1-(s-glutathionyl)-2,4-dinitrobenzene (BioDeep_00000008530)

 

Secondary id: BioDeep_00001871576

human metabolite


代谢物信息卡片


(2S)-2-amino-4-{[(1R)-1-[(carboxymethyl)carbamoyl]-2-[(2,4-dinitrophenyl)sulfanyl]ethyl]carbamoyl}butanoic acid

化学式: C16H19N5O10S (473.0853)
中文名称: S-(2,4-二硝基苯基)-谷胱甘肽
谱图信息: 最多检出来源 Homo sapiens(not specific) 29.86%

分子结构信息

SMILES: C1=CC(=C(C=C1[N+](=O)[O-])[N+](=O)[O-])SCC(C(=O)NCC(=O)O)NC(=O)CCC(C(=O)O)N
InChI: InChI=1S/C16H19N5O10S/c17-9(16(26)27)2-4-13(22)19-10(15(25)18-6-14(23)24)7-32-12-3-1-8(20(28)29)5-11(12)21(30)31/h1,3,5,9-10H,2,4,6-7,17H2,(H,18,25)(H,19,22)(H,23,24)(H,26,27)

描述信息

1-(s-glutathionyl)-2,4-dinitrobenzene, also known as Dinitrophenyl-S-glutathione or GS-DNP, is classified as a member of the Oligopeptides. Oligopeptides are organic compounds containing a sequence of between three and ten alpha-amino acids joined by peptide bonds. 1-(s-glutathionyl)-2,4-dinitrobenzene is considered to be practically insoluble (in water) and acidic

同义名列表

11 个代谢物同义名

(2S)-2-amino-4-{[(1R)-1-[(carboxymethyl)carbamoyl]-2-[(2,4-dinitrophenyl)sulfanyl]ethyl]carbamoyl}butanoic acid; 1-(s-glutathionyl)-2,4-dinitrobenzene; S-(2,4-Dinitrophenyl)-Glutathione; S-(2,4-dinitrophenyl)glutathione; Dinitrophenyl-S-glutathione; DNP-S-Glutathione; S-DNP-Glutathione; GSH-S-DNP; DNP-SG; GS-DNP; S-(2,4-Dinitrophenyl)glutathione



数据库引用编号

16 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

4 个相关的代谢反应过程信息。

Reactome(4)

BioCyc(0)

WikiPathways(0)

Plant Reactome(0)

INOH(0)

PlantCyc(0)

COVID-19 Disease Map(0)

PathBank(0)

PharmGKB(0)

2 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。

亚细胞结构定位 关联基因列表
Cytoplasm 7 ABCB1, ABCB4, AIMP2, ALOX5, CAT, ELANE, HPGDS
Peripheral membrane protein 2 ALOX5, RALBP1
Mitochondrion membrane 1 ABCG2
Nucleus 3 AIMP2, NR1I2, RALBP1
cytosol 9 ABCB4, AIMP2, ALOX5, CAT, ELANE, GSR, HPGDS, PRKCQ, RALBP1
mitochondrial membrane 1 ABCG2
nuclear body 2 NR1I2, RALBP1
phagocytic vesicle 1 ELANE
nucleoplasm 7 ABCB4, ABCG2, ALOX5, ATP2B1, HPGDS, NR1I2, RALBP1
Cell membrane 8 ABCB1, ABCB4, ABCC1, ABCG2, ATP2B1, CYSLTR2, OATP1, RALBP1
Multi-pass membrane protein 9 ABCB1, ABCB4, ABCC1, ABCC2, ABCC3, ABCG2, ATP2B1, CYSLTR2, OATP1
Synapse 1 ATP2B1
cell surface 3 ABCB1, ABCC2, ELANE
glutamatergic synapse 1 ATP2B1
presynaptic membrane 1 ATP2B1
Cytoplasm, cytosol 3 AIMP2, ALOX5, RALBP1
plasma membrane 12 ABCB1, ABCB4, ABCC1, ABCC2, ABCC3, ABCG2, ATP2B1, CYSLTR2, GCG, OATP1, PRKCQ, RALBP1
synaptic vesicle membrane 1 ATP2B1
Membrane 10 ABCB1, ABCB4, ABCC1, ABCC2, ABCC3, ABCG2, AIMP2, ATP2B1, CAT, RALBP1
apical plasma membrane 6 ABCB1, ABCB4, ABCC1, ABCC2, ABCG2, OATP1
basolateral plasma membrane 4 ABCC1, ABCC3, ATP2B1, OATP1
extracellular exosome 7 ABCB1, ABCB4, ABCC1, ATP2B1, CAT, ELANE, GSR
extracellular space 3 ALOX5, ELANE, GCG
perinuclear region of cytoplasm 1 ALOX5
intercellular canaliculus 2 ABCB4, ABCC2
mitochondrion 3 CAT, GSR, RALBP1
protein-containing complex 1 CAT
intracellular membrane-bounded organelle 3 ATP2B1, CAT, HPGDS
Secreted 1 GCG
extracellular region 4 ALOX5, CAT, ELANE, GCG
mitochondrial matrix 2 CAT, GSR
transcription regulator complex 1 NR1I2
centriolar satellite 1 PRKCQ
Cytoplasmic vesicle, secretory vesicle, synaptic vesicle membrane 1 ATP2B1
Nucleus membrane 1 ALOX5
nuclear membrane 1 ALOX5
external side of plasma membrane 1 GSR
nucleolus 1 PNMA2
Apical cell membrane 4 ABCB1, ABCB4, ABCC2, ABCG2
Cytoplasm, perinuclear region 1 ALOX5
Membrane raft 2 ABCB4, ABCG2
focal adhesion 2 ABCB4, CAT
Peroxisome 1 CAT
Peroxisome matrix 1 CAT
peroxisomal matrix 1 CAT
peroxisomal membrane 1 CAT
collagen-containing extracellular matrix 1 ELANE
secretory granule 1 ELANE
lateral plasma membrane 2 ABCC1, ATP2B1
chromatin 1 NR1I2
cell projection 1 ATP2B1
brush border membrane 1 ABCG2
Nucleus, nucleolus 1 PNMA2
spindle pole 1 RALBP1
Basolateral cell membrane 2 ABCC3, ATP2B1
Cytoplasm, cytoskeleton, spindle pole 1 RALBP1
nuclear envelope 1 ALOX5
Nucleus envelope 1 ALOX5
Presynaptic cell membrane 1 ATP2B1
intermediate filament cytoskeleton 1 NR1I2
basal plasma membrane 3 ABCC1, ABCC3, OATP1
clathrin-coated vesicle 1 ABCB4
ficolin-1-rich granule lumen 2 ALOX5, CAT
secretory granule lumen 3 ALOX5, CAT, GCG
endoplasmic reticulum lumen 1 GCG
nuclear matrix 1 ALOX5
transcription repressor complex 1 ELANE
specific granule lumen 1 ELANE
Cytoplasmic vesicle, clathrin-coated vesicle 1 ABCB4
azurophil granule lumen 1 ELANE
immunological synapse 2 ATP2B1, PRKCQ
aggresome 1 PRKCQ
Nucleus matrix 1 ALOX5
nuclear envelope lumen 1 ALOX5
Basal cell membrane 2 ABCC3, OATP1
external side of apical plasma membrane 2 ABCB1, ABCG2
aminoacyl-tRNA synthetase multienzyme complex 1 AIMP2
Cytoplasmic vesicle, phagosome 1 ELANE
[Glucagon-like peptide 1]: Secreted 1 GCG
catalase complex 1 CAT
Nucleus intermembrane space 1 ALOX5
photoreceptor ribbon synapse 1 ATP2B1


文献列表

  • Julio C Painefilú, Virginia A Bianchi, Bernd Krock, Julieta S De Anna, Gisela Kristoff, Carlos M Luquet. Effects of paralytic shellfish toxins on the middle intestine of Oncorhynchus mykiss: Glutathione metabolism, oxidative status, lysosomal function and ATP-binding cassette class C (ABCC) proteins activity. Ecotoxicology and environmental safety. 2020 Nov; 204(?):111069. doi: 10.1016/j.ecoenv.2020.111069. [PMID: 32758696]
  • Aoi Matsushima, Keisuke Oda, Nobuhiro Mori, Teruo Murakami. Modulation of multidrug resistance-associated proteins function in erythrocytes in glycerol-induced acute renal failure rats. The Journal of pharmacy and pharmacology. 2017 Feb; 69(2):172-181. doi: 10.1111/jphp.12664. [PMID: 27859255]
  • Silvina S M Villanueva, Virginia G Perdomo, María L Ruiz, Juan P Rigalli, Agostina Arias, Marcelo G Luquita, Mary Vore, Viviana A Catania, Aldo D Mottino. Effect of glucagon-like peptide 2 on hepatic, renal, and intestinal disposition of 1-chloro-2,4-dinitrobenzene. Drug metabolism and disposition: the biological fate of chemicals. 2012 Jul; 40(7):1252-8. doi: 10.1124/dmd.111.044339. [PMID: 22453052]
  • Sonali Dubey, Prashant Misra, Sanjay Dwivedi, Sandipan Chatterjee, Sumit K Bag, Shrikant Mantri, Mehar H Asif, Arti Rai, Smita Kumar, Manju Shri, Preeti Tripathi, Rudra D Tripathi, Prabodh K Trivedi, Debasis Chakrabarty, Rakesh Tuli. Transcriptomic and metabolomic shifts in rice roots in response to Cr (VI) stress. BMC genomics. 2010 Nov; 11(?):648. doi: 10.1186/1471-2164-11-648. [PMID: 21092124]
  • Tomoharu Yokooji, Nobuhiro Mori, Teruo Murakami. Modulated function of tissue efflux transporters under hyperbilirubinemia in rats. European journal of pharmacology. 2010 Jun; 636(1-3):166-72. doi: 10.1016/j.ejphar.2010.03.042. [PMID: 20362568]
  • T Yokooji, M Kida, M Mori, H Akashi, N Mori, S Yoshihara, T Murakami. Interaction of Rhei Rhizoma extract with cytochrome P450 3A and efflux transporters in rats. Die Pharmazie. 2010 May; 65(5):367-74. doi: ". [PMID: 20503931]
  • Katja Berginc, Simon Zakelj, Darko Ursic, Albin Kristl. Aged garlic extract stimulates p-glycoprotein and multidrug resistance associated protein 2 mediated effluxes. Biological & pharmaceutical bulletin. 2009 Apr; 32(4):694-9. doi: 10.1248/bpb.32.694. [PMID: 19336907]
  • Tomoharu Yokooji, Teruo Murakami, Ryoko Yumoto, Junya Nagai, Mikihisa Takano. Site-specific bidirectional efflux of 2,4-dinitrophenyl-S-glutathione, a substrate of multidrug resistance-associated proteins, in rat intestine and Caco-2 cells. The Journal of pharmacy and pharmacology. 2007 Apr; 59(4):513-20. doi: 10.1211/jpp.59.4.0005. [PMID: 17430634]
  • Tomoharu Yokooji, Teruo Murakami, Ryoko Yumoto, Junya Nagai, Mikihisa Takano. Function of multidrug resistance-associated protein 2 in acute hepatic failure rats. European journal of pharmacology. 2006 Sep; 546(1-3):152-60. doi: 10.1016/j.ejphar.2006.06.079. [PMID: 16899240]
  • Kumiko Ogawa, Ryoko Yumoto, Natsuki Hamada, Junya Nagai, Mikihisa Takano. Interaction of valproic acid and carbapenem antibiotics with multidrug resistance-associated proteins in rat erythrocyte membranes. Epilepsy research. 2006 Sep; 71(1):76-87. doi: 10.1016/j.eplepsyres.2006.05.016. [PMID: 16806827]
  • Silvina S M Villanueva, María L Ruiz, Carol J Soroka, Shi-Ying Cai, Marcelo G Luquita, Adriana M Torres, Enrique J Sánchez Pozzi, José M Pellegrino, James L Boyer, Viviana A Catania, Aldo D Mottino. Hepatic and extrahepatic synthesis and disposition of dinitrophenyl-S-glutathione in bile duct-ligated rats. Drug metabolism and disposition: the biological fate of chemicals. 2006 Aug; 34(8):1301-9. doi: 10.1124/dmd.106.009415. [PMID: 16679389]
  • Chung-Pu Wu, Anna Maria Calcagno, Stephen B Hladky, Suresh V Ambudkar, Margery A Barrand. Modulatory effects of plant phenols on human multidrug-resistance proteins 1, 4 and 5 (ABCC1, 4 and 5). The FEBS journal. 2005 Sep; 272(18):4725-40. doi: 10.1111/j.1742-4658.2005.04888.x. [PMID: 16156793]
  • Tomoharu Yokooji, Teruo Murakami, Kumiko Ogawa, Ryoko Yumoto, Junya Nagai, Mikihisa Takano. Modulation of intestinal transport of 2,4-dinitrophenyl-S-glutathione, a multidrug resistance-associated protein 2 substrate, by bilirubin treatment in rats. The Journal of pharmacy and pharmacology. 2005 May; 57(5):579-85. doi: 10.1211/0022357056019. [PMID: 15901347]
  • Masakazu Hirouchi, Hiroshi Suzuki, Yuichi Sugiyama. Treatment of hyperbilirubinemia in Eisai hyperbilirubinemic rat by transfecting human MRP2/ABCC2 gene. Pharmaceutical research. 2005 Apr; 22(4):661-6. doi: 10.1007/s11095-005-2502-1. [PMID: 15846474]
  • Carolina I Ghanem, Paula C Gómez, María C Arana, María Perassolo, María L Ruiz, Silvina S M Villanueva, Elena J Ochoa, Viviana A Catania, Laura A Bengochea, Aldo D Mottino. Effect of acetaminophen on expression and activity of rat liver multidrug resistance-associated protein 2 and P-glycoprotein. Biochemical pharmacology. 2004 Aug; 68(4):791-8. doi: 10.1016/j.bcp.2004.05.014. [PMID: 15276087]
  • Marcela A Gonzalez, Marcelo G Roma, Claudio A Bernal, Maria de Lujan Alvarez, Maráia C Carrillo. Biliary secretory function in rats chronically intoxicated with aluminum. Toxicological sciences : an official journal of the Society of Toxicology. 2004 May; 79(1):189-95. doi: 10.1093/toxsci/kfh085. [PMID: 14976346]
  • Young-Joo Lee, Hiroyuki Kusuhara, Yuichi Sugiyama. Do multidrug resistance-associated protein-1 and -2 play any role in the elimination of estradiol-17 beta-glucuronide and 2,4-dinitrophenyl-S-glutathione across the blood-cerebrospinal fluid barrier?. Journal of pharmaceutical sciences. 2004 Jan; 93(1):99-107. doi: 10.1002/jps.10521. [PMID: 14648640]
  • Rajendra Sharma, Yusong Yang, Abha Sharma, Seema Dwivedi, Vsevolod L Popov, Paul J Boor, Sharad S Singhal, Sanjay Awasthi, Yogesh C Awasthi. Mechanisms and physiological significance of the transport of the glutathione conjugate of 4-hydroxynonenal in human lens epithelial cells. Investigative ophthalmology & visual science. 2003 Aug; 44(8):3438-49. doi: 10.1167/iovs.03-0051. [PMID: 12882793]
  • Jingsong Cao, Bruno Stieger, Peter J Meier, Mary Vore. Expression of rat hepatic multidrug resistance-associated proteins and organic anion transporters in pregnancy. American journal of physiology. Gastrointestinal and liver physiology. 2002 Sep; 283(3):G757-66. doi: 10.1152/ajpgi.00126.2002. [PMID: 12181192]
  • Aldo D Mottino, Jingsong Cao, Luis M Veggi, Fernando Crocenzi, Marcelo G Roma, Mary Vore. Altered localization and activity of canalicular Mrp2 in estradiol-17beta-D-glucuronide-induced cholestasis. Hepatology (Baltimore, Md.). 2002 Jun; 35(6):1409-19. doi: 10.1053/jhep.2002.33327. [PMID: 12029626]
  • Rémon A M H van Aubel, Pascal H E Smeets, Janny G P Peters, René J M Bindels, Frans G M Russel. The MRP4/ABCC4 gene encodes a novel apical organic anion transporter in human kidney proximal tubules: putative efflux pump for urinary cAMP and cGMP. Journal of the American Society of Nephrology : JASN. 2002 Mar; 13(3):595-603. doi: 10.1681/asn.v133595. [PMID: 11856762]
  • Y Cui, J König, D Keppler. Vectorial transport by double-transfected cells expressing the human uptake transporter SLC21A8 and the apical export pump ABCC2. Molecular pharmacology. 2001 Nov; 60(5):934-43. doi: 10.1124/mol.60.5.934. [PMID: 11641421]
  • I Podgorski, A W Bull. Energy-dependent export of the 13-oxooctadecadienoic acid-glutathione conjugate from HT-29 cells and plasma membrane vesicles. Biochimica et biophysica acta. 2001 Aug; 1533(1):55-65. doi: 10.1016/s1388-1981(01)00140-8. [PMID: 11514236]
  • M J Harris, M Kuwano, M Webb, P G Board. Identification of the apical membrane-targeting signal of the multidrug resistance-associated protein 2 (MRP2/MOAT). The Journal of biological chemistry. 2001 Jun; 276(24):20876-81. doi: 10.1074/jbc.m010566200. [PMID: 11274200]
  • H Zeng, G Liu, P A Rea, G D Kruh. Transport of amphipathic anions by human multidrug resistance protein 3. Cancer research. 2000 Sep; 60(17):4779-84. doi: . [PMID: 10987286]
  • J F Rebbeor, G C Connolly, J H Henson, J L Boyer, N Ballatori. ATP-dependent GSH and glutathione S-conjugate transport in skate liver: role of an Mrp functional homologue. American journal of physiology. Gastrointestinal and liver physiology. 2000 Aug; 279(2):G417-25. doi: 10.1152/ajpgi.2000.279.2.g417. [PMID: 10915652]
  • R Wheeler, S Y Neo, J Chew, S B Hladky, M A Barrand. Use of membrane vesicles to investigate drug interactions with transporter proteins, P-glycoprotein and multidrug resistance-associated protein. International journal of clinical pharmacology and therapeutics. 2000 Mar; 38(3):122-9. doi: 10.5414/cpp38122. [PMID: 10739115]
  • S K Srivastava, X Hu, H Xia, A Pal, J Guo, J L Orchard, S V Singh. Gender related differences in ATP-dependent transport of dinitrophenyl-glutathione conjugate across murine canalicular liver plasma membrane. FEBS letters. 1999 Feb; 445(2-3):291-4. doi: 10.1016/s0014-5793(99)00140-4. [PMID: 10094475]
  • C A Hinchman, J F Rebbeor, N Ballatori. Efficient hepatic uptake and concentrative biliary excretion of a mercapturic acid. The American journal of physiology. 1998 10; 275(4):G612-9. doi: 10.1152/ajpgi.1998.275.4.g612. [PMID: 9756488]
  • J F Rebbeor, G C Connolly, M E Dumont, N Ballatori. ATP-dependent transport of reduced glutathione in yeast secretory vesicles. The Biochemical journal. 1998 Sep; 334 ( Pt 3)(?):723-9. doi: 10.1042/bj3340723. [PMID: 9729482]
  • I Onaran, A Ozaydin, M Gültepe, G Sultuybek. Transport of glutathione conjugate in erythrocytes from aged subjects and susceptibility to oxidative stress following inhibition of the glutathione S-conjugate pump. Mechanisms of ageing and development. 1998 Jun; 103(2):195-207. doi: 10.1016/s0047-6374(98)00042-6. [PMID: 9701771]
  • R Evers, M Kool, L van Deemter, H Janssen, J Calafat, L C Oomen, C C Paulusma, R P Oude Elferink, F Baas, A H Schinkel, P Borst. Drug export activity of the human canalicular multispecific organic anion transporter in polarized kidney MDCK cells expressing cMOAT (MRP2) cDNA. The Journal of clinical investigation. 1998 Apr; 101(7):1310-9. doi: 10.1172/jci119886. [PMID: 9525973]
  • A Sokal, L Pułaski, B Rychlik, A Fortuniak, G Bartosz. Is the glutathione S-conjugate pump a flippase?. Biochemistry and molecular biology international. 1998 Jan; 44(1):97-105. doi: 10.1080/15216549800201102. [PMID: 9503152]
  • J H Hooijberg, H J Broxterman, M Heijn, D L Fles, J Lankelma, H M Pinedo. Modulation by (iso)flavonoids of the ATPase activity of the multidrug resistance protein. FEBS letters. 1997 Aug; 413(2):344-8. doi: 10.1016/s0014-5793(97)00940-x. [PMID: 9280310]
  • M Heijn, J H Hooijberg, G L Scheffer, G Szabó, H V Westerhoff, J Lankelma. Anthracyclines modulate multidrug resistance protein (MRP) mediated organic anion transport. Biochimica et biophysica acta. 1997 May; 1326(1):12-22. doi: 10.1016/s0005-2736(97)00003-5. [PMID: 9188796]
  • Z S Li, Y P Lu, R G Zhen, M Szczypka, D J Thiele, P A Rea. A new pathway for vacuolar cadmium sequestration in Saccharomyces cerevisiae: YCF1-catalyzed transport of bis(glutathionato)cadmium. Proceedings of the National Academy of Sciences of the United States of America. 1997 Jan; 94(1):42-7. doi: 10.1073/pnas.94.1.42. [PMID: 8990158]
  • K Zhang, K P Wong. Inhibition of the efflux of glutathione S-conjugates by plant polyphenols. Biochemical pharmacology. 1996 Nov; 52(10):1631-8. doi: 10.1016/s0006-2952(96)00570-9. [PMID: 8937479]
  • R Tommasini, R Evers, E Vogt, C Mornet, G J Zaman, A H Schinkel, P Borst, E Martinoia. The human multidrug resistance-associated protein functionally complements the yeast cadmium resistance factor 1. Proceedings of the National Academy of Sciences of the United States of America. 1996 Jun; 93(13):6743-8. doi: 10.1073/pnas.93.13.6743. [PMID: 8692889]
  • R Evers, G J Zaman, L van Deemter, H Jansen, J Calafat, L C Oomen, R P Oude Elferink, P Borst, A H Schinkel. Basolateral localization and export activity of the human multidrug resistance-associated protein in polarized pig kidney cells. The Journal of clinical investigation. 1996 Mar; 97(5):1211-8. doi: 10.1172/jci118535. [PMID: 8636432]
  • K Niinuma, H Suzuki, M Yamazaki, Y Sugiyama. [Preparation of plasma membrane and the analysis of transport kinetics and driving forces]. Nihon rinsho. Japanese journal of clinical medicine. 1996 Mar; 54(3):692-703. doi: NULL. [PMID: 8904225]
  • Y Matsuda, L F Epstein, Z Gatmaitan, I M Arias. The role of thiols in ATP-dependent transport of S-(2,4-dinitrophenyl)glutathione by rat liver plasma membrane vesicles. Biochimica et biophysica acta. 1996 Feb; 1279(1):35-42. doi: 10.1016/0005-2736(95)00241-3. [PMID: 8624358]
  • H Roelofsen, C T Bakker, B Schoemaker, M Heijn, P L Jansen, R P Elferink. Redistribution of canalicular organic anion transport activity in isolated and cultured rat hepatocytes. Hepatology (Baltimore, Md.). 1995 Jun; 21(6):1649-57. doi: NULL. [PMID: 7768511]
  • T P Akerboom, H Sies. Transport of glutathione disulfide and glutathione S-conjugates in hepatocyte plasma membrane vesicles. Methods in enzymology. 1994; 233(?):416-25. doi: 10.1016/s0076-6879(94)33048-4. [PMID: 8015477]
  • R Bossard, B Stieger, B O'Neill, G Fricker, P J Meier. Ethinylestradiol treatment induces multiple canalicular membrane transport alterations in rat liver. The Journal of clinical investigation. 1993 Jun; 91(6):2714-20. doi: 10.1172/jci116511. [PMID: 8514879]
  • G Bartosz, H Sies, T P Akerboom. Organic anions exhibit distinct inhibition patterns on the low-Km and high-Km transport of S-(2,4-dinitrophenyl)glutathione through the human erythrocyte membrane. The Biochemical journal. 1993 May; 292 ( Pt 1)(?):171-4. doi: 10.1042/bj2920171. [PMID: 8503844]
  • T P Akerboom, G Bartosz, H Sies. Low- and high-Km transport of dinitrophenyl glutathione in inside out vesicles from human erythrocytes. Biochimica et biophysica acta. 1992 Jan; 1103(1):115-9. doi: 10.1016/0005-2736(92)90064-s. [PMID: 1730013]
  • T W Simmons, C A Hinchman, N Ballatori. Polarity of hepatic glutathione and glutathione S-conjugate efflux, and intraorgan mercapturic acid formation in the skate. Biochemical pharmacology. 1991 Nov; 42(11):2221-8. doi: 10.1016/0006-2952(91)90359-d. [PMID: 1958237]
  • T P Akerboom, V Narayanaswami, M Kunst, H Sies. ATP-dependent S-(2,4-dinitrophenyl)glutathione transport in canalicular plasma membrane vesicles from rat liver. The Journal of biological chemistry. 1991 Jul; 266(20):13147-52. doi: . [PMID: 2071597]
  • K Kobayashi, S Komatsu, T Nishi, H Hara, K Hayashi. ATP-dependent transport for glucuronides in canalicular plasma membrane vesicles. Biochemical and biophysical research communications. 1991 Apr; 176(2):622-6. doi: 10.1016/s0006-291x(05)80229-3. [PMID: 2025276]
  • K Kobayashi, Y Sogame, H Hara, K Hayashi. Mechanism of glutathione S-conjugate transport in canalicular and basolateral rat liver plasma membranes. The Journal of biological chemistry. 1990 May; 265(14):7737-41. doi: 10.1016/s0021-9258(19)38990-2. [PMID: 2335503]
  • R P Oude Elferink, R Ottenhoff, W G Liefting, B Schoemaker, A K Groen, P L Jansen. ATP-dependent efflux of GSSG and GS-conjugate from isolated rat hepatocytes. The American journal of physiology. 1990 May; 258(5 Pt 1):G699-706. doi: 10.1152/ajpgi.1990.258.5.g699. [PMID: 2333997]
  • T Ishikawa, K Kobayashi, Y Sogame, K Hayashi. Evidence for leukotriene C4 transport mediated by an ATP-dependent glutathione S-conjugate carrier in rat heart and liver plasma membranes. FEBS letters. 1989 Dec; 259(1):95-8. doi: 10.1016/0014-5793(89)81503-0. [PMID: 2599115]
  • Y C Awasthi, S V Singh, H Ahmad, L W Wronski, S K Srivastava, E F LaBelle. ATP dependent primary active transport of xenobiotic-glutathione conjugates by human erythrocyte membrane. Molecular and cellular biochemistry. 1989 Nov; 91(1-2):131-6. doi: 10.1007/bf00228088. [PMID: 2533663]
  • M Kunst, H Sies, T P Akerboom. ATP-stimulated uptake of S-(2,4-dinitrophenyl)glutathione by plasma membrane vesicles from rat liver. Biochimica et biophysica acta. 1989 Jul; 983(1):123-5. doi: 10.1016/0005-2736(89)90389-1. [PMID: 2758047]
  • K Kobayashi, Y Sogame, K Hayashi, P Nicotera, S Orrenius. ATP stimulates the uptake of S-dinitrophenylglutathione by rat liver plasma membrane vesicles. FEBS letters. 1988 Nov; 240(1-2):55-8. doi: 10.1016/0014-5793(88)80339-9. [PMID: 3191999]