Review on the analysis of 2-amino-1-methyl-6-phenylimidazo[4,5-b]pyridine and its phase I and phase II metabolites in biological matrices, foodstuff and beverages

Teunissen, S.F.; Rosing, Hilde; Schinkel, Alfred H.; Schellens, Jan H.M.; Beijnen, Jos H.

doi:10.1016/j.jchromb.2010.10.018

Cited by 9 publications

(10 citation statements)

References 77 publications

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“…A combination of hydroxylation and subsequent glucuronidation of PhIP results in five known phase II metabolites [12,32]. We observed only four of them which might be due to sensitivity constraints.…”

Section: (4) N2-methyl-phipmentioning

confidence: 82%

“…The LC gradient which was used for LC-MS-MS analysis, was previously developed for the quantification of PhIP and N2-OH-PhIP in various matrices [33].…”

Section: Chromatographymentioning

confidence: 99%

“…Their retention time, parent and product mass and UV absorbance spectra were compared with authentic standards and literature [12,38]. One other known hydroxylated PhIP metabolite, namely 4 0 -OH-PhIP, was not identified in urine [32].…”

Section: (1) Phip (2) N2-oh-phip (3) 5-oh-phipmentioning

confidence: 99%

“…(8) PhIP-N2-glucuronide, (9) PhIP-N3-glucuronide 2-Amino-1-methyl-6-phenylimidazo [4,5-b]pyridine is known to have two locations which are preferred for addition of a glucuronide group: the N2, located at the terminal amine, and the N3, located in the imidazole moiety (Table 1) [32]. Both metabolites differ predominantly from each other in terms of UV absorbance and polarity and have a distinct mass transition of 401/225 m/z due to the loss of glucuronic acid.…”

Section: (4) N2-methyl-phipmentioning

confidence: 99%

“…Data on whether these metabolites can be considered detoxified or activated products is lacking and so is data on the extent of formation in vivo. Numerous assays have been developed for the quantification of PhIP in various matrices [32,33]. However, the number of publications reporting on the quantification of PhIP metabolites is very scarce and includes only minor fractions of currently known PhIP metabolites [24,30,34,35].…”

Section: Introductionmentioning

confidence: 99%

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Analysis of 2-Amino-1-methyl-6-phenylimidazo[4,5-b]pyridine and Its Phase I and Phase II Metabolites in Mouse Urine Using LC–UV–MS–MS

et al. 2011

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2-Amino-1-methyl-6-phenylimidazo [4,5-b]pyridine (PhIP) is an abundantly present heterocyclic aromatic amine which is found to be carcinogenic in rodents, mice and rats. The biotransformation of PhIP is extensive and involves both the formation of bioactivated as well as detoxification metabolites. In order to understand its carcinogenicity, the metabolism of PhIP needs to be studied. Numerous metabolites of PhIP have been described but, so far, assays for their quantitative determination in biological matrices are scarce. We present the development and application of an assay, using reversed phase liquid chromatography coupled to ultraviolet and mass spectrometry detectors for the quantification of PhIP, three phase I and nine phase II metabolites in urine. Additionally, the identification of two PhIP-sulfates by the use of NMR is presented. Sample pretreatment consisted of straightforward dilution of urine. PhIP and its metabolites were shown to be stable in diluted urine for at least 22 h when stored at 2-8°C. Precision of the analysis was within 15%. The assay has been successfully applied for the quantification of PhIP and 12 of its metabolites in urine from mice that received 200 mg kg -1 PhIP via oral gavage.

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Section: (4) N2-methyl-phipmentioning

confidence: 82%

“…The LC gradient which was used for LC-MS-MS analysis, was previously developed for the quantification of PhIP and N2-OH-PhIP in various matrices [33].…”

Section: Chromatographymentioning

confidence: 99%

Section: (1) Phip (2) N2-oh-phip (3) 5-oh-phipmentioning

confidence: 99%

Section: (4) N2-methyl-phipmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

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Analysis of 2-Amino-1-methyl-6-phenylimidazo[4,5-b]pyridine and Its Phase I and Phase II Metabolites in Mouse Urine Using LC–UV–MS–MS

et al. 2011

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MicroRNA profiling of carcinogen‐induced rat colon tumors and the influence of dietary spinach

Parasramka

Dashwood

Wang

et al. 2012

Molecular Nutrition Food Res

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Scope MicroRNA (miRNA) profiles are altered in chronic conditions such as cardiovascular disease, diabetes, neurological disorders, and cancer. A systems biology approach was used to examine, for the first time, miRNAs altered in rat colon tumors induced by 2-amino-1-methyl-6-phenylimidazo[4,5-b]pyridine (PhIP), a heterocyclic amine carcinogen from cooked meat. Methods and Results Among the most highly dysregulated miRNAs were those belonging to the let-7 family. Subsequent computational modeling and target validation identified c-Myc and miRNA-binding proteins Lin28A/Lin28B (Lin28) as key players, along with Sox2, Nanog and Oct-3/4. These targets of altered miRNAs in colon cancers have been implicated in tumor recurrence and reduced patient survival, in addition to their role as pluripotency factors. In parallel with these findings, the tumor-suppressive effects of dietary spinach given post-initiation correlated with elevated levels of let-7 family members and partial normalization of c-myc, Sox2, Nanog, Oct-3/4, HmgA2, Dnmt3b and P53 expression. Conclusion We conclude that the let-7/c-Myc/Lin28 axis is dysregulated in heterocyclic amine-induced colon carcinogenesis, and that the tumor suppressive effects of dietary spinach are associated with partial normalization of this pathway.

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Identification of In Vivo Metabolites of Levophencynonate in Human Plasma and Urine by High-Performance Liquid Chromatography Tandem Triple-Time-of-Flight Mass Spectrometry

Si³

et al. 2017

Chromatographia

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Review on the analysis of 2-amino-1-methyl-6-phenylimidazo[4,5-b]pyridine and its phase I and phase II metabolites in biological matrices, foodstuff and beverages

Cited by 9 publications

References 77 publications

Analysis of 2-Amino-1-methyl-6-phenylimidazo[4,5-b]pyridine and Its Phase I and Phase II Metabolites in Mouse Urine Using LC–UV–MS–MS

Analysis of 2-Amino-1-methyl-6-phenylimidazo[4,5-b]pyridine and Its Phase I and Phase II Metabolites in Mouse Urine Using LC–UV–MS–MS

MicroRNA profiling of carcinogen‐induced rat colon tumors and the influence of dietary spinach

Identification of In Vivo Metabolites of Levophencynonate in Human Plasma and Urine by High-Performance Liquid Chromatography Tandem Triple-Time-of-Flight Mass Spectrometry

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