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Chemical Compound Review

homocysteine     2-amino-4-sulfanyl-butanoic acid

Synonyms: homo-cys, PubChem19432, CHEMBL310604, ACMC-1B2D6, AG-F-57853, ...
 
 
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Disease relevance of homocysteine

 

Psychiatry related information on homocysteine

 

High impact information on homocysteine

 

Chemical compound and disease context of homocysteine

  • CONCLUSIONS: We conclude that Cys, Met, N-acetylcysteine, and DL-homocysteine differentially inhibit DDP toxicity and uptake in cultured S1, S3, and DCT cells, and that the inhibition of uptake, as well as the complexation of DDP with Cys within the cell, may prevent toxicity [13].
 

Biological context of homocysteine

 

Anatomical context of homocysteine

  • DL-Homocysteine (1200 mg/kg; i.p. injection) produced epileptic activity in hippocampus in an inconsistent manner [19].
  • Upon Hcy treatment of hepatocytes, there was a significant increase in HMG-CoA reductase mRNA expression in these cells [2].
  • 3. The effect of D,L-homocysteine (200 microM or 2 mM) cannot be ascribed to a direct antimuscarinic effect since 30 min pretreatment of rat ileum with these concentrations did not significantly change the contractile effect of increasing concentrations of acetylcholine (0.015-15 microM) [15].
  • We tested the hypothesis that recovery from ailing to failing myocardium in diabetes by PPARgamma agonist is in part due to decreased matrix metalloproteinase-9 (MMP-9) activation and left ventricular (LV) tissue levels of homocysteine (Hcy) [20].
  • METHODS: For the proliferation study, bovine aortic smooth muscle cells (BASMC, 10, 000/well) were allowed to grow for 2 days before 2 mmol/L D,L -homocysteine was added for 2, 4, 6, and 8 days to simulate the clinical hyperhomocysteinemic condition [17].
 

Associations of homocysteine with other chemical compounds

  • However, Hcy-mediated brain MVEC collagen constriction was abrogated with anti-beta-1 integrin [9].
  • Gels in the absence or presence of Hcy were incubated with muscimol or baclofen, a GABA-B receptor agonist [9].
  • Elevated plasma homocysteine (Hcy) concentration is associated with other cardiovascular risk factors [2].
  • In vitro, S-adenosylhomocysteine acted similar to but more potently than DL-homocysteine, augmenting KYNA production at 0.03-0.08 mM and reducing it at > or =0.5 mM [21].
  • Two groups of six male weanling Sprague-Dawley rats were provided with deionized water and pair-fed diets that were adequate (14.0 mg/kg) or deficient (1.3 mg/kg) in Cu to groups fed diets similarly adequate or deficient in Cu but containing DL-homocysteine (10 g/kg) [22].
  • Mass spectrometric analysis showed that, by means of an arginine (Arg)-thiol electrostatic interaction, homocysteine forms noncovalent complexes with the two Arg-rich epitopes of the third intracellular loop of the D2 receptor, one of them involved in A(2A)-D2 receptor heteromerization [23].
  • T24/83 cells stably overexpressing the Ca(2+)-binding ER chaperone GRP78 showed diminished cytosolic Ca(2+) transients induced by homocysteine and reduced ER-Ca(2+) emptying evoked by thapsigargin [24].
  • Supplementation with folate and vitamins B-6 and B-12 lowered plasma homocysteine but had no beneficial effect on bone turnover at the end of 2 y, as assessed by biomarkers of bone formation and resorption [25].
  • Lower levels of folate and vitamin B(12) and higher homocysteine levels at baseline were associated with a higher risk of incident depression at follow-up [26].
 

Gene context of homocysteine

  • FV G1691A was found in 14 babies (heterozygous: RVT n = 9, PVT n = 4; homozygous HVT n = 1) and five controls, the MTHFR TT677 genotype together with increased HCY in four infants with thrombosis (RVT n = 2; PVT n = 1; HVT n = 1) compared with one control, and the PT G20210A variant was present in one control only [27].
  • Patients had mild to moderate renal insufficiency and showed, in the plasma, higher fluorescent AGE and carboxymethyllysine (CML) levels, as well as elevated concentrations of AOPPs, lipofuscin and Hcy when compared with CTRL [28].
  • Pretreatment of hepatocytes with inhibitors for transcription factors not only blocked the activation of SREBP-2, CREB, and NF-Y but also attenuated Hcy-induced HMG-CoA reductase mRNA expression [2].
  • The activation of SREBP-2, CREB, and NF-Y preceded the increase in HMG-CoA reductase expression in Hcy-treated cells [2].
  • In the presence of D,L-homocysteine (1 mM), mean TXB2 and 12-hydroxy-5,8,10-heptadecatrienoic acid production was also significantly increased [12.7% +/- 1.5 to 16.9% +/- 1.5 (P less than 0.01) TXB2 and 27% +/- 4 to 31% +/- 4.1 (P less than 0.02) HHT] [29].
  • No association between MTRR 66A>G and immediate postoperative plasma total homocysteine after nitrous oxide anesthesia was detected [30].
 

Analytical, diagnostic and therapeutic context of homocysteine

References

  1. Methionine requirement and replacement by homocysteine in tissue cultures of selected rodent and human malignant and normal cells. Kreis, W., Goodenow, M. Cancer Res. (1978) [Pubmed]
  2. Hyperhomocysteinemia induces hepatic cholesterol biosynthesis and lipid accumulation via activation of transcription factors. Woo, C.W., Siow, Y.L., Pierce, G.N., Choy, P.C., Minuk, G.Y., Mymin, D., O, K. Am. J. Physiol. Endocrinol. Metab. (2005) [Pubmed]
  3. Factors affecting methionine toxicity and its alleviation in the chick. Harter, J.M., Baker, D.H. J. Nutr. (1978) [Pubmed]
  4. Hyperhomocysteinemia, hyperfibrinogenemia, and lipoprotein (a) excess in maintenance dialysis patients: a matched case-control study. Bostom, A.G., Shemin, D., Lapane, K.L., Sutherland, P., Nadeau, M.R., Wilson, P.W., Yoburn, D., Bausserman, L., Tofler, G., Jacques, P.F., Selhub, J., Rosenberg, I.H. Atherosclerosis (1996) [Pubmed]
  5. Experimental secondarily generalized convulsive status epilepticus induced by D,L-homocysteine thiolactone. Walton, N.Y., Treiman, D.M. Epilepsy Res. (1988) [Pubmed]
  6. Homocysteine, vitamins, and vascular disease prevention. McCully, K.S. Am. J. Clin. Nutr. (2007) [Pubmed]
  7. Vascular and cellular stress in inflammatory bowel disease: revisiting the role of homocysteine. Peyrin-Biroulet, L., Rodriguez-Guéant, R.M., Chamaillard, M., Desreumaux, P., Xia, B., Bronowicki, J.P., Bigard, M.A., Guéant, J.L. Am. J. Gastroenterol. (2007) [Pubmed]
  8. Effect of homocysteine on calcium mobilization and platelet function in type 2 diabetes mellitus. Alexandru, N., Jardín, I., Popov, D., Simionescu, M., García-Estañ, J., Salido, G.M., Rosado, J.A. J. Cell. Mol. Med. (2008) [Pubmed]
  9. GABA receptors and nitric oxide ameliorate constrictive collagen remodeling in hyperhomocysteinemia. Shastry, S., Moning, L., Tyagi, N., Steed, M., Tyagi, S.C. J. Cell. Physiol. (2005) [Pubmed]
  10. Homocysteine-induced modulation of tissue plasminogen activator binding to its endothelial cell membrane receptor. Hajjar, K.A. J. Clin. Invest. (1993) [Pubmed]
  11. Tyrosinase inhibition due to interaction of homocyst(e)ine with copper: the mechanism for reversible hypopigmentation in homocystinuria due to cystathionine beta-synthase deficiency. Reish, O., Townsend, D., Berry, S.A., Tsai, M.Y., King, R.A. Am. J. Hum. Genet. (1995) [Pubmed]
  12. Inhibition of ceramide-redox signaling pathway blocks glomerular injury in hyperhomocysteinemic rats. Yi, F., Zhang, A.Y., Li, N., Muh, R.W., Fillet, M., Renert, A.F., Li, P.L. Kidney Int. (2006) [Pubmed]
  13. Sulfur-containing amino acids decrease cisplatin cytotoxicity and uptake in renal tubule epithelial cell lines. Kröning, R., Lichtenstein, A.K., Nagami, G.T. Cancer Chemother. Pharmacol. (2000) [Pubmed]
  14. A study of micturition inducing sites in the periaqueductal gray of the mesencephalon. Taniguchi, N., Miyata, M., Yachiku, S., Kaneko, S., Yamaguchi, S., Numata, A. J. Urol. (2002) [Pubmed]
  15. Effects of homocysteine on acetylcholine- and adenosine-induced vasodilatation of pancreatic vascular bed in rats. Quéré, I., Hillaire-Buys, D., Brunschwig, C., Chapal, J., Janbon, C., Blayac, J.P., Petit, P., Loubatières-Mariani, M.M. Br. J. Pharmacol. (1997) [Pubmed]
  16. Is mutated serine hydroxymethyltransferase (SHMT) involved in the etiology of neural tube defects? Heil, S.G., Van der Put, N.M., Waas, E.T., den Heijer, M., Trijbels, F.J., Blom, H.J. Mol. Genet. Metab. (2001) [Pubmed]
  17. Homocysteine stimulates MAP kinase in bovine aortic smooth muscle cells. Woo, D.K., Dudrick, S.J., Sumpio, B.E. Surgery (2000) [Pubmed]
  18. The sigma receptor ligand (+)-pentazocine prevents apoptotic retinal ganglion cell death induced in vitro by homocysteine and glutamate. Martin, P.M., Ola, M.S., Agarwal, N., Ganapathy, V., Smith, S.B. Brain Res. Mol. Brain Res. (2004) [Pubmed]
  19. Homocysteine-induced alterations in extracellular amino acids in rat hippocampus. Butcher, S.P., Cameron, D., Kendall, L., Griffiths, R. Neurochem. Int. (1992) [Pubmed]
  20. Pioglitazone prevents cardiac remodeling in high-fat, high-calorie-induced Type 2 diabetes mellitus. Rodriguez, W.E., Joshua, I.G., Falcone, J.C., Tyagi, S.C. Am. J. Physiol. Heart Circ. Physiol. (2006) [Pubmed]
  21. Dual effect of DL-homocysteine and S-adenosylhomocysteine on brain synthesis of the glutamate receptor antagonist, kynurenic acid. Luchowska, E., Luchowski, P., Paczek, R., Ziembowicz, A., Kocki, T., Turski, W.A., Wielosz, M., Lazarewicz, J., Urbanska, E.M. J. Neurosci. Res. (2005) [Pubmed]
  22. Effect of dietary homocysteine on copper status in rats. Brown, J.C., Strain, J.J. J. Nutr. (1990) [Pubmed]
  23. Allosteric modulation of dopamine D2 receptors by homocysteine. Agnati, L.F., Ferré, S., Genedani, S., Leo, G., Guidolin, D., Filaferro, M., Carriba, P., Casadó, V., Lluis, C., Franco, R., Woods, A.S., Fuxe, K. J. Proteome Res. (2006) [Pubmed]
  24. Role of endoplasmic reticulum calcium disequilibria in the mechanism of homocysteine-induced ER stress. Dickhout, J.G., Sood, S.K., Austin, R.C. Antioxid. Redox Signal. (2007) [Pubmed]
  25. Lowering homocysteine with B vitamins has no effect on biomarkers of bone turnover in older persons: a 2-y randomized controlled trial. Green, T.J., McMahon, J.A., Skeaff, C.M., Williams, S.M., Whiting, S.J. Am. J. Clin. Nutr. (2007) [Pubmed]
  26. Predictive value of folate, vitamin B12 and homocysteine levels in late-life depression. Kim, J.M., Stewart, R., Kim, S.W., Yang, S.J., Shin, I.S., Yoon, J.S. Br. J. Psychiatry (2008) [Pubmed]
  27. Abdominal venous thrombosis in neonates and infants: role of prothrombotic risk factors - a multicentre case-control study. For the Childhood Thrombophilia Study Group. Heller, C., Schobess, R., Kurnik, K., Junker, R., Günther, G., Kreuz, W., Nowak-Göttl, U. Br. J. Haematol. (2000) [Pubmed]
  28. Effects of ramipril in nondiabetic nephropathy: improved parameters of oxidatives stress and potential modulation of advanced glycation end products. Sebeková, K., Gazdíková, K., Syrová, D., Blazícek, P., Schinzel, R., Heidland, A., Spustová, V., Dzúrik, R. Journal of human hypertension. (2003) [Pubmed]
  29. Effect of homocysteine and homocystine on platelet and vascular arachidonic acid metabolism. Graeber, J.E., Slott, J.H., Ulane, R.E., Schulman, J.D., Stuart, M.J. Pediatr. Res. (1982) [Pubmed]
  30. A common gene variant in methionine synthase reductase is not associated with peak homocysteine concentrations after nitrous oxide anesthesia. Nagele, P., Zeugswetter, B., Eberle, C., Hüpfl, M., Mittlböck, M., Födinger, M. Pharmacogenet. Genomics (2009) [Pubmed]
  31. Hyperhomocysteinemia and vitamin B6 deficiency: new risk markers for nonvalvular atrial fibrillation? Marcucci, R., Betti, I., Cecchi, E., Poli, D., Giusti, B., Fedi, S., Lapini, I., Abbate, R., Gensini, G.F., Prisco, D. Am. Heart J. (2004) [Pubmed]
 
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