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N(6)-Carboxymethyllysine

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N(6)-Carboxymethyllysine
Stereo, skeletal formula of N(6)-carboxymethyllysine (S)
Stereo, skeletal formula of N(6)-carboxymethyllysine (S)
Names
IUPAC name N-(Carboxymethyl)-L-lysine
Systematic IUPAC name (2S)-2-Amino-6-hexanoic acid
Identifiers
CAS Number
3D model (JSmol)
Beilstein Reference 4989963 S
ChEBI
ChemSpider
MeSH N(6)-carboxymethyllysine
PubChem CID
UNII
CompTox Dashboard (EPA)
InChI
  • InChI=1S/C8H16N2O4/c9-6(8(13)14)3-1-2-4-10-5-7(11)12/h6,10H,1-5,9H2,(H,11,12)(H,13,14)Key: NUXSIDPKKIEIMI-UHFFFAOYSA-N
SMILES
  • NC(CCCCNCC(=O)O)C(=O)O
Properties
Chemical formula C8H16N2O4
Molar mass 204.226 g·mol
Related compounds
Related alkanoic acids gamma-Glutamylcysteine
Except where otherwise noted, data are given for materials in their standard state (at 25 °C , 100 kPa). ☒N verify (what is  ?) Infobox references
Chemical compound

N(6)-Carboxymethyllysine (CML), also known as N-(carboxymethyl)lysine, is an advanced glycation endproduct (AGE). CML has been the most used marker for AGEs in food analysis.

Recently, it has been demonstrated that gut microbiota mediates an aging-associated decline in gut barrier function, allowing AGEs to leak into the bloodstream from the gut and impairing microglial function in the brain. It is suggested that the amount of CML in human blood samples may correlated with age.

A humanized monoclonal antibody which binds to N6 – carboxymethyl lysine shows considerable promise as a possible therapeutic agent for treating pancreatic cancer.

References

  1. Semba RD, Nicklett EJ, Ferrucci L (2010). "Does accumulation of advanced glycation end products contribute to the aging phenotype?". The Journals of Gerontology. 65A (9): 963–975. doi:10.1093/gerona/glq074. PMC 2920582. PMID 20478906.
  2. O. Mossad, B. Batut, B. Yilmaz, N. Dokalis, C. Mezö, E. Nent, L. S. Nabavi, M. Mayer, F. J. M. Maron, J. M. Buescher, M. G. de Agüero, A. Szalay, T. Lämmermann, A. J. Macpherson, S. C. Ganal-Vonarburg, R. Backofen, D. Erny, M. Prinz, T. Blank (2022). "Gut microbiota drives age-related oxidative stress and mitochondrial damage in microglia via the metabolite N6-carboxymethyllysine". Nat. Neurosci. 25 (3): 295–305. doi:10.1038/s41593-022-01027-3. PMID 35241804. S2CID 247228807.{{cite journal}}: CS1 maint: multiple names: authors list (link)
  3. Rossi, Gabriela R.; Jensen, Ashley; Ng, Serina; Yin, Zhirong; Li, Aimin; Misra, Anjan; Von Hoff, Daniel D.; Gruber, Lewis; Gruber, Misty; Han, Haiyong (7 October 2023). "Advanced glycation end product (AGE) targeting antibody SIWA318H is efficacious in preclinical models for pancreatic cancer". Scientific Reports. 13 (1): 16953. Bibcode:2023NatSR..1316953R. doi:10.1038/s41598-023-44211-6. PMC 10560265. PMID 37805542.


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