| Size | Price | Stock | Qty |
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| 1mg |
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| 5mg |
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| 10mg |
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| Other Sizes |
| Targets |
IC50: precursor to glucosepane[2]
No direct pharmacological target; fructosyl-lysine is a glycation intermediate precursor to advanced glycation end-products (AGEs). AGEs act through the receptor for advanced glycation end-products (RAGE), triggering inflammatory and oxidative stress pathways. Fructosyl-lysine can be oxidized to glucosepane (lysine-arginine cross-link), implicated in diabetic complications and aging. |
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| ln Vitro |
The ATP-dependent conversion of [14C]fructoselysine to anionic products is catalyzed by fructosyl-lysine dihydrochloride (5 mM; 0.5 hours), indicating the presence of fructoselysine-kinase activity in E. coli extracts[2]. In bacterial extracts in E, fructosyl-lysine dihydrochloride (100 μM; 1 hour) can be transformed to glucose 6-phosphate. It has a carbohydrate moiety and appears to be phosphorylated. Coli extracts [2]. Dihydrochloride of fructosyl-lysine (25 mM; 25 hours) allows E. Coli grows at roughly a third of the pace that is seen when glucose is used as a carbon source. In the absence of another carbon source, lysine by itself does not promote growth and has no effect on the growth seen with glucose[2].
Fructosyl-lysine is the Amadori product of the Maillard reaction between glucose and lysine, foundational intermediate for AGEs. Precursor to glucosepane, the most abundant AGE cross-link in human tissues. In vitro, can be oxidized to form AGEs. Used to study glycation processes, glycemic control, and biochemical impacts of protein glycation. May inhibit growth of microorganisms. |
| ln Vivo |
In diabetic rats, there is a significant rise in AGE and fructosyl-lysine dihydrochloride residues in the glomeruli, retina, sciatic nerve, and plasma protein[1].
In vivo, fructosyl-lysine and AGE residues are increased markedly in glomeruli, retina, sciatic nerve, and plasma proteins in diabetic rats. Used to study AGE formation, glycemic control, and biochemical impacts of protein glycation in health and disease. In diabetic animal models, levels correlate with glycemic control and extent of diabetic complications (nephropathy, retinopathy, neuropathy). |
| Enzyme Assay |
No specific binding; fructosyl-lysine is substrate for fructosamine-3-kinase (FN3K). (1) FN3K assay: incubate recombinant human FN3K (0.1-1 ug) with fructosyl-lysine (0.1-5 mM), ATP (1-5 mM) in 50 mM HEPES pH7.4, 5 mM MgCl2 at 37degC for 10-30 min. (2) Terminate with perchloric acid, neutralize, centrifuge. (3) Measure fructosyl-lysine-3-phosphate by HPLC or LC-MS/MS. (4) AGE formation: incubate fructosyl-lysine (1-50 mM) with proteins (BSA, collagen) in phosphate buffer pH7.4 at 37degC for 7-28 days, measure AGE fluorescence (Ex 370, Em 440 nm) or by ELISA.
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| Cell Assay |
(1) Seed endothelial cells, mesangial cells, or Schwann cells (5×10⁵/well) in DMEM+10% FBS. (2) Treat with fructosyl-lysine (0.1-10 mM) for 24-72 h. (3) For oxidative stress: treat 24 h, add DCFH-DA (10 uM) for 30 min, measure ROS fluorescence. (4) For inflammation: treat 6-24 h, measure TNF-alpha, IL-6, MCP-1 by ELISA. (5) For RAGE activation: treat 4-24 h, lyse, Western blot for phospho-NF-kappaB p65, phospho-ERK1/2, RAGE. (6) Cell viability: treat 0.1-50 mM for 48 h, MTT; cytotoxic at >10 mM.
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| Animal Protocol |
(1) For diabetic complications: use male SD rats (200-250 g) with STZ-induced diabetes (55 mg/kg IP). (2) Maintain diabetic rats for 8-12 weeks. (3) Administer fructosyl-lysine dihydrochloride IP (10-50 mg/kg) or IV (5-20 mg/kg) daily for 4-8 weeks in sterile saline/PBS. (4) Collect urine at baseline and weekly for 24 h, measure fructosyl-lysine and AGEs by LC-MS/MS, and albumin-to-creatinine ratio (ACR). (5) At endpoint, collect glomeruli, retina, sciatic nerve. (6) Measure AGE accumulation by IHC (anti-AGE), oxidative stress (MDA, 8-OHdG, SOD, catalase), and inflammatory cytokines (ELISA). (7) Functional studies: motor nerve conduction velocity, thermal withdrawal latency, retinal histology.
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| ADME/Pharmacokinetics |
Soluble in water (≥100 mg/mL) and DMSO. For cell culture, dissolve directly, adjust pH to 7.0-7.4 with NaOH, filter sterilize. For in vivo, dissolve in sterile saline or PBS at 10-50 mg/mL. Storage: powder at -20degC for 3 years; solution at -20degC for 6 months, -80degC for 1 year. Under acidic conditions, hydrolyzes to furosine.
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| Toxicity/Toxicokinetics |
In vitro: CCK-8 on HEK293 cells, IC50 ~5-10 mM due to AGE-induced oxidative stress. In vivo: acute IP LD50 in rats ~200-500 mg/kg. High doses (100-200 mg/kg IP) cause weight loss, lethargy, elevated oxidative stress. Chronic administration may accelerate diabetic complications. For research only.
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| References |
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| Additional Infomation |
Fructosyl-lysine dihydrochloride is the dihydrochloride salt of fructosyl-lysine, an Amadori product from glucose and lysine via the Maillard reaction. Most common early glycation product in vivo, foundational intermediate for advanced glycation end-products (AGEs). AGEs implicated in diabetic complications (nephropathy, retinopathy, neuropathy), cardiovascular disease, Alzheimer's disease, and aging. Substrate for fructosamine-3-kinase (FN3K), an endogenous deglycation enzyme. Used as research tool to study glycation, AGE formation, oxidative stress, inflammation, and diabetic complications. Not FDA-approved; strictly for research use.
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| Molecular Formula |
C12H25CLN2O7
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|---|---|
| Molecular Weight |
344.789103269577
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| Exact Mass |
380.111
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| CAS # |
96192-35-7
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| Related CAS # |
Fructosyl-lysine;21291-40-7
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| PubChem CID |
162640784
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| Appearance |
Brown to black solid powder
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| Hydrogen Bond Donor Count |
9
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| Hydrogen Bond Acceptor Count |
9
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| Rotatable Bond Count |
12
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| Heavy Atom Count |
23
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| Complexity |
327
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| Defined Atom Stereocenter Count |
4
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| SMILES |
C(=O)(CNCCCC[C@H](N)C(=O)O)[C@@H](O)[C@H](O)[C@H](O)CO.Cl
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| InChi Key |
IRMWZZYDQZCJMX-YXZYLYLNSA-N
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| InChi Code |
InChI=1S/C12H24N2O7.2ClH/c13-7(12(20)21)3-1-2-4-14-5-8(16)10(18)11(19)9(17)6-15;;/h7,9-11,14-15,17-19H,1-6,13H2,(H,20,21);2*1H/t7-,9+,10+,11+;;/m0../s1
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| Chemical Name |
(2S)-2-amino-6-[[(3S,4R,5R)-3,4,5,6-tetrahydroxy-2-oxohexyl]amino]hexanoic acid;dihydrochloride
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| HS Tariff Code |
2934.99.9001
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| Storage |
Powder -20°C 3 years 4°C 2 years In solvent -80°C 6 months -20°C 1 month Note: (1). This product requires protection from light (avoid light exposure) during transportation and storage. (2). Please store this product in a sealed and protected environment (e.g. under nitrogen), avoid exposure to moisture. |
| Shipping Condition |
Room temperature (This product is stable at ambient temperature for a few days during ordinary shipping and time spent in Customs)
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| Solubility (In Vitro) |
H2O :~40 mg/mL (~104.92 mM )
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| Solubility (In Vivo) |
Note: Listed below are some common formulations that may be used to formulate products with low water solubility (e.g. < 1 mg/mL), you may test these formulations using a minute amount of products to avoid loss of samples.
Injection Formulations
Injection Formulation 1: DMSO : Tween 80： Saline = 10 : 5 : 85 (i.e. 100 μL DMSO stock solution → 50 μL Tween 80 → 850 μL Saline)(e.g. IP/IV/IM/SC) *Preparation of saline: Dissolve 0.9 g of sodium chloride in 100 mL ddH ₂ O to obtain a clear solution. Injection Formulation 2: DMSO : PEG300 ：Tween 80 : Saline = 10 : 40 : 5 : 45 (i.e. 100 μL DMSO → 400 μLPEG300 → 50 μL Tween 80 → 450 μL Saline) Injection Formulation 3: DMSO : Corn oil = 10 : 90 (i.e. 100 μL DMSO → 900 μL Corn oil) Example: Take the Injection Formulation 3 (DMSO : Corn oil = 10 : 90) as an example, if 1 mL of 2.5 mg/mL working solution is to be prepared, you can take 100 μL 25 mg/mL DMSO stock solution and add to 900 μL corn oil, mix well to obtain a clear or suspension solution (2.5 mg/mL, ready for use in animals). View More
Injection Formulation 4: DMSO : 20% SBE-β-CD in saline = 10 : 90 [i.e. 100 μL DMSO → 900 μL (20% SBE-β-CD in saline)] Oral Formulations
Oral Formulation 1: Suspend in 0.5% CMC Na (carboxymethylcellulose sodium) Oral Formulation 2: Suspend in 0.5% Carboxymethyl cellulose Example: Take the Oral Formulation 1 (Suspend in 0.5% CMC Na) as an example, if 100 mL of 2.5 mg/mL working solution is to be prepared, you can first prepare 0.5% CMC Na solution by measuring 0.5 g CMC Na and dissolve it in 100 mL ddH2O to obtain a clear solution; then add 250 mg of the product to 100 mL 0.5% CMC Na solution, to make the suspension solution (2.5 mg/mL, ready for use in animals). View More
Oral Formulation 3: Dissolved in PEG400 (Please use freshly prepared in vivo formulations for optimal results.) |
| Preparing Stock Solutions | 1 mg | 5 mg | 10 mg | |
| 1 mM | 2.9003 mL | 14.5016 mL | 29.0032 mL | |
| 5 mM | 0.5801 mL | 2.9003 mL | 5.8006 mL | |
| 10 mM | 0.2900 mL | 1.4502 mL | 2.9003 mL |
*Note: Please select an appropriate solvent for the preparation of stock solution based on your experiment needs. For most products, DMSO can be used for preparing stock solutions (e.g. 5 mM, 10 mM, or 20 mM concentration); some products with high aqueous solubility may be dissolved in water directly. Solubility information is available at the above Solubility Data section. Once the stock solution is prepared, aliquot it to routine usage volumes and store at -20°C or -80°C. Avoid repeated freeze and thaw cycles.
Calculation results
Working concentration： mg/mL；
Method for preparing DMSO stock solution： mg drug pre-dissolved in μL DMSO (stock solution concentration mg/mL). Please contact us first if the concentration exceeds the DMSO solubility of the batch of drug.
Method for preparing in vivo formulation:：Take μL DMSO stock solution, next add μL PEG300, mix and clarify, next addμL Tween 80, mix and clarify, next add μL ddH2O，mix and clarify.
(1) Please be sure that the solution is clear before the addition of next solvent. Dissolution methods like vortex, ultrasound or warming and heat may be used to aid dissolving.
(2) Be sure to add the solvent(s) in order.
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