Lipid X
Lipid X is a 2,3-diacylglucosamine-1-phosphate that serves as the monosaccharide precursor of lipid A, possessing both LPS antagonist and weak agonist activities. Lipid X exerts protective effects by inhibiting tumor necrosis factor production, monocyte procoagulant activity, and neutrophil priming. Lipid X may induce transient pulmonary hypertension, neutropenia, and mild pyrogenic effects in laboratory animals. Lipid X has low toxicity and no in vitro antibacterial activity, but it significantly reduces mortality following Gram-negative bacterial infection and endotoxin exposure. Lipid X tends to accumulate in liver tissue, binds to circulating cellular components, and can be converted to lipid Y through transesterification. Lipid X can be used in research on Gram-negative bacterial sepsis, endotoxemia, and associated pulmonary hypertension.
For research use only. We do not sell to patients.
- CAS No.: 86559-73-1
- Formula: C34H66NO12P
- Molecular Weight:711.86
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Storage:
Please store the product under the recommended conditions in the Certificate of Analysis.
To place orders, for customer services and technical support, please contact: MedChemExpress USA
Tel: 609-228-6898 E-mail: [email protected] [email protected]
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Biological Activity
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Chemical Information
- Purity & Documentation
- References
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Help & FAQs
Biological Activity
Lipid X (0-1.0 mM; 0-60 min) is converted to lipid Y by E. coli membrane-bound palmitoyltransferase, with formation linear with incubation time for up to 60 min and linear with membrane protein concentration up to 1.5 mg/mL, and exhibiting a concentration-dependent increase in product formation that approaches saturation at 1 mM lipid X[1].
Lipid X (10 μg/mL) exhibits no in vitro antimicrobial activity against E. coli (ATCC 25922) and does not enhance ticarcillin-mediated bacterial killing[2].
MedChemExpress (MCE) has not independently confirmed the accuracy of these methods. They are for reference only.
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Cell Line:E. coli
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Concentration:0-1.0 mM
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Incubation Time:0-60 min
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Result:Converted to lipid Y by E. coli membrane-bound palmitoyltransferase, with formation linear with incubation time for up to 60 min and linear with membrane protein concentration up to 1.5 mg/mL.
Exhibited a concentration-dependent increase in product formation that approaches saturation at 1 mM.
A single dose of Lipid X (750 μg) reduces the mortality rate of LPS-induced endotoxemia in C57BL/10 mice[3].
Lipid X protects sheep from LPS-induced death, alleviates LPS-induced pulmonary hypertension in both early and late stages, and protects neutropenic mice from fatal Gram-negative bacterial infection[3].
Pretreatment with Lipid X (100-200 μg/kg; intravenous injection; bolus; single administration 1 hour prior to endotoxin challenge) results in 100% survival of sheep subjected to lethal E. coli endotoxin challenge, and significantly alleviates endotoxin-induced pulmonary arterial hypertension and fever[4].
MedChemExpress (MCE) has not independently confirmed the accuracy of these methods. They are for reference only.
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Animal Model:ICR mice (female)[2]
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Dosage:1000 μg total (single dose); 500 μg (two doses, 6 hours before and after inoculation)
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Administration:i.v.; single dose; two doses (6 hours before and after inoculation)
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Result:Reduced cumulative mortality at 18 hours post-inoculation to 13-45% when administered alone.
Achieved 18% cumulative mortality at 18 hours post-inoculation with two 500-μg dose schedule (6 hours before and after inoculation).
Improved 24-hour survival to 67%, 48-hour survival to 23%, and 5-day cure rate to 18% when combined with ticarcillin 1200 mg/kg every 6 hours.
Increased survival 2- to 4-fold at 24 hours, 48 hours, and 5 days post-inoculation across a range of ticarcillin doses.
Reduced the ticarcillin dose required to protect 50% of mice by 4.5-fold at 1 day, 2-fold at 2 days, and 2.6-fold at 5 days.
Resulted in 94% survival during 48-hour antibiotic treatment period (6% cumulative mortality at 48 hours post-inoculation) when administered as single 1000-μg dose 6 hours post-inoculation alongside ticarcillin 150 mg/kg every 8 hours.
Chemical Information
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CAS No. 86559-73-1
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Molecular Weight 711.86
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Formula C34H66NO12P
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SMILES
O[C@H]1[C@H](OC(C[C@H](O)CCCCCCCCCCC)=O)[C@@H](NC(C[C@H](O)CCCCCCCCCCC)=O)[C@@H](OP(O)(O)=O)O[C@@H]1CO
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Shipping
Room temperature in continental US; may vary elsewhere.
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Storage
Please store the product under the recommended conditions in the Certificate of Analysis.
Purity & Documentation
References
[2]. Golenbock DT, et al. Lipid X protects mice against fatal Escherichia coli infection. Infect Immun. 1988;56(4):779-784. [Content Brief]
[3]. Golenbock DT, et al. Elimination and tissue distribution of the monosaccharide lipid A precursor, lipid X, in mice and sheep. Antimicrob Agents Chemother. 1988;32(1):37-41. [Content Brief]
[4]. Golenbock DT, et al. Lipid X ameliorates pulmonary hypertension and protects sheep from death due to endotoxin. Infect Immun. 1987;55(10):2471-2476. [Content Brief]
Calculators
Concentration (start) × Volume (start) = Concentration (final) × Volume (final)
Lipid X Related Classifications
HY-130581 Related Classifications
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