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Chemical Compound Review

cysteinate(2-)     2-amino-3-sulfido-propanoate

Synonyms: AC1NUTZG, CHEBI:32457, cysteine dianion, 2-amino-3-sulfidopropanoate
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Disease relevance of carbocysteine


Psychiatry related information on carbocysteine

  • We undertook this study to assess the patterns of regional cerebral perfusion (RCP) with SPECT using Technetium- 99m-ethyl cysteinate dimer (Tc-99m-ECD) in children with Tourette's Syndrome (TS), and to compare these with the patterns in a group of normal controls [6].
  • Tc-99m ethyl cysteinate dimer SPECT and 2-[F-18]fluoro-2-deoxy-D-glucose PET in Alzheimer's disease. Comparison of perfusion and metabolic patterns [7].
  • OBJECTIVE: The authors hypothesized that there is a pattern difference in cerebralperfusion of the 99-Technitium L, L-ethyl cysteinate dimer Single Photon Emission Computer Tomography (99-Tc ECD SPECT) between mild and moderate to severe dementia [8].

High impact information on carbocysteine

  • The probable active-site cluster, previously termed the H-cluster, was found to be an unexpected arrangement of six iron atoms existing as a [4Fe-4S] cubane subcluster covalently bridged by a cysteinate thiol to a [2Fe] subcluster [9].
  • The results support a catalytic mechanism for SOR, with the first step involving oxidative addition of superoxide to form a ferric-peroxo intermediate, and indicate the important roles that the Fe spin state and the trans cysteinate ligand play in effecting superoxide reduction and peroxide release [10].
  • Given the proven fingerprinting capability of MCD spectroscopy, this provides convincing evidence for endogenous thiolate (cysteinate) ligation to the heme iron of NOS [11].
  • The aim of this study was to investigate the efficacy of pre- and posttreatment 99mTc-ethyl cysteinate dimer (99mTc-ECD) single photon emission computed tomography (SPECT) for predicting the ischemic outcome of embolic middle cerebral artery occlusion after treatment with local intraarterial thrombolysis [12].
  • The usefulness of technetium-99m-labeled cysteinate dimer as a marker in the measurement of regional cerebral blood flow was tested in five cynomolgus monkeys [13].

Biological context of carbocysteine

  • Biophysical characterization of this enzyme has led to the assignment of the heme ligands as histidine and cysteinate, respectively, which has recently been confirmed by crystal structure determination of the catalytic core of the protein [14].
  • The safety, biodistribution and kinetics of a new perfusion imaging agent [99mTc-L,L]-ethyl cysteinate dimer (ECD) was evaluated in normal volunteers [15].
  • Silver cysteinate appeared to have the greatest effect on fecundity, with a no-observable-effect concentration (NOEC) less than 0.001 microg/L [16].
  • In order to quantitatively characterize the risk associated with silver in aquatic ecosystems, the bioavailabilities and toxicities of silver cysteinate and silver glutathionate were characterized [16].
  • Enzymatic hydrolysis of the pendant ester group of [99mTc](SNS/S) mixed ligand complexes by esterase was investigated in vitro and compared with that of the ethyl cysteinate dimer, [99mTc]ECD [17].

Anatomical context of carbocysteine


Associations of carbocysteine with other chemical compounds

  • In one-electron-reduced analogues, cleavage of the active-site disulfide is accompanied by coordination of one of the cysteine residues that form the active-site disulfide to yield a [Fe(4)S(4)](3+) cluster with two cysteinate ligands at a unique Fe site [23].
  • OBJECTIVE: To investigate the cerebral perfusion patterns of the subcortical structures by using serial technetium Tc 99m-ethyl cysteinate dimer SPECT in a case of SC, which may provide a clue for the pathophysiological mechanisms [24].
  • The rate of P420 formation is accelerated at lower pH, consistent with protonation of the cysteinate (Cys 394) to a thiol underlying the P450-P420 transition [25].
  • The energy of the porphyrin(pi)-to-Fe(III) charge-transfer band (8930 cm(-)(1)) and the presence of cysteinate S-to-Fe(III) charge-transfer bands between 600 and 700 nm confirm cysteinate axial ligation to the low-spin Fe(III) hemes in oxidized wild-type and H77Y CooA [26].
  • Together, these data support assignment of the axial ligands as cysteinate and imidazole in ferric cystathionine beta-synthase [27].

Gene context of carbocysteine

  • The results establish that the metal-binding domains bind Cu(I) predominantly in a bis cysteinate environment, and are able to bind exogenous ligands such as DTT in a similar fashion to Atox1 [28].
  • We studied the effects of MPH on brain activity in male children and adolescents with ADHD, using the blood flow radiotracer technetium-99m ethyl cysteinate dimer ((99m)Tc-ECD) and single-photon emission tomography (SPET) [29].
  • Using L,L-ethyl cysteinate dimer (99mTc ECD) SPECT and SPM, we aimed to clarify the association of rCBF changes with psychiatric symptoms in SLE patients whose magnetic resonance imaging (MRI) showed no morphological abnormalities [30].
  • METHODS: Ictal and interictal (99m)Tc-ethyl cysteinate dimer SPECT images were acquired for 6 children with partial epilepsy (age range, 2-10 y) [31].
  • METHODS: Brain perfusion SPECT with 99mTc-ethyl cysteinate dimer (99mTc-ECD) was used in 16 right-handed patients with aphasia after a left-sided cerebrovascular accident (CVA) in the early chronic period after the onset of CVA [32].

Analytical, diagnostic and therapeutic context of carbocysteine


  1. Differentiation between transient ischemic attack and ischemic stroke within the first six hours after onset of symptoms by using 99mTc-ECD-SPECT. Berrouschot, J., Barthel, H., Hesse, S., Köster, J., Knapp, W.H., Schneider, D. J. Cereb. Blood Flow Metab. (1998) [Pubmed]
  2. Combined SPECT and diffusion-weighted MRI as a predictor of infarct growth in acute ischemic stroke. Karonen, J.O., Nuutinen, J., Kuikka, J.T., Vanninen, E.J., Vanninen, R.L., Partanen, P.L., Vainio, P.A., Roivainen, R., Sivenius, J., Aronen, H.J. J. Nucl. Med. (2000) [Pubmed]
  3. Abnormal regional cerebral blood flow on 99mTc ECD brain SPECT in patients with primary Sjögren's syndrome and normal findings on brain magnetic resonance imaging. Chang, C.P., Shiau, Y.C., Wang, J.J., Ho, S.T., Kao, A. Ann. Rheum. Dis. (2002) [Pubmed]
  4. Technetium Tc-99m ethyl cysteinate dimer brain single-photon emission CT in mild traumatic brain injury: a prospective study. Gowda, N.K., Agrawal, D., Bal, C., Chandrashekar, N., Tripati, M., Bandopadhyaya, G.P., Malhotra, A., Mahapatra, A.K. AJNR. American journal of neuroradiology. (2006) [Pubmed]
  5. Tc-99m ethylene cysteinate dimer SPECT in the differential diagnosis of parkinsonism. Feigin, A., Antonini, A., Fukuda, M., De Notaris, R., Benti, R., Pezzoli, G., Mentis, M.J., Moeller, J.R., Eidelberg, D. Mov. Disord. (2002) [Pubmed]
  6. Tc-99m-ECD SPECT brain imaging in children with Tourette's syndrome. Diler, R.S., Reyhanli, M., Toros, F., Kibar, M., Avci, A. Yonsei Med. J. (2002) [Pubmed]
  7. Tc-99m ethyl cysteinate dimer SPECT and 2-[F-18]fluoro-2-deoxy-D-glucose PET in Alzheimer's disease. Comparison of perfusion and metabolic patterns. Ishii, K., Sasaki, M., Sakamoto, S., Yamaji, S., Kitagaki, H., Mori, E. Clinical nuclear medicine. (1999) [Pubmed]
  8. Patterns of single photon emission tomography (SPECT) among patients with dementia in the memory clinic at Siriraj Hospital. Nako, A., Siritho, S., Chotinaiwattarakul, W., Ratanamart, V., Udompunthuruk, S., Jamjumrus, P., Senanarong, V. Journal of the Medical Association of Thailand = Chotmaihet thangphaet (2006) [Pubmed]
  9. X-ray crystal structure of the Fe-only hydrogenase (CpI) from Clostridium pasteurianum to 1.8 angstrom resolution. Peters, J.W., Lanzilotta, W.N., Lemon, B.J., Seefeldt, L.C. Science (1998) [Pubmed]
  10. Nitric oxide binding at the mononuclear active site of reduced Pyrococcus furiosus superoxide reductase. Clay, M.D., Cosper, C.A., Jenney, F.E., Adams, M.W., Johnson, M.K. Proc. Natl. Acad. Sci. U.S.A. (2003) [Pubmed]
  11. Identification of nitric oxide synthase as a thiolate-ligated heme protein using magnetic circular dichroism spectroscopy. Comparison with cytochrome P-450-CAM and chloroperoxidase. Sono, M., Stuehr, D.J., Ikeda-Saito, M., Dawson, J.H. J. Biol. Chem. (1995) [Pubmed]
  12. Prediction of acute embolic stroke outcome after local intraarterial thrombolysis: value of pretreatment and posttreatment 99mTc-ethyl cysteinate dimer single photon emission computed tomography. Ogasawara, K., Ogawa, A., Doi, M., Konno, H., Suzuki, M., Yoshimoto, T. J. Cereb. Blood Flow Metab. (2000) [Pubmed]
  13. Regional cerebral blood flow and distribution of [99mTc]ethyl cysteinate dimer in nonhuman primates. Orlandi, C., Crane, P.D., Platts, S.H., Walovitch, R.C. Stroke (1990) [Pubmed]
  14. Effects of heme ligand mutations including a pathogenic variant, H65R, on the properties of human cystathionine beta-synthase. Ojha, S., Wu, J., LoBrutto, R., Banerjee, R. Biochemistry (2002) [Pubmed]
  15. Characterization of technetium-99m-L,L-ECD for brain perfusion imaging, Part 2: Biodistribution and brain imaging in humans. Léveillé, J., Demonceau, G., De Roo, M., Rigo, P., Taillefer, R., Morgan, R.A., Kupranick, D., Walovitch, R.C. J. Nucl. Med. (1989) [Pubmed]
  16. Effects of ligand-bound silver on Ceriodaphnia dubia. Bielmyer, G.K., Bell, R.A., Klaine, S.J. Environ. Toxicol. Chem. (2002) [Pubmed]
  17. Characterization and preliminary evaluation of ester-modified technetium-99m SNS/S mixed ligand complexes as potential brain perfusion agents. Tsoukalas, C., Papadopoulos, M.S., Maina, T., Pirmettis, I.C., Nock, B.A., Raptopoulou, C., Terzis, A., Chiotellis, E. Nucl. Med. Biol. (1999) [Pubmed]
  18. Quantitative assessment of cerebral blood flow in genetically confirmed spinocerebellar ataxia type 6. Honjo, K., Ohshita, T., Kawakami, H., Naka, H., Imon, Y., Maruyama, H., Mimori, Y., Matsumoto, M. Arch. Neurol. (2004) [Pubmed]
  19. Characterization of technetium-99m-L,L-ECD for brain perfusion imaging, Part 1: Pharmacology of technetium-99m ECD in nonhuman primates. Walovitch, R.C., Hill, T.C., Garrity, S.T., Cheesman, E.H., Burgess, B.A., O'Leary, D.H., Watson, A.D., Ganey, M.V., Morgan, R.A., Williams, S.J. J. Nucl. Med. (1989) [Pubmed]
  20. A comparative study of 99Tcm-HMPAO and 99Tcm-ECD as a leukocyte labelling agent. Kao, C.H., Huang, W.T., Wang, Y.L., Lin, K.S., Lo, J.M., Wang, S.J. Nuclear medicine communications. (1994) [Pubmed]
  21. Cognitive deterioration associated with focal cortical dysplasia. Oki, J., Miyamoto, A., Takahashi, S., Takei, H. Pediatric neurology. (1999) [Pubmed]
  22. Ictal (99m)Tc ECD SPECT in paroxysmal kinesigenic choreoathetosis. Ko, C.H., Kong, C.K., Ngai, W.T., Ma, K.M. Pediatric neurology. (2001) [Pubmed]
  23. Spectroscopic characterization of site-specific [Fe(4)S(4)] cluster chemistry in ferredoxin:thioredoxin reductase: implications for the catalytic mechanism. Walters, E.M., Garcia-Serres, R., Jameson, G.N., Glauser, D.A., Bourquin, F., Manieri, W., Schürmann, P., Johnson, M.K., Huynh, B.H. J. Am. Chem. Soc. (2005) [Pubmed]
  24. Serial brain SPECT images in a case of Sydenham chorea. Lee, P.H., Nam, H.S., Lee, K.Y., Lee, B.I., Lee, J.D. Arch. Neurol. (1999) [Pubmed]
  25. Biophysical characterization of the sterol demethylase P450 from Mycobacterium tuberculosis, its cognate ferredoxin, and their interactions. McLean, K.J., Warman, A.J., Seward, H.E., Marshall, K.R., Girvan, H.M., Cheesman, M.R., Waterman, M.R., Munro, A.W. Biochemistry (2006) [Pubmed]
  26. Probing the heme axial ligation in the CO-sensing CooA protein with magnetic circular dichroism spectroscopy. Dhawan, I.K., Shelver, D., Thorsteinsson, M.V., Roberts, G.P., Johnson, M.K. Biochemistry (1999) [Pubmed]
  27. Characterization of the heme in human cystathionine beta-synthase by X-ray absorption and electron paramagnetic resonance spectroscopies. Ojha, S., Hwang, J., Kabil, O., Penner-Hahn, J.E., Banerjee, R. Biochemistry (2000) [Pubmed]
  28. Copper transfer to the N-terminal domain of the Wilson disease protein (ATP7B): X-ray absorption spectroscopy of reconstituted and chaperone-loaded metal binding domains and their interaction with exogenous ligands. Ralle, M., Lutsenko, S., Blackburn, N.J. J. Inorg. Biochem. (2004) [Pubmed]
  29. The acute effect of methylphenidate on cerebral blood flow in boys with attention-deficit/hyperactivity disorder. Szobot, C.M., Ketzer, C., Cunha, R.D., Parente, M.A., Langleben, D.D., Acton, P.D., Kapczinski, F., Rohde, L.A. Eur. J. Nucl. Med. Mol. Imaging (2003) [Pubmed]
  30. Abnormal regional cerebral blood flow in systemic lupus erythematosus patients with psychiatric symptoms. Oda, K., Matsushima, E., Okubo, Y., Ohta, K., Murata, Y., Koike, R., Miyasaka, N., Kato, M. The Journal of clinical psychiatry. (2005) [Pubmed]
  31. Computer-aided intrapatient comparison of brain SPECT images: the gray-level normalization issue applied to children with epilepsy. Pérault, C., Papathanassiou, D., Wampach, H., Véra, P., Kaminska, A., Chiron, C., Peruzzi, P., Liehn, J.C. J. Nucl. Med. (2002) [Pubmed]
  32. Prognostic value of brain perfusion single-photon emission computed tomography (SPECT) for language recovery in patients with aphasia. Nakagawa, T., Murata, Y., Kojima, T., Shinkai, Y., Yamaya, Y., Kato, M., Shibuya, H. Nuclear medicine communications. (2005) [Pubmed]
  33. Endogenous cysteine ligation in ferric and ferrous cytochrome P-450. Direct evidence from x-ray absorption spectroscopy. Hahn, J.E., Hodgson, K.O., Andersson, L.A., Dawson, J.H. J. Biol. Chem. (1982) [Pubmed]
  34. Spectroscopic investigations of ferric cytochrome P-450-CAM ligand complexes. Identification of the ligand trans to cysteinate in the native enzyme. Dawson, J.H., Andersson, L.A., Sono, M. J. Biol. Chem. (1982) [Pubmed]
  35. Reperfusion and metabolic recovery of brain tissue and clinical outcome after ischemic stroke and thrombolytic therapy. Berrouschot, J., Barthel, H., Hesse, S., Knapp, W.H., Schneider, D., von Kummer, R. Stroke (2000) [Pubmed]
  36. Comparison of technetium-99m-HMPAO and technetium-99m-ECD cerebral SPECT images in Alzheimer's disease. van Dyck, C.H., Lin, C.H., Smith, E.O., Wisniewski, G., Cellar, J., Robinson, R., Narayan, M., Bennett, A., Delaney, R.C., Bronen, R.A., Hoffer, P.B. J. Nucl. Med. (1996) [Pubmed]
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