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Leukotriene B4 ethanolamide 877459-63-7

Leukotriene B4 ethanolamide 877459-63-7

CAS No.: 877459-63-7

Leukotriene B4 ethanolamide (LTB4 ethanolamide) is an antagonist and partial agonist of leukotriene B4 receptor 1 (BLTR1
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Leukotriene B4 ethanolamide (LTB4 ethanolamide) is an antagonist and partial agonist of leukotriene B4 receptor 1 (BLTR1). Leukotriene B4 ethanolamide improves tumor progression associated with inflammation alone.

Physicochemical Properties


Molecular Formula C22H37NO4
Molecular Weight 379.53
Exact Mass 379.272
CAS # 877459-63-7
PubChem CID 5283127
Appearance Typically exists as solid at room temperature
Density 1.0±0.1 g/cm3
Boiling Point 617.6±55.0 °C at 760 mmHg
Flash Point 327.3±31.5 °C
Vapour Pressure 0.0±4.0 mmHg at 25°C
Index of Refraction 1.527
LogP 2.72
Hydrogen Bond Donor Count 4
Hydrogen Bond Acceptor Count 4
Rotatable Bond Count 16
Heavy Atom Count 27
Complexity 469
Defined Atom Stereocenter Count 2
SMILES

CCCCC/C=C\C[C@@H](O)/C=C/C=C/C=C\[C@@H](O)CCCC(NCCO)=O

InChi Key DQLVVNIINUTUIU-XLFGVTECSA-N
InChi Code

InChI=1S/C22H37NO4/c1-2-3-4-5-6-9-13-20(25)14-10-7-8-11-15-21(26)16-12-17-22(27)23-18-19-24/h6-11,14-15,20-21,24-26H,2-5,12-13,16-19H2,1H3,(H,23,27)/b8-7+,9-6-,14-10+,15-11-/t20-,21-/m1/s1
Chemical Name

(5S,6Z,8E,10E,12R,14Z)-5,12-dihydroxy-N-(2-hydroxyethyl)icosa-6,8,10,14-tetraenamide
Synonyms

LTB4 ethanolamide
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)

Biological Activity


Targets Human Endogenous Metabolite
ln Vitro Leukotriene B4 ethanolamide inhibits the contractile effect of LTB 4 in isolated guinea pig lung parenchyma with a Kb of 7.28 nM[1]. Leukotriene B4 ethanolamide (1 μM) acts as a partial agonist of BLT receptors in PMN cells, inducing PMN migration with a pEC50 of 7[2]. Leukotriene B4 ethanolamide (1 μM) stimulates Ca2+ release in TRPV1-expressing rat CHO cells with a pEC50 of 7.28[2].
ln Vivo Leukotriene B4 ethanolamide (100 nM/mouse/day, subcutaneous injection for 5 days) inhibits inflammation-related tumor progression in the C57BL/6 mouse model [2].
Cell Assay Cell Migration Assay [2]
Cell Types: PMN Concentration: 1 μM
Incubation Duration:
Experimental Results: Induced migration of neutrophils.
Animal Protocol Animal/Disease Models:Melanoma tumor in C57BL/6 mouse models[2]
Doses: 100 nM/mouse
Route of Administration: s.c., once a day for 5 days
Experimental Results: Inhibited melanoma tumor growth in mice coinjected with apoptotic Tm1 melanoma cells and a subtumorigenic dose of Tm1.
References

[1]. Novel compounds that interact with both leukotriene B4 receptors and vanilloid TRPV1 receptors. J Pharmacol Exp Ther. 2006 Feb;316(2):955-65.

[2]. , Leukotriene B4 creates a favorable microenvironment for murine melanoma growth. Mol Cancer Res. 2009 Sep;7(9):1417-24.

Additional Infomation LTB4 ethanol amide is a N-acylethanolamine.

Solubility Data


Solubility (In Vitro) May dissolve in DMSO (in most cases), if not, try other solvents such as H2O, Ethanol, or DMF with a minute amount of products to avoid loss of samples
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 : 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).
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 : PEG300:Tween 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).
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 2.6348 mL 13.1742 mL 26.3484 mL
5 mM 0.5270 mL 2.6348 mL 5.2697 mL
10 mM 0.2635 mL 1.3174 mL 2.6348 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.