Cysteinyldopa

Last updated
Cysteinyldopa [1]
Cysteinyldopa.svg
Names
IUPAC name
2-Amino-3-[3-[(2-amino-3-hydroxy-3-oxopropyl)thio]-4,5-dihydroxyphenyl]propanoic acid
Other names
5-S-Cysteinyldopa
Identifiers
3D model (JSmol)
ChEMBL
ChemSpider
MeSH Cysteinyldopa
PubChem CID
UNII
  • InChI=1S/C12H16N2O6S/c13-6(11(17)18)1-5-2-8(15)10(16)9(3-5)21-4-7(14)12(19)20/h2-3,6-7,15-16H,1,4,13-14H2,(H,17,18)(H,19,20) Yes check.svgY
    Key: SXISMOAILJWTID-UHFFFAOYSA-N Yes check.svgY
  • InChI=1/C12H16N2O6S/c13-6(11(17)18)1-5-2-8(15)10(16)9(3-5)21-4-7(14)12(19)20/h2-3,6-7,15-16H,1,4,13-14H2,(H,17,18)(H,19,20)
    Key: SXISMOAILJWTID-UHFFFAOYAI
  • O=C(O)C(N)Cc1cc(SCC(C(=O)O)N)c(O)c(O)c1
Properties
C12H16N2O6S
Molar mass 316.33 g·mol−1
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
Yes check.svgY  verify  (what is  Yes check.svgYX mark.svgN ?)

Cysteinyldopa is a catecholamine. Excessive cysteinyldopa in plasma and urine has been linked to malignant melanoma. [1] [2] [3] Cysteinyldopa is found in large amounts in the plasma and urine of patients with malignant melanoma. It is therefore used in the diagnosis of melanoma and for the detection of postoperative metastases. Cysteinyldopa is believed to be formed by the rapid enzymatic hydrolysis of 5-S-glutathionedopa found in melanin-producing cells.

See also

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References

  1. 1 2 Cysteinyldopa - Compound Summary, PubChem.
  2. Agrup G, Agrup P, Andersson T, Hafström L, Hansson C, Jacobsson S, Jönsson PE, Rorsman H, Rosengren AM, Rosengren E (1979). "5 years' experience of 5-S-cysteinyldopa in melanoma diagnosis". Acta Derm Venereol. 59 (5): 381–388. PMID   93360.{{cite journal}}: CS1 maint: multiple names: authors list (link)
  3. Goto H, Usui M, Wakamatsu K, Ito S (2001). "5-S-cysteinyldopa as diagnostic tumor marker for uveal malignant melanoma". Jpn J Ophthalmol. 45 (5): 538–542. doi:10.1016/s0021-5155(01)00393-8. PMID   11583680.{{cite journal}}: CS1 maint: multiple names: authors list (link)