Synthesis and disposition of 14C-labelled gentian violet in F344 rats and B6C3F1 mice

McDonald, Jerome J.; North, Betty M.; Breeden, Cloyd R.; Lai, Ching-Cheng; Roth, Robert W.

doi:10.1016/0278-6915(84)90360-0

Cited by 5 publications

(22 citation statements)

References 10 publications

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“…Appropriate portions were pooled, concentrated, and recrystal- lized from ethyl acetate and hexane to give 1.44 g (88%) of pure LMG (mp 86-88 °C) as a beige-colored solid. The UV, MS, 1 H and 13 C NMR data of this sample match those of standard (see Tables 1 and 2).…”

Section: Methodssupporting

confidence: 62%

“…The residue was purified by column chromatography on silica using a 9:1 ratio of chloroform:methanol, which afforded 1.94 g of MG (53%) as a dark green residue. The UV, MS, 1 H and 13 C NMR data of this sample match those of the standard (see Tables 1-3).…”

Section: Methodssupporting

confidence: 55%

“…THF was distilled fresh from sodium/benzophenone prior to use. 13 C-labeled benzaldehyde was purchased from Isotec (Miamisburg, OH). All reagents and solvents were purchased from Aldrich, Inc. (Milwaukee, WI).…”

Section: Methodsmentioning

confidence: 99%

“…HRMS were obtained in the University of Illinois Mass Spectrometry Laboratory, School of Chemical Science, Urbana-Champaign, IL. 1 H and 13 C NMR spectra were recorded on a Bruker AM500 spectrometer operating at 500 and 126 MHz, respectively. Chemical shifts are expressed in ppm with respect to the internal standard tetramethylsilane.…”

Section: Methodsmentioning

confidence: 99%

“…1 H NMR (DMSO-d6): δ 2.83 (s, 12 H, 2 -N(CH3)2), 5.87 (s, 1H, D2O exchangeable OH), 6.60 (d, 4H, H3,5,3′,5′, J ) 8.9 Hz), 6.96 (d, 4H, H2,6,2′,6′, J ) 8.9 Hz), 7.15 (m, 1H, H4′′), 7.18 (m, 2H, H3′′,5′′), 7.25 (m, 2H, H2′′,6′′). 13 C NMR (DMSO-d6): δ 42.84 (-N(CH3)2), 82.52 (C7), 113.93 (C3,5,3′,5′), 131.06 (C2,6,2′,6′). The remaining carbinolic residue was transferred to a flask containing 100 mL of methanol and 1 mL of concentrated HCl.…”

Section: Methodsmentioning

confidence: 99%

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Synthesis and Characterization of N-Demethylated Metabolites of Malachite Green and Leucomalachite Green

Cho

Yang

Blankenship

et al. 2003

Chem. Res. Toxicol.

137

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Malachite green (MG), a triphenylmethane dye used to treat fungal and protozoan infections in fish, undergoes sequential oxidation to produce various N-demethylated derivatives (monodes-, dides(sym)-, dides(unsym)-, trides-, and tetrades-) both before and after reduction to leucomalachite green (LMG). The close structure resemblance of the metabolites with aromatic amine carcinogens implicates a potential genotoxicity from exposure to MG. The availability of the synthetic standards is important for metabolic and DNA adduct studies of MG. This paper describes a simple and versatile method for the synthesis of MG, LMG, and their N-demethylated metabolites. The synthesis involves a coupling of 4-(dimethylamino)benzophenone or 4-nitrobenzophenone with the aryllithium reagents derived from appropriately substituted 4-bromoaniline derivatives, followed by treatment with HCl in methanol. The resulting cationic MG and their leuco analogues showed systematic UV/vis spectral and tandem mass fragmentation patterns consistent with sequential N-demethylation. The extensive (1)H and (13)C spectral assignments of the metabolites were aided by the availability of (13)C(7)-labeled MG and LMG. The results indicate the existence of a resonance structure with the cationic charge located in the central methane carbon (C(7)). The synthetic procedure is general in scope so that it can be extended to the preparation of N-demethylated metabolites of other structurally related N-methylated triphenylmethane dyes.

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Section: Methodssupporting

confidence: 62%

Section: Methodssupporting

confidence: 55%

Section: Methodsmentioning

confidence: 99%

Section: Methodsmentioning

confidence: 99%

Section: Methodsmentioning

confidence: 99%

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Synthesis and Characterization of N-Demethylated Metabolites of Malachite Green and Leucomalachite Green

Cho

Yang

Blankenship

et al. 2003

Chem. Res. Toxicol.

137

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Reductive Aminations of Carbonyl Compounds with Borohydride and Borane Reducing Agents

2002

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Reductive amination is an important tool for synthetic organic chemists in the construction of carbon‐nitrogen bonds. This reaction, also termed reductive alkylation, involves condensation of an aldehyde or ketone with an amine in the presence of a reducing agent. A wide variety of substrates can be used including aliphatic and aromatic aldehydes and ketones, and even benzophenones. A range of amines from ammonia to aromatic amines, including those with electron‐withdrawing substituents, can be employed. For particularly sluggish reactions, such as those involving weakly electrophilic carbonyl groups, poorly nucleophilic amines, or sterically congested reactive centers, additives such as molecular sieves or Lewis acids are often useful. This chapter focuses on those conditions in which the carbonyl component, amine, and reducing reagent react in the same vessel. This review is restricted to reductive aminations using borohydride and borane reducing agents. This chapter concentrates on reductive amination chemistry mediated by borohydride and other boron‐containing reducing agents from 1971, the year when sodium cyanoborohydride was introduced, through the middle of 1999. In addition to reductive aminations of aldehyde and ketone substrates, reactions of related structures including acetals, aminals, ketals, carboxylic acids, nitriles, and dicarbonyls that form a nitrogen‐containing ring are reviewed. Intramolecular processes in which the substrate contains both the carbonyl and amine moieties are described. The intramolecular variant is a useful method for preparing cyclic amines. All of the various boron‐containing hydride sources in reductive aminations, including labeled metal hydrides, are reviewed. Instances of reductive aminations that failed are described. Applications of this method to a solid support in parallel synthesis in combinatorial chemistry as well as reductive aminations that proceed in tandem with a second reaction such as reductive lactamizations are discussed.

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Chronic toxicity/carcinogenicity studies of gentian violet in fischer 344 rats: Two-generation exposure

Littlefield

Gaylor

Blackwell

et al. 1989

Food and Chemical Toxicology

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Synthesis and disposition of 14C-labelled gentian violet in F344 rats and B6C3F1 mice

Cited by 5 publications

References 10 publications

Synthesis and Characterization of N-Demethylated Metabolites of Malachite Green and Leucomalachite Green

Synthesis and Characterization of N-Demethylated Metabolites of Malachite Green and Leucomalachite Green

Reductive Aminations of Carbonyl Compounds with Borohydride and Borane Reducing Agents

Chronic toxicity/carcinogenicity studies of gentian violet in fischer 344 rats: Two-generation exposure

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