1-Methyl-6-phenyl-1H-imidazo[4,5-b]pyridin-2-amine (BioDeep_00000003046)
Secondary id: BioDeep_00001871333
human metabolite
代谢物信息卡片
1H-imidazo(4,5-b)Pyridin-2-amine, 1-methyl-6-phenyl- (9ci)
化学式: C13H12N4 (224.1062)
中文名称: 2-氨基-1-甲基-6-苯基咪唑[4,5-b]吡啶
谱图信息:
最多检出来源 Homo sapiens(plant) 7.84%
分子结构信息
SMILES: Cn1c(=N)[nH]c2ncc(-c3ccccc3)cc21
InChI: InChI=1S/C13H12N4/c1-17-11-7-10(9-5-3-2-4-6-9)8-15-12(11)16-13(17)14/h2-8H,1H3,(H2,14,15,16)
描述信息
1-Methyl-6-phenyl-1H-imidazo[4,5-b]pyridin-2-amine is a food-related mutagen, reported to be the most abundant heterocyclic amine found in cooked meat and fish.
Food-related mutagen, reported to be the most abundant heterocyclic amine found in cooked meat and fish
CONFIDENCE standard compound; INTERNAL_ID 8317
CONFIDENCE standard compound; INTERNAL_ID 2293
CONFIDENCE standard compound; INTERNAL_ID 9
D009676 - Noxae > D002273 - Carcinogens
D009676 - Noxae > D009153 - Mutagens
同义名列表
15 个代谢物同义名
1H-imidazo(4,5-b)Pyridin-2-amine, 1-methyl-6-phenyl- (9ci); 2-amino-1-Methyl-6-phenylimidazo [4,5-b]pyridine (phip); 1-Methyl-6-phenyl-1H-imidazo[4,5-b]pyridin-2-amine, 9ci; 2-Amino-1-methyl-6-phenylimidazo[4,5-b]pyridine (PhIP); 2-amino-1-Methyl-6-phenyl-1H-imidazo[4,5-b]pyridine; 1-Methyl-6-phenyl-1H-imidazo[4,5-b]pyridin-2-amine; 2-amino-1-Methyl-6-phenyl-imidazo [4,5-b] pyridine; 1-Methyl-6-phenyl-1H-imidazo(4,5-b)pyridin-2-amine; 2-amino-1-Methyl-6-phenyl-imidazo(4,5-b)pyridine; 2-amino-1-Methyl-6-phenylimidazo(4,5-b)pyridine; 2-Amino-1-methyl-6-phenylimidazo[4,5-b]pyridine; 1H-imidazo(4,5-b)Pyridine; PhIP; PIQ; 2-Amino-1-methyl-6-phenylimidazo[4,5-b]pyridine
数据库引用编号
35 个数据库交叉引用编号
- ChEBI: CHEBI:76290
- KEGG: C16038
- PubChem: 1530
- HMDB: HMDB0041008
- Metlin: METLIN71126
- DrugBank: DB08398
- ChEMBL: CHEMBL1213271
- Wikipedia: 2-Amino-1-methyl-6-phenylimidazo(4,5-b)pyridine
- foodb: FDB020870
- chemspider: 1476
- CAS: 1185024-97-8
- CAS: 105650-23-5
- CAS: 138370-35-1
- CAS: 106105-17-3
- MoNA: UA000901
- MoNA: SM831754
- MoNA: UA000903
- MoNA: AU229301
- MoNA: AU229302
- MoNA: AU229360
- MoNA: AU229359
- MoNA: AU229305
- MoNA: AU229362
- MoNA: AU229358
- MoNA: UA000904
- MoNA: AU229357
- MoNA: AU229303
- MoNA: AU229304
- MoNA: SM831701
- MoNA: AU229306
- PMhub: MS000007825
- PubChem: 47205348
- PDB-CCD: PIQ
- NIKKAJI: J258.694K
- KNApSAcK: 76290
分类词条
相关代谢途径
Reactome(0)
BioCyc(0)
PlantCyc(0)
代谢反应
0 个相关的代谢反应过程信息。
Reactome(0)
BioCyc(0)
WikiPathways(0)
Plant Reactome(0)
INOH(0)
PlantCyc(0)
COVID-19 Disease Map(0)
PathBank(0)
PharmGKB(0)
1 个相关的物种来源信息
在这里通过桑基图来展示出与当前的这个代谢物在我们的BioDeep知识库中具有相关联信息的其他代谢物。在这里进行关联的信息来源主要有：
- PubMed: 来源于PubMed文献库中的文献信息，我们通过自然语言数据挖掘得到的在同一篇文献中被同时提及的相关代谢物列表，这个列表按照代谢物同时出现的文献数量降序排序，取前10个代谢物作为相关研究中关联性很高的代谢物集合展示在桑基图中。
- NCBI Taxonomy: 通过文献数据挖掘，得到的代谢物物种来源信息关联。这个关联信息同样按照出现的次数降序排序，取前10个代谢物作为高关联度的代谢物集合展示在桑吉图上。
- Chemical Taxonomy: 在物质分类上处于同一个分类集合中的其他代谢物
- Chemical Reaction: 在化学反应过程中，存在为当前代谢物相关联的生化反应过程中的反应底物或者反应产物的关联代谢物信息。
点击图上的相关代谢物的名称，可以跳转到相关代谢物的信息页面。
文献列表
- Liwen Jiang, Yong Li, Chaoyi Xue, Zhiyong He, Zhaojun Wang, Fang Qin, Jie Chen, Maomao Zeng. The inhibitory effects of yellow mustard (Brassica juncea) and its characteristic pungent ingredient allyl isothiocyanate (AITC) on PhIP formation: Focused on the inhibitory pathways of AITC.
Food chemistry.
2022 Mar; 373(Pt A):131398. doi:
10.1016/j.foodchem.2021.131398. [PMID: 34710679] - Xiuli Zhao, Zeping Shao, Xiaofei Zhou, Yongxi Lin, Jingting Guo, Jun Guo, Yan Zhang, Shuo Wang. Sub-chronic exposure to PhIP induces oxidative damage and DNA damage, and disrupts the amino acid metabolism in the colons of Wistar rats.
Food and chemical toxicology : an international journal published for the British Industrial Biological Research Association.
2021 Jul; 153(?):112249. doi:
10.1016/j.fct.2021.112249. [PMID: 33945839] - Yong Li, Wei Quan, Junhui Wang, Zhiyong He, Fang Qin, Zhaojun Wang, Maomao Zeng, Jie Chen. Effects of ten vegetable oils on heterocyclic amine profiles in roasted beef patties using UPLC-MS/MS combined with principal component analysis.
Food chemistry.
2021 Jun; 347(?):128996. doi:
10.1016/j.foodchem.2020.128996. [PMID: 33508588] - Xiuli Zhao, Hengchao Liu, Xiaofei Zhou, Xiaoxu Chen, Nan Hu, Yan Zhang, Shuo Wang. 2-Amino-1-methyl-6-phenylimidazo[4,5-b]pyridine Induced Colon Injury by Disrupting the Intestinal Bacterial Composition and Lipid Metabolic Pathways in Rats.
Journal of agricultural and food chemistry.
2021 Jan; 69(1):437-446. doi:
10.1021/acs.jafc.0c06588. [PMID: 33373210] - Vivek Lawana, Se Young Um, Rachel M Foguth, Jason R Cannon. Neuromelanin formation exacerbates HAA-induced mitochondrial toxicity and mitophagy impairments.
Neurotoxicology.
2020 12; 81(?):147-160. doi:
10.1016/j.neuro.2020.10.005. [PMID: 33058929] - Samaria L Gutiérrez-Pacheco, Martin Valenzuela-Melendres, Adrián Hernández-Mendoza, Armando Burgos-Hernández, Ramón E Robles-Zepeda, E Aída Peña-Ramos. Antimutagenic effect of an Asclepias subulata extract against heterocyclic aromatic amines commonly found in cooked meat and its heat stability.
Food chemistry.
2020 Aug; 322(?):126725. doi:
10.1016/j.foodchem.2020.126725. [PMID: 32283373] - I-Jeng Yeh, Szu-Chia Chen, Meng-Chi Yen, Yen-Hung Wu, Chih-Hsing Hung, Po-Lin Kuo. 6-Shogaol Suppresses 2-Amino-1-Methyl-6-Phenylimidazo [4,5-b] Pyridine (PhIP)-Induced Human 786-O Renal Cell Carcinoma Osteoclastogenic Activity and Metastatic Potential.
Nutrients.
2019 Sep; 11(10):. doi:
10.3390/nu11102306. [PMID: 31569368] - A E El-Sisi, S S Sokar, M E El-Sayad, E A Moussa, E I Salim. Anticancer effect of metformin against 2-amino-1-methyl-6-phenylimidazo [4,5-b]pyridine-induced rat mammary carcinogenesis is through AMPK pathway and modulation of oxidative stress markers.
Human & experimental toxicology.
2019 Jun; 38(6):703-712. doi:
10.1177/0960327119839192. [PMID: 30924377] - Jianbo Zhang, Christophe Lacroix, Esther Wortmann, Hans-Joachim Ruscheweyh, Shinichi Sunagawa, Shana J Sturla, Clarissa Schwab. Gut microbial beta-glucuronidase and glycerol/diol dehydratase activity contribute to dietary heterocyclic amine biotransformation.
BMC microbiology.
2019 05; 19(1):99. doi:
10.1186/s12866-019-1483-x. [PMID: 31096909] - Medjda Bellamri, Yi Wang, Kim Yonemori, Kami K White, Lynne R Wilkens, Loïc Le Marchand, Robert J Turesky. Biomonitoring an albumin adduct of the cooked meat carcinogen 2-amino-1-methyl-6-phenylimidazo[4,5-b]pyridine in humans.
Carcinogenesis.
2018 12; 39(12):1455-1462. doi:
10.1093/carcin/bgy125. [PMID: 30247550] - Ram B Jain. Concentrations of selected heterocyclic aromatic amines among US population aged ≥ 6 years: data from NHANES 2013-2014.
Environmental science and pollution research international.
2018 Jul; 25(20):19859-19874. doi:
10.1007/s11356-018-2210-0. [PMID: 29737487] - Chundi Yu, Zeping Shao, Jinhui Zhang, Bing Liu, Lingjie Kong, Yan Zhang, Shuo Wang. Dual Effects of Creatinine on the Formation of 2-Amino-1-Methyl-6-Phenylimidazo [4,5-b]pyridine (PhIP).
Journal of food science.
2018 Feb; 83(2):294-299. doi:
10.1111/1750-3841.14035. [PMID: 29341141] - Francisco J Hidalgo, José L Navarro, Rosario Zamora. Structure-Activity Relationship (SAR) of Phenolics for 2-Amino-1-methyl-6-phenylimidazo[4,5-b]pyridine (PhIP) Formation in Phenylalanine/Creatinine Reaction Mixtures Including (or Not) Oxygen and Lipid Hydroperoxides.
Journal of agricultural and food chemistry.
2018 Jan; 66(1):255-264. doi:
10.1021/acs.jafc.7b04859. [PMID: 29224335] - Katia Sayyed, Marc Le Vee, Ziad Abdel-Razzak, Olivier Fardel. Inhibition of organic anion transporter (OAT) activity by cigarette smoke condensate.
Toxicology in vitro : an international journal published in association with BIBRA.
2017 Oct; 44(?):27-35. doi:
10.1016/j.tiv.2017.06.014. [PMID: 28629854] - Rong Wang, Ying-Shiuan Chen, Wan-Mohaiza Dashwood, Qingjie Li, Christiane V Löhr, Kay Fischer, Emily Ho, David E Williams, Roderick H Dashwood. Divergent roles of p120-catenin isoforms linked to altered cell viability, proliferation, and invasiveness in carcinogen-induced rat skin tumors.
Molecular carcinogenesis.
2017 07; 56(7):1733-1742. doi:
10.1002/mc.22630. [PMID: 28218467] - Jae Kyeom Kim, Daniel D Gallaher, Chi Chen, Cynthia M Gallaher, Dan Yao, Sabrina P Trudo. Phenethyl isothiocyanate and indole-3-carbinol from cruciferous vegetables, but not furanocoumarins from apiaceous vegetables, reduced PhIP-induced DNA adducts in Wistar rats.
Molecular nutrition & food research.
2016 09; 60(9):1956-66. doi:
10.1002/mnfr.201500790. [PMID: 27133590] - Chundi Yu, Zeping Shao, Bing Liu, Yan Zhang, Shuo Wang. Inhibition of 2-Amino-1-methyl-6-phenylimidazo [4,5-b]pyridine (PhIP) Formation by Alkoxy Radical Scavenging of Flavonoids and Their Quantitative Structure-Activity Relationship in a Model System.
Journal of food science.
2016 Aug; 81(8):C1908-13. doi:
10.1111/1750-3841.13381. [PMID: 27384350] - Loïc Le Marchand, Kim Yonemori, Kami K White, Adrian A Franke, Lynne R Wilkens, Robert J Turesky. Dose validation of PhIP hair level as a biomarker of heterocyclic aromatic amines exposure: a feeding study.
Carcinogenesis.
2016 07; 37(7):685-691. doi:
10.1093/carcin/bgw049. [PMID: 27207666] - Jonathan Sheng, Yi Wang, Robert J Turesky, Kerri Kluetzman, Qing-Yu Zhang, Xinxin Ding. Novel Transgenic Mouse Model for Studying Human Serum Albumin as a Biomarker of Carcinogenic Exposure.
Chemical research in toxicology.
2016 05; 29(5):797-809. doi:
10.1021/acs.chemrestox.5b00529. [PMID: 27028147] - Di Yu, Shu-Juan Yu. Effects of waxy rice starch and short chain amylose (SCA) on the formation of 2-amino-1-methyl-6-phenylimidazo[4,5-b]pyridine (PhIP) in a model system.
Food & function.
2016 Mar; 7(3):1339-44. doi:
10.1039/c5fo01495f. [PMID: 26887688] - Annette M Krais, Ewoud N Speksnijder, Joost P M Melis, Rajinder Singh, Anna Caldwell, Gonçalo Gamboa da Costa, Mirjam Luijten, David H Phillips, Volker M Arlt. Metabolic activation of 2-amino-1-methyl-6-phenylimidazo [4,5-b]pyridine and DNA adduct formation depends on p53: Studies in Trp53(+/+),Trp53(+/-) and Trp53(-/-) mice.
International journal of cancer.
2016 Feb; 138(4):976-82. doi:
10.1002/ijc.29836. [PMID: 26335255] - Sandra Halwachs, Carsten Kneuer, Katrin Gohlsch, Marian Müller, Vera Ritz, Walther Honscha. The ABCG2 efflux transporter from rabbit placenta: Cloning and functional characterization.
Placenta.
2016 Feb; 38(?):8-15. doi:
10.1016/j.placenta.2015.12.005. [PMID: 26907376] - Stephanie C Melkonian, Carrie R Daniel, Yuanqing Ye, Nizar M Tannir, Jose A Karam, Surena F Matin, Christopher G Wood, Xifeng Wu. Gene-environment interaction of genome-wide association study-identified susceptibility loci and meat-cooking mutagens in the etiology of renal cell carcinoma.
Cancer.
2016 Jan; 122(1):108-15. doi:
10.1002/cncr.29543. [PMID: 26551148] - Anja Hortemo Høie, Camilla Svendsen, Gunnar Brunborg, Hansruedi Glatt, Jan Alexander, Walter Meinl, Trine Husøy. Genotoxicity of three food processing contaminants in transgenic mice expressing human sulfotransferases 1A1 and 1A2 as assessed by the in vivo alkaline single cell gel electrophoresis assay.
Environmental and molecular mutagenesis.
2015 Oct; 56(8):709-14. doi:
10.1002/em.21963. [PMID: 26270892] - Renato Tavares dos Santos Pereira, Felipe Augusto Dörr, Ernani Pinto, Marina Yazigi Solis, Guilherme Giannini Artioli, Alan Lins Fernandes, Igor Hisashi Murai, Wagner Silva Dantas, Antônio Carlos Seguro, Mirela Aparecida Rodrigues Santinho, Hamilton Roschel, Alain Carpentier, Jacques Remi Poortmans, Bruno Gualano. Can creatine supplementation form carcinogenic heterocyclic amines in humans?.
The Journal of physiology.
2015 Sep; 593(17):3959-71. doi:
10.1113/jp270861. [PMID: 26148133] - Karen S Sfanos, Kirstie Canene-Adams, Heidi Hempel, Shu-Han Yu, Brian W Simons, Anthony J Schaeffer, Edward M Schaeffer, William G Nelson, Angelo M De Marzo. Bacterial Prostatitis Enhances 2-Amino-1-Methyl-6-Phenylimidazo[4,5-b]Pyridine (PhIP)-Induced Cancer at Multiple Sites.
Cancer prevention research (Philadelphia, Pa.).
2015 Aug; 8(8):683-92. doi:
10.1158/1940-6207.capr-15-0090. [PMID: 25990088] - Yi Wang, Lijuan Peng, Medjda Bellamri, Sophie Langouët, Robert J Turesky. Mass Spectrometric Characterization of Human Serum Albumin Adducts Formed with N-Oxidized Metabolites of 2-Amino-1-methylphenylimidazo[4,5-b]pyridine in Human Plasma and Hepatocytes.
Chemical research in toxicology.
2015 May; 28(5):1045-59. doi:
10.1021/acs.chemrestox.5b00075. [PMID: 25815793] - Jae Kyeom Kim, Daniel D Gallaher, Chi Chen, Dan Yao, Sabrina P Trudo. Apiaceous vegetable consumption decreases PhIP-induced DNA adducts and increases methylated PhIP metabolites in the urine metabolome in rats.
The Journal of nutrition.
2015 Mar; 145(3):442-51. doi:
10.3945/jn.114.202622. [PMID: 25733458] - Francisco J Hidalgo, Esmeralda Alcón, Rosario Zamora. Reactive carbonyl-scavenging ability of 2-aminoimidazoles: 2-amino-1-methylbenzimidazole and 2-amino-1-methyl-6-phenylimidazo[4,5-b]pyridine (PhIP).
Journal of agricultural and food chemistry.
2014 Dec; 62(49):12045-51. doi:
10.1021/jf504320a. [PMID: 25418848] - Kevin M Cooper, Natcha Jankhaikhot, Geraldine Cuskelly. Optimised extraction of heterocyclic aromatic amines from blood using hollow fibre membrane liquid-phase microextraction and triple quadrupole mass spectrometry.
Journal of chromatography. A.
2014 Sep; 1358(?):20-8. doi:
10.1016/j.chroma.2014.06.061. [PMID: 25037778] - Amy M Griggs, Zeynep S Agim, Vartika R Mishra, Mitali A Tambe, Alison E Director-Myska, Kenneth W Turteltaub, George P McCabe, Jean-Christophe Rochet, Jason R Cannon. 2-Amino-1-methyl-6-phenylimidazo[4,5-b]pyridine (PhIP) is selectively toxic to primary dopaminergic neurons in vitro.
Toxicological sciences : an official journal of the Society of Toxicology.
2014 Jul; 140(1):179-89. doi:
10.1093/toxsci/kfu060. [PMID: 24718704] - Lijuan Peng, Robert J Turesky. Optimizing proteolytic digestion conditions for the analysis of serum albumin adducts of 2-amino-1-methyl-6-phenylimidazo[4,5-b]pyridine, a potential human carcinogen formed in cooked meat.
Journal of proteomics.
2014 May; 103(?):267-78. doi:
10.1016/j.jprot.2014.03.023. [PMID: 24698664] - Yan Zhang, Zhou Luo, Zeping Shao, Chundi Yu, Shuo Wang. Effects of antioxidants of bamboo leaves and flavonoids on 2-amino-1-methyl-6-phenylimidazo[4,5-b]pyridine (PhIP) formation in chemical model systems.
Journal of agricultural and food chemistry.
2014 May; 62(20):4798-802. doi:
10.1021/jf500483y. [PMID: 24806809] - Ricardo Salazar, Gerónimo Arámbula-Villa, Francisco J Hidalgo, Rosario Zamora. Structural characteristics that determine the inhibitory role of phenolic compounds on 2-amino-1-methyl-6-phenylimidazo[4,5-b]pyridine (PhIP) formation.
Food chemistry.
2014 May; 151(?):480-6. doi:
10.1016/j.foodchem.2013.11.105. [PMID: 24423560] - Luca Dominici, Milena Villarini, Francesca Trotta, Ermanno Federici, Giovanni Cenci, Massimo Moretti. Protective effects of probiotic Lactobacillus rhamnosus IMC501 in mice treated with PhIP.
Journal of microbiology and biotechnology.
2014 Mar; 24(3):371-8. doi:
10.4014/jmb.1309.09072. [PMID: 24346468] - Maria L H Vlaming, Sebastiaan F Teunissen, Evita van de Steeg, Anita van Esch, Els Wagenaar, Luc Brunsveld, Tom F A de Greef, Hilde Rosing, Jan H M Schellens, Jos H Beijnen, Alfred H Schinkel. Bcrp1;Mdr1a/b;Mrp2 combination knockout mice: altered disposition of the dietary carcinogen PhIP (2-amino-1-methyl-6-phenylimidazo[4,5-b]pyridine) and its genotoxic metabolites.
Molecular pharmacology.
2014 Mar; 85(3):520-30. doi:
10.1124/mol.113.088823. [PMID: 24334255] - Yukari Totsuka, Tetsushi Watanabe, Souleymane Coulibaly, Sae Kobayashi, Marina Nishizaki, Miho Okazaki, Tomohiro Hasei, Keiji Wakabayashi, Hitoshi Nakagama. In vivo genotoxicity of a novel heterocyclic amine, aminobenzoazepinoquinolinone-derivative (ABAQ), produced by the Maillard reaction between glucose and l-tryptophan.
Mutation research. Genetic toxicology and environmental mutagenesis.
2014 Jan; 760(?):48-55. doi:
10.1016/j.mrgentox.2013.12.002. [PMID: 24333690] - Rui Jin Li, Jing Jing Tian, Wan Qing Li, Fang Qin Cheng, Gang Shuan Gao. Effect of 2-amino-1-methyl-6-phenylimidazo [4, 5-b] pyridine on oxidative stress and gene expression of c-fos, c-jun, p16 and Rb in rat colons and protective role of seabuckthorn seed oil.
Journal of environmental science and health. Part. B, Pesticides, food contaminants, and agricultural wastes.
2014; 49(4):279-89. doi:
10.1080/03601234.2014.868667. [PMID: 24502215] - Rosario Zamora, Esmeralda Alcón, Francisco J Hidalgo. Effect of amino acids on the formation of 2-amino-1-methyl-6-phenylimidazo[4,5-b]pyridine (PhIP) in creatinine/phenylalanine and creatinine/phenylalanine/4-oxo-2-nonenal reaction mixtures.
Food chemistry.
2013 Dec; 141(4):4240-5. doi:
10.1016/j.foodchem.2013.06.036. [PMID: 23993611] - Louise Wassermann, Sandra Halwachs, Daniela Baumann, Ingo Schaefer, Peter Seibel, Walther Honscha. Assessment of ABCG2-mediated transport of xenobiotics across the blood-milk barrier of dairy animals using a new MDCKII in vitro model.
Archives of toxicology.
2013 Sep; 87(9):1671-82. doi:
10.1007/s00204-013-1066-9. [PMID: 23652544] - Yoon Jung Lee, Yun-Jin Hong, Ji Yeon Kim, Kwang Won Lee, Oran Kwon. Dietary Chlorella protects against heterocyclic amine-induced aberrant gene expression in the rat colon by increasing fecal excretion of unmetabolized PhIP.
Food and chemical toxicology : an international journal published for the British Industrial Biological Research Association.
2013 Jun; 56(?):272-7. doi:
10.1016/j.fct.2013.01.028. [PMID: 23466459] - Rosario Zamora, Esmeralda Alcón, Francisco J Hidalgo. Comparative formation of 2-amino-1-methyl-6-phenylimidazo[4,5-b]pyridine (PhIP) in creatinine/phenylalanine and creatinine/phenylalanine/4-oxo-2-nonenal reaction mixtures.
Food chemistry.
2013 May; 138(1):180-5. doi:
10.1016/j.foodchem.2012.09.116. [PMID: 23265474] - Robert J Turesky, Lin Liu, Dan Gu, Kim M Yonemori, Kami K White, Lynne R Wilkens, Loïc Le Marchand. Biomonitoring the cooked meat carcinogen 2-amino-1-methyl-6-phenylimidazo[4,5-b]pyridine in hair: impact of exposure, hair pigmentation, and cytochrome P450 1A2 phenotype.
Cancer epidemiology, biomarkers & prevention : a publication of the American Association for Cancer Research, cosponsored by the American Society of Preventive Oncology.
2013 Mar; 22(3):356-64. doi:
10.1158/1055-9965.epi-12-1206. [PMID: 23329727] - Jehan A Khan, Jalaluddin A Jalal, C Ioanndes, Said S Moselhy. Impact of aqueous doash extract on urinary mutagenicity in rats exposed to heterocyclic amines.
Toxicology and industrial health.
2013 Mar; 29(2):142-8. doi:
10.1177/0748233711427053. [PMID: 22173956] - Rosa Busquets, Henrik Frandsen, Jan Åke Jönsson, Lluís Puignou, Maria Teresa Galceran, Kerstin Skog. Biomonitoring of dietary heterocyclic amines and metabolites in urine by liquid phase microextraction: 2-amino-1-methyl-6-phenylimidazo[4,5-b]pyridine (PhIP), a possible biomarker of exposure to dietary PhIP.
Chemical research in toxicology.
2013 Feb; 26(2):233-40. doi:
10.1021/tx3003966. [PMID: 23276304] - Dojung Kim, Young-Joo Lee, Heui-Young Ryu, Jin-Hee Lee, Hyun-Kyung Kim, Eunhee Kim, Jae-Dong Moon, Dong Deuk Chang, Hae-Seong Yoon. Genetic polymorphisms in metabolism of 2-amino-1-methyl-6-phenylimidazo[4,5-b] pyridine.
Journal of applied toxicology : JAT.
2013 Jan; 33(1):63-70. doi:
10.1002/jat.1712. [PMID: 22131055] - Yan Zhang, Chundi Yu, Jingbo Mei, Shuo Wang. Formation and mitigation of heterocyclic aromatic amines in fried pork.
Food additives & contaminants. Part A, Chemistry, analysis, control, exposure & risk assessment.
2013; 30(9):1501-7. doi:
10.1080/19440049.2013.809627. [PMID: 23862679] - Rosario Zamora, Esmeralda Alcón, Francisco J Hidalgo. Effect of lipid oxidation products on the formation of 2-amino-1-methyl-6-phenylimidazo[4,5-b]pyridine (PhIP) in model systems.
Food chemistry.
2012 Dec; 135(4):2569-74. doi:
10.1016/j.foodchem.2012.06.062. [PMID: 22980844] - Elżbieta Klewicka, Adriana Nowak, Zenon Zduńczyk, Jerzy Juśkiewicz, Bożena Cukrowska. Protective effect of lactofermented red beetroot juice against aberrant crypt foci formation, genotoxicity of fecal water and oxidative stress induced by 2-amino-1-methyl-6-phenylimidazo[4,5-b] pyridine in rats model.
Environmental toxicology and pharmacology.
2012 Nov; 34(3):895-904. doi:
10.1016/j.etap.2012.08.009. [PMID: 22995401] - Lijuan Peng, Surendra Dasari, David L Tabb, Robert J Turesky. Mapping serum albumin adducts of the food-borne carcinogen 2-amino-1-methyl-6-phenylimidazo[4,5-b]pyridine by data-dependent tandem mass spectrometry.
Chemical research in toxicology.
2012 Oct; 25(10):2179-93. doi:
10.1021/tx300253j. [PMID: 22827630] - Nicole C Deziel, Timothy J Buckley, Rashmi Sinha, Salahaddhin Abubaker, Elizabeth A Platz, Paul T Strickland. Comparability and repeatability of methods for estimating the dietary intake of the heterocyclic amine contaminant 2-amino-1-methyl-6-phenylimidazo[4,5b]pyridine (PhIP).
Food additives & contaminants. Part A, Chemistry, analysis, control, exposure & risk assessment.
2012 Aug; 29(8):1202-11. doi:
10.1080/19440049.2012.682657. [PMID: 22571725] - Liliana Rounds, Cody M Havens, Yelena Feinstein, Mendel Friedman, Sadhana Ravishankar. Plant extracts, spices, and essential oils inactivate Escherichia coli O157:H7 and reduce formation of potentially carcinogenic heterocyclic amines in cooked beef patties.
Journal of agricultural and food chemistry.
2012 Apr; 60(14):3792-9. doi:
10.1021/jf204062p. [PMID: 22397498] - Gregory J Anger, Alex M Cressman, Micheline Piquette-Miller. Expression of ABC Efflux transporters in placenta from women with insulin-managed diabetes.
PloS one.
2012; 7(4):e35027. doi:
10.1371/journal.pone.0035027. [PMID: 22558111] - Shinji Takasu, Michihiro Mutoh, Mami Takahashi, Hitoshi Nakagama. Lipoprotein lipase as a candidate target for cancer prevention/therapy.
Biochemistry research international.
2012; 2012(?):398697. doi:
10.1155/2012/398697. [PMID: 22028972] - Ruijin Li, Wanqing Li, Jingfang Xie, Yuexia Zhang. [Lipid peroxidation in different tissues of rats treated with 2-amino-1-methyl-6-phenylimidazo [4,5-b] pyridine].
Wei sheng yan jiu = Journal of hygiene research.
2012 Jan; 41(1):102-5. doi:
. [PMID: 22443067] - Lijuan Peng, Robert J Turesky. Mass spectrometric characterization of 2-amino-1-methyl-6-phenylimidazo[4,5-b]pyridine N-oxidized metabolites bound at Cys34 of human serum albumin.
Chemical research in toxicology.
2011 Nov; 24(11):2004-17. doi:
10.1021/tx2003504. [PMID: 21916490] - Gisela Dobbernack, Walter Meinl, Nicole Schade, Simone Florian, Korinna Wend, Ingo Voigt, Heinz Himmelbauer, Madeleine Gross, Thomas Liehr, Hansruedi Glatt. Altered tissue distribution of 2-amino-1-methyl-6-phenylimidazo[4,5-b]pyridine-DNA adducts in mice transgenic for human sulfotransferases 1A1 and 1A2.
Carcinogenesis.
2011 Nov; 32(11):1734-40. doi:
10.1093/carcin/bgr204. [PMID: 21900212] - Kanithaporn Puangsombat, Wannee Jirapakkul, J Scott Smith. Inhibitory activity of Asian spices on heterocyclic amines formation in cooked beef patties.
Journal of food science.
2011 Oct; 76(8):T174-80. doi:
10.1111/j.1750-3841.2011.02338.x. [PMID: 21913920] - Bojana Zegura, David Dobnik, Maša Hojnik Niderl, Metka Filipič. Antioxidant and antigenotoxic effects of rosemary (Rosmarinus officinalis L.) extracts in Salmonella typhimurium TA98 and HepG2 cells.
Environmental toxicology and pharmacology.
2011 Sep; 32(2):296-305. doi:
10.1016/j.etap.2011.06.002. [PMID: 21843811] - Dan Gu, Melissa M Raymundo, Fred F Kadlubar, Robert J Turesky. Ultraperformance liquid chromatography-tandem mass spectrometry method for biomonitoring cooked meat carcinogens and their metabolites in human urine.
Analytical chemistry.
2011 Feb; 83(3):1093-101. doi:
10.1021/ac102918b. [PMID: 21194225] - Ming Xi Tang, Kumiko Ogawa, Makoto Asamoto, Teera Chewonarin, Shugo Suzuki, Takuji Tanaka, Tomoyuki Shirai. Effects of nobiletin on PhIP-induced prostate and colon carcinogenesis in F344 rats.
Nutrition and cancer.
2011; 63(2):227-33. doi:
10.1080/01635581.2011.523506. [PMID: 21298591] - K L Platt, R Edenharder, S Aderhold, E Muckel, H Glatt. Fruits and vegetables protect against the genotoxicity of heterocyclic aromatic amines activated by human xenobiotic-metabolizing enzymes expressed in immortal mammalian cells.
Mutation research.
2010 Dec; 703(2):90-8. doi:
10.1016/j.mrgentox.2010.08.007. [PMID: 20713174] - S F Teunissen, H Rosing, A H Schinkel, J H M Schellens, J H Beijnen. 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.
Journal of chromatography. B, Analytical technologies in the biomedical and life sciences.
2010 Dec; 878(31):3199-216. doi:
10.1016/j.jchromb.2010.10.018. [PMID: 21071289] - Nicole Schupp, August Heidland, Helga Stopper. Genomic damage in endstage renal disease-contribution of uremic toxins.
Toxins.
2010 10; 2(10):2340-58. doi:
10.3390/toxins2102340. [PMID: 22069557] - Hiromitsu Watanabe. Intestinal metaplasia -the effect of Acid on the gastric mucosa and gastric carcinogenesis-.
Journal of toxicologic pathology.
2010 Sep; 23(3):115-23. doi:
10.1293/tox.23.115. [PMID: 22272022] - S F Teunissen, M L H Vlaming, H Rosing, J H M Schellens, A H Schinkel, J H Beijnen. Development and validation of a liquid chromatography-tandem mass spectrometry assay for the analysis of 2-amino-1-methyl-6-phenylimidazo[4,5-b]pyridine (PhIP) and its metabolite 2-hydroxyamino-1-methyl-6-phenylimidazo[4,5-b]pyridine (N-OH-PhIP) in plasma, urine, bile, intestinal contents, faeces and eight selected tissues from mice.
Journal of chromatography. B, Analytical technologies in the biomedical and life sciences.
2010 Sep; 878(25):2353-62. doi:
10.1016/j.jchromb.2010.07.012. [PMID: 20708442] - Rebecca Kuriyan, Divya R Kumar, Rajendran R, Anura V Kurpad. An evaluation of the hypolipidemic effect of an extract of Hibiscus Sabdariffa leaves in hyperlipidemic Indians: a double blind, placebo controlled trial.
BMC complementary and alternative medicine.
2010 Jun; 10(?):27. doi:
10.1186/1472-6882-10-27. [PMID: 20553629] - Fernando De Andrés, Mohammed Zougagh, Gregorio Castañeda, Angel Ríos. Determination of heterocyclic amines in urine samples by capillary liquid chromatography with evaporated light-scattering detection.
Analytical and bioanalytical chemistry.
2010 May; 397(1):223-231. doi:
10.1007/s00216-009-3370-z. [PMID: 20396988] - Dan Gu, Lynn McNaughton, David Lemaster, Brian G Lake, Nigel J Gooderham, Fred F Kadlubar, Robert J Turesky. A comprehensive approach to the profiling of the cooked meat carcinogens 2-amino-3,8-dimethylimidazo[4,5-f]quinoxaline, 2-amino-1-methyl-6-phenylimidazo[4,5-b]pyridine, and their metabolites in human urine.
Chemical research in toxicology.
2010 Apr; 23(4):788-801. doi:
10.1021/tx900436m. [PMID: 20192249] - Hala A Awney, Heba Sindi. The effect of rosemary on the mutagenic activity of heterocyclic amines extracted from common food consumed in Saudi Arabia.
International journal of food sciences and nutrition.
2010 Mar; 61(2):192-203. doi:
10.3109/09637480903294953. [PMID: 19939197] - Kanithaporn Puangsombat, J Scott Smith. Inhibition of heterocyclic amine formation in beef patties by ethanolic extracts of rosemary.
Journal of food science.
2010 Mar; 75(2):T40-7. doi:
10.1111/j.1750-3841.2009.01491.x. [PMID: 20492265] - Rosa Busquets, Jan Ake Jönsson, Henrik Frandsen, Lluís Puignou, Maria Teresa Galceran, Kerstin Skog. Hollow fibre-supported liquid membrane extraction and LC-MS/MS detection for the analysis of heterocyclic amines in urine samples.
Molecular nutrition & food research.
2009 Dec; 53(12):1496-504. doi:
10.1002/mnfr.200800577. [PMID: 19810020] - Volker Mai, Quintece M McCrary, Rashmi Sinha, Michael Glei. Associations between dietary habits and body mass index with gut microbiota composition and fecal water genotoxicity: an observational study in African American and Caucasian American volunteers.
Nutrition journal.
2009 Oct; 8(?):49. doi:
10.1186/1475-2891-8-49. [PMID: 19845958] - Jean-Marie Fede, Anup P Thakur, Nigel J Gooderham, Robert J Turesky. Biomonitoring of 2-amino-1-methyl-6-phenylimidazo[4,5-b]pyridine (PhIP) and its carcinogenic metabolites in urine.
Chemical research in toxicology.
2009 Jun; 22(6):1096-105. doi:
10.1021/tx900052c. [PMID: 19441775] - Valon Llabjani, Kevin C Jones, Gareth O Thomas, Lee A Walker, Richard F Shore, Francis L Martin. Polybrominated diphenyl ether-associated alterations in cell biochemistry as determined by attenuated total reflection Fourier-transform infrared spectroscopy: a comparison with DNA-reactive and/or endocrine-disrupting agents.
Environmental science & technology.
2009 May; 43(9):3356-64. doi:
10.1021/es8036127. [PMID: 19534158] - Bo Wang, Shu-Feng Zhou. Synthetic and natural compounds that interact with human cytochrome P450 1A2 and implications in drug development.
Current medicinal chemistry.
2009; 16(31):4066-218. doi:
10.2174/092986709789378198. [PMID: 19754423] - Veronika A Ehrlich, Armen K Nersesyan, Kambis Atefie, Christine Hoelzl, Franziska Ferk, Julia Bichler, Eva Valic, Andreas Schaffer, Rolf Schulte-Hermann, Michael Fenech, Karl-Heinz Wagner, Siegfried Knasmüller. Inhalative exposure to vanadium pentoxide causes DNA damage in workers: results of a multiple end point study.
Environmental health perspectives.
2008 Dec; 116(12):1689-93. doi:
10.1289/ehp.11438. [PMID: 19079721] - H Frandsen. Biomonitoring of urinary metabolites of 2-amino-1-methyl-6-phenylimidazo[4,5-b]pyridine (PhIP) following human consumption of cooked chicken.
Food and chemical toxicology : an international journal published for the British Industrial Biological Research Association.
2008 Sep; 46(9):3200-5. doi:
10.1016/j.fct.2008.07.008. [PMID: 18692111] - Sam De Coster, Gudrun Koppen, Marc Bracke, Carmen Schroijen, Elly Den Hond, Vera Nelen, Els Van de Mieroop, Liesbeth Bruckers, Maaike Bilau, Willy Baeyens, Greet Schoeters, Nik van Larebeke. Pollutant effects on genotoxic parameters and tumor-associated protein levels in adults: a cross sectional study.
Environmental health : a global access science source.
2008 Jun; 7(?):26. doi:
10.1186/1476-069x-7-26. [PMID: 18522717] - Junichi Enokizono, Hiroyuki Kusuhara, Atsushi Ose, Alfred H Schinkel, Yuichi Sugiyama. Quantitative investigation of the role of breast cancer resistance protein (Bcrp/Abcg2) in limiting brain and testis penetration of xenobiotic compounds.
Drug metabolism and disposition: the biological fate of chemicals.
2008 Jun; 36(6):995-1002. doi:
10.1124/dmd.107.019257. [PMID: 18322075] - Mary Vore, Markos Leggas. Progesterone acts via progesterone receptors A and B to regulate breast cancer resistance protein expression.
Molecular pharmacology.
2008 Mar; 73(3):613-5. doi:
10.1124/mol.107.044289. [PMID: 18086804] - Lynn Vanhaecke, Filip Vercruysse, Nico Boon, Willy Verstraete, Ilse Cleenwerck, Marjan De Wachter, Paul De Vos, Tom van de Wiele. Isolation and characterization of human intestinal bacteria capable of transforming the dietary carcinogen 2-amino-1-methyl-6-phenylimidazo[4,5-b]pyridine.
Applied and environmental microbiology.
2008 Mar; 74(5):1469-77. doi:
10.1128/aem.02064-07. [PMID: 18192423] - Christine Hoelzl, Hansruedi Glatt, Walter Meinl, Gerhard Sontag, Gerald Haidinger, Michael Kundi, Tatjana Simic, Asima Chakraborty, Julia Bichler, Franziska Ferk, Karel Angelis, Armen Nersesyan, Siegfried Knasmüller. Consumption of Brussels sprouts protects peripheral human lymphocytes against 2-amino-1-methyl-6-phenylimidazo[4,5-b]pyridine (PhIP) and oxidative DNA-damage: results of a controlled human intervention trial.
Molecular nutrition & food research.
2008 Mar; 52(3):330-41. doi:
10.1002/mnfr.200700406. [PMID: 18293303] - L Vanhaecke, M G Knize, H Noppe, H De Brabander, W Verstraete, T Van de Wiele. Intestinal bacteria metabolize the dietary carcinogen 2-amino-1-methyl-6-phenylimidazo[4,5-b]pyridine following consumption of a single cooked chicken meal in humans.
Food and chemical toxicology : an international journal published for the British Industrial Biological Research Association.
2008 Jan; 46(1):140-8. doi:
10.1016/j.fct.2007.07.008. [PMID: 17766021] - Jon Lezamiz, Thaer Barri, Jan Ake Jönsson, Kerstin Skog. A simplified hollow-fibre supported liquid membrane extraction method for quantification of 2-amino-1-methyl-6-phenylimidazo[4,5-b]pyridine (PhIP) in urine and plasma samples.
Analytical and bioanalytical chemistry.
2008 Jan; 390(2):689-96. doi:
10.1007/s00216-007-1702-4. [PMID: 17985119] - Lynnette R Ferguson, Martin Philpott. Nutrition and mutagenesis.
Annual review of nutrition.
2008; 28(?):313-29. doi:
10.1146/annurev.nutr.28.061807.155449. [PMID: 18399774] - Ka-Wing Cheng, Qingli Wu, Zong Ping Zheng, Xiaofang Peng, James E Simon, Feng Chen, Mingfu Wang. Inhibitory effect of fruit extracts on the formation of heterocyclic amines.
Journal of agricultural and food chemistry.
2007 Dec; 55(25):10359-65. doi:
10.1021/jf071820z. [PMID: 18004801] - Carola Funk, Annett Braune, John H Grabber, Hans Steinhart, Mirko Bunzel. Model studies of lignified fiber fermentation by human fecal microbiota and its impact on heterocyclic aromatic amine adsorption.
Mutation research.
2007 Nov; 624(1-2):41-8. doi:
10.1016/j.mrfmmm.2007.03.010. [PMID: 17475287] - J H Beumer, R C Garner, M B Cohen, S Galbraith, G F Duncan, T Griffin, J H Beijnen, J H M Schellens. Human mass balance study of the novel anticancer agent ixabepilone using accelerator mass spectrometry.
Investigational new drugs.
2007 Aug; 25(4):327-34. doi:
10.1007/s10637-007-9041-z. [PMID: 17347871] - Robert J Turesky, Jian-Min Yuan, Renwei Wang, Sabrina Peterson, Mimi C Yu. Tobacco smoking and urinary levels of 2-amino-9H-pyrido[2,3-b]indole in men of Shanghai, China.
Cancer epidemiology, biomarkers & prevention : a publication of the American Association for Cancer Research, cosponsored by the American Society of Preventive Oncology.
2007 Aug; 16(8):1554-60. doi:
10.1158/1055-9965.epi-07-0132. [PMID: 17684128] - H Frandsen. Deconjugation of N-glucuronide conjugated metabolites with hydrazine hydrate--biomarkers for exposure to the food-borne carcinogen 2-amino-1-methyl-6-phenylimidazo[4,5-b]pyridine (PhIP).
Food and chemical toxicology : an international journal published for the British Industrial Biological Research Association.
2007 May; 45(5):863-70. doi:
10.1016/j.fct.2006.11.006. [PMID: 17184892] - Chantell Wilson, Ayoola Aboyade-Cole, Oneil Newell, Selina Darling-Reed, Ebenezer Oriaku, Ronald Thomas. Diallyl sulfide inhibits PhIP-induced DNA strand breaks in normal human breast epithelial cells.
Oncology reports.
2007 Apr; 17(4):807-11. doi:
. [PMID: 17342319] - Peter Viberg, Karl-Gustav Wahlund, Kerstin Skog. On-line capillary based quantitative analysis of a heterocyclic amine in human urine.
Journal of chromatography. A.
2006 Nov; 1133(1-2):347-52. doi:
10.1016/j.chroma.2006.08.034. [PMID: 16962602] - Michael A Malfatti, Karen H Dingley, Susan Nowell-Kadlubar, Esther A Ubick, Nisha Mulakken, David Nelson, Nicholas P Lang, James S Felton, Kenneth W Turteltaub. The urinary metabolite profile of the dietary carcinogen 2-amino-1-methyl-6-phenylimidazo[4,5-b]pyridine is predictive of colon DNA adducts after a low-dose exposure in humans.
Cancer research.
2006 Nov; 66(21):10541-7. doi:
10.1158/0008-5472.can-06-1573. [PMID: 17079477] - M L H Vlaming, K Mohrmann, E Wagenaar, D R de Waart, R P J Oude Elferink, J S Lagas, O van Tellingen, L D Vainchtein, H Rosing, J H Beijnen, J H M Schellens, A H Schinkel. Carcinogen and anticancer drug transport by Mrp2 in vivo: studies using Mrp2 (Abcc2) knockout mice.
The Journal of pharmacology and experimental therapeutics.
2006 Jul; 318(1):319-27. doi:
10.1124/jpet.106.101774. [PMID: 16611851] - Lynn Vanhaecke, Nathalie Van Hoof, Willem Van Brabandt, Bram Soenen, Arne Heyerick, Norbert De Kimpe, Denis De Keukeleire, Willy Verstraete, Tom Van de Wiele. Metabolism of the food-associated carcinogen 2-amino-1-methyl-6-phenylimidazo[4,5-b]pyridine by human intestinal microbiota.
Journal of agricultural and food chemistry.
2006 May; 54(9):3454-61. doi:
10.1021/jf053170+. [PMID: 16637707] - Sunita B Jones, James D Brooks. Modest induction of phase 2 enzyme activity in the F-344 rat prostate.
BMC cancer.
2006 Mar; 6(?):62. doi:
10.1186/1471-2407-6-62. [PMID: 16539699] - Michael A Malfatti, Esther A Ubick, James S Felton. The impact of glucuronidation on the bioactivation and DNA adduction of the cooked-food carcinogen 2-amino-1-methyl-6-phenylimidazo[4,5-b]pyridine in vivo.
Carcinogenesis.
2005 Nov; 26(11):2019-28. doi:
10.1093/carcin/bgi151. [PMID: 15944213] - Connie Cheung, Xiaochao Ma, Kristopher W Krausz, Shioko Kimura, Lionel Feigenbaum, Timothy P Dalton, Daniel W Nebert, Jeffrey R Idle, Frank J Gonzalez. Differential metabolism of 2-amino-1-methyl-6-phenylimidazo[4,5-b]pyridine (PhIP) in mice humanized for CYP1A1 and CYP1A2.
Chemical research in toxicology.
2005 Sep; 18(9):1471-8. doi:
10.1021/tx050136g. [PMID: 16167840]
