitoylphosphatidylcholine, albumin, lactose) produced dose-dependent pulmonary vasodilation and increased transpulmonary cGMP release without significant effect on mean arterial pressure. Inhalation of microparticles containing BAY 41-8543 or BAY 58-2667 increased systemic arterial oxygenation. The magnitude and duration of pulmonary vasodilation induced by iNO were augmented after inhaling BAY 41-8543 microparticles. Intravenous administration of 1H-[1,2,4]oxadiazolo[4,3-a]quinoxalin-1-one (ODQ), which oxidizes the prosthetic heme group of sGC, markedly reduced the pulmonary vasodilator effect of iNO. In contrast, pulmonary vasodilation and transpulmonary cGMP release induced by inhaling BAY 58-2667 microparticles were greatly enhanced after treatment with ODQ. Inhalation of microparticles containing agonists of sGC may provide an effective novel treatment for patients with pulmonary hypertension, particularly when responsiveness to iNO is impaired by oxidation of sGC.
    Subject(s): Abridged Index Medicus ; Administration, Inhalation ; Aerosols ; Anesthesia. Intensive care medicine. Transfusions. Cell therapy and gene therapy ; Animals ; BAY 41-2272 ; BAY 41-8543 ; BAY 58-2667 ; Benzoates - administration & dosage ; Benzoates - pharmacology ; Biological and medical sciences ; Cyclic GMP - metabolism ; Dose-Response Relationship, Drug ; Drug Combinations ; Guanylate Cyclase ; H. Pulmonary Vascular Disease ; Injections, Intravenous ; Intensive care medicine ; Lung - drug effects ; Lung - metabolism ; Medical sciences ; Morpholines - administration & dosage ; Morpholines - pharmacology ; Nitric Oxide - administration & dosage ; Nitric Oxide - pharmacology ; Oxadiazoles - administration & dosage ; Oxadiazoles - pharmacology ; Particle Size ; Pharmacology. Drug treatments ; Phosphodiesterase Inhibitors - administration & dosage ; Phosphodiesterase Inhibitors - pharmacology ; Pneumology ; Powders ; Pulmonary Circulation - drug effects ; pulmonary hypertension ; Pulmonary hypertension. Acute cor pulmonale. Pulmonary embolism. Pulmonary vascular diseases ; Purinones - administration & dosage ; Purinones - pharmacology ; Pyrazoles - administration & dosage ; Pyrazoles - pharmacology ; Pyridines - administration & dosage ; Pyridines - pharmacology ; Pyrimidines - administration & dosage ; Pyrimidines - pharmacology ; Quinoxalines - administration & dosage ; Quinoxalines - pharmacology ; Receptors, Cytoplasmic and Nuclear - agonists ; Respiratory system ; Sheep ; soluble guanylate cyclase ; Soluble Guanylyl Cyclase ; Vasodilation - drug effects
    ISSN: 1073-449X
    E-ISSN: 1535-4970
    DOI: 10.1164/rccm.200707-1121OC
    Source: Elektronische Zeitschriftenbibliothek - Frei zugängliche E-Journals
    Source: ProQuest Central
    URL: http://pascal-francis.inist.fr/vibad/index.php?action=getRecordDetail&idt=19893884$$DView record in Pascal Francis
    URL: https://www.ncbi.nlm.nih.gov/pubmed/17872487$$D View this record in MEDLINE/PubMed
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  • 4
    Article
    Article
    Design and Synthesis of Potent and Selective Azaindole-Based Rho Kinase (ROCK) Inhibitors
    2008
    ISSN: 1860-7179 
    Details
    Language: English
    In: ChemMedChem, 2008-12-15, Vol.3 (12), p.1893-1904
    Description: Rho kinase plays a pivotal role in several cellular processes such as vasoregulation, making it a suitable target for the treatment of hypertension and related disorders. We discovered a new compound class of Rho kinase (ROCK) inhibitors containing a 7‐azaindole hinge‐binding scaffold tethered to an aminopyrimidine core. Herein we describe the structure–activity relationships elucidated through biochemical and functional assays. The introduction of suitable substituents at the 3‐position of the bicyclic moiety led to an increase in activity, which was required to design compounds with favorable pharmacokinetic profile. Azaindole 32 was identified as a highly selective and orally available ROCK inhibitor able to cause a sustained blood pressure reduction in vivo. A new compound class of Rho kinase (ROCK) inhibitors containing a 7‐azaindole hinge‐binding moiety was discovered. The introduction of substituents at the 3‐position of the bicyclic ring system led to a significant increase in activity and permitted the design of compounds with a favorable pharmacokinetic profile. The ROCK inhibitors are orally bioavailable and mediate a sustained blood pressure lowering effect in vivo.
    Subject(s): 7-azaindole ; Animals ; Drug Design ; Enzyme Inhibitors - chemical synthesis ; Enzyme Inhibitors - chemistry ; Enzyme Inhibitors - pharmacology ; Indoles - chemical synthesis ; Indoles - chemistry ; Indoles - pharmacology ; inhibitors ; Inhibitory Concentration 50 ; Models, Molecular ; Pyrimidines - chemical synthesis ; Pyrimidines - chemistry ; Pyrimidines - pharmacology ; Rats ; Rats, Wistar ; Rho kinase ; rho-Associated Kinases - antagonists & inhibitors ; rho-Associated Kinases - pharmacology ; Structure-Activity Relationship ; structure-activity relationships ; vasorelaxation
    ISSN: 1860-7179
    E-ISSN: 1860-7187
    DOI: 10.1002/cmdc.200800211
    Source: Get It Now
    Source: Wiley-Blackwell Full Collection 2014
    URL: https://www.ncbi.nlm.nih.gov/pubmed/18973168$$D View this record in MEDLINE/PubMed
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  • 5
    Article
    Article
    Investigations of the in Vitro Transport of Human Milk Oligosaccharides by a Caco-2 Monolayer Using a Novel High Performance Liquid Chromatography-Mass Spectrometry Technique
    2001
    ISSN: 0021-9258 
    Details
    Language: English
    In: The Journal of biological chemistry, 2001-09-14, Vol.276 (37), p.34363-34370
    Description: Complex lactose-derived oligosaccharides belong to the main components of human milk and are believed to exert multiple functions in the breast-fed infant. Therefore, we investigated the transepithelial transport of human milk oligosaccharides over Caco-2 monolayers. Main human milk oligosaccharides (HMOs) in the apical, basolateral, or intracellular compartment were separated by high performance liquid chromatography using a HypercarbTM column and analyzed on line by mass spectrometry. This method allowed the identification and quantification of these components in intra- and extracellular fractions without prior purification. Using this technique we were able to show that acidic and neutral HMOs cross the epithelial barrier. The transepithelial flux of neutral, but not acidic, oligosaccharides was temperature-sensitive and partly inhibited by brefeldin A and bafilomycin A. Furthermore, net flux from the apical to the basolateral compartment was only observed for the neutral components. Similarly, apical cellular uptake was only found for neutral components but not for acidic oligosaccharides. Intracellular concentrations of neutral HMOs were significantly increased by inhibitors of transcytosis such as brefeldin A,N-ethylmaleimide, or bafilomycin A. The cellular uptake was saturable, and an apparent Km for lacto-N-fucopentaose I of 1.7 ± 0.1 mmol/liter and for lacto-N-tetraose of 1.8 ± 0.4 mmol/liter was determined. Furthermore, the uptake of lacto-N-fucopentaose I could be inhibited by the addition of the stereoisomer lacto-N-fucopentaose II but not by lacto-N-tetraose. These findings suggest that neutral HMOs are transported across the intestinal epithelium by receptor-mediated transcytosis as well as via paracellular pathways, whereas translocation of acidic HMOs solely represents paracellular flux.
    Subject(s): Biological Transport ; Caco-2 Cells ; Chromatography, High Pressure Liquid ; Humans ; Intestinal Mucosa - metabolism ; Mass Spectrometry ; Milk, Human - chemistry ; Oligosaccharides - analysis ; Oligosaccharides - metabolism
    ISSN: 0021-9258
    E-ISSN: 1083-351X
    DOI: 10.1074/jbc.M104805200
    Source: HighWire Press (Free Journals)
    Source: Alma/SFX Local Collection
    URL: https://www.ncbi.nlm.nih.gov/pubmed/11423546$$D View this record in MEDLINE/PubMed
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  • 6
    Article
    Article
    In Vitro to In Vivo Comparison of the Substrate Characteristics of Sorafenib Tosylate toward P-Glycoprotein
    2010
    ISSN: 0090-9556 
    Details
    Language: English
    In: Drug metabolism and disposition, 2010, Vol.38 (8), p.1341-1346
    Description: Sorafenib (Nexavar) is a novel oral Raf kinase and vascular endothelial growth factor receptor inhibitor. Most anticancer drugs are substrates for ATP-binding cassette efflux pumps especially for P-glycoprotein (P-gp). To evaluate the influence of P-gp on the pharmacokinetics of sorafenib substrate properties for this transporter were investigated. Therefore, permeability of sorafenib across Caco-2 and P-gp-overexpressing cells was determined. To determine the in vivo relevance of these in vitro findings, pharmacokinetics of sorafenib in mdr1a/1b(-/-) and wild-type (WT) mice was studied. Sorafenib is highly permeable and exhibits a slight efflux across Caco-2 cells. In P-gp-overexpressing cells, a small concentration-dependent efflux was observed, which was completely blocked by the addition of ivermectin. In mdr1a/1b(-/-) and WT mice, unchanged compound represented by far the majority of radioactivity in plasma. After intravenous and oral administration, brain/plasma concentration ratios in mdr1a/1b(-/-) mice were 1.3- to 1.5-fold higher than those in WT mice. However, after intravenous or oral administration, plasma concentrations were similar in both mouse strains. In conclusion, sorafenib is highly permeable and a weak P-gp substrate in vitro. These findings were confirmed by the small factor of 1.3 to 1.5 observed for the brain/plasma ratios in mdr1a/1b(-/-) versus WT mice in vivo. Based on these in vitro and in vivo results, it is unlikely that P-gp has a major effect on the plasma concentrations of sorafenib in humans. Because of the high permeability and low P-gp-mediated transport, sorafenib might be able to cross the blood-brain barrier and target tumors within the brain.
    Subject(s): Animals ; Anti-Arrhythmia Agents - metabolism ; Anti-Arrhythmia Agents - pharmacokinetics ; ATP-Binding Cassette, Sub-Family B, Member 1 - metabolism ; ATP-Binding Cassette, Sub-Family B, Member 1 - pharmacokinetics ; Benzenesulfonates - blood ; Benzenesulfonates - metabolism ; Benzenesulfonates - pharmacokinetics ; Biological and medical sciences ; Brain - metabolism ; Caco-2 Cells ; Digoxin - metabolism ; Digoxin - pharmacokinetics ; Humans ; LLC-PK1 Cells ; Male ; Medical sciences ; Mice ; Mice, Knockout ; Niacinamide - analogs & derivatives ; Permeability ; Pharmacology. Drug treatments ; Phenylurea Compounds ; Protein Kinase Inhibitors - blood ; Protein Kinase Inhibitors - metabolism ; Protein Kinase Inhibitors - pharmacokinetics ; Pyridines - blood ; Pyridines - metabolism ; Pyridines - pharmacokinetics ; Swine
    ISSN: 0090-9556
    E-ISSN: 1521-009X
    DOI: 10.1124/dmd.110.032052
    Source: Alma/SFX Local Collection
    URL: http://pascal-francis.inist.fr/vibad/index.php?action=getRecordDetail&idt=23060533$$DView record in Pascal Francis
    URL: https://www.ncbi.nlm.nih.gov/pubmed/20413726$$D View this record in MEDLINE/PubMed
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  • 7
    Article
    Article
    Cover Picture: Design and Synthesis of Potent and Selective Azaindole-Based Rho Kinase (ROCK) Inhibitors (ChemMedChem 12/2008)
    2008
    ISSN: 1860-7179 
    Details
    Language: English
    In: ChemMedChem, 2008-12-15, Vol.3 (12), p.1797-1797
    Subject(s): 7-azaindole ; inhibitors ; Rho kinase ; structure-activity relationships ; vasorelaxation
    ISSN: 1860-7179
    E-ISSN: 1860-7187
    DOI: 10.1002/cmdc.200890046
    Source: Get It Now
    Source: Wiley-Blackwell Full Collection 2014
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  • 8
    Article
    Article
    Soluble guanylate cyclase activator reverses acute pulmonary hypertension and augments the pulmonary vasodilator response to inhaled nitric oxide in awake lambs
    2004
    ISSN: 0009-7322 
    Details
    Language: English
    In: Circulation (New York, N.Y.), 2004, Vol.110 (15), p.2253-2259
    Description: Inhaled nitric oxide (NO) is a potent and selective pulmonary vasodilator, which induces cGMP synthesis by activating soluble guanylate cyclase (sGC) in ventilated lung regions. Carbon monoxide (CO) has also been proposed to influence smooth muscle tone via activation of sGC. We examined whether direct stimulation of sGC by BAY 41-2272 would produce pulmonary vasodilation and augment the pulmonary responses to inhaled NO or CO. In awake, instrumented lambs, the thromboxane analogue U-46619 was intravenously administered to increase mean pulmonary arterial pressure to 35 mm Hg. Intravenous infusion of BAY 41-2272 (0.03, 0.1, and 0.3 mg x kg(-1) x h(-1)) reduced mean pulmonary arterial pressure and pulmonary vascular resistance and increased transpulmonary cGMP release in a dose-dependent manner. Larger doses of BAY 41-2272 also produced systemic vasodilation and elevated the cardiac index. N(omega)-nitro-l-arginine methyl ester abolished the systemic but not the pulmonary vasodilator effects of BAY 41-2272. Furthermore, infusing BAY 41-2272 at 0.1 mg x kg(-1) x h(-1) potentiated and prolonged the pulmonary vasodilation induced by inhaled NO (2, 10, and 20 ppm). In contrast, inhaled CO (50, 250, and 500 ppm) had no effect on U-46619-induced pulmonary vasoconstriction before or during administration of BAY 41-2272. In lambs with acute pulmonary hypertension, BAY 41-2272 is a potent pulmonary vasodilator that augments and prolongs the pulmonary vasodilator response to inhaled NO. Direct pharmacological stimulation of sGC, either alone or in combination with inhaled NO, may provide a novel approach for the treatment of pulmonary hypertension.
    Subject(s): 15-Hydroxy-11 alpha,9 alpha-(epoxymethano)prosta-5,13-dienoic Acid - toxicity ; Administration, Inhalation ; Animals ; Biological and medical sciences ; Blood and lymphatic vessels ; Blood Pressure - drug effects ; Calcium-Binding Proteins - agonists ; Calcium-Binding Proteins - physiology ; Carbon Dioxide - blood ; Carbon Monoxide - pharmacology ; Cardiology. Vascular system ; Coronary heart disease ; Cyclic GMP - biosynthesis ; Cyclic GMP - secretion ; Diseases of the peripheral vessels. Diseases of the vena cava. Miscellaneous ; Drug Evaluation, Preclinical ; Drug Interactions ; Guanylate Cyclase-Activating Proteins ; Heart ; Hypertension, Pulmonary - chemically induced ; Hypertension, Pulmonary - drug therapy ; Hypertension, Pulmonary - physiopathology ; Infusions, Intravenous ; Medical sciences ; NG-Nitroarginine Methyl Ester - administration & dosage ; NG-Nitroarginine Methyl Ester - pharmacology ; Nitric Oxide - administration & dosage ; Nitric Oxide - pharmacology ; Nitric Oxide - therapeutic use ; Oxygen - blood ; Pneumology ; Pulmonary Artery ; Pulmonary hypertension. Acute cor pulmonale. Pulmonary embolism. Pulmonary vascular diseases ; Pyrazoles - administration & dosage ; Pyrazoles - pharmacology ; Pyrazoles - therapeutic use ; Pyridines - administration & dosage ; Pyridines - pharmacology ; Pyridines - therapeutic use ; Sheep ; Vascular Resistance - drug effects ; Vasodilator Agents - administration & dosage ; Vasodilator Agents - pharmacology ; Vasodilator Agents - therapeutic use ; Wakefulness
    ISSN: 0009-7322
    E-ISSN: 1524-4539
    DOI: 10.1161/01.CIR.0000144469.01521.8A
    Source: Hellenic Academic Libraries Link
    Source: American Heart Association Journals
    Source: Elektronische Zeitschriftenbibliothek - Frei zugängliche E-Journals
    Source: Alma/SFX Local Collection
    URL: http://pascal-francis.inist.fr/vibad/index.php?action=getRecordDetail&idt=16548944$$DView record in Pascal Francis
    URL: https://www.ncbi.nlm.nih.gov/pubmed/15466650$$D View this record in MEDLINE/PubMed
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  • 9
    Article
    Article
    Soluble guanylate cyclase stimulator attenuates acute pulmonary hypertension and augments the pulmonary vasodilator response to inhaled nitric oxide in awake lambs
    2005
    ISSN: 1471-2210 
    Details
    Language: English
    In: BMC pharmacology, 2005-06-16, Vol.5 (S1), p.S28-S28
    ISSN: 1471-2210
    E-ISSN: 1471-2210
    DOI: 10.1186/1471-2210-5-S1-S28
    Source: PubMed Central
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