Guanidinosuccinic acid (BioDeep_00000001349)

 

Secondary id: BioDeep_00000399984, BioDeep_00000412658

human metabolite PANOMIX_OTCML-2023 Endogenous blood metabolite Toxin BioNovoGene_Lab2019 natural product


代谢物信息卡片


(2S)-2-(diaminomethylideneamino)butanedioic acid

化学式: C5H9N3O4 (175.0593)
中文名称: 2-胍基琥珀酸
谱图信息: 最多检出来源 Homo sapiens(blood) 22.54%

Reviewed

Last reviewed on 2024-10-28.

Cite this Page

Guanidinosuccinic acid. BioDeep Database v3. PANOMIX ltd, a top metabolomics service provider from China. https://query.biodeep.cn/s/guanidinosuccinic_acid (retrieved 2024-12-22) (BioDeep RN: BioDeep_00000001349). Licensed under the Attribution-Noncommercial 4.0 International License (CC BY-NC 4.0).

分子结构信息

SMILES: C(C(C(=O)O)N=C(N)N)C(=O)O
InChI: InChI=1S/C5H9N3O4/c6-5(7)8-2(4(11)12)1-3(9)10/h2H,1H2,(H,9,10)(H,11,12)(H4,6,7,8)/t2-/m0/s1

描述信息

Guanidinosuccinic acid (GSA) has been identified as a uremic toxin according to the European Uremic Toxin Working Group (PMID:22626821). It is one of the earliest uremic toxins isolated and its toxicity identified. Its metabolic origins show that it arose from the oxidation of argininosuccinic acid (ASA) by free radicals. The stimulus for this oxidation, occurring optimally in the presence of the failed kidney, is the rising level of urea which, through enzyme inhibition, results in a decline in hepatic levels of the semi-essential amino acid, arginine. It is further noted that concentrations of GSA in both serum and urine decline sharply in animals and humans exposed to the essential amino acid, methionine. Uremic patients suffer from a defective ability to generate methyl groups due to anorexia, dietary restrictions and renal protein leakage. This leads to the accumulation of homocysteine, a substance known to produce vascular damage. Even in healthy subjects intake of choline together with methionine is insufficient to satisfy total metabolic requirements for methyl groups. In end-stage renal disease, therefore, protein restriction contributes to the build-up of toxins in uremia. Replacement using specific amino acid mixtures should be directed toward identified deficiencies and adequacy monitored by following serum levels of the related toxins, in this case GSA and homocysteine. (PMID 12701806).
Guanidinosuccinic acid (GSA) is one of the earliest uremic toxins isolated and its toxicity identified. Its metabolic origins show that it arose from the oxidation of argininosuccinic acid (ASA) by free radicals. The stimulus for this oxidation, occurring optimally in the presence of the failed kidney, is the rising level of urea which, through enzyme inhibition, results in a decline in hepatic levels of the semi-essential amino acid, arginine. It is further noted that concentrations of GSA in both serum and urine decline sharply in animals and humans exposed to the essential amino acid, methionine. Uremic patients suffer from a defective ability to generate methyl groups due to anorexia, dietary restrictions and renal protein leakage. This leads to the accumulation of homocysteine, a substance known to produce vascular damage. Even in healthy subjects intake of choline together with methionine is insufficient to satisfy total metabolic requirements for methyl groups. In end-stage renal disease, therefore, protein restriction contributes to the build-up of toxins in uremia. Replacement using specific amino acid mixtures should be directed toward identified deficiencies and adequacy monitored by following serum levels of the related toxins, in this case GSA and homocysteine. (PMID 12701806) [HMDB]
Guanidinosuccinic acid is a nitrogenous metabolite.

同义名列表

14 个代谢物同义名

(2S)-2-(diaminomethylideneamino)butanedioic acid; (2S)-2-Carbamimidamidobutanedioic acid; N-(Aminoiminomethyl)-L-aspartic acid; Guanidinosuccinic acid, (DL)-isomer; (2S)-2-Carbamimidamidobutanedioate; N-(Aminoiminomethyl)-L-aspartate; N-Carbamimidoyl-L-aspartic acid; N-Amidino-L-aspartic acid; L-N-Amidinoaspartic acid; Guanidinosuccinic acid; N-Amidino-L-aspartate; L-N-Amidinoaspartate; Guanidinosuccinate; N-Amidino-L-aspartate



数据库引用编号

20 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)

33 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 11 AHSP, ARG1, ASL, ASS1, AXIN2, CA1, CAT, FH, NLN, PKM, XDH
Endoplasmic reticulum membrane 1 TKT
Nucleus 4 ARG1, AXIN2, FH, PKM
cytosol 12 ARG1, ASL, ASS1, AXIN2, CA1, CAT, FH, GPT, NLN, PKM, TKT, XDH
nuclear body 1 TKT
centrosome 1 AXIN2
nucleoplasm 2 ASS1, TKT
Cell membrane 2 ADGRE5, TKT
Cytoplasmic granule 1 ARG1
Multi-pass membrane protein 3 ABCC3, ADGRE5, SLCO4C1
Synapse 1 TAC1
mitochondrial inner membrane 1 GATM
neuronal cell body 1 TAC1
Cytoplasm, cytosol 2 ASS1, NLN
plasma membrane 7 ABCC3, ADGRE5, AXIN2, ICAM3, NLN, SLCO4C1, TKT
Membrane 4 ABCC3, ADGRE5, CAT, ICAM3
apical plasma membrane 1 TKT
axon 1 TAC1
basolateral plasma membrane 2 ABCC3, SLCO4C1
extracellular exosome 12 ADGRE5, ASL, ASS1, CA1, CAT, FH, GATM, GPT, ICAM3, PKM, SLCO4C1, TKT
extracellular space 4 ARG1, PTH, TAC1, XDH
mitochondrion 5 CAT, FH, GATM, NLN, PKM
protein-containing complex 1 CAT
intracellular membrane-bounded organelle 1 CAT
Single-pass type I membrane protein 2 ICAM3, TKT
extracellular region 6 ARG1, CAT, NLN, PKM, PTH, TAC1
mitochondrial outer membrane 1 ASS1
mitochondrial matrix 2 CAT, FH
Extracellular vesicle 1 PKM
actin cytoskeleton 1 TKT
perikaryon 1 ASS1
beta-catenin destruction complex 1 AXIN2
vesicle 2 PKM, TKT
Mitochondrion inner membrane 1 GATM
focal adhesion 3 ADGRE5, CAT, TKT
Peroxisome 3 CAT, TKT, XDH
sarcoplasmic reticulum 1 XDH
Peroxisome matrix 1 CAT
peroxisomal matrix 1 CAT
peroxisomal membrane 1 CAT
Mitochondrion intermembrane space 1 NLN
mitochondrial intermembrane space 2 GATM, NLN
collagen-containing extracellular matrix 1 PKM
receptor complex 1 TKT
cilium 1 PKM
Chromosome 1 FH
Basolateral cell membrane 2 ABCC3, SLCO4C1
site of double-strand break 1 FH
cell body fiber 1 ASS1
specific granule membrane 1 SLCO4C1
basal plasma membrane 1 ABCC3
ficolin-1-rich granule lumen 2 CAT, PKM
secretory granule lumen 2 CAT, PKM
secretory granule membrane 1 ADGRE5
specific granule lumen 1 ARG1
azurophil granule membrane 1 SLCO4C1
azurophil granule lumen 1 ARG1
Basal cell membrane 1 ABCC3
Rough endoplasmic reticulum 1 PKM
hemoglobin complex 1 AHSP
catalase complex 1 CAT
[Isoform Mitochondrial]: Mitochondrion 1 FH
[Isoform Cytoplasmic]: Cytoplasm, cytosol 1 FH
[Isoform M2]: Cytoplasm 1 PKM
[Isoform M1]: Cytoplasm 1 PKM
[Adhesion G protein-coupled receptor E5 subunit alpha]: Secreted, extracellular space 1 ADGRE5


文献列表

  • Mahim I Qureshi, Michele Greco, Panagiotis A Vorkas, Elaine Holmes, Alun H Davies. Application of Metabolic Profiling to Abdominal Aortic Aneurysm Research. Journal of proteome research. 2017 07; 16(7):2325-2332. doi: 10.1021/acs.jproteome.6b00894. [PMID: 28287739]
  • Rizwan Ali Zounr, Mumammad Yar Khuhawar, Taj Muhammad Jahangir, Malik Alamgir. Improved Gas Chromatographic Determination of Guanidino Compounds Using Isovaleroylacetone and Ethyl Chloroformate as Derivatizing Reagents. Analytical sciences : the international journal of the Japan Society for Analytical Chemistry. 2016; 32(2):141-6. doi: 10.2116/analsci.32.141. [PMID: 26860556]
  • Liqiang Gu, Xiaofan Wang, Yuanyuan Zhang, Yu Jiang, Huan Lu, Kaishun Bi, Xiaohui Chen. Determination of 12 potential nephrotoxicity biomarkers in rat serum and urine by liquid chromatography with mass spectrometry and its application to renal failure induced by Semen Strychni. Journal of separation science. 2014 May; 37(9-10):1058-66. doi: 10.1002/jssc.201400053. [PMID: 24610835]
  • S A Majidano, M Y Khuhawar. Gas chromatographic determination of guanidino compounds in uremic patients using glyoxal as derivatizing reagent. Journal of chromatographic science. 2012 May; 50(5):380-6. doi: 10.1093/chromsci/bms013. [PMID: 22392369]
  • Masanori Tachikawa, Saori Ikeda, Jun Fujinawa, Shirou Hirose, Shin-ichi Akanuma, Ken-ichi Hosoya. γ-Aminobutyric acid transporter 2 mediates the hepatic uptake of guanidinoacetate, the creatine biosynthetic precursor, in rats. PloS one. 2012; 7(2):e32557. doi: 10.1371/journal.pone.0032557. [PMID: 22384273]
  • Michal Ciborowski, Joanna Teul, Jose Luis Martin-Ventura, Jesús Egido, Coral Barbas. Metabolomics with LC-QTOF-MS permits the prediction of disease stage in aortic abdominal aneurysm based on plasma metabolic fingerprint. PloS one. 2012; 7(2):e31982. doi: 10.1371/journal.pone.0031982. [PMID: 22384120]
  • Takafumi Toyohara, Takaaki Abe. [Analysis of transporter function and development to clinical application]. Seikagaku. The Journal of Japanese Biochemical Society. 2011 Apr; 83(4):323-8. doi: NULL. [PMID: 21626887]
  • Daisuke Saigusa, Naoto Suzuki, Mai Takahashi, Kanako Shiba, Satoshi Tanaka, Takaaki Abe, Takanori Hishinuma, Yoshihisa Tomioka. Simultaneous determination of guanidinosuccinic acid and guanidinoacetic acid in urine using high performance liquid chromatography/tandem mass spectrometry. Analytica chimica acta. 2010 Sep; 677(2):169-75. doi: 10.1016/j.aca.2010.08.005. [PMID: 20837184]
  • Eva Schepers, Griet Glorieux, Laetitia Dou, Claire Cerini, Nathalie Gayrard, Loïc Louvet, Charlotte Maugard, Pierre Preus, Maria Rodriguez-Ortiz, Angel Argiles, Philippe Brunet, Gerald Cohen, Joachim Jankowski, Vera Jankowski, Ziad Massy, Mariano Rodriguez, Raymond Vanholder. Guanidino compounds as cause of cardiovascular damage in chronic kidney disease: an in vitro evaluation. Blood purification. 2010; 30(4):277-87. doi: 10.1159/000320765. [PMID: 21079396]
  • Min Fu, Zhao-Hui Sun, Huan-Cong Zuo. Neuroprotective effect of piperine on primarily cultured hippocampal neurons. Biological & pharmaceutical bulletin. 2010; 33(4):598-603. doi: 10.1248/bpb.33.598. [PMID: 20410592]
  • Kazuharu Ienaga, Hiroki Mikami, Takako Yokozawa. First indications demonstrating the preventive effects of NZ-419, a novel intrinsic antioxidant, on the initiation and/or progression of chronic renal failure in rats. Biological & pharmaceutical bulletin. 2009 Jul; 32(7):1204-8. doi: 10.1248/bpb.32.1204. [PMID: 19571386]
  • Don J Durzan. Arginine, scurvy and Cartier's 'tree of life'. Journal of ethnobiology and ethnomedicine. 2009 Feb; 5(?):5. doi: 10.1186/1746-4269-5-5. [PMID: 19187550]
  • Olivier Levillain, Bart Marescau, Ilse Possemiers, Peter Paul De Deyn. Accumulation of methylguanidine and changes in guanidino compound levels in plasma, urine, and kidneys of furosemide-treated rats. Metabolism: clinical and experimental. 2008 Jun; 57(6):802-10. doi: 10.1016/j.metabol.2008.01.025. [PMID: 18502263]
  • Youri E C Taes, Bart Marescau, An De Vriese, Peter P De Deyn, Eva Schepers, Raymond Vanholder, Joris R Delanghe. Guanidino compounds after creatine supplementation in renal failure patients and their relation to inflammatory status. Nephrology, dialysis, transplantation : official publication of the European Dialysis and Transplant Association - European Renal Association. 2008 Apr; 23(4):1330-5. doi: 10.1093/ndt/gfm793. [PMID: 18048424]
  • Burton D Cohen. Premature aging in uremia. Molecular and cellular biochemistry. 2007 Apr; 298(1-2):195-8. doi: 10.1007/s11010-006-9351-z. [PMID: 17136440]
  • R Gatti, M G Gioia. Anisoin: a useful pre-chromatographic derivatization fluorogenic reagent for LC analysis of guanidino compounds. Journal of pharmaceutical and biomedical analysis. 2006 Sep; 42(1):11-6. doi: 10.1016/j.jpba.2005.12.035. [PMID: 16460903]
  • A Torremans, B Marescau, B Kränzlin, N Gretz, J-M Billiouw, R Vanholder, R De Smet, K Bouwman, R Brouns, P P De Deyn. Biochemical validation of a rat model for polycystic kidney disease: comparison of guanidino compound profile with the human condition. Kidney international. 2006 Jun; 69(11):2003-12. doi: 10.1038/sj.ki.5000443. [PMID: 16641922]
  • R O Law. Cerebrocellular swelling in the presence of uraemic guanidino compounds: ameliorative effects of taurine. Neurochemical research. 2005 Dec; 30(12):1465-70. doi: 10.1007/s11064-005-8823-y. [PMID: 16362765]
  • Sunny Eloot, An Torremans, Rita De Smet, Bart Marescau, Dirk De Wachter, Peter Paul De Deyn, Norbert Lameire, Pascal Verdonck, Raymond Vanholder. Kinetic behavior of urea is different from that of other water-soluble compounds: the case of the guanidino compounds. Kidney international. 2005 Apr; 67(4):1566-75. doi: 10.1111/j.1523-1755.2005.00238.x. [PMID: 15780113]
  • Birgitta C Burckhardt, Julia Lorenz, Christoph Kobbe, Gerhard Burckhardt. Substrate specificity of the human renal sodium dicarboxylate cotransporter, hNaDC-3, under voltage-clamp conditions. American journal of physiology. Renal physiology. 2005 Apr; 288(4):F792-9. doi: 10.1152/ajprenal.00360.2004. [PMID: 15561973]
  • An Torremans, Bart Marescau, Debby Van Dam, Chris Van Ginneken, Frans Van Meir, Pierre-Paul Van Bogaert, Rudi D'Hooge, Jan de Vente, Peter Paul De Deyn. GSA: behavioral, histological, electrophysiological and neurochemical effects. Physiology & behavior. 2005 Feb; 84(2):251-64. doi: 10.1016/j.physbeh.2004.12.001. [PMID: 15708777]
  • Wim Derave, Bart Marescau, Els Vanden Eede, Bert O Eijnde, Peter P De Deyn, Peter Hespel. Plasma guanidino compounds are altered by oral creatine supplementation in healthy humans. Journal of applied physiology (Bethesda, Md. : 1985). 2004 Sep; 97(3):852-7. doi: 10.1152/japplphysiol.00206.2004. [PMID: 15107411]
  • Griet L Glorieux, Annemieke W Dhondt, Peter Jacobs, Joke Van Langeraert, Norbert H Lameire, Peter Paul De Deyn, Raymond C Vanholder. In vitro study of the potential role of guanidines in leukocyte functions related to atherogenesis and infection. Kidney international. 2004 Jun; 65(6):2184-92. doi: 10.1111/j.1523-1755.2004.00631.x. [PMID: 15149331]
  • Rudi D'Hooge, Gerda Van de Vijver, Pierre-Paul Van Bogaert, Bart Marescau, Raymond Vanholder, Peter P De Deyn. Involvement of voltage- and ligand-gated Ca2+ channels in the neuroexcitatory and synergistic effects of putative uremic neurotoxins. Kidney international. 2003 May; 63(5):1764-75. doi: 10.1046/j.1523-1755.2003.00912.x. [PMID: 12675852]
  • Kazumasa Aoyagi. Inhibition of arginine synthesis by urea: a mechanism for arginine deficiency in renal failure which leads to increased hydroxyl radical generation. Molecular and cellular biochemistry. 2003 Feb; 244(1-2):11-5. doi: NULL. [PMID: 12701804]
  • Burton D Cohen. Methyl group deficiency and guanidino production in uremia. Molecular and cellular biochemistry. 2003 Feb; 244(1-2):31-6. doi: . [PMID: 12701806]
  • Olivier Levillain, Bart Marescau, Ilse Possemiers, Paul De Deyn. Dehydration modifies guanidino compound concentrations in the different zones of the rat kidney. Pflugers Archiv : European journal of physiology. 2002 May; 444(1-2):143-52. doi: 10.1007/s00424-002-0787-z. [PMID: 11976926]
  • M Al Banchaabouchi, B Marescau, E Van Marck, R D'hooge, P P De Deyn. Long-term effect of partial nephrectomy on biological parameters, kidney histology, and guanidino compound levels in mice. Metabolism: clinical and experimental. 2001 Dec; 50(12):1418-25. doi: 10.1053/meta.2001.26763. [PMID: 11735086]
  • M Al Banchaabouchi, B Marescau, R D'Hooge, P P De Deyn. The effect of high protein diet on urea and guanidino compound levels in renal insufficient mice. Amino acids. 2001 Dec; 21(4):401-15. doi: 10.1007/s007260170005. [PMID: 11858699]
  • I Pietrzak, M Komarnicki, D Zaremba-Drobnik. Platelet aggregation and prostaglandin metabolism in uremic patients. American journal of kidney diseases : the official journal of the National Kidney Foundation. 2001 Oct; 38(4 Suppl 1):S111-4. doi: 10.1053/ajkd.2001.27416. [PMID: 11576934]
  • M J Smogorzewski. Central nervous dysfunction in uremia. American journal of kidney diseases : the official journal of the National Kidney Foundation. 2001 Oct; 38(4 Suppl 1):S122-8. doi: 10.1053/ajkd.2001.27419. [PMID: 11576937]
  • O Levillain, B Marescau, I Possemiers, M Al Banchaabouchi, P P De Deyn. Influence of 72\% injury in one kidney on several organs involved in guanidino compound metabolism: a time course study. Pflugers Archiv : European journal of physiology. 2001 Jul; 442(4):558-69. doi: 10.1007/s004240100581. [PMID: 11510889]
  • P P De Deyn, R D'Hooge, P P Van Bogaert, B Marescau. Endogenous guanidino compounds as uremic neurotoxins. Kidney international. Supplement. 2001 Feb; 78(?):S77-83. doi: 10.1046/j.1523-1755.2001.59780077.x. [PMID: 11168988]
  • K Aoyagi, S Shahrzad, S Iida, C Tomida, A Hirayama, S Nagase, K Takemura, A Koyama, S Ohba, M Narita, B D Cohen. Role of nitric oxide in the synthesis of guanidinosuccinic acid, an activator of the N-methyl-D-aspartate receptor. Kidney international. Supplement. 2001 Feb; 78(?):S93-6. doi: 10.1046/j.1523-1755.2001.59780093.x. [PMID: 11168991]
  • I Pietrzak, K Baczyk. Erythrocyte transketolase activity and guanidino compounds in hemodialysis patients. Kidney international. Supplement. 2001 Feb; 78(?):S97-101. doi: 10.1046/j.1523-1755.2001.59780097.x. [PMID: 11168992]
  • C Parikh, G Gyamlani, N Panlilio, C P Carvounis. Unmeasured cations: probable cause of relatively low anion gap in chronic renal failure. Renal failure. 2001 Jan; 23(1):91-6. doi: 10.1081/jdi-100001288. [PMID: 11256534]
  • M Noris, G Remuzzi. Uremic bleeding: closing the circle after 30 years of controversies?. Blood. 1999 Oct; 94(8):2569-74. doi: NULL. [PMID: 10515859]
  • Y Nohara, T Hanai, J Suzuki, G Matsumoto, F Iinuma, H Kubo, T Kinoshita. Automatic system for the assay of guanidino compounds to assess uremic status and effect of hemodialysis. Chemical & pharmaceutical bulletin. 1998 Nov; 46(11):1844-5. doi: 10.1248/cpb.46.1844. [PMID: 9845964]
  • M Al Banchaabouchi, B Marescau, R D'Hooge, E Van Marck, A Van Daele, O Levillain, P P De Deyn. Biochemical and histopathological changes in nephrectomized mice. Metabolism: clinical and experimental. 1998 Mar; 47(3):355-61. doi: 10.1016/s0026-0495(98)90271-2. [PMID: 9500577]
  • T Yokozawa, E Dong, H Oura, G Nonaka, I Nishioka. Magnesium lithospermate B ameliorates cisplatin-induced injury in cultured renal epithelial cells. Experimental and toxicologic pathology : official journal of the Gesellschaft fur Toxikologische Pathologie. 1997 Dec; 49(5):343-6. doi: 10.1016/s0940-2993(97)80104-2. [PMID: 9455679]
  • T Kinoshita. [Chronic renal failure and guanidino compounds]. Yakugaku zasshi : Journal of the Pharmaceutical Society of Japan. 1997 Nov; 117(10-11):673-80. doi: 10.1248/yakushi1947.117.10-11_673. [PMID: 9414581]
  • J Verhelst, J Berwaerts, B Marescau, R Abs, H Neels, C Mahler, P P De Deyn. Serum creatine, creatinine, and other guanidino compounds in patients with thyroid dysfunction. Metabolism: clinical and experimental. 1997 Sep; 46(9):1063-7. doi: 10.1016/s0026-0495(97)90279-1. [PMID: 9284897]
  • O Levillain, B Marescau, P P De Deyn. Renal handling of guanidino compounds in rat and rabbit. The Journal of physiology. 1997 Mar; 499 ( Pt 2)(?):561-70. doi: 10.1113/jphysiol.1997.sp021949. [PMID: 9080382]
  • J C Pan, Y Q Pei, L An, L Lai, R D'Hooge, P P De Deyn. Epileptiform activity and hippocampal damage produced by intrahippocampal injection of guanidinosuccinic acid in rat. Neuroscience letters. 1996 May; 209(2):121-4. doi: 10.1016/0304-3940(96)12615-x. [PMID: 8761997]
  • I Pietrzak, R Czarnecki, K Baczyk, K Antoniewicz. [Uremic polyneuropathy in patients treated conservatively (nondialyzed) or treated with dialysis]. Przeglad lekarski. 1996; 53(7):544-8. doi: . [PMID: 8975290]
  • K Aoyagi, S Nagase, M Gotoh, K Akiyama, M Satoh, A Hirayama, A Koyama. Role of reactive oxygen and argininosuccinate in guanidinosuccinate synthesis in isolated rat hepatocytes. Enzyme & protein. 1996; 49(4):205-11. doi: 10.1159/000468630. [PMID: 9030887]
  • P P De Deyn, P Robitaille, M Vanasse, I A Qureshi, B Marescau. Serum guanidino compound levels in uremic pediatric patients treated with hemodialysis or continuous cycle peritoneal dialysis. Correlations between nerve conduction velocities and altered guanidino compound concentrations. Nephron. 1995; 69(4):411-7. doi: 10.1159/000188511. [PMID: 7777105]
  • R D'Hooge, Y Q Pei, B Marescau, P P De Deyn. Ontogenetic differences in convulsive action and cerebral uptake of uremic guanidino compounds in juvenile mice. Neurochemistry international. 1994 Mar; 24(3):215-20. doi: 10.1016/0197-0186(94)90078-7. [PMID: 8025530]
  • A Dasgupta, S Malik. Fast atom bombardment mass spectrometric determination of the molecular weight range of uremic compounds that displace phenytoin from protein binding: absence of midmolecular uremic toxins. American journal of nephrology. 1994; 14(3):162-8. doi: 10.1159/000168708. [PMID: 7977474]
  • M R Gyetko, C H Hsu, C C Wilkinson, S Patel, E Young. Monocyte 1 alpha-hydroxylase regulation: induction by inflammatory cytokines and suppression by dexamethasone and uremia toxin. Journal of leukocyte biology. 1993 Jul; 54(1):17-22. doi: 10.1002/jlb.54.1.17. [PMID: 8336075]
  • K L Meert, D R Deshmukh, B Marescau, V S Ghole, P P De Deyn, A P Sarnaik. Effect of urease-induced hyperammonemia on metabolism of guanidino compounds. Biochemical medicine and metabolic biology. 1993 Feb; 49(1):51-6. doi: 10.1006/bmmb.1993.1005. [PMID: 8439450]
  • Y Suzuki. [Guanidino compounds and aliphatic monoamines in acute and chronic renal failure]. Nihon Jinzo Gakkai shi. 1992 Oct; 34(10):1077-85. doi: . [PMID: 1289608]
  • B Marescau, P P De Deyn, I A Qureshi, M E De Broe, I Antonozzi, S D Cederbaum, R Cerone, N Chamoles, R Gatti, S S Kang. The pathobiochemistry of uremia and hyperargininemia further demonstrates a metabolic relationship between urea and guanidinosuccinic acid. Metabolism: clinical and experimental. 1992 Sep; 41(9):1021-4. doi: 10.1016/0026-0495(92)90131-s. [PMID: 1518417]
  • Z Kopczyński, T Dryl-Rydzyńska. [Studies of the effects of low-molecular uremic toxins on anaerobic metabolism of human erythrocytes]. Polskie Archiwum Medycyny Wewnetrznej. 1991 Oct; 86(4):232-8. doi: NULL. [PMID: 1813877]
  • Z Kopczyński, T Dryl-Rydzyńska. [Effect of methylguanidine and guanidine succinic acid on methemoglobin reductase activity in human red cells]. Polski tygodnik lekarski (Warsaw, Poland : 1960). 1991 Feb; 46(6-7):140-2. doi: . [PMID: 1845732]
  • M Maejima, S Takahashi, M Hatano. [Platelet aggregation in chronic renal failure--whole blood aggregation and effect of guanidino compounds]. Nihon Jinzo Gakkai shi. 1991 Feb; 33(2):201-12. doi: NULL. [PMID: 2051648]
  • T Yokozawa, K Fujioka, H Oura, G Nonaka, I Nishioka. Effects of rhubarb tannins on uremic toxins. Nephron. 1991; 58(2):155-60. doi: 10.1159/000186406. [PMID: 1865970]
  • S Patel, C H Hsu. Effect of polyamines, methylguanidine, and guanidinosuccinic acid on calcitriol synthesis. The Journal of laboratory and clinical medicine. 1990 Jan; 115(1):69-73. doi: NULL. [PMID: 2299258]
  • M Miura, Y Nomoto, H Sakai. Short term effect of lactulose therapy in patients with chronic renal failure. The Tokai journal of experimental and clinical medicine. 1989 Mar; 14(1):29-34. doi: NULL. [PMID: 2699952]
  • T Yokozawa, Z L Mo, H Oura. Comparison of toxic effects of methylguanidine, guanidinosuccinic acid and creatinine in rats with adenine-induced chronic renal failure. Nephron. 1989; 51(3):388-92. doi: 10.1159/000185328. [PMID: 2918950]
  • K Haruki, M Hirata, H Muramoto, Y Tofuku, R Takeda. [A striking rise of serum guanidinosuccinic acid (s-GSA) in the critical period of CRF]. Nihon Jinzo Gakkai shi. 1988 Jul; 30(7):821-5. doi: . [PMID: 3249449]
  • Z Kopczyński, T Dryl-Rydzyńska. Studies on the effect of low-molecule uremic toxins on the activity of glucose-6-phosphate dehydrogenase (E.C.1.1.1.49) and transketolase (E.C.2.2.1.1) in human red blood cells. Acta physiologica Polonica. 1988 Jul; 39(4):269-75. doi: . [PMID: 3252690]
  • S Shindo, Y Watanabe, A Mori. Effects of starvation on guanidino compound metabolism in mice. Research communications in chemical pathology and pharmacology. 1986 Oct; 54(1):73-85. doi: . [PMID: 3797807]
  • P De Deyn, B Marescau, W Lornoy, I Becaus, A Lowenthal. Guanidino compounds in uraemic dialysed patients. Clinica chimica acta; international journal of clinical chemistry. 1986 Jun; 157(2):143-50. doi: 10.1016/0009-8981(86)90220-2. [PMID: 3719996]
  • D Powell, J Bergstrom, R Dzurik, P Gulyassy, D Lockwood, L Phillips. Toxins and inhibitors in chronic renal failure. American journal of kidney diseases : the official journal of the National Kidney Foundation. 1986 Apr; 7(4):292-9. doi: 10.1016/s0272-6386(86)80070-1. [PMID: 3515909]
  • Y Tofuku, M Kuroda, H Muramoto, R Takeda. [A study of guanidine metabolism in uremia, with special reference to serum guanidinoacetic acid in anephric patients]. Nihon Jinzo Gakkai shi. 1984 Feb; 26(2):171-81. doi: NULL. [PMID: 6748335]
  • K Aoyagi, S Ohba, M Narita, S Tojo. Regulation of biosynthesis of guanidinosuccinic acid in isolated rat hepatocytes and in vivo. Kidney international. Supplement. 1983 Dec; 16(?):S224-8. doi: . [PMID: 6588254]
  • A Fujimura, M Kawato, H Nakabayashi, Y Tofuku, M Noto, T Akiyama, C Kido, M Kuroda, R Takeda. [Hyperprolactinemia and guanidinosuccinic acid in chronic renal failure]. Nihon Jinzo Gakkai shi. 1983 Feb; 25(2):199-204. doi: NULL. [PMID: 6620688]
  • H Böhles, B D Cohen, D Michalk. Guanidinosuccinic acid excretion in argininosuccinic aciduria. Advances in experimental medicine and biology. 1982; 153(?):443-8. doi: 10.1007/978-1-4757-6903-6_54. [PMID: 7164917]
  • T Hoshino. Recommended deproteinizing methods for plasma guanidino compound analysis by liquid chromatography. Advances in experimental medicine and biology. 1982; 153(?):391-400. doi: 10.1007/978-1-4757-6903-6_48. [PMID: 6299066]
  • Y Ochiai, S Abe, T Yamada, K Tada, F Kosaka. Guanidino compounds and hemodialysis. Advances in experimental medicine and biology. 1982; 153(?):459-64. doi: 10.1007/978-1-4757-6903-6_56. [PMID: 7164919]
  • H Mikami, Y Orita, A Ando, M Fujii, T Kikuchi, K Yoshihara, A Okada, H Abe. Metabolic pathway of guanidino compounds in chronic renal failure. Advances in experimental medicine and biology. 1982; 153(?):449-58. doi: 10.1007/978-1-4757-6903-6_55. [PMID: 7164918]
  • B Marescau, A Lowenthal, H G Terheggen, E Esmans, F Alderweireldt. Guanidino compounds in hyperargininemia. Advances in experimental medicine and biology. 1982; 153(?):427-34. doi: 10.1007/978-1-4757-6903-6_52. [PMID: 7164915]
  • N Riccioni, M T Monari, S Gualandi, R Tazzari, F Corsini. [Urinary guanidinosuccinic acid in uremic children]. Bollettino della Societa italiana di biologia sperimentale. 1980 Oct; 56(19):1936-41. doi: . [PMID: 7459104]
  • Y Tofuku, M Kuroda, T Kita, R Takeda. [Studies on guanidine compounds in uremia: reevaluation of serum GSA in relation to acute symptoms of uremia (author's transl)]. Nihon Jinzo Gakkai shi. 1980 Mar; 22(3):249-58. doi: NULL. [PMID: 7382166]
  • W M Keane, W P Potsic, L J Perloff, C F Barker, R A Grossman. Aspergillus thyroiditis. Otolaryngology. 1978 Sep; 86(5):ORL-761. doi: 10.1177/019459987808600519. [PMID: 114945]
  • M Y Liang, M Toporek, B Schepartz. Screening uremic 'toxins' using bromsulfophthalein clearance by the isolated perfused rat liver. Nephron. 1978; 22(4-6):306-11. doi: 10.1159/000181467. [PMID: 740090]
  • J D Kopple, S I Gordon, M Wang, M E Swendseid. Factors affecting serum and urinary guanidinosuccinic acid levels in normal and uremic subjects. The Journal of laboratory and clinical medicine. 1977 Aug; 90(2):303-11. doi: . [PMID: 886215]
  • G Perez, C Abraira, A Rey, M Horn. Removal of guanidinosuccinic acid by hemodialysis. Nephron. 1977; 19(4):214-9. doi: 10.1159/000180891. [PMID: 917168]
  • G Perez, A Rey, E Schiff. The biosynthesis of guanidinosuccinic acid by perfused rat liver. The Journal of clinical investigation. 1976 Mar; 57(3):807-9. doi: 10.1172/jci108340. [PMID: 1249211]