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Lacto-N-fucopentaose III (LNFP-III)

Cat No.:V73024 Purity: ≥98%
Lacto-N-fucopentaose III (LNFP-III) is an immunomodulator.
Lacto-N-fucopentaose III (LNFP-III)
Lacto-N-fucopentaose III (LNFP-III) Chemical Structure CAS No.: 25541-09-7
Product category: Arginase
This product is for research use only, not for human use. We do not sell to patients.
Size Price Stock Qty
1mg
Other Sizes
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Product Description
Lacto-N-fucopentaose III (LNFP-III) is an immunomodulator. Lacto-N-fucopentaose III reduces the severity of experimental autoimmune encephalomyelitis (EAE) and central nervous system/CNS inflammation.
Lacto-N-fucopentaose III (LNFP-III) is a complex oligosaccharide belonging to the family of human milk oligosaccharides (HMOs). It is a human milk oligosaccharide that can inhibit the adherence of pathogens to the intestinal epithelium. LNFP-III functions as an immunomodulator.
Biological Activity I Assay Protocols (From Reference)
Targets
LNFP-III targets the immune system, acting as an immunomodulatory agent. It reduces the severity of experimental autoimmune encephalomyelitis (EAE) and central nervous system (CNS) inflammation. The compound's mechanism likely involves modulation of immune cell function and cytokine production, although specific molecular targets remain to be fully elucidated.
ln Vitro
Thrombocytes stimulated by lacto-N-fucopentaose III glycan (LNFP-III; 50 μg/mL; 48 h) produce nitric oxide. Dendritic cell migration across the brain endothelium is decreased by lacto-N-fucopentaose III [1]. The mRNA expression of arginase I (Aldh1a2), aldehyde dehydrogenase 1, A2 subfamily (Aldh1a2), indoleamine 2,3-dioxygenation enzyme 1 (Ido1), and heme oxygenase 1 (Homx1) is significantly increased by lacto-N-fucopentaose III glycan (50 μg/mL; 48 h) [1].
In vitro, LNFP-III has been shown to modulate immune responses in various cell-based assays. It inhibits pathogen adherence to intestinal epithelial cells, suggesting a role in preventing infections. The compound's immunomodulatory effects are likely mediated through interactions with immune cell receptors, leading to altered cytokine profiles and immune cell activation states.
ln Vivo
In mice with dominant spectrum peripheral immune response, lacto-N-fucopentaose III glycan (50 μg/mouse; iv; twice weekly for two weeks) dramatically lowers the severity of experimental autoimmune encephalomyelitis (EAE) and central nervous system inflammation while also distorting Th2 response [1]. In the Gulf War Illness mouse model, lacto-N-fucopentaose III (35 μg dextran conjugate/mouse; sc; daily for 2 weeks) improves both acute and persistent hippocampus synaptic plasticity and transmission deficits [2].
In vivo, LNFP-III reduces the severity of experimental autoimmune encephalomyelitis (EAE) and central nervous system inflammation in animal models. These findings indicate potent immunomodulatory activity with therapeutic potential in autoimmune and inflammatory diseases of the CNS. Further studies are needed to confirm efficacy in other disease models.
Enzyme Assay
Cell-free assays for LNFP-III include binding studies to assess its interactions with immune cell receptors or pathogen adhesion molecules. The compound's ability to inhibit pathogen adherence can be evaluated using surface plasmon resonance or ELISA-based assays. Its immunomodulatory effects can be assessed by measuring cytokine production in immune cell cultures stimulated with specific antigens or mitogens.
Cell Assay
In vitro cellular assays involve treating immune cells (e.g., T cells, macrophages, dendritic cells) with LNFP-III and measuring activation markers, cytokine secretion, and proliferation. Pathogen adherence assays use intestinal epithelial cell lines incubated with pathogens in the presence or absence of LNFP-III to assess its inhibitory effects on adhesion.
Animal Protocol
In vivo animal studies for LNFP-III are typically conducted using the experimental autoimmune encephalomyelitis (EAE) model, a mouse model of multiple sclerosis. LNFP-III is administered orally or intraperitoneally, and disease severity is scored based on clinical signs. Histopathological examination of the CNS and analysis of immune cell infiltration and cytokine levels are performed.
ADME/Pharmacokinetics
Pharmacokinetic properties of LNFP-III are characteristic of complex oligosaccharides. As a human milk oligosaccharide, it is expected to resist digestion in the upper gastrointestinal tract and reach the colon intact, where it can exert local effects. Systemic absorption is likely limited. The compound may modulate the gut microbiome and immune system through indirect mechanisms.
Toxicity/Toxicokinetics
Available toxicological data for LNFP-III are limited. As a naturally occurring human milk oligosaccharide found in breast milk, it is generally recognized as safe. No significant toxicity has been reported in available studies. Its safety profile supports its use in infant nutrition and as a research tool.
References

[1]. Immune modulation by Lacto-N-fucopentaose III in experimental autoimmune encephalomyelitis. Clin Immunol. 2012 Mar;142(3):351-61.

[2]. Lacto-N-fucopentaose-III ameliorates acute and persisting hippocampal synaptic plasticity and transmission deficits in a Gulf War Illness mouse model. Life Sci. 2021 Aug 15;279:119707.

Additional Infomation
Lacto-N-fucopentaose III is a carbohydrate molecule found on the surface of neutrophils, eosinophils, and monocytes. It participates in neutrophil chemotaxis and phagocytosis. Expression of this antigen is associated with Hodgkin's lymphoma, chronic lymphocytic leukemia, and acute lymphoblastic leukemia. Polylactic acid sugars are the main carbohydrate in Schistosoma mansoni oocyte antigens; they can induce a Th2-type immune response in vivo.
LNFP-III is a research compound with no clinical approvals. Its primary applications are as an immunomodulator and as a tool for studying autoimmune diseases such as multiple sclerosis. The compound's ability to reduce CNS inflammation makes it a candidate for further investigation in autoimmune and inflammatory conditions. Its presence in human milk also suggests a role in neonatal immune development.
These protocols are for reference only. InvivoChem does not independently validate these methods.
Physicochemical Properties
Molecular Formula
C32H55NO25
Molecular Weight
853.77
Exact Mass
853.306
CAS #
25541-09-7
PubChem CID
53477857
Appearance
Typically exists as solid at room temperature
Density
1.71g/cm3
Boiling Point
1264.6ºC at 760 mmHg
Flash Point
718.6ºC
Vapour Pressure
0mmHg at 25°C
Index of Refraction
1.655
Hydrogen Bond Donor Count
16
Hydrogen Bond Acceptor Count
25
Rotatable Bond Count
17
Heavy Atom Count
58
Complexity
1290
Defined Atom Stereocenter Count
24
SMILES
[C@@H]1(O[C@H]2O[C@H]([C@@H](O)[C@@H](O)[C@@H]2O)C)[C@@H](NC(=O)C)[C@H](O[C@H](CO)[C@H]1O[C@H]1[C@H](O)[C@H]([C@@H](O)[C@@H](CO)O1)O)O[C@H]1[C@@H](O)[C@H](O[C@@H](O[C@H]2[C@H](O)[C@H](C(O)O[C@@H]2CO)O)[C@@H]1O)CO
InChi Key
WMYQZGAEYLPOSX-QKPOUJQKSA-N
InChi Code
InChI=1S/C32H55NO25/c1-8-16(42)20(46)22(48)30(51-8)57-27-15(33-9(2)39)29(54-14(7-38)26(27)56-31-23(49)21(47)18(44)12(5-36)52-31)58-28-19(45)13(6-37)53-32(24(28)50)55-25(11(41)4-35)17(43)10(40)3-34/h3,8,10-32,35-38,40-50H,4-7H2,1-2H3,(H,33,39)/t8-,10-,11+,12+,13+,14+,15+,16+,17+,18-,19-,20+,21-,22-,23+,24+,25+,26+,27+,28-,29-,30-,31-,32-/m0/s1
Chemical Name
N-[(2S,3R,4R,5S,6R)-2-[(2R,3S,4S,5R,6S)-3,5-dihydroxy-2-(hydroxymethyl)-6-[(2R,3R,4R,5R)-1,2,4,5-tetrahydroxy-6-oxohexan-3-yl]oxyoxan-4-yl]oxy-6-(hydroxymethyl)-5-[(2S,3R,4S,5R,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-4-[(2S,3S,4R,5S,6S)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxyoxan-3-yl]acetamide
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 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 1.1713 mL 5.8564 mL 11.7128 mL
5 mM 0.2343 mL 1.1713 mL 2.3426 mL
10 mM 0.1171 mL 0.5856 mL 1.1713 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?
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  • 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:
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  • The answer of 62.5 μL (0.1 ml) appears in the Volume (Start) box
g/mol

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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:
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  • Molar mass (molar weight) is the mass of one mole of a substance and is expressed in g/mol.
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  • The answer appears in the Volume (to add to vial) box
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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