2-Amino-3-methylimidazo(4,5-F)quinoline (BioDeep_00000409806)

Main id: BioDeep_00000003641

 


代谢物信息卡片


2-Amino-3-methyl-imidazo[4,5-f]quinoline (IQ)

化学式: C11H10N4 (198.090542)
中文名称: 2-氨基-3-甲基-3H-咪唑并[4,5-F]喹啉
谱图信息: 最多检出来源 () 0%

分子结构信息

SMILES: CN1C(N)=NC2=C1C=CC1=NC=CC=C21
InChI: InChI=1S/C11H10N4/c1-15-9-5-4-8-7(3-2-6-13-8)10(9)14-11(15)12/h2-6H,1H3,(H2,12,14)

描述信息

CONFIDENCE standard compound; INTERNAL_ID 2437

同义名列表

3 个代谢物同义名

3-methyl-3H-imidazo[4,5-f]quinolin-2-amine; 2-Amino-3-methylimidazo(4,5-F)quinoline; 2-Amino-3-methyl-imidazo[4,5-f]quinoline (IQ)



数据库引用编号

13 个数据库交叉引用编号

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)

0 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

  • Adriana Nowak, Agata Czyżowska, Krzysztof Huben, Michał Sójka, Sławomir Kuberski, Anna Otlewska, Katarzyna Śliżewska. Prebiotics and age, but not probiotics affect the transformation of 2-amino-3-methyl-3H-imidazo[4,5-f]quinoline (IQ) by fecal microbiota - An in vitro study. Anaerobe. 2016 Jun; 39(?):124-35. doi: 10.1016/j.anaerobe.2016.03.009. [PMID: 27034248]
  • Adriana Nowak, Agata Czyżowska, Małgorzata Stańczyk. Protective activity of probiotic bacteria against 2-amino-3-methyl-3H-imidazo[4,5-f]quinoline (IQ) and 2-amino-1-methyl-6-phenyl-1H-imidazo[4,5-b]pyridine (PhIP) - an in vitro study. Food additives & contaminants. Part A, Chemistry, analysis, control, exposure & risk assessment. 2015; 32(11):1927-38. doi: 10.1080/19440049.2015.1084651. [PMID: 26295367]
  • Adriana Nowak, Katarzyna Śliżewska. β-Glucuronidase and β-glucosidase activity and human fecal water genotoxicity in the presence of probiotic lactobacilli and the heterocyclic aromatic amine IQ in vitro. Environmental toxicology and pharmacology. 2014 Jan; 37(1):66-73. doi: 10.1016/j.etap.2013.10.014. [PMID: 24309132]
  • Xiao-Li Xie, Min Wei, Anna Kakehashi, Shotaro Yamano, Kyoko Okabe, Masaki Tajiri, Hideki Wanibuchi. Dammar resin, a non-mutagen, induces [corrected] oxidative stress and metabolic enzymes in the liver of gpt delta transgenic mouse which is different from a mutagen, 2-amino-3-methylimidazo[4,5-f]quinoline. Mutation research. 2012 Oct; 748(1-2):29-35. doi: 10.1016/j.mrgentox.2012.06.005. [PMID: 22766412]
  • Ezar Hafez, Tetsuyuki Takahashi, Hirohisa Ogawa, Makoto Sato, Tokiko Nakai, Chie Takasu, Hisanori Uehara, Keisuke Izumi. High susceptibility to zymbal gland and intestinal carcinogenesis in diabetic Otsuka long-evans Tokushima Fatty rats. Journal of toxicologic pathology. 2011 Dec; 24(4):187-93. doi: 10.1293/tox.24.187. [PMID: 22319230]
  • Marek Banasik, Todd Stedeford, Robert P Strosznajder, Masanori Takehashi, Seigo Tanaka, Kunihiro Ueda. Inhibition of poly(ADP-ribose) polymerase-1 attenuates the toxicity of carbon tetrachloride. Journal of enzyme inhibition and medicinal chemistry. 2011 Dec; 26(6):883-9. doi: 10.3109/14756366.2011.557315. [PMID: 21395487]
  • Lynnette R Ferguson, Philip J Harris, Philip Kestell, Shuotun Zhu, Rex Munday, Christine M Munday. Comparative effects in rats of intact wheat bran and two wheat bran fractions on the disposition of the mutagen 2-amino-3-methylimidazo[4,5-f]quinoline. Mutation research. 2011 Nov; 716(1-2):59-65. doi: 10.1016/j.mrfmmm.2011.08.005. [PMID: 21939672]
  • 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]
  • Alva Biran, Hadar Ben Yoav, Sharon Yagur-Kroll, Rami Pedahzur, Sebastian Buchinger, Yosi Shacham-Diamand, Georg Reifferscheid, Shimshon Belkin. Microbial genotoxicity bioreporters based on sulA activation. Analytical and bioanalytical chemistry. 2011 Jul; 400(9):3013-24. doi: 10.1007/s00216-011-5007-2. [PMID: 21533638]
  • Monica Borgatti, Irene Mancini, Nicoletta Bianchi, Alessandra Guerrini, Ilaria Lampronti, Damiano Rossi, Gianni Sacchetti, Roberto Gambari. Bergamot (Citrus bergamia Risso) fruit extracts and identified components alter expression of interleukin 8 gene in cystic fibrosis bronchial epithelial cell lines. BMC biochemistry. 2011 Apr; 12(?):15. doi: 10.1186/1471-2091-12-15. [PMID: 21496221]
  • Natalya Hanlon, Nattaya Konsue, Nick Coldham, Maurice J Sauer, Costas Ioannides. Exposure to isothiocyanates suppresses urinary mutagenicity in rats treated with heterocyclic amine IQ: lack of association with CYP1 activity. Nutrition and cancer. 2011; 63(2):300-5. doi: 10.1080/01635581.2011.530735. [PMID: 21298592]
  • 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]
  • Paromita Raychaudhury, Ashis K Basu. Replication Past the γ-Radiation-Induced Guanine-Thymine Cross-Link G[8,5-Me]T by Human and Yeast DNA Polymerase η. Journal of nucleic acids. 2010 Sep; 2010(?):. doi: 10.4061/2010/101495. [PMID: 20936176]
  • Catherine Cornu, Laurent Remontet, Florence Noel-Baron, Alain Nicolas, Nathalie Feugier-Favier, Pascal Roy, Bruno Claustrat, Mitra Saadatian-Elahi, Behrouz Kassaï. A dietary supplement to improve the quality of sleep: a randomized placebo controlled trial. BMC complementary and alternative medicine. 2010 Jun; 10(?):29. doi: 10.1186/1472-6882-10-29. [PMID: 20569455]
  • Hwan-Goo Kang, Sang-Hee Jeong, Joon-Hyoung Cho. Antimutagenic and anticarcinogenic effect of methanol extracts of Petasites japonicus Maxim leaves. Journal of veterinary science. 2010 Mar; 11(1):51-8. doi: 10.4142/jvs.2010.11.1.51. [PMID: 20195065]
  • Chiung-Huei Peng, Wen-Ta Chiu, Chi-Wen Juan, Jeng-Leun Mau, Chien-Chou Chen, Chiung-Chi Peng, Eric-Yc Lai, Charng-Cherng Chyau. Pivotal role of curcuminoids on the antimutagenic activity of Curcuma zedoaria extracts. Drug and chemical toxicology. 2010; 33(1):64-76. doi: 10.3109/01480540903170738. [PMID: 19995306]
  • Fong-Fu Hsu, Vijaya M Lakshmi, Terry V Zenser. Characterization of new metabolites from in vivo biotransformation of 2-amino-3-methylimidazo[4,5-f]quinoline in mouse by mass spectrometry. Journal of mass spectrometry : JMS. 2009 Sep; 44(9):1359-68. doi: 10.1002/jms.1620. [PMID: 19629964]
  • Mojgan Najafzadeh, P Dominic Reynolds, Adolf Baumgartner, Diana Anderson. Flavonoids inhibit the genotoxicity of hydrogen peroxide (H(2)O(2)) and of the food mutagen 2-amino-3-methylimadazo[4,5-f]-quinoline (IQ) in lymphocytes from patients with inflammatory bowel disease (IBD). Mutagenesis. 2009 Sep; 24(5):405-11. doi: 10.1093/mutage/gep016. [PMID: 19553277]
  • Vijaya M Lakshmi, Fong-Fu Hsu, Terry V Zenser. Identification of new 2-amino-3-methylimidazo[4,5-f]quinoline urinary metabolites from beta-naphthoflavone-treated mice. Drug metabolism and disposition: the biological fate of chemicals. 2009 Aug; 37(8):1690-7. doi: 10.1124/dmd.109.027342. [PMID: 19451400]
  • N Konsue, C Ioannides. Tissue differences in the modulation of rat cytochromes P450 and phase II conjugation systems by dietary doses of phenethyl isothiocyanate. Food and chemical toxicology : an international journal published for the British Industrial Biological Research Association. 2008 Dec; 46(12):3677-83. doi: 10.1016/j.fct.2008.09.046. [PMID: 18929617]
  • Vijaya M Lakshmi, Fong Fu Hsu, Terry V Zenser. N-Demethylation is a major route of 2-amino-3-methylimidazo[4,5-f]quinoline metabolism in mouse. Drug metabolism and disposition: the biological fate of chemicals. 2008 Jun; 36(6):1143-52. doi: 10.1124/dmd.107.019166. [PMID: 18356269]
  • Javor Kac, Janja Plazar, Ales Mlinaric, Bojana Zegura, Tamara T Lah, Metka Filipic. Antimutagenicity of hops (Humulus lupulus L.): bioassay-directed fractionation and isolation of xanthohumol. Phytomedicine : international journal of phytotherapy and phytopharmacology. 2008 Mar; 15(3):216-20. doi: 10.1016/j.phymed.2007.09.008. [PMID: 17959367]
  • Christèle Humblot, Michaël Murkovic, Lionel Rigottier-Gois, Martine Bensaada, Anthony Bouclet, Claude Andrieux, Jamila Anba, Sylvie Rabot. Beta-glucuronidase in human intestinal microbiota is necessary for the colonic genotoxicity of the food-borne carcinogen 2-amino-3-methylimidazo[4,5-f]quinoline in rats. Carcinogenesis. 2007 Nov; 28(11):2419-25. doi: 10.1093/carcin/bgm170. [PMID: 17660508]
  • Janja Plazar, Bojana Zegura, Tamara T Lah, Metka Filipic. Protective effects of xanthohumol against the genotoxicity of benzo(a)pyrene (BaP), 2-amino-3-methylimidazo[4,5-f]quinoline (IQ) and tert-butyl hydroperoxide (t-BOOH) in HepG2 human hepatoma cells. Mutation research. 2007 Aug; 632(1-2):1-8. doi: 10.1016/j.mrgentox.2007.03.013. [PMID: 17590382]
  • Harvey J Armbrecht, Vijaya M Lakshmi, Jason Wickstra, Fong Fu Hsu, Terry V Zenser. Metabolism of a heterocyclic amine colon carcinogen in young and old rats. Drug metabolism and disposition: the biological fate of chemicals. 2007 Apr; 35(4):633-9. doi: 10.1124/dmd.106.013532. [PMID: 17251306]
  • Daniela Diehl, Doris Oesterle, Martin W Elmlinger, Andreas Hoeflich, Eckhard Wolf, Harald Lahm. IGF-II transgenic mice display increased aberrant colon crypt multiplicity and tumor volume after 1,2-dimethylhydrazine treatment. Journal of carcinogenesis. 2006 Nov; 5(?):24. doi: 10.1186/1477-3163-5-24. [PMID: 17118177]
  • 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]
  • Yasuki Kitamura, Takashi Umemura, Kazushi Okazaki, Keita Kanki, Takayoshi Imazawa, Toshiaki Masegi, Akiyoshi Nishikawa, Masao Hirose. Enhancing effects of simultaneous treatment with sodium nitrite on 2-amino-3-methylimidazo[4,5-f]quinoline-induced rat liver, colon and Zymbal's gland carcinogenesis after initiation with diethylnitrosamine and 1,2-dimethylhydrazine. International journal of cancer. 2006 May; 118(10):2399-404. doi: 10.1002/ijc.21649. [PMID: 16353153]
  • Yasuki Kitamura, Takashi Umemura, Keita Kanki, Yuji Ishii, Yuichi Kuroiwa, Toshiaki Masegi, Akiyoshi Nishikawa, Masao Hirose. Lung as a new target in rats of 2-amino-3-methylimidazo[4,5-f]quinoline carcinogenesis: results of a two-stage model initiated with N-bis(2-hydroxypropyl)nitrosamine. Cancer science. 2006 May; 97(5):368-73. doi: 10.1111/j.1349-7006.2006.00191.x. [PMID: 16630133]
  • 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]
  • Antonius E van Herwaarden, Els Wagenaar, Barbara Karnekamp, Gracia Merino, Johan W Jonker, Alfred H Schinkel. Breast cancer resistance protein (Bcrp1/Abcg2) reduces systemic exposure of the dietary carcinogens aflatoxin B1, IQ and Trp-P-1 but also mediates their secretion into breast milk. Carcinogenesis. 2006 Jan; 27(1):123-30. doi: 10.1093/carcin/bgi176. [PMID: 16000399]
  • Sevtap Aydin, A Ahmet Başaran, Nurşen Başaran. The effects of thyme volatiles on the induction of DNA damage by the heterocyclic amine IQ and mitomycin C. Mutation research. 2005 Mar; 581(1-2):43-53. doi: 10.1016/j.mrgentox.2004.10.017. [PMID: 15725604]
  • Ricky D Holland, Theresa Gehring, Jason Taylor, Brian G Lake, Nigel J Gooderham, Robert J Turesky. Formation of a mutagenic heterocyclic aromatic amine from creatinine in urine of meat eaters and vegetarians. Chemical research in toxicology. 2005 Mar; 18(3):579-90. doi: 10.1021/tx049675w. [PMID: 15777097]
  • C L Chepanoske, K Brown, K W Turteltaub, K H Dingley. Characterization of a peptide adduct formed by N-acetoxy-2-amino-1-methyl-6-phenylimidazo[4,5-b]pyridine (PhIP), a reactive intermediate of the food carcinogen PhIP. Food and chemical toxicology : an international journal published for the British Industrial Biological Research Association. 2004 Aug; 42(8):1367-72. doi: 10.1016/j.fct.2003.11.012. [PMID: 15207388]
  • V R Yoxall, D A Parker, P A Kentish, C Ioannides. Short-term black tea intake modulates the excretion of urinary mutagens in rats treated with 2-amino-3-methylimidazo-[4,5-f]quinoline (IQ): role of CYP1A2 upregulation. Archives of toxicology. 2004 Aug; 78(8):477-82. doi: 10.1007/s00204-004-0562-3. [PMID: 15034640]
  • Victoria Yoxall, Judith Wilson, Costas Ioannides. An improved method for the extraction of mutagens from human urine and cooked meat using blue rayon. Mutation research. 2004 Apr; 559(1-2):121-30. doi: 10.1016/j.mrgentox.2004.01.006. [PMID: 15066580]
  • P Kestell, S Zhu, L R Ferguson. Mechanisms by which resistant starches and non-starch polysaccharide sources affect the metabolism and disposition of the food carcinogen, 2-amino-3-methylimidazo[4,5-f]quinoline. Journal of chromatography. B, Analytical technologies in the biomedical and life sciences. 2004 Mar; 802(1):201-10. doi: 10.1016/j.jchromb.2003.10.046. [PMID: 15036012]
  • F Kassie, E F Lhoste, A Bruneau, M Zsivkovits, F Ferk, M Uhl, T Zidek, S Knasmüller. Effect of intestinal microfloras from vegetarians and meat eaters on the genotoxicity of 2-amino-3-methylimidazo[4,5-f]quinoline, a carcinogenic heterocyclic amine. Journal of chromatography. B, Analytical technologies in the biomedical and life sciences. 2004 Mar; 802(1):211-5. doi: 10.1016/j.jchromb.2003.10.045. [PMID: 15036013]
  • Tian-Wei Yu, Meirong Xu, Roderick H Dashwood. Antimutagenic activity of spearmint. Environmental and molecular mutagenesis. 2004; 44(5):387-93. doi: 10.1002/em.20063. [PMID: 15529323]
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  • Markus Zsivkovits, Kassie Fekadu, Gerhard Sontag, Ursula Nabinger, Wolfgang W Huber, Michael Kundi, Asima Chakraborty, Helmuth Foissy, Siegfried Knasmüller. Prevention of heterocyclic amine-induced DNA damage in colon and liver of rats by different lactobacillus strains. Carcinogenesis. 2003 Dec; 24(12):1913-8. doi: 10.1093/carcin/bgg167. [PMID: 12970070]
  • Vibeke M Breinholt, Anne Marie Mølck, Gitte W Svendsen, Bahram Daneshvar, Anne M Vinggaard, Morten Poulsen, Lars O Dragsted. Effects of dietary antioxidants and 2-amino-3-methylimidazo[4,5-f]- quinoline (IQ) on preneoplastic lesions and on oxidative damage, hormonal status, and detoxification capacity in the rat. Food and chemical toxicology : an international journal published for the British Industrial Biological Research Association. 2003 Oct; 41(10):1315-23. doi: 10.1016/s0278-6915(03)00122-4. [PMID: 12909264]
  • R H Dashwood, M Xu. The disposition and metabolism of 2-amino-3-methylimidazo-[4,5-f]quinoline in the F344 rat at high versus low doses of indole-3-carbinol. Food and chemical toxicology : an international journal published for the British Industrial Biological Research Association. 2003 Aug; 41(8):1185-92. doi: 10.1016/s0278-6915(03)00110-8. [PMID: 12842187]
  • Peter Møller, Max Hansen, Herman Autrup, Jette Bornholt, Ulla Vogel, Anne-Marie Mølck, Håkan Wallin, Lars O Dragsted, Lotte Risom, Henrik E Poulsen, Steffen Loft. Dietary low-dose sucrose modulation of IQ-induced genotoxicity in the colon and liver of Big Blue rats. Mutation research. 2003 Jun; 527(1-2):91-7. doi: 10.1016/s0027-5107(03)00058-7. [PMID: 12787917]
  • Lynnette R Ferguson, Shuotun Zhu, Philip Kestell. Contrasting effects of non-starch polysaccharide and resistant starch-based diets on the disposition and excretion of the food carcinogen, 2-amino-3-methylimidazo[4,5-f]quinoline (IQ), in a rat model. Food and chemical toxicology : an international journal published for the British Industrial Biological Research Association. 2003 Jun; 41(6):785-92. doi: 10.1016/s0278-6915(03)00012-7. [PMID: 12738184]
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