Ethenodeoxyadenosine (BioDeep_00000026834)

   

human metabolite Endogenous


代谢物信息卡片


(2R,3S,5R)-2-(hydroxymethyl)-5-{3H-imidazo[2,1-f]purin-3-yl}oxolan-3-ol

化学式: C12H13N5O3 (275.1018348)
中文名称:
谱图信息: 最多检出来源 () 0%

分子结构信息

SMILES: C1C(C(OC1N2C=NC3=C2N=CN4C3=NC=C4)CO)O
InChI: InChI=1S/C12H13N5O3/c18-4-8-7(19)3-9(20-8)17-6-14-10-11-13-1-2-16(11)5-15-12(10)17/h1-2,5-9,18-19H,3-4H2

描述信息

Etheno nucleosides are a new class of chemically modified components of nucleic acids. These base-modified nucleosides demonstrate significant biological properties, acting, among others, as antiviral or antitumor agents. One of the possible modifications of the nucleoside is their transformation into ethenonucleosides. Thus, nucleosides or their respective heterocyclic bases, possessing an exocyclic amino group, as well as a neighboring endocyclic nitrogen, can react with some bifunctional reagents (e.g., α-halocarbonyl compounds) to form products with an additional five-membered ring of the imidazole type. The ethenonucleosides basically do not occur in nature; some of the only exceptions are Y-nucleosides. Etheno modified DNA bases are generated from the carcinogens vinyl chloride and urethane, but also by reactions of DNA with products derived from lipid peroxidation (LPO) and oxidative stress via endogenous pathways. Highly variable background levels of epsilon-adducts were detected in DNA from different organs of unexposed humans and rodents. Several known cancer risk factors increased the level of these DNA lesions in target organs: elevated epsilon-adducts were found in hepatic DNA from patients with metal storage diseases, after overproduction of nitric oxide (NO) by inducible NO synthase (iNOS) in a mouse model, and in colonic polyps of familial adenomatous polyposis patients. A high omega-6-polyunsaturated fatty acid diet increased epsilon-DNA adducts in white blood cells of female subjects. (PMID:10882861).
Etheno (epsilon) modified DNA bases are generated from the carcinogens vinyl chloride and urethane, but also by reactions of DNA with products derived from lipid peroxidation (LPO) and oxidative stress via endogenous pathways. Highly variable background levels of epsilon-adducts were detected in DNA from different organs of unexposed humans and rodents. Several known cancer risk factors increased the level of these DNA lesions in target organs: elevated epsilon-adducts were found in hepatic DNA from patients with metal storage diseases, after overproduction of nitric oxide (NO) by inducible NO synthase (iNOS) in a mouse model, and in colonic polyps of familial adenomatous polyposis patients. A high omega-6-polyunsaturated fatty acid diet increased epsilon-DNA adducts in white blood cells of female subjects. (PMID: 10882861) [HMDB]
N6-Etheno 2'-deoxyadenosine is a reactive oxygen species (ROS)/reactive nitrogen species (RNS)-induced DNA oxidation product, used as a biomarker to evaluate chronic inflammation and lipid peroxidation in animal or human tissues[1].

同义名列表

12 个代谢物同义名

(2R,3S,5R)-2-(hydroxymethyl)-5-{3H-imidazo[2,1-f]purin-3-yl}oxolan-3-ol; 2-Deoxy-2-deuteroethenoadenosine; N1,N6-etheno-2-Deoxyadenosine; 1,N6-Etheno-2-deoxyadenosine; 1,N2-Etheno-2-deoxyguanosine; 1,N(6)-Ethenodeoxyadenosine; 1,N(6)-Deoxyethenoadenosine; N6-Etheno 2-deoxyadenosine; 1,N6-Ethenodeoxyadenosine; Ethenodeoxyadenosine; 1,N6-etheno-DA; N6-Etheno 2'-deoxyadenosine



数据库引用编号

10 个数据库交叉引用编号

分类词条

相关代谢途径

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代谢反应

0 个相关的代谢反应过程信息。

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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

  • M L Shen, Z N He, X Zhang, H W Duan, Y Niu, P Bin, M Ye, T Meng, Y F Dai, S F Yu, W Chen, Y X Zheng. [Association of etheno-DNA adduct and DNA methylation level among workers exposed to diesel engine exhaust]. Zhonghua yu fang yi xue za zhi [Chinese journal of preventive medicine]. 2017 Jun; 51(6):556-561. doi: 10.3760/cma.j.issn.0253-9624.2017.06.019. [PMID: 28592103]
  • Somkid Dechakhamphu, Somchai Pinlaor, Paiboon Sitthithaworn, Helmut Bartsch, Puangrat Yongvanit. Accumulation of miscoding etheno-DNA adducts and highly expressed DNA repair during liver fluke-induced cholangiocarcinogenesis in hamsters. Mutation research. 2010 Sep; 691(1-2):9-16. doi: 10.1016/j.mrfmmm.2010.06.003. [PMID: 20541562]
  • Plamen P Christov, Katya V Petrova, Ganesh Shanmugam, Ivan D Kozekov, Albena Kozekova, F Peter Guengerich, Michael P Stone, Carmelo J Rizzo. Comparison of the in vitro replication of the 7-(2-oxoheptyl)-1,N2-etheno-2'-deoxyguanosine and 1,N2-etheno-2'-deoxyguanosine lesions by Sulfolobus solfataricus P2 DNA polymerase IV (Dpo4). Chemical research in toxicology. 2010 Aug; 23(8):1330-41. doi: 10.1021/tx100082e. [PMID: 20578729]
  • Mayura Meerang, Jagadeesan Nair, Pornpan Sirankapracha, Chonthida Thephinlap, Somdet Srichairatanakool, Khelifa Arab, Ruchaneekorn Kalpravidh, Jim Vadolas, Suthat Fucharoen, Helmut Bartsch. Accumulation of lipid peroxidation-derived DNA lesions in iron-overloaded thalassemic mouse livers: comparison with levels in the lymphocytes of thalassemia patients. International journal of cancer. 2009 Aug; 125(4):759-66. doi: 10.1002/ijc.24412. [PMID: 19480008]
  • K Arab, M Pedersen, J Nair, M Meerang, L E Knudsen, H Bartsch. Typical signature of DNA damage in white blood cells: a pilot study on etheno adducts in Danish mother-newborn child pairs. Carcinogenesis. 2009 Feb; 30(2):282-5. doi: 10.1093/carcin/bgn264. [PMID: 19037091]
  • Somkid Dechakhamphu, Puangrat Yongvanit, Jagadeesan Nair, Somchai Pinlaor, Paiboon Sitthithaworn, Helmut Bartsch. High excretion of etheno adducts in liver fluke-infected patients: protection by praziquantel against DNA damage. Cancer epidemiology, biomarkers & prevention : a publication of the American Association for Cancer Research, cosponsored by the American Society of Preventive Oncology. 2008 Jul; 17(7):1658-64. doi: 10.1158/1055-9965.epi-08-0191. [PMID: 18628417]
  • Mayura Meerang, Jagadeesan Nair, Pornpan Sirankapracha, Chonthida Thephinlap, Somdet Srichairatanakool, Suthat Fucharoen, Helmut Bartsch. Increased urinary 1,N6-ethenodeoxyadenosine and 3,N4-ethenodeoxycytidine excretion in thalassemia patients: markers for lipid peroxidation-induced DNA damage. Free radical biology & medicine. 2008 May; 44(10):1863-8. doi: 10.1016/j.freeradbiomed.2008.02.009. [PMID: 18342016]
  • Qingming Fang, Jagadeesan Nair, Xin Sun, Dimiter Hadjiolov, Helmut Bartsch. Etheno-DNA adduct formation in rats gavaged with linoleic acid, oleic acid and coconut oil is organ- and gender specific. Mutation research. 2007 Nov; 624(1-2):71-9. doi: 10.1016/j.mrfmmm.2007.04.002. [PMID: 17521682]
  • Katya V Petrova, Ravikumar S Jalluri, Ivan D Kozekov, Carmelo J Rizzo. Mechanism of 1,N2-etheno-2'-deoxyguanosine formation from epoxyaldehydes. Chemical research in toxicology. 2007 Nov; 20(11):1685-92. doi: 10.1021/tx7001433. [PMID: 17907786]
  • Jagadeesan Nair, Silvio De Flora, Alberto Izzotti, Helmut Bartsch. Lipid peroxidation-derived etheno-DNA adducts in human atherosclerotic lesions. Mutation research. 2007 Aug; 621(1-2):95-105. doi: 10.1016/j.mrfmmm.2007.02.013. [PMID: 17412369]
  • Andreas Brink, Ursula Lutz, Wolfgang Völkel, Werner K Lutz. Simultaneous determination of O6-methyl-2'-deoxyguanosine, 8-oxo-7,8-dihydro-2'-deoxyguanosine, and 1,N6-etheno-2'-deoxyadenosine in DNA using on-line sample preparation by HPLC column switching coupled to ESI-MS/MS. Journal of chromatography. B, Analytical technologies in the biomedical and life sciences. 2006 Jan; 830(2):255-61. doi: 10.1016/j.jchromb.2005.10.046. [PMID: 16298174]
  • Jagadeesan Nair, Olga Sinitsina, Elena A Vasunina, Georgy A Nevinsky, Jacques Laval, Helmut Bartsch. Age-dependent increase of etheno-DNA-adducts in liver and brain of ROS overproducing OXYS rats. Biochemical and biophysical research communications. 2005 Oct; 336(2):478-82. doi: 10.1016/j.bbrc.2005.08.114. [PMID: 16137653]
  • Peter R Hillestrøm, Kristiina Nyssönen, Tomi-Pekka Tuomainen, Eero Pukkala, Jukka T Salonen, Henrik E Poulsen. Urinary excretion of epsilondA is not predictive of cancer development: a prospective nested case-control study. Free radical research. 2005 Jan; 39(1):51-3. doi: 10.1080/10715760400022103. [PMID: 15875811]
  • Peter R Hillestrøm, Anne-Mette Hoberg, Allan Weimann, Henrik E Poulsen. Quantification of 1,N6-etheno-2'-deoxyadenosine in human urine by column-switching LC/APCI-MS/MS. Free radical biology & medicine. 2004 Jun; 36(11):1383-92. doi: 10.1016/j.freeradbiomed.2004.02.068. [PMID: 15135174]
  • Alexander Frank, Helmut K Seitz, Helmut Bartsch, Norbert Frank, Jagadeesan Nair. Immunohistochemical detection of 1,N6-ethenodeoxyadenosine in nuclei of human liver affected by diseases predisposing to hepato-carcinogenesis. Carcinogenesis. 2004 Jun; 25(6):1027-31. doi: 10.1093/carcin/bgh089. [PMID: 14742317]
  • Alain Barbin, Rong Wang, Peter J O'Connor, Rhoderick H Elder. Increased formation and persistence of 1,N(6)-ethenoadenine in DNA is not associated with higher susceptibility to carcinogenesis in alkylpurine-DNA-N-glycosylase knockout mice treated with vinyl carbamate. Cancer research. 2003 Nov; 63(22):7699-703. doi: ". [PMID: 14633693]
  • R Godschalk, J Nair, F J van Schooten, A Risch, P Drings, K Kayser, H Dienemann, H Bartsch. Comparison of multiple DNA adduct types in tumor adjacent human lung tissue: effect of cigarette smoking. Carcinogenesis. 2002 Dec; 23(12):2081-6. doi: 10.1093/carcin/23.12.2081. [PMID: 12507931]
  • Tomoyuki Hanaoka, Jagadeesan Nair, Yoshiko Takahashi, Satoshi Sasaki, Helmut Bartsch, Shoichiro Tsugane. Urinary level of 1,N(6) -ethenodeoxyadenosine, a marker of oxidative stress, is associated with salt excretion and omega 6-polyunsaturated fatty acid intake in postmenopausal Japanese women. International journal of cancer. 2002 Jul; 100(1):71-5. doi: 10.1002/ijc.10437. [PMID: 12115589]
  • T Hagenlocher, J Nair, N Becker, A Korfmann, H Bartsch. Influence of dietary fatty acid, vegetable, and vitamin intake on etheno-DNA adducts in white blood cells of healthy female volunteers: a pilot study. Cancer epidemiology, biomarkers & prevention : a publication of the American Association for Cancer Research, cosponsored by the American Society of Preventive Oncology. 2001 Nov; 10(11):1187-91. doi: NULL. [PMID: 11700267]
  • P Navasumrit, T H Ward, P J O'Connor, J Nair, N Frank, H Bartsch. Ethanol enhances the formation of endogenously and exogenously derived adducts in rat hepatic DNA. Mutation research. 2001 Aug; 479(1-2):81-94. doi: 10.1016/s0027-5107(01)00156-7. [PMID: 11470483]
  • D Rindgen, S H Lee, M Nakajima, I A Blair. Formation of a substituted 1,N(6)-etheno-2'-deoxyadenosine adduct by lipid hydroperoxide-mediated generation of 4-oxo-2-nonenal. Chemical research in toxicology. 2000 Sep; 13(9):846-52. doi: 10.1021/tx0000771. [PMID: 10995257]
  • J Nair, G Fürstenberger, F Bürger, F Marks, H Bartsch. Promutagenic etheno-DNA adducts in multistage mouse skin carcinogenesis: correlation with lipoxygenase-catalyzed arachidonic acid metabolism. Chemical research in toxicology. 2000 Aug; 13(8):703-9. doi: 10.1021/tx000045d. [PMID: 10956057]
  • K Schmid, J Nair, G Winde, I Velic, H Bartsch. Increased levels of promutagenic etheno-DNA adducts in colonic polyps of FAP patients. International journal of cancer. 2000 Jul; 87(1):1-4. doi: 10.1002/1097-0215(20000701)87:1<1::aid-ijc1>3.0.co;2-c. [PMID: 10861445]
  • H Bartsch, J Nair. New DNA-based biomarkers for oxidative stress and cancer chemoprevention studies. European journal of cancer (Oxford, England : 1990). 2000 Jun; 36(10):1229-34. doi: 10.1016/s0959-8049(00)00095-2. [PMID: 10882861]
  • Y Yang, J Nair, A Barbin, H Bartsch. Immunohistochemical detection of 1,N(6)-ethenodeoxyadenosine, a promutagenic DNA adduct, in liver of rats exposed to vinyl chloride or an iron overload. Carcinogenesis. 2000 Apr; 21(4):777-81. doi: 10.1093/carcin/21.4.777. [PMID: 10753215]
  • M Moriya, G A Pandya, F Johnson, A P Grollman. Cellular response to exocyclic DNA adducts. IARC scientific publications. 1999; ?(150):263-70. doi: NULL. [PMID: 10626226]
  • J Nair. Lipid peroxidation-induced etheno-DNA adducts in humans. IARC scientific publications. 1999; ?(150):55-61. doi: NULL. [PMID: 10626208]
  • W P Watson, J P Aston, T Barlow, A E Crane, D Potter, T Brown. Detection of 1,N6-etheno-2'-deoxyadenosine and 3,N4-etheno-2'-deoxycytidine occurring endogenously in DNA. IARC scientific publications. 1999; ?(150):63-73. doi: ". [PMID: 10626209]
  • J Nair, A Gal, S Tamir, S R Tannenbaum, G N Wogan, H Bartsch. Etheno adducts in spleen DNA of SJL mice stimulated to overproduce nitric oxide. Carcinogenesis. 1998 Dec; 19(12):2081-4. doi: 10.1093/carcin/19.12.2081. [PMID: 9886560]
  • J Nair, P L Carmichael, R C Fernando, D H Phillips, A J Strain, H Bartsch. Lipid peroxidation-induced etheno-DNA adducts in the liver of patients with the genetic metal storage disorders Wilson's disease and primary hemochromatosis. Cancer epidemiology, biomarkers & prevention : a publication of the American Association for Cancer Research, cosponsored by the American Society of Preventive Oncology. 1998 May; 7(5):435-40. doi: ". [PMID: 9610794]
  • J Nair, C E Vaca, I Velic, M Mutanen, L M Valsta, H Bartsch. High dietary omega-6 polyunsaturated fatty acids drastically increase the formation of etheno-DNA base adducts in white blood cells of female subjects. Cancer epidemiology, biomarkers & prevention : a publication of the American Association for Cancer Research, cosponsored by the American Society of Preventive Oncology. 1997 Aug; 6(8):597-601. doi: ". [PMID: 9264272]
  • G A Pandya, M Moriya. 1,N6-ethenodeoxyadenosine, a DNA adduct highly mutagenic in mammalian cells. Biochemistry. 1996 Sep; 35(35):11487-92. doi: 10.1021/bi960170h. [PMID: 8784204]
  • Y Guichard, F el Ghissassi, J Nair, H Bartsch, A Barbin. Formation and accumulation of DNA ethenobases in adult Sprague-Dawley rats exposed to vinyl chloride. Carcinogenesis. 1996 Aug; 17(8):1553-9. doi: 10.1093/carcin/17.8.1553. [PMID: 8761409]
  • J Nair, A Barbin, Y Guichard, H Bartsch. 1,N6-ethenodeoxyadenosine and 3,N4-ethenodeoxycytine in liver DNA from humans and untreated rodents detected by immunoaffinity/32P-postlabeling. Carcinogenesis. 1995 Mar; 16(3):613-7. doi: 10.1093/carcin/16.3.613. [PMID: 7697821]
  • J A Swenberg, N Fedtke, F Ciroussel, A Barbin, H Bartsch. Etheno adducts formed in DNA of vinyl chloride-exposed rats are highly persistent in liver. Carcinogenesis. 1992 Apr; 13(4):727-9. doi: 10.1093/carcin/13.4.727. [PMID: 1576725]