An advanced glycation endproduct
Related Products
Isomer(s)
33093Octopinic Acid
Labeled Version(s)
26785Nε-(1-Carboxymethyl)-L-lysine-d3
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Nε-(1-Carboxymethyl)-L-lysine

Item No. 16483

Product Insert (PDF)Safety Data Sheet (SDS) (PDF)
Technical Information
Formal Name
N6-(carboxymethyl)-L-lysine
CAS Number
5746-04-3
Synonyms
  • CML
Molecular Formula
C8H16N2O4
Formula Weight
204.2
Purity
≥95%
Formulation
A crystalline solid
Solubility(Learn about Variance in Solubility)
PBS (pH 7.2): 10 mg/ml
SMILES
OC(CNCCCC[C@H](N)C(O)=O)=O
InChi Code
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)/t6-/m0/s1
InChi Key
NUXSIDPKKIEIMI-LURJTMIESA-N
Shipping & Storage Information
Storage
-20°C
Shipping
Room temperature in continental US; may vary elsewhere
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    1 mg

    $61

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    5 mg

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    10 mg

    $242

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    25 mg

    $530

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    Cayman Chemical
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    OBESITY RESEARCH SOLUTIONS
    Product Description

    Nε-(1-Carboxymethyl)-L-lysine (CML) is an advanced glycation end product (AGE), produced by the oxidative modification of glycated proteins during oxidative stress.1,2,3 Levels of CML increase with aging and during diabetes, cancer, vascular disease, and other pathologies marked by oxidative stress.1,4,5 CML activates the membrane-bound receptor for AGEs (RAGE), triggering signaling through MAPKs and NF-κB, whereas truncation of RAGE produces a soluble protein that binds CML and reduces signaling.6,7

    WARNING This product is not for human or veterinary use.

    References & Product Citations
    Product Description References

    1. Requena, J.R., Ahemd, M.U., Fountain, C.W., et al. Carboxymethylethanolamine, a biomarker of phospholipid modification during the maillard reaction in vivo. The Journal of Biological Chemisty 272(28), 17473-17479 (1997).

    2. Ahmed, M.U., Brinkmann, F.E., Degenhardt, T.P., et al. Nε-(carboxyethyl)lysine, a product of the chemical modification of proteins by methylglyoxal, increases with age in human lens proteins. Biochem. J. 324(Pt 2), 565-570 (1997).

    3. Schleicher, E.D., Wagner, E., and Nerlich, A.G. Increased accumulation of the glycoxidation product Nε-(carboxymethyl)lysine in human tissues in diabetes and aging. J. Clin. Invest. 99(3), 457-468 (1997).

    4. Campbell, D.J., Somaratne, J.B., Jenkins, A.J., et al. Impact of type 2 diabetes and the metabolic syndrome on myocardial structure and microvasculature of men with coronary artery disease. Cardiovasc. Diabetol. 10, 1-14 (2011).

    5. Brouwers, O., de Vos-Houben, J.M.J., Niessen, P.M.G., et al. Mild oxidative damage in the diabetic rat heart is attenuated by glyoxalase-1 overexpression. Int. J. Mol. Sci. 14(8), 15724-15739 (2013).

    6. Schmidt, A.M., Yan, S.D., Yan, S.F., et al. The biology of the receptor for advanced glycation end products and its ligands. Biochim. Biophys. Acta 1498(2-3), 99-111 (2000).

    7. Moy, K.A., Jiao, L., Freedman, N.D., et al. Soluble receptor for advanced glycation end products and risk of liver cancer. Hepatology 57(6), 2338-2345 (2013).