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L-Lysinamide dihydrochloride

L-Lysine amide dihydrochloride is the amide form of L-lysine.
L-Lysinamide dihydrochloride
L-Lysinamide dihydrochloride Chemical Structure CAS No.: 51127-08-3
Product category: Amino Acid Derivatives
This product is for research use only, not for human use. We do not sell to patients.
Size Price Stock Qty
100mg
Other Sizes

Other Forms of L-Lysinamide dihydrochloride:

  • L-Lysyl-L-lysinamide
  • L-Lysinamide
Official Supplier of:
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Top Publications Citing lnvivochem Products
Product Description
L-Lysinamide dihydrochloride is the amide form of L-Lysine. L-Lysinamide dihydrochloride can be conjugated with Cholesterol and L-guanine to act as a DNA delivery agent.
L-Lysinamide dihydrochloride (CAS 51127-08-3) is the amide form of the essential amino acid L-lysine. Its molecular formula is C6H17Cl2N3O and molecular weight is 218.12. The IUPAC name is (S)-2,6-diaminohexanamide dihydrochloride. This compound is used as a research tool in drug delivery, particularly as a DNA delivery agent, and as a building block in peptide synthesis. It has also been investigated for binding to enzymes such as iridoid synthase. It is supplied as a white to off-white solid powder. For research use only; not for human therapy.
Biological Activity I Assay Protocols (From Reference)
Targets
L-Lysinamide dihydrochloride targets the process of DNA delivery rather than a specific biological receptor. It can be conjugated with cholesterol and L-ornithinamide to form a DNA delivery agent that binds and condenses DNA, facilitating its transfer into cells. It has also been reported to bind to the enzyme iridoid synthase, which is involved in the formation of imines and aldehydes in plant metabolism. However, its primary use is as a cationic molecule for nucleic acid complexation and non-viral gene delivery. It operates within the gene therapy and drug delivery pathways.
ln Vitro
In vitro, L-Lysinamide dihydrochloride is used to form complexes with DNA (lipoplexes or polyplexes) for transfection studies. A typical protocol: dissolve the compound in water or PBS to prepare a 10-50 mM stock. Mix with plasmid DNA at various N/P ratios (amine/phosphate ratio) and incubate for 15-30 min at room temperature to form complexes. Add to cells (e.g., HEK293, HeLa) in serum-free medium. After 4-6 h, replace with complete medium. Measure transfection efficiency after 24-48 h using a reporter gene assay (e.g., luciferase or GFP). No significant cytotoxicity is observed at N/P ratios up to 20. L-Lysinamide is less potent than polyethylenimine but provides a biodegradable alternative. DMSO is not used; compound is water-soluble.
ln Vivo
No in vivo activity data are available for L-Lysinamide dihydrochloride as a drug candidate. It is used as a reagent for in vitro DNA delivery studies. In some research contexts, it may be formulated with DNA for local administration in animal models to study gene delivery, but no detailed in vivo protocols are available in the sources. For research use only.
Enzyme Assay
Not applicable. L-Lysinamide dihydrochloride is a chemical reagent and analytical standard, not a drug candidate. For non-cellular characterization, a standard HPLC method can be used: dissolve the compound in water or 0.1% TFA to 1 mg/mL. Inject onto a C18 column (250×4.6 mm, 5 microm). Mobile phase: 0.1% TFA in water (A) and acetonitrile (B). Gradient: 0-30% B over 20 min. Flow rate: 1.0 mL/min, UV detection at 210 nm. Retention time is approximately 3-5 min. For LC-MS/MS, positive ESI mode, m/z 146 [M-2HCl+H]+ for the free base. Melting point: 222-224degC. Purity typically >98% (HPLC). No enzyme/receptor binding assays.
Cell Assay
For in vitro cell transfection assays, culture HEK293 or HeLa cells in DMEM with 10% FBS at 37degC, 5% CO2. Seed cells in 24-well plates (1×10⁵ cells/well) 24 h before transfection. Prepare L-Lysinamide dihydrochloride in water to a concentration of 1-10 mM. Prepare DNA solution (0.5-1 ug plasmid DNA in 50 uL Opti-MEM). Mix the compound with DNA at various N/P ratios (e.g., 5:1, 10:1, 20:1) and incubate for 15-30 min. Add the complexes to cells in serum-free medium. After 4-6 h, add 1 mL of complete medium (20% FBS) to each well. Incubate for 24-48 h. For GFP reporter, visualize by fluorescence microscopy. For luciferase, lyse cells and measure luminescence. Positive control: Lipofectamine 2000. Negative control: naked DNA. DMSO not used. All experiments in triplicate.
Animal Protocol
No in vivo animal studies are performed with L-Lysinamide dihydrochloride as a drug candidate. It is a chemical reagent for in vitro use. For research use only.
ADME/Pharmacokinetics
Not applicable. L-Lysinamide dihydrochloride is a chemical reagent, not a drug candidate; its pharmacokinetic properties are not characterized. If administered systemically, as a small cationic molecule (MW 218.12), it would likely be rapidly cleared renally and metabolized to lysine. For storage, powder at -20degC for up to 3 years, protected from light and moisture. Solubility: water (freely soluble), DMSO (slightly). Appearance: white to off-white solid powder. Melting point: 222-224degC. Purity >98% (HPLC).
Toxicity/Toxicokinetics
No formal toxicity data are available for L-Lysinamide dihydrochloride. In cell transfection assays, no significant cytotoxicity is observed at effective N/P ratios. L-Lysine and its derivatives are generally considered safe. Standard laboratory safety precautions for handling chemical reagents should be followed: avoid inhalation, ingestion, skin/eye contact; use PPE (gloves, lab coat, safety goggles); work in a fume hood. For research use only-not for human use. Dispose of waste according to local regulations for chemical waste.
References

[1]. New cationic liposomes for gene transfer into mammalian cells with high efficiency and low toxicity. Bioconjug Chem. 2001 Jan-Feb;12(1):108-13.

Additional Infomation
CAS: 51127-08-3. Molecular formula: C6H17Cl2N3O, molecular weight: 218.12. IUPAC name: (S)-2,6-diaminohexanamide dihydrochloride. Also known as L-lysine amide dihydrochloride. Appearance: white to off-white solid powder. Melting point: 222-224degC. Solubility: water (freely soluble), DMSO (slightly). Purity: >98% (HPLC). Storage: -20degC, protected from light and moisture. Use: DNA delivery reagent, peptide synthesis building block. Not for human use. For research only.
These protocols are for reference only. InvivoChem does not independently validate these methods.
Physicochemical Properties
Molecular Formula
C6H17CL2N3O
Molecular Weight
218.12
Exact Mass
217.075
CAS #
51127-08-3
Related CAS #
L-Lysinamide; 32388-19-5
PubChem CID
20760365
Appearance
White to off-white solid powder
Hydrogen Bond Donor Count
5
Rotatable Bond Count
5
Heavy Atom Count
12
Complexity
105
Defined Atom Stereocenter Count
1
SMILES
C(CCN)C[C@@H](C(=O)N)N.Cl.Cl
InChi Key
AIYVJLPYZQDCKV-XRIGFGBMSA-N
InChi Code
InChI=1S/C6H15N3O.2ClH/c7-4-2-1-3-5(8)6(9)10;;/h5H,1-4,7-8H2,(H2,9,10);2*1H/t5-;;/m0../s1
Chemical Name
(2S)-2,6-diaminohexanamide;dihydrochloride
HS Tariff Code
2934.99.9001
Storage

Powder      -20°C    3 years

                     4°C     2 years

In solvent   -80°C    6 months

                  -20°C    1 month

Shipping Condition
Room temperature (This product is stable at ambient temperature for a few days during ordinary shipping and time spent in Customs)
Solubility Data
Solubility (In Vitro)
DMSO : ~50 mg/mL (~229.23 mM; with sonication)
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
(e.g. IP/IV/IM/SC)
Injection Formulation 1: DMSO : Tween 80: Saline = 10 : 5 : 85 (i.e. 100 μL DMSO stock solution 50 μL Tween 80 850 μL Saline)
*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 : PEG300Tween 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).
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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)]
*Preparation of 20% SBE-β-CD in Saline (4°C,1 week): Dissolve 2 g SBE-β-CD in 10 mL saline to obtain a clear solution.
Injection Formulation 5: 2-Hydroxypropyl-β-cyclodextrin : Saline = 50 : 50 (i.e. 500 μL 2-Hydroxypropyl-β-cyclodextrin 500 μL Saline)
Injection Formulation 6: DMSO : PEG300 : castor oil : Saline = 5 : 10 : 20 : 65 (i.e. 50 μL DMSO 100 μLPEG300 200 μL castor oil 650 μL Saline)
Injection Formulation 7: Ethanol : Cremophor : Saline = 10: 10 : 80 (i.e. 100 μL Ethanol 100 μL Cremophor 800 μL Saline)
Injection Formulation 8: Dissolve in Cremophor/Ethanol (50 : 50), then diluted by Saline
Injection Formulation 9: EtOH : Corn oil = 10 : 90 (i.e. 100 μL EtOH 900 μL Corn oil)
Injection Formulation 10: EtOH : PEG300Tween 80 : Saline = 10 : 40 : 5 : 45 (i.e. 100 μL EtOH 400 μLPEG300 50 μL Tween 80 450 μL 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).
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Oral Formulation 3: Dissolved in PEG400
Oral Formulation 4: Suspend in 0.2% Carboxymethyl cellulose
Oral Formulation 5: Dissolve in 0.25% Tween 80 and 0.5% Carboxymethyl cellulose
Oral Formulation 6: Mixing with food powders


Note: Please be aware that the above formulations are for reference only. InvivoChem strongly recommends customers to read literature methods/protocols carefully before determining which formulation you should use for in vivo studies, as different compounds have different solubility properties and have to be formulated differently.

 (Please use freshly prepared in vivo formulations for optimal results.)
Preparing Stock Solutions 1 mg 5 mg 10 mg
1 mM 4.5846 mL 22.9232 mL 45.8463 mL
5 mM 0.9169 mL 4.5846 mL 9.1693 mL
10 mM 0.4585 mL 2.2923 mL 4.5846 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.

Calculator

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An example of molarity calculation using the molarity calculator is shown below:
What is the mass of compound required to make a 10 mM stock solution in 5 ml of DMSO given that the molecular weight of the compound is 350.26 g/mol?
  • Enter 350.26 in the Molecular Weight (MW) box
  • Enter 10 in the Concentration box and choose the correct unit (mM)
  • Enter 5 in the Volume box and choose the correct unit (mL)
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  • The answer of 17.513 mg appears in the Mass box. In a similar way, you may calculate the volume and concentration.

Dilution Calculator allows you to calculate how to dilute a stock solution of known concentrations. For example, you may Enter C1, C2 & V2 to calculate V1, as detailed below:

What volume of a given 10 mM stock solution is required to make 25 ml of a 25 μM solution?
Using the equation C1V1 = C2V2, where C1=10 mM, C2=25 μM, V2=25 ml and V1 is the unknown:
  • Enter 10 into the Concentration (Start) box and choose the correct unit (mM)
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  • Enter 25 into the Volume (End) box and choose the correct unit (mL)
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  • The answer of 62.5 μL (0.1 ml) appears in the Volume (Start) box
g/mol

Molecular Weight Calculator allows you to calculate the molar mass and elemental composition of a compound, as detailed below:

Note: Chemical formula is case sensitive: C12H18N3O4  c12h18n3o4
Instructions to calculate molar mass (molecular weight) of a chemical compound:
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Definitions of molecular mass, molecular weight, molar mass and molar weight:
  • Molecular mass (or molecular weight) is the mass of one molecule of a substance and is expressed in the unified atomic mass units (u). (1 u is equal to 1/12 the mass of one atom of carbon-12)
  • Molar mass (molar weight) is the mass of one mole of a substance and is expressed in g/mol.
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In vivo Formulation Calculator (Clear solution)
Step 1: Enter information below (Recommended: An additional animal to make allowance for loss during the experiment)
Step 2: Enter in vivo formulation (This is only a calculator, not the exact formulation for a specific product. Please contact us first if there is no in vivo formulation in the solubility section.)
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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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