Effect of 2-(4-aminophenylmethyl)-6-hydroxy-3,4-dihydronaphthalen-1(2H)-one on all-transand 13-cis-retinoic acid levels in plasma quantified by high perfomance liquid chromatography coupled to tandem mass spectrometry

Angotti, Marc; Hartmann, Rolf W.; Kirby, Amanda; Simons, Claire; Nicholls, P. J.; Sewell, Robert David Edmund; Smith, H. J.

doi:10.1080/14756360400008889

Cited by 8 publications

(2 citation statements)

References 27 publications

(26 reference statements)

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“…We have recently described several classes of RAMBAs in rat liver microsomal assays, other systems (human placenta and human liver microsomes, human skin homogenates), and RA-induced cell cultures (human male genital fibroblasts and HaCat cells). − The most potent inhibitor of retinoic acid metabolism was the 2-(4-aminobenzyl)-6-hydroxytetralone (Figure ). , With this compound as a lead, a range of tetralone derivatives were prepared to probe requirements for optimal retinoic acid metabolism inhibitory activity using two in vitro assay systems: rat liver microsomes and human breast cancer MCF-7 cells expressing CYP26A1 activity.…”

Section: Introductionmentioning

confidence: 99%

“…[22][23][24] The most potent inhibitor of retinoic acid metabolism was the 2-(4-aminobenzyl)-6-hydroxytetralone (Figure 2). 24,25 With this compound as a lead, a range of tetralone derivatives were prepared to probe requirements for optimal retinoic acid metabolism inhibitory activity using two in vitro assay systems: rat liver microsomes and human breast cancer MCF-7 cells expressing CYP26A1 activity.…”

Section: Introductionmentioning

confidence: 99%

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Novel Tetralone-Derived Retinoic Acid Metabolism Blocking Agents: Synthesis and in Vitro Evaluation with Liver Microsomal and MCF-7 CYP26A1 Cell Assays

et al. 2005

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The potent inhibitory activity of novel 2-benzyltetralone and 2-benzylidenetetralone derivatives vs liver microsomal retinoic acid metabolizing enzymes and a MCF-7 CYP26A1 cell assay is described. In the liver microsomal assay, the 2-biphenylmethyl-6-hydroxytetralone derivatives 16a and 16b were found to be potent inhibitors (IC50 = 0.5 and 0.8 microM) compared with the broad spectrum P450 inhibitor ketoconazole and the retinoid mimetic R115866 (IC50 = 18.0 and 9.0 microM, respectively). In the MCF-7 CYP26A1 cell assay, the 2-(4-hydroxybenzyl)-6-methoxytetralone 5 and unsaturated benzylidene precursor 6 were found to be the most potent (IC50 = 7 and 5 microM, respectively), which was comparable with liarozole (7 microM) but considerably less active than R115866 (IC50 = 5 nM). With a CYP26A1 homology model, the tetralones were shown to be positioned in a hydrophobic tunnel with additional interactions, e.g., transition metal coordination and hydrogen-bonding interactions with GLY300, observed for the potent 4-hydroxyphenyl substituted inhibitors.

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Section: Introductionmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

Novel Tetralone-Derived Retinoic Acid Metabolism Blocking Agents: Synthesis and in Vitro Evaluation with Liver Microsomal and MCF-7 CYP26A1 Cell Assays

et al. 2005

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Isotretinoin Oxidation and Electroanalysis in a Pharmaceutical Drug Using a Boron‐doped Diamond Electrode

et al. 2016

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Isotretinoin redox behaviour, by voltammetry, at the cathodic pre‐treated boron doped diamond electrode by cyclic, differential pulse and square wave voltammetry, and by spectrophotometry in a wide pH range, was investigated. The isotretinoin oxidation was an irreversible, diffusion‐controlled process, occurred in a three‐step cascade mechanism, and the isotretinoin diffusion coefficient D13‐cis‐RA=7.35×10−6 cm2 s−1, was calculated. The UV‐Vis isotretinoin maximum absorption was pH‐dependent. The detection limits LOD=0.53 μM, by differential pulse voltammetry, and LOD=0.38 μM, by UV‐Vis spectroscopy, were obtained. The isotretinoin in the pharmaceutical drug Roacutan®, using differential pulse voltammetry, was determined.

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Current literature in mass spectrometry

2006

J. Mass Spectrom.

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In order to keep subscribers up‐to‐date with the latest developments in their field, John Wiley & Sons are providing a current awareness service in each issue of the journal. The bibliography contains newly published material in the field of mass spectrometry. Each bibliography is divided into 11 sections: 1 Books, Reviews & Symposia; 2 Instrumental Techniques & Methods; 3 Gas Phase Ion Chemistry; 4 Biology/Biochemistry: Amino Acids, Peptides & Proteins; Carbohydrates; Lipids; Nucleic Acids; 5 Pharmacology/Toxicology; 6 Natural Products; 7 Analysis of Organic Compounds; 8 Analysis of Inorganics/Organometallics; 9 Surface Analysis; 10 Environmental Analysis; 11 Elemental Analysis. Within each section, articles are listed in alphabetical order with respect to author (4 Weeks journals ‐ Search completed at 28th. Dec. 2005)

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Effect of 2-(4-aminophenylmethyl)-6-hydroxy-3,4-dihydronaphthalen-1(2H)-one on all-transand 13-cis-retinoic acid levels in plasma quantified by high perfomance liquid chromatography coupled to tandem mass spectrometry

Cited by 8 publications

References 27 publications

Novel Tetralone-Derived Retinoic Acid Metabolism Blocking Agents: Synthesis and in Vitro Evaluation with Liver Microsomal and MCF-7 CYP26A1 Cell Assays

Novel Tetralone-Derived Retinoic Acid Metabolism Blocking Agents: Synthesis and in Vitro Evaluation with Liver Microsomal and MCF-7 CYP26A1 Cell Assays

Isotretinoin Oxidation and Electroanalysis in a Pharmaceutical Drug Using a Boron‐doped Diamond Electrode

Current literature in mass spectrometry

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