An advanced glycation end product
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Nε-(1-Carboxyethyl)-L-lysine

Item No. 25333

Product Insert (PDF)Safety Data Sheet (SDS) (PDF)
Technical Information
Formal Name
N6-(1-carboxyethyl)-L-lysine
CAS Number
5746-03-2
Synonyms
  • CEL
Molecular Formula
C9H18N2O4
Formula Weight
218.3
Purity
≥95% (mixture of diastereomers)
Formulation (Request formulation change)
A solid
Solubility(Learn about Variance in Solubility)
Water: Slightly soluble
SMILES
OC(C(NCCCC[C@H](N)C(O)=O)C)=O
InChi Code
InChI=1S/C9H18N2O4/c1-6(8(12)13)11-5-3-2-4-7(10)9(14)15/h6-7,11H,2-5,10H2,1H3,(H,12,13)(H,14,15)/t6?,7-/m0/s1
InChi Key
XCYPSOHOIAZISD-MLWJPKLSSA-N
Shipping & Storage Information
Storage
-20°C
Shipping
Room temperature in continental US; may vary elsewhere
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    1 mg

    $41

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    5 mg

    $178

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    10 mg

    $332

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    Cayman Chemical
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    Product Description

    Nε-(1-Carboxyethyl)-L-lysine (CEL) is an advanced glycation end product (AGE) produced by the reaction of methyl glyoxal with lysine residues in proteins.1 Protein bound, but not free, CEL binds to the receptor for AGEs (RAGE).2 CEL levels are elevated in the lens of diabetic patients with cataract.3 Long-term caloric restriction decreases CEL levels in rat heart mitochondria.4 It decreases glutamate uptake and secretion of S100B in rat hippocampal slices in a RAGE-independent manner when used at a concentration of 1 mM.5

    WARNING This product is not for human or veterinary use.

    References & Product Citations
    Product Description References

    1. 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).

    2. Xue, J., Ray, R., Singer, D., et al. The receptor for advanced glycation end products (RAGE) specifically recognizes methylglyoxal-derived AGEs. Biochemistry 53(20), 3327-3335 (2014).

    3. Hashim, Z., and Zarina, S. Advanced glycation end products in diabetic and non-diabetic human subjects suffering from cataract. Age (Dordr) 33(3), 377-384 (2011).

    4. Pamplona, R., Portero-Otín, M., Bellmunt, M.J., et al. Aging increases Nepsilon-(carboxymethyl)lysine and caloric restriction decreases Nepsilon-(carboxyethyl)lysine and Nepsilon-(malondialdehyde)lysine in rat heart mitochondrial proteins. Free Radic. Res. 36(1), 47-54 (2002).

    5. Hansen, F.K., Battú, C.E., Dutra, M.F., et al. Methylglyoxal and carboxyethyllysine reduce glutamate uptake and S100B secretion in the hippocampus independently of RAGE activation. Amino Acids 48(2), 375-385 (2016).