m-Phenylenediamine (BioDeep_00001868029)
Main id: BioDeep_00000002886
代谢物信息卡片
m-Phenylenediamine
化学式: C6H8N2 (108.0687)
中文名称: 间苯二胺
谱图信息:
最多检出来源 () 0%
分子结构信息
SMILES: C1=CC(=CC(=C1)N)N
InChI: InChI=1S/C6H8N2/c7-5-2-1-3-6(8)4-5/h1-4H,7-8H2
数据库引用编号
11 个数据库交叉引用编号
- ChEBI: CHEBI:8092
- KEGG: C02454
- KEGGdrug: D92171
- PubChem: 7935
- ChEMBL: CHEMBL1595914
- CAS: 108-45-2
- PubChem: 5474
- CAS: 25265-76-3
- NIKKAJI: J369G
- NIKKAJI: J600.168H
- KNApSAcK: 8092
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
- Sarah R Dennison, David A Phoenix, Timothy J Snape. Synthetic oligoureas of metaphenylenediamine mimic host defence peptides in their antimicrobial behaviour.
Bioorganic & medicinal chemistry letters.
2013 May; 23(9):2518-21. doi:
10.1016/j.bmcl.2013.03.018. [PMID: 23541668] - Jian-qiu Chen, Zhi-jun Hu, Nan-xi Wang, Rong Ji. Interactions between m-phenylenediamine and bovine serum albumin measured by spectroscopy.
Luminescence : the journal of biological and chemical luminescence.
2013 Mar; 28(2):226-31. doi:
10.1002/bio.2369. [PMID: 22511621] - Yuhui Wang, Zhengjun Wu, Zhihong Liu. Upconversion fluorescence resonance energy transfer biosensor with aromatic polymer nanospheres as the lable-free energy acceptor.
Analytical chemistry.
2013 Jan; 85(1):258-64. doi:
10.1021/ac302659b. [PMID: 23186324] - Sandra Jahn, Helene Faber, Raniero Zazzeroni, Uwe Karst. Electrochemistry/liquid chromatography/mass spectrometry to demonstrate irreversible binding of the skin allergen p-phenylenediamine to proteins.
Rapid communications in mass spectrometry : RCM.
2012 Jun; 26(12):1415-25. doi:
10.1002/rcm.6247. [PMID: 22592985] - Pablo J Almeida, Leopoldo Borrego, Elisenda Pulido-Melián, Oscar González-Díaz. Quantification of p-phenylenediamine and 2-hydroxy-1,4-naphthoquinone in henna tattoos.
Contact dermatitis.
2012 Jan; 66(1):33-7. doi:
10.1111/j.1600-0536.2011.01992.x. [PMID: 21972791] - Mei-Rong Huang, Xue-Wu Rao, Xin-Gui Li, Yong-Bo Ding. Lead ion-selective electrodes based on polyphenylenediamine as unique solid ionophores.
Talanta.
2011 Sep; 85(3):1575-84. doi:
10.1016/j.talanta.2011.06.049. [PMID: 21807224] - M Gube, K Heinrich, P Dewes, P Brand, T Kraus, T Schettgen. Internal exposure of hairdressers to permanent hair dyes: a biomonitoring study using urinary aromatic diamines as biomarkers of exposure.
International archives of occupational and environmental health.
2011 Mar; 84(3):287-92. doi:
10.1007/s00420-010-0539-x. [PMID: 20443120] - Thomas Schettgen, K Heinrich, T Kraus, Monika Gube. Determination of 2,5-toluylenediamine (2,5-TDA) and aromatic amines in urine after personal application of hair dyes: kinetics and doses.
Archives of toxicology.
2011 Feb; 85(2):127-33. doi:
10.1007/s00204-010-0563-3. [PMID: 20549195] - Yingwei Zhang, Hailong Li, Yonglan Luo, Xu Shi, Jingqi Tian, Xuping Sun. Poly(m-phenylenediamine) nanospheres and nanorods: selective synthesis and their application for multiplex nucleic acid detection.
PloS one.
2011; 6(6):e20569. doi:
10.1371/journal.pone.0020569. [PMID: 21731617] - Gero P Hooff, Nick A van Huizen, Roland J W Meesters, Eduard E Zijlstra, Mohamed Abdelraheem, Waleed Abdelraheem, Mohamed Hamdouk, Jan Lindemans, Theo M Luider. Analytical investigations of toxic p-phenylenediamine (PPD) levels in clinical urine samples with special focus on MALDI-MS/MS.
PloS one.
2011; 6(8):e22191. doi:
10.1371/journal.pone.0022191. [PMID: 21829608] - Helga Rothe, Katherine Sarlo, Heike Scheffler, Carsten Goebel. The hair dyes PPD and PTD fail to induce a T(H)2 immune response following repeated topical application in BALB/c mice.
Journal of immunotoxicology.
2011 Jan; 8(1):46-55. doi:
10.3109/1547691x.2010.543096. [PMID: 21299354] - Mariusz Nowak, Tomasz Wielkoszyński, Bogdan Marek, Beata Kos-Kudła, Elzbieta Swietochowska, Lucyna Siemińska, Jacek Karpe, Dariusz Kajdaniuk, Joanna Głogowska-Szelag, Katarzyna Nowak. Antioxidant potential, paraoxonase 1, ceruloplasmin activity and C-reactive protein concentration in diabetic retinopathy.
Clinical and experimental medicine.
2010 Sep; 10(3):185-92. doi:
10.1007/s10238-009-0084-7. [PMID: 20012460] - Yun-Yang Wan, Rong Lu, Kazuhiro Akiyama, Katsuhisa Okamoto, Takayuki Honda, Yu-Min Du, Takashi Yoshida, Tetsuo Miyakoshi, Charles J Knill, John F Kennedy. Effects of lacquer polysaccharides, glycoproteins and isoenzymes on the activity of free and immobilised laccase from Rhus vernicifera.
International journal of biological macromolecules.
2010 Jul; 47(1):76-81. doi:
10.1016/j.ijbiomac.2010.03.016. [PMID: 20363247] - S C Chen, C H Chen, Y L Tioh, P Y Zhong, Y S Lin, S M Chye. Para-phenylenediamine induced DNA damage and apoptosis through oxidative stress and enhanced caspase-8 and -9 activities in Mardin-Darby canine kidney cells.
Toxicology in vitro : an international journal published in association with BIBRA.
2010 Jun; 24(4):1197-202. doi:
10.1016/j.tiv.2010.02.011. [PMID: 20156547] - Alaina Terzulli, Daniel J Kosman. Analysis of the high-affinity iron uptake system at the Chlamydomonas reinhardtii plasma membrane.
Eukaryotic cell.
2010 May; 9(5):815-26. doi:
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Toxicology and industrial health.
2010 Mar; 26(2):81-7. doi:
10.1177/0748233709360200. [PMID: 20103579] - Boulos Zacharie, Shaun D Abbott, Jean-François Bienvenu, Alan D Cameron, Josée Cloutier, Jean-Simon Duceppe, Abdallah Ezzitouni, Daniel Fortin, Karine Houde, Caroline Lauzon, Nancie Moreau, Valérie Perron, Nicole Wilb, Michel Asselin, André Doucet, Marie-Eve Fafard, Dannyck Gaudreau, Brigitte Grouix, François Sarra-Bournet, Natalie St-Amant, Lyne Gagnon, Christopher L Penney. 2,4,6-trisubstituted triazines as protein a mimetics for the treatment of autoimmune diseases.
Journal of medicinal chemistry.
2010 Feb; 53(3):1138-45. doi:
10.1021/jm901403r. [PMID: 20047277] - Falguni Parikh. Changing trends in poisoning.
The Journal of the Association of Physicians of India.
2009 Nov; 57(?):739. doi:
NULL. [PMID: 20329437] - Manisha Sahay, R Vani, Sharmas Vali. Hair dye ingestion--an uncommon cause of acute kidney injury.
The Journal of the Association of Physicians of India.
2009 Nov; 57(?):743-4. doi:
NULL. [PMID: 20329439] - Padmarajaiah Nagaraja, Anantharaman Shivakumar, Ashwinee Kumar Shrestha. Development and evaluation of kinetic spectrophotometric assays for horseradish peroxidase by catalytic coupling of paraphenylenediamine and mequinol.
Analytical sciences : the international journal of the Japan Society for Analytical Chemistry.
2009 Oct; 25(10):1243-8. doi:
10.2116/analsci.25.1243. [PMID: 19822971] - Padmarajaiah Nagaraja, Anantharaman Shivakumar, Ashwinee Kumar Shrestha. Peroxidase-catalyzed oxidative coupling of paraphenylenediamine with 3-dimethylaminobenzoic acid: application in crude plant extracts.
Journal of agricultural and food chemistry.
2009 Jun; 57(12):5173-7. doi:
10.1021/jf900696p. [PMID: 19456130] - John Farrell, Claire Jenkinson, Sidonie N Lavergne, James L Maggs, B Kevin Park, Dean J Naisbitt. Investigation of the immunogenicity of p-phenylenediamine and Bandrowski's base in the mouse.
Toxicology letters.
2009 Mar; 185(3):153-9. doi:
10.1016/j.toxlet.2008.12.008. [PMID: 19136049] - Dragan L Jovanovic, Maja R Slavkovic-Jovanovic. Allergic contact dermatitis from temporary henna tattoo.
The Journal of dermatology.
2009 Jan; 36(1):63-5. doi:
10.1111/j.1346-8138.2008.00588.x. [PMID: 19207440] - Sang-Hee Lee, Hyun-Gug Cho, Sang-Il Lee. The effects of tungstate on skin lesions caused by PPD in rats.
Biological & pharmaceutical bulletin.
2008 Apr; 31(4):681-4. doi:
10.1248/bpb.31.681. [PMID: 18379062] - Eve Marie Coulter, Claire Jenkinson, Ying Wu, John Farrell, Brian Foster, Andrew Smith, Carolann McGuire, Camilla Pease, David Basketter, Clodagh King, Peter Simon Friedmann, Munir Pirmohamed, Brian Kevin Park, Dean J Naisbitt. Activation of T-cells from allergic patients and volunteers by p-phenylenediamine and Bandrowski's base.
The Journal of investigative dermatology.
2008 Apr; 128(4):897-905. doi:
10.1038/sj.jid.5701071. [PMID: 17914451] - Sonali Rathour Hansen, Susanne Kroon. [Patch testing and nickel allergy].
Tidsskrift for den Norske laegeforening : tidsskrift for praktisk medicin, ny raekke.
2008 Feb; 128(4):433-5. doi:
. [PMID: 18274576] - Gerald Weissmann. Apply directly to the forehead: Holmes, Nana, and hennapecia.
FASEB journal : official publication of the Federation of American Societies for Experimental Biology.
2007 Apr; 21(4):963-5. doi:
10.1096/fj.07-0401ufm. [PMID: 17389564] - Jacob Urkin. Henna tattooing dermatitis: consider an additive as the culprit.
The British journal of general practice : the journal of the Royal College of General Practitioners.
2006 Oct; 56(531):794-5. doi:
". [PMID: 17007712] - Ssu-Ching Chen, Ching-Hsein Chen, Chi-Liang Chern, Li-Sung Hsu, Ya-Chun Huang, King-Thom Chung, Soi-Moi Chye. p-Phenylenediamine induces p53-mediated apoptosis in Mardin-Darby canine kidney cells.
Toxicology in vitro : an international journal published in association with BIBRA.
2006 Sep; 20(6):801-7. doi:
10.1016/j.tiv.2005.12.003. [PMID: 16469477] - T Oppel, A Schnuch. [The most frequent allergens in allergic contact dermatitis].
Deutsche medizinische Wochenschrift (1946).
2006 Jul; 131(28-29):1584-9. doi:
10.1055/s-2006-947800. [PMID: 16823706] - Ik-Joon Kang, Mu-Hyoung Lee. Quantification of para-phenylenediamine and heavy metals in henna dye.
Contact dermatitis.
2006 Jul; 55(1):26-9. doi:
10.1111/j.0105-1873.2006.00845.x. [PMID: 16842550] - William E Dressler, Terence Appelqvist. Plasma/blood pharmacokinetics and metabolism after dermal exposure to para-aminophenol or para-phenylenediamine.
Food and chemical toxicology : an international journal published for the British Industrial Biological Research Association.
2006 Mar; 44(3):371-9. doi:
10.1016/j.fct.2005.08.009. [PMID: 16239057] - Wen-Hua Chen, Xue-Bin Shao, Steven L Regen. Poly(choloyl)-based amphiphiles as pore-forming agents: transport-active monomers by design.
Journal of the American Chemical Society.
2005 Sep; 127(36):12727-35. doi:
10.1021/ja053527q. [PMID: 16144423] - A K Mathur, R B Raizada, M K Srivastava, A Singh. Effect of dermal exposure to paraphenylenediamine and linear alkylbenzene sulphonate in guinea pigs.
Biomedical and environmental sciences : BES.
2005 Aug; 18(4):238-40. doi:
. [PMID: 16274105] - Robert P Eager. Atopy to henna tattoos in children.
European journal of emergency medicine : official journal of the European Society for Emergency Medicine.
2005 Aug; 12(4):189-90. doi:
10.1097/00063110-200508000-00008. [PMID: 16034265] - José M Martín, Angeles Revert, Vicent Alonso, Laura García, Inmaculada Molina, Carolina Pereda, Esperanza Jordá. [Acute contact eczema from paraphenylenediamine contained in temporary henna tattoos].
Actas dermo-sifiliograficas.
2005 Jul; 96(6):382-5. doi:
10.1016/s0001-7310(05)73096-9. [PMID: 16476259] - Hatem Kallel, Hedi Chelly, Hassen Dammak, Mabrouk Bahloul, Hichem Ksibi, Chokri Ben Hamida, Adel Chaari, Noureddine Rekik, Marc E De Broe, Mounir Bouaziz. Clinical manifestations of systemic paraphenylene diamine intoxication.
Journal of nephrology.
2005 May; 18(3):308-11. doi:
NULL. [PMID: 16013020] - Petteri Nieminen, Anne-Mari Mustonen, Markku Kirsi. Increased plasma creatine kinase activities triggered by edible wild mushrooms.
Food and chemical toxicology : an international journal published for the British Industrial Biological Research Association.
2005 Jan; 43(1):133-8. doi:
10.1016/j.fct.2004.09.002. [PMID: 15582205] - Josefina Cortés-Eslava, Sandra Gómez-Arroyo, Rafael Villalobos-Pietrini, Jesús Javier Espinosa-Aguirre. Antimutagenicity of coriander (Coriandrum sativum) juice on the mutagenesis produced by plant metabolites of aromatic amines.
Toxicology letters.
2004 Nov; 153(2):283-92. doi:
10.1016/j.toxlet.2004.05.011. [PMID: 15451560] - Jean Blair, Robert T Brodell, Susan T Nedorost. Dermatitis associated with henna tattoo. 'Safe' alternative to permanent tattoos carries risk.
Postgraduate medicine.
2004 Sep; 116(3):63-5. doi:
10.3810/pgm.2004.09.1590. [PMID: 15460091] - Jin Li, Lang-Tao Xiao, Xuan-Ming Liu, Guang-Ming Zeng, Guo-He Huang, Guo-Li Shen, Ru-Qin Yu. Amperometric biosensor with HRP immobilized on a sandwiched nano-Au / polymerized m-phenylenediamine film and ferrocene mediator.
Analytical and bioanalytical chemistry.
2003 Jul; 376(6):902-7. doi:
10.1007/s00216-003-1989-8. [PMID: 12802559] - H Yokozeki, M-H Wu, K Sumi, K Igawa, Y Miyazaki, I Katayama, K Takeda, S Akira, K Nishioka. Th2 cytokines, IgE and mast cells play a crucial role in the induction of para-phenylenediamine-induced contact hypersensitivity in mice.
Clinical and experimental immunology.
2003 Jun; 132(3):385-92. doi:
10.1046/j.1365-2249.2003.02164.x. [PMID: 12780683] - J Cortés-Eslava, S Gómez-Arroyo, R Villalobos-Pietrini, J J Espinosa-Aguirre. Metabolic activation of three arylamines and two organophosphorus insecticides by coriander (Coriandrum sativum) a common edible vegetable.
Toxicology letters.
2001 Dec; 125(1-3):39-49. doi:
10.1016/s0378-4274(01)00414-3. [PMID: 11701221] - M Ferrer, A Sánchez-Lamar, J L Fuentes, J Barbé, M Llagostera. Studies on the antimutagenesis of Phyllanthus orbicularis: mechanisms involved against aromatic amines.
Mutation research.
2001 Nov; 498(1-2):99-105. doi:
10.1016/s1383-5718(01)00270-4. [PMID: 11673075] - A A Cherkashin, A A Bulychev, W J Vredenberg. The outward component of photoinduced current in chloroplasts of Peperomia metallica.
Membrane & cell biology.
2001; 14(4):475-85. doi:
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Biochemical Society transactions.
2000 Feb; 28(2):89-93. doi:
10.1042/bst0280089. [PMID: 10816106] - D A Stavreva, E D Wagner, M J Plewa, T Gichner. Characterization of a macromolecular matrix isolated from tobacco suspension cell cultures and its role in the activation of promutagenic m-phenylenediamine.
Mutation research.
1997 Oct; 379(2):191-9. doi:
10.1016/s0027-5107(97)00137-1. [PMID: 9357548] - D Vlcek, E Miadoková, V Vlckova, M Slaninová, S Podstavková. Metabolic activation of meta-phenylenediamine by the alga Chlamydomonas reinhardtii.
Mutation research.
1997 Jul; 391(3):143-51. doi:
10.1016/s1383-5718(97)00061-2. [PMID: 9268039] - E D Wagner, K Repetny, J S Tan, T Gichner, M J Plewa. Mutagenic synergy between paraoxon and mammalian or plant-activated aromatic amines.
Environmental and molecular mutagenesis.
1997; 30(3):312-20. doi:
10.1002/(sici)1098-2280(1997)30:3<312::aid-em10>3.0.co;2-g. [PMID: 9366910] - M J Plewa, E D Wagner, D A Stavreva, T Gichner. Plant activation and its role in environmental mutagenesis and antimutagenesis.
Mutation research.
1996 Feb; 350(1):163-71. doi:
10.1016/0027-5107(95)00115-8. [PMID: 8657177] - T Gichner, J Veleminský, E D Wagner, M J Plewa. Mutagenic synergy between paraoxon and plant-activated m-phenylenediamine or 2-acetoxyacetylaminofluorene.
Environmental and molecular mutagenesis.
1996; 27(1):59-66. doi:
10.1002/(sici)1098-2280(1996)27:1<59::aid-em8>3.0.co;2-9. [PMID: 8625949] - T Gichner, D A Stavreva, N Cerovská, E D Wagner, M J Plewa. Metabolic activation of m-phenylenediamine to products mutagenic in Salmonella typhimurium by medium isolated from tobacco suspension cell cultures.
Mutation research.
1995 Sep; 331(1):127-32. doi:
10.1016/0027-5107(95)00058-q. [PMID: 7666860] - M J Plewa, E D Wagner, T W Yu, D Anderson. Genotoxicity of m-phenylenediamine and 2-aminofluorene in Salmonella typhimurium and human lymphocytes with and without plant activation.
Environmental and molecular mutagenesis.
1995; 26(2):171-7. doi:
10.1002/em.2850260211. [PMID: 7556114] - T Gichner, G Cabrera Lopez, E D Wagner, M J Plewa. Induction of somatic mutations in Tradescantia clone 4430 by three phenylenediamine isomers and the antimutagenic mechanisms of diethyldithiocarbamate and ammonium meta-vanadate.
Mutation research.
1994 Apr; 306(2):165-72. doi:
10.1016/0027-5107(94)90027-2. [PMID: 7512215] - K Y Seo, J Riley, D Cortez, E D Wagner, M J Plewa. Characterization of stable high molecular weight mutagenic product(s) of plant-activated m-phenylenediamine.
Mutation research.
1993 Apr; 299(2):111-20. doi:
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Mutation research.
1991 Mar; 247(1):57-64. doi:
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Environmental and molecular mutagenesis.
1990; 15(4):236-44. doi:
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Progress in clinical and biological research.
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Food and chemical toxicology : an international journal published for the British Industrial Biological Research Association.
1989 Nov; 27(11):741-9. doi:
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Mutation research.
1988 Feb; 197(2):303-12. doi:
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Mutation research.
1988 Feb; 197(2):207-19. doi:
10.1016/0027-5107(88)90094-2. [PMID: 3277040] - M A Lhotka, M J Plewa, J M Gentile. Plant activation of m-phenylenediamine by tobacco, cotton, and carrot cell suspension cultures.
Environmental and molecular mutagenesis.
1987; 10(1):79-88. doi:
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Mutation research.
1984 Nov; 138(2-3):137-43. doi:
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