C12-iE-DAP hydrochloride
Based on 1 publication(s) in Google Scholar
C12-iE-DAP hydrochloride (Lauroyl-γ-D-glutamyl-meso-diaminopimelic acid hydrochloride) is a highly potent and selective NOD1 agonist, with an EC50 of 0.027 nM in HEK-Blue cells expressing human NOD1. C12-iE-DAP hydrochloride activates the NOD1/RIPK2 signaling pathway and its downstream p38 MAPK and NF-κB, induces the expression of inflammatory mediators such as IL6 and IL8, and exerts synergistic effects with TLR4, Dectin-1 or Mincle signaling. C12-iE-DAP hydrochloride can be used in studies related to vascular inflammation, tumor metastasis and neuroinflammation.
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- Pureté: 96.59%
- Formule: C24H44ClN3O8
- Masse moléculaire:538.07
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Stockage:
Sealed storage, away from moisture.
Powder -80°C, 2 years , -20°C, 1 year* In solvent : -80°C, 6 months; -20°C, 1 month (sealed storage, away from moisture)
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Activité biologique
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Chemical Information
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Solvant et solubilité
- Pureté et documentation
- Références
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Help & FAQs
Publications Citing Use of MedChemExpress (MCE) C12-iE-DAP hydrochloride
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Activité biologique
Description
IC50 & Target
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hNOD1 0.027 nM (EC50) |
In Vitro
C12-iE-DAP (compound 16) hydrochloride (Lauroyl-γ-D-glutamyl-meso-diaminopimelic acid hydrochloride) hydrochloride induces NF-κB/AP-1-dependent SEAP signaling in HEK-Blue cells expressing human NOD1, with an EC50 of 0.027 nM[5].
C12-iE-DAP (0.01-10 μg/mL; 18 h) hydrochloride acts synergistically with Curdlan (HY-131166) or TDB to enhance NF-κB/AP-1-dependent SEAP expression in the human monocytic cell line THP1-XBlue-CD14, with activity levels exceeding the additive effect of stimulation by each agonist alone[2].
C12-iE-DAP (1-100 μg/mL; 24 h) hydrochloride acts synergistically with Curdlan or TDB to enhance the production of the IL-8 cytokine in the human monocyte cell line THP-1, with the production level exceeding the additive effect of stimulation by individual agonists[2].
C12-iE-DAP (10-9-10-8 M; 1 h) hydrochloride upregulates CD11b in granulocytes from fresh human whole blood in a dose-dependent manner, with a stronger induction effect at 10-8 M than at 10-9 M; whereas compound 27 exhibits stronger activity at both of the above concentrations[5].
C12-iE-DAP (5 μg/mL; 6 h) hydrochloride induces IL6 and IL8 mRNA expression in primary human brain pericytes and increases IL-8 release in cell culture supernatants[1].
C12-iE-DAP (1 μg/mL; 6 h) hydrochloride-induced IL8 expression in human brain pericytes depends on the NOD1/RIPK2/p38/NF-κB signaling pathway. NOD1 knockdown reduces IL8 induction by >62%, while inhibitors of RIPK2, p38 or NF-κB can significantly suppress this response[1].
C12-iE-DAP (1 μg/mL) hydrochloride acts synergistically with LPS (5 ng/mL) for 6 h to enhance IL8 mRNA expression in primary human brain pericytes, and the induced level is higher than that of LPS (100 ng/mL) alone[1].
C12-iE-DAP (2,000 ng/mL) hydrochloride increases the adhesion of HT29 cells to fibronectin, collagen I and collagen IV by approximately 2-fold, 2-fold and 1.5-fold, respectively, enhances the migration of HT29 cells by approximately 2-fold, and simultaneously increases the adhesion of MC38 cells to both collagen I and fibronectin by approximately 1.5-fold[4].
C12-iE-DAP (up to 2,000 ng/mL; up to 80 min) hydrochloride increases p38 phosphorylation in colorectal cancer cells by up to approximately 7-fold in a dose- and time-dependent manner, but does not induce corresponding changes in IκBα degradation[4].
MedChemExpress (MCE) has not independently confirmed the accuracy of these methods. They are for reference only.
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Cell Line:human monocytic THP-1 cells
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Concentration:1-100 μg/mL
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Incubation Time:24 h
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Result:Induced IL-8 production in a dose-dependent manner.
Produced IL-8 production levels greater than the sum of levels induced by individual stimulation when combined with Curdlan or TDB, demonstrating a synergistic potentiation effect.
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Cell Line:human monocytic THP-1 cells
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Concentration:10 μg/mL
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Incubation Time:24 h (agonist incubation); inhibitors added 1 h prior to agonist treatment
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Result:Abrogated IL-8 production induced by individual treatment when RIP2 was inhibited via gefitinib.
Reduced IL-8 production induced by combined treatment with TDB to near baseline levels when RIP2 was inhibited via gefitinib.
Showed no significant effect on IL-8 production induced by individual treatment when Syk was inhibited via piceatannol.
Reduced IL-8 production induced by combined treatment with TDB to levels equivalent to individual treatment when Syk was inhibited via piceatannol.
Completely abrogated IL-8 production induced by both individual and combined treatment when dexamethasone was used.
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Cell Line:human colorectal cancer HT29 cells
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Concentration:2000 ng/mL
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Incubation Time:60 min (following 30 min DMSO pre-incubation)
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Result:Induced a 2-fold increase in HT29 cell migration compared to DMSO vehicle control, with statistical significance.
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Cell Line:human colorectal cancer HT29 cells
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Concentration:500-2000 ng/mL (fixed incubation time); 2000 ng/mL (time-dependent analysis)
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Incubation Time:fixed time (dose-dependent analysis); 20-80 min (2000 ng/mL)
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Result:Induced a dose-dependent increase in p38 phosphorylation, with up to a 7-fold increase at 2000 ng/mL compared to DMSO contro.
Induced a time-dependent increase in p38 phosphorylation, with up to a 2.3-fold increase at 80 min compared to baseline.
In Vivo
Activation of the NOD1 signaling pathway via C12-iE-DAP (1 mM; intracerebroventricular injection; once every 3 days for 4 weeks) hydrochloride abolishes the cognitive-improving, anti-inflammatory and anti-Aβ plaque effects of Avn-C in obese 5×FAD mice, with significant reversals observed in key indicators including the novel object recognition index, time spent in the target quadrant of the MWM, pro-inflammatory cytokine levels and Aβ load[3].
When MC38 cells pretreated with C12-iE-DAP (2,000 ng/mL) hydrochloride are injected intrasplenically into C57BL/6 mice, 37 metastatic nodules form on the liver surface on day 21[4].
Intrasplenic injection of HT29 or MC38 cells pretreated with C12-iE-DAP (2,000 ng/mL) hydrochloride increases their adhesion to liver sinusoids in C57BL/6 mice by approximately 2-fold, and this effect is blocked by ML130 (10 μM)[4].
MedChemExpress (MCE) has not independently confirmed the accuracy of these methods. They are for reference only.
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Animal Model:BALB/c (female, SPF, 5-6 weeks old)[2]
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Dosage:C12-iE-DAP: 1 μg/mouse; Curdlan; TDB: 10 μg/mouse
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Administration:i.m.; single dose
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Result:Co-stimulation synergistically increased serum IL-6 and KC levels at 3 h.
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Animal Model:5×FAD (male, 2 months old, high-fat diet-induced obesity-accelerated Alzheimer's disease)[3]
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Dosage:1 mM
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Administration:i.c.v.; once every three days; 4 weeks
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Result:Reduced object-recognition and spatial-memory performance.
Reversed the reductions in NOD1/RIP2/NF-κB signaling, inflammatory cytokines and Aβ deposition induced by Avenanthramide-C.
Chemical Information
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Appearance Solid
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Masse moléculaire 538.07
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Formule C24H44ClN3O8
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Color White to off-white
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Synonyms
Lauroyl-γ-D-glutamyl-meso-diaminopimelic acid hydrochloride; γ-D-glutamyl-meso-diaminopimelic acid hydrochloride
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Sequence
Lauroyl-γ-d-Glu-meso-diaminopimelic acid
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Livraison
Room temperature in continental US; may vary elsewhere.
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Stockage
Sealed storage, away from moisture
Powder -80°C 2 years -20°C 1 year * In solvent : -80°C, 6 months; -20°C, 1 month (sealed storage, away from moisture)
Publications (1)
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Journal Impact Factor
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Most Recent
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J Extracell Vesicles
Tumour-Derived Extracellular Vesicles Reprogramme Tumour-Associated Macrophages Into Immunosuppressive Phenotype via NOD1 Signalling in Clear Cell Renal Cell Carcinoma. [Abstract]2026 Jun;15(6):e70317. PMID: 42226559
Solvant et solubilité
In Vitro:
DMSO : 100 mg/mL (185.85 mM; Need ultrasonic; Hygroscopic DMSO has a significant impact on the solubility of product, please use newly opened DMSO)
Please refer to the solubility information to select the appropriate solvent. Once prepared, please aliquot and store the solution to prevent product inactivation from repeated freeze-thaw cycles.
Storage method and period of stock solution: -80°C, 6 months; -20°C, 1 month (sealed storage, away from moisture). When stored at -80°C, please use it within 6 months. When stored at -20°C, please use it within 1 month.
Please refer to the solubility information to select the appropriate solvent. Once prepared, please aliquot and store the solution to prevent product inactivation from repeated freeze-thaw cycles.
Storage method and period of stock solution: -80°C, 6 months; -20°C, 1 month (sealed storage, away from moisture). When stored at -80°C, please use it within 6 months. When stored at -20°C, please use it within 1 month.
Concentration (start) × Volume (start) = Concentration (final) × Volume (final)
Pureté et documentation
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Fiche technique (283 KB)
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SDS (252 KB)
- English - EN (252 KB)
- Français - FR (252 KB)
- Deutsch - DE (252 KB)
- Norwegian - NO (252 KB)
- Español - ES (252 KB)
- Swedish - SV (252 KB)
- Italian - IT (252 KB)
- Korean - KR (252 KB)
- Portuguese - PT (252 KB)
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Instruction de manipulation (2659 KB)
Références
[1]. Navarro R, et al. Role of nucleotide-binding oligomerization domain 1 (NOD1) in pericyte-mediated vascular inflammation. Journal of cellular and molecular medicine. 2016 May;20(5):980-6. [Content Brief]
[2]. Tukhvatulin AI, et al. NOD1/2 and the C-Type Lectin Receptors Dectin-1 and Mincle Synergistically Enhance Proinflammatory Reactions Both In Vitro and In Vivo. Journal of inflammation research. 2020;13:357-368. [Content Brief]
[3]. Wang M, et al. Avenanthramide-C Mitigates High-Fat Diet-Accelerated Alzheimer's Pathologies via NOD1-Driven Neuroinflammation in 5×FAD Mice. Nutrients. 2025 Aug 19;17(16):2679. [Content Brief]
[4]. Jiang HY, et al. Activation of the pattern recognition receptor NOD1 augments colon cancer metastasis. Protein & cell. 2020 Mar;11(3):187-201. [Content Brief]
[5]. Agnihotri G, et al. Structure-activity relationships in nucleotide oligomerization domain 1 (Nod1) agonistic γ-glutamyldiaminopimelic acid derivatives. Journal of medicinal chemistry. 2011 Mar 10;54(5):1490-510. [Content Brief]
Complete Stock Solution Preparation Table
Please refer to the solubility information to select the appropriate solvent. Once prepared, please aliquot and store the solution to prevent product inactivation from repeated freeze-thaw cycles.
Storage method and period of stock solution: -80°C, 6 months; -20°C, 1 month (sealed storage, away from moisture). When stored at -80°C, please use it within 6 months. When stored at -20°C, please use it within 1 month.
| Optional Solvent | Concentration Solvent Mass | 1 mg | 5 mg | 10 mg | 25 mg |
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| DMSO | 1 mM | 1.8585 mL | 9.2925 mL | 18.5849 mL | 46.4624 mL |
| 5 mM | 0.3717 mL | 1.8585 mL | 3.7170 mL | 9.2925 mL | |
| 10 mM | 0.1858 mL | 0.9292 mL | 1.8585 mL | 4.6462 mL | |
| 15 mM | 0.1239 mL | 0.6195 mL | 1.2390 mL | 3.0975 mL | |
| 20 mM | 0.0929 mL | 0.4646 mL | 0.9292 mL | 2.3231 mL | |
| 25 mM | 0.0743 mL | 0.3717 mL | 0.7434 mL | 1.8585 mL | |
| 30 mM | 0.0619 mL | 0.3097 mL | 0.6195 mL | 1.5487 mL | |
| 40 mM | 0.0465 mL | 0.2323 mL | 0.4646 mL | 1.1616 mL | |
| 50 mM | 0.0372 mL | 0.1858 mL | 0.3717 mL | 0.9292 mL | |
| 60 mM | 0.0310 mL | 0.1549 mL | 0.3097 mL | 0.7744 mL | |
| 80 mM | 0.0232 mL | 0.1162 mL | 0.2323 mL | 0.5808 mL | |
| 100 mM | 0.0186 mL | 0.0929 mL | 0.1858 mL | 0.4646 mL |
C12-iE-DAP hydrochloride Related Classifications
HY-P5524A Related Classifications
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