Dimethylarsinous acid (BioDeep_00000013356)

 

Secondary id: BioDeep_00001868952

human metabolite Endogenous Cytotoxicity


代谢物信息卡片


Dimethylarsinous-acid

化学式: C2H7AsO (121.9712832)
中文名称:
谱图信息: 最多检出来源 Homo sapiens(blood) 40%

分子结构信息

SMILES: C[As](C)O
InChI: InChI=1S/C2H7AsO/c1-3(2)4/h4H,1-2H3

描述信息

Dimethylarsinous acid is a reactive organic intermediate of dimethylarsinic acid involved in toxicity. Dimethylarsinous acid is detected in the urine of individuals who ingest arsenic-polluted drinking water. The cytogenetic study in V79 cells using iododimethylarsine, which is easily hydrolyzed to dimethylarsinous acid in water, revealed that dimethylarsinous acid was very cytotoxic (50\\% growth inhibition concentration; 1.1 (+-) 0.14 uM), and either induced aneuploids or a high rate of tetraploids (73\\% at 2.5 μM). Dimethylarsinous acid caused mitotic arrest, since the mitotic index at toxic dose (5 μM) was 13.9\\%, significantly higher than the control (2.7\\%). Dimethylarsinous acid significantly increased sister chromatid exchange (SCE) and chromosomal aberrations, most of which were chromatid gaps and chromatid breaks. The cytotoxicity and the activity of dimethylarsinous acid in inducing chromosomal aberration or SCE was as effective as arsenite, but the activity was much lower than that of mitomycin C, which was used as a positive control. The most potent effects of dimethylarsinous acid on the cells were induction of aneuploids, tetraploids and c-mitosis. The toxicity of dimethylarsinous acid is strongly related to the disturbance of the normal cell cycle.(PMID: 15276414).
Dimethylarsinous acid is a reactive organic intermediate of dimethylarsinic acid involved in toxicity.

同义名列表

6 个代谢物同义名

Dimethylarsinous-acid; dimethylarsinous acid; Dimethylarsinite; [As(CH3)2(OH)]; Me2asoh; DmaIII



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

Reactome(0)

BioCyc(0)

PlantCyc(0)

代谢反应

1 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(1)

  • Arsenate Detoxification: Dimethylarsinate + Hydrogen Ion + reduced electron acceptor ⟶ Dimethylarsinous acid + Water + oxidized electron acceptor

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

  • Chao-Yuan Huang, Ying-Chin Lin, Horng-Sheng Shiue, Wei-Jen Chen, Chien-Tien Su, Yeong-Shiau Pu, Pui-Lam Ao, Yu-Mei Hsueh. Comparison of arsenic methylation capacity and polymorphisms of arsenic methylation genes between bladder cancer and upper tract urothelial carcinoma. Toxicology letters. 2018 Oct; 295(?):64-73. doi: 10.1016/j.toxlet.2018.05.035. [PMID: 29859237]
  • Binggan Wei, Jiangping Yu, Jing Wang, Linsheng Yang, Hairong Li, Chang Kong, Yajuan Xia, Kegong Wu. The relationships between arsenic methylation and both skin lesions and hypertension caused by chronic exposure to arsenic in drinking water. Environmental toxicology and pharmacology. 2017 Jul; 53(?):89-94. doi: 10.1016/j.etap.2017.05.009. [PMID: 28528304]
  • Birget Moe, Hanyong Peng, Xiufen Lu, Baowei Chen, Lydia W L Chen, Stephan Gabos, Xing-Fang Li, X Chris Le. Comparative cytotoxicity of fourteen trivalent and pentavalent arsenic species determined using real-time cell sensing. Journal of environmental sciences (China). 2016 Nov; 49(?):113-124. doi: 10.1016/j.jes.2016.10.004. [PMID: 28007166]
  • Binggan Wei, Jiangping Yu, Hairong Li, Linsheng Yang, Yajuan Xia, Kegong Wu, Jianwei Gao, Zhiwei Guo, Na Cui. Arsenic Metabolites and Methylation Capacity Among Individuals Living in a Rural Area with Endemic Arseniasis in Inner Mongolia, China. Biological trace element research. 2016 Apr; 170(2):300-8. doi: 10.1007/s12011-015-0490-5. [PMID: 26335574]
  • S Piñol, A Sala, C Guzman, S Marcos, X Joya, C Puig, M Velasco, D Velez, O Vall, O Garcia-Algar. Arsenic levels in immigrant children from countries at risk of consuming arsenic polluted water compared to children from Barcelona. Environmental monitoring and assessment. 2015 Nov; 187(11):661. doi: 10.1007/s10661-015-4869-8. [PMID: 26431705]
  • Jenna M Currier, María C Ishida, Carmen González-Horta, Blanca Sánchez-Ramírez, Lourdes Ballinas-Casarrubias, Daniela S Gutiérrez-Torres, Roberto Hernández Cerón, Damián Viniegra Morales, Francisco A Baeza Terrazas, Luz M Del Razo, Gonzalo G García-Vargas, R Jesse Saunders, Zuzana Drobná, Rebecca C Fry, Tomáš Matoušek, John B Buse, Michelle A Mendez, Dana Loomis, Miroslav Stýblo. Associations between arsenic species in exfoliated urothelial cells and prevalence of diabetes among residents of Chihuahua, Mexico. Environmental health perspectives. 2014 Oct; 122(10):1088-94. doi: 10.1289/ehp.1307756. [PMID: 25000461]
  • Mayukh Banerjee, Michael W Carew, Barbara A Roggenbeck, Brayden D Whitlock, Hua Naranmandura, X Chris Le, Elaine M Leslie. A novel pathway for arsenic elimination: human multidrug resistance protein 4 (MRP4/ABCC4) mediates cellular export of dimethylarsinic acid (DMAV) and the diglutathione conjugate of monomethylarsonous acid (MMAIII). Molecular pharmacology. 2014 Aug; 86(2):168-79. doi: 10.1124/mol.113.091314. [PMID: 24870404]
  • Puttappa R Dodmane, Lora L Arnold, David E Muirhead, Shugo Suzuki, Masanao Yokohira, Karen L Pennington, Bhavana J Dave, Xiufen Lu, X Chris Le, Samuel M Cohen. Characterization of intracellular inclusions in the urothelium of mice exposed to inorganic arsenic. Toxicological sciences : an official journal of the Society of Toxicology. 2014 Jan; 137(1):36-46. doi: 10.1093/toxsci/kft227. [PMID: 24097667]
  • Puttappa R Dodmane, Lora L Arnold, Satoko Kakiuchi-Kiyota, Fang Qiu, Xiangde Liu, Stephen I Rennard, Samuel M Cohen. Cytotoxicity and gene expression changes induced by inorganic and organic trivalent arsenicals in human cells. Toxicology. 2013 Oct; 312(?):18-29. doi: 10.1016/j.tox.2013.07.008. [PMID: 23876855]
  • Hanjun Li, Jing Lin, Yufeng Li, Jinting Yan, Bai Li, Wei Zhang, Zeqin Dong, Chunying Chen. [Distribution of arsenic species and its DNA damage in subchronic arsenite-exposed mice]. Wei sheng yan jiu = Journal of hygiene research. 2013 Sep; 42(5):764-9, 776. doi: NULL. [PMID: 24218882]
  • M Calatayud, V Devesa, D Vélez. Differential toxicity and gene expression in Caco-2 cells exposed to arsenic species. Toxicology letters. 2013 Mar; 218(1):70-80. doi: 10.1016/j.toxlet.2013.01.013. [PMID: 23353816]
  • Hua Naranmandura, Shi Xu, Shota Koike, Li Qiang Pan, Bin Chen, Yan Wei Wang, Kanwal Rehman, Bin Wu, Zhe Chen, Noriyuki Suzuki. The endoplasmic reticulum is a target organelle for trivalent dimethylarsinic acid (DMAIII)-induced cytotoxicity. Toxicology and applied pharmacology. 2012 May; 260(3):241-9. doi: 10.1016/j.taap.2012.02.017. [PMID: 22425709]
  • Luz M Del Razo, Gonzalo G García-Vargas, Olga L Valenzuela, Erika Hernández Castellanos, Luz C Sánchez-Peña, Jenna M Currier, Zuzana Drobná, Dana Loomis, Miroslav Stýblo. Exposure to arsenic in drinking water is associated with increased prevalence of diabetes: a cross-sectional study in the Zimapán and Lagunera regions in Mexico. Environmental health : a global access science source. 2011 Aug; 10(?):73. doi: 10.1186/1476-069x-10-73. [PMID: 21864395]
  • M Calatayud, V Devesa, R Montoro, D Vélez. In vitro study of intestinal transport of arsenite, monomethylarsonous acid, and dimethylarsinous acid by Caco-2 cell line. Toxicology letters. 2011 Jul; 204(2-3):127-33. doi: 10.1016/j.toxlet.2011.04.023. [PMID: 21554932]
  • Xuefeng Ren, Maria Aleshin, William J Jo, Russel Dills, David A Kalman, Christopher D Vulpe, Martyn T Smith, Luoping Zhang. Involvement of N-6 adenine-specific DNA methyltransferase 1 (N6AMT1) in arsenic biomethylation and its role in arsenic-induced toxicity. Environmental health perspectives. 2011 Jun; 119(6):771-7. doi: 10.1289/ehp.1002733. [PMID: 21193388]
  • Kristin E Porter, Anamika Basu, Alan E Hubbard, Michael N Bates, David Kalman, Omar Rey, Allan Smith, Martyn T Smith, Craig Steinmaus, Christine F Skibola. Association of genetic variation in cystathionine-beta-synthase and arsenic metabolism. Environmental research. 2010 Aug; 110(6):580-7. doi: 10.1016/j.envres.2010.05.001. [PMID: 20670920]
  • Hua Naranmandura, Katsuya Iwata, Kazuo T Suzuki, Yasumitsu Ogra. Distribution and metabolism of four different dimethylated arsenicals in hamsters. Toxicology and applied pharmacology. 2010 May; 245(1):67-75. doi: 10.1016/j.taap.2010.02.001. [PMID: 20144633]
  • Shugo Suzuki, Lora L Arnold, Karen L Pennington, Baowei Chen, X Chris Le, Samuel M Cohen. Effects of an epidermal growth factor receptor inhibitor on arsenic associated toxicity in the rat bladder epithelium. Toxicology letters. 2009 Jun; 187(2):124-9. doi: 10.1016/j.toxlet.2009.02.013. [PMID: 19429254]
  • E M Kenyon, M F Hughes, B M Adair, J H Highfill, E A Crecelius, H J Clewell, J W Yager. Tissue distribution and urinary excretion of inorganic arsenic and its methylated metabolites in C57BL6 mice following subchronic exposure to arsenate in drinking water. Toxicology and applied pharmacology. 2008 Nov; 232(3):448-55. doi: 10.1016/j.taap.2008.07.018. [PMID: 18706920]
  • Hua Naranmandura, Kazuo T Suzuki. Identification of the major arsenic-binding protein in rat plasma as the ternary dimethylarsinous-hemoglobin-haptoglobin complex. Chemical research in toxicology. 2008 Mar; 21(3):678-85. doi: 10.1021/tx700383g. [PMID: 18247522]
  • Badal K Mandal, Kazuo T Suzuki, Kazunori Anzai. Impact of arsenic in foodstuffs on the people living in the arsenic-affected areas of West Bengal, India. Journal of environmental science and health. Part A, Toxic/hazardous substances & environmental engineering. 2007 Oct; 42(12):1741-52. doi: 10.1080/10934520701564244. [PMID: 17952775]
  • Samuel M Cohen, Takamasa Ohnishi, Lora L Arnold, X Chris Le. Arsenic-induced bladder cancer in an animal model. Toxicology and applied pharmacology. 2007 Aug; 222(3):258-63. doi: 10.1016/j.taap.2006.10.010. [PMID: 17109909]
  • Kathleen M McCarty, Yen-Ching Chen, Quazi Quamruzzaman, Mahmuder Rahman, Golam Mahiuddin, Yu-Mei Hsueh, Li Su, Thomas Smith, Louise Ryan, David C Christiani. Arsenic methylation, GSTT1, GSTM1, GSTP1 polymorphisms, and skin lesions. Environmental health perspectives. 2007 Mar; 115(3):341-5. doi: 10.1289/ehp.9152. [PMID: 17431481]
  • Tsing-Cheng Wang, Kun-Yan Jan, Alexander S S Wang, Jia-Ran Gurr. Trivalent arsenicals induce lipid peroxidation, protein carbonylation, and oxidative DNA damage in human urothelial cells. Mutation research. 2007 Feb; 615(1-2):75-86. doi: 10.1016/j.mrfmmm.2006.10.003. [PMID: 17134727]
  • Meiling Lu, Hailin Wang, Xing-Fang Li, Lora L Arnold, Samuel M Cohen, X Chris Le. Binding of dimethylarsinous acid to cys-13alpha of rat hemoglobin is responsible for the retention of arsenic in rat blood. Chemical research in toxicology. 2007 Jan; 20(1):27-37. doi: 10.1021/tx060195+. [PMID: 17226924]
  • T Sakurai, C Kojima, Y Kobayashi, S Hirano, M H Sakurai, M P Waalkes, S Himeno. Toxicity of a trivalent organic arsenic compound, dimethylarsinous glutathione in a rat liver cell line (TRL 1215). British journal of pharmacology. 2006 Dec; 149(7):888-97. doi: 10.1038/sj.bjp.0706899. [PMID: 17043674]
  • Hua Naranmandura, Noriyuki Suzuki, Kazuo T Suzuki. Trivalent arsenicals are bound to proteins during reductive methylation. Chemical research in toxicology. 2006 Aug; 19(8):1010-8. doi: 10.1021/tx060053f. [PMID: 16918239]
  • E Dopp, L M Hartmann, U von Recklinghausen, A M Florea, S Rabieh, U Zimmermann, B Shokouhi, S Yadav, A V Hirner, A W Rettenmeier. Forced uptake of trivalent and pentavalent methylated and inorganic arsenic and its cyto-/genotoxicity in fibroblasts and hepatoma cells. Toxicological sciences : an official journal of the Society of Toxicology. 2005 Sep; 87(1):46-56. doi: 10.1093/toxsci/kfi218. [PMID: 15947026]
  • Olga L Valenzuela, Victor H Borja-Aburto, Gonzalo G Garcia-Vargas, Martha B Cruz-Gonzalez, Eliud A Garcia-Montalvo, Emma S Calderon-Aranda, Luz M Del Razo. Urinary trivalent methylated arsenic species in a population chronically exposed to inorganic arsenic. Environmental health perspectives. 2005 Mar; 113(3):250-4. doi: 10.1289/ehp.7519. [PMID: 15743710]
  • Helle R Hansen, Andrea Raab, Marcel Jaspars, Bruce F Milne, Jörg Feldmann. Sulfur-containing arsenical mistaken for dimethylarsinous acid [DMA(III)] and identified as a natural metabolite in urine: major implications for studies on arsenic metabolism and toxicity. Chemical research in toxicology. 2004 Aug; 17(8):1086-91. doi: 10.1021/tx049978q. [PMID: 15310240]
  • Zhongwen Wang, Jin Zhou, Xiufen Lu, Zhilong Gong, X Chris Le. Arsenic speciation in urine from acute promyelocytic leukemia patients undergoing arsenic trioxide treatment. Chemical research in toxicology. 2004 Jan; 17(1):95-103. doi: 10.1021/tx0341714. [PMID: 14727923]
  • Xiufen Lu, Lora L Arnold, Samuel M Cohen, William R Cullen, X Chris Le. Speciation of dimethylarsinous acid and trimethylarsine oxide in urine from rats fed with dimethylarsinic acid and dimercaptopropane sulfonate. Analytical chemistry. 2003 Dec; 75(23):6463-8. doi: 10.1021/ac034868u. [PMID: 14640715]
  • Kaoru Yoshida, Koichi Kuroda, Xu Zhou, Yoshinori Inoue, Yukiko Date, Hideki Wanibuchi, Shoji Fukushima, Ginji Endo. Urinary sulfur-containing metabolite produced by intestinal bacteria following oral administration of dimethylarsinic acid to rats. Chemical research in toxicology. 2003 Sep; 16(9):1124-9. doi: 10.1021/tx030008x. [PMID: 12971800]
  • Guifeng Jiang, Zhilong Gong, Xing-Fang Li, William R Cullen, X Chris Le. Interaction of trivalent arsenicals with metallothionein. Chemical research in toxicology. 2003 Jul; 16(7):873-80. doi: 10.1021/tx034053g. [PMID: 12870890]
  • Stephen Nesnow, Barbara C Roop, Guy Lambert, Maria Kadiiska, Ronald P Mason, William R Cullen, Marc J Mass. DNA damage induced by methylated trivalent arsenicals is mediated by reactive oxygen species. Chemical research in toxicology. 2002 Dec; 15(12):1627-34. doi: 10.1021/tx025598y. [PMID: 12482246]
  • Samuel M Cohen, Lora L Arnold, Eva Uzvolgyi, Martin Cano, Margaret St John, Shinji Yamamoto, Xiufen Lu, X Chris Le. Possible role of dimethylarsinous acid in dimethylarsinic acid-induced urothelial toxicity and regeneration in the rat. Chemical research in toxicology. 2002 Sep; 15(9):1150-7. doi: 10.1021/tx020026z. [PMID: 12230408]