C14-Tri-LAN-Gly

Notification:  This product will be removed from our catalog in December 2024.

NOD1 Agonist - Meso‑lanthionine tri-peptide

NOD1 is a pattern recognition receptor that senses Gram‑ bacterial peptidoglycans (PGN), and more specifically the minimal motif γ-glutamyl-meso-diaminopimelic acid (iE-DAP) [1]. Synthetic agonists of NOD1 have been developed in various ways to enhance their potency and intracellular delivery: NOD1 preferentially detects tri-DAP peptides with an N-terminal lipophilic chain [1,2].

InvivoGen has developed C14-Tri-LAN-Gly which contains meso‑lanthionine instead of the meso-DAP moiety, a myristic lipophilic chain, and three peptides (Ala, Glu, Gly) [3]. Meso‑lanthionine is a diamino-type amino acid specific to the PGN of some Gram- bacteria such as Fusobacterium nucleatum [4]. C14-Tri-LAN-Gly has the advantage of being a single diastereoisomer, as opposed to other synthetic NOD1 agonists which are a mixture of L and D isomers.

Recognition of C14-Tri-LAN-Gly by NOD1 induces the activation of the NF-κB signaling pathway. While it activates both human and murine NOD1, it is the agonist of choice for murine NOD1 as it exhibits a ~10-fold better potency than the C12-iE-DAP and a ~100-fold better potency than the Tri-DAP.

References:

1. Girardin SE. et al., 2013. Nod1 detects a unique muropeptide from Gram-negative bacterial peptidoglycan. Science. 300: 1584-87.
2. Nielsen AE. et al., 2017. Synthetic agonists of NOD-like, RIG-like, and C-type lectin receptors for probing the inflammatory immune response. Future Med Chem. (in press).
3. Kingston Mills, Patrick Kelly, Jean-Gerard Tiraby, Thierry Lioux, Eric Perouzel, Patent online 2016, Novel compounds, WO 2016008946 A1
4. Uehara A. et al., 2006. Meso-diaminopimelic acid and meso-lanthionine, amino acids specific to bacterial peptidoglycans, activate human epithelial cells through NOD1. J Immunol. 177(3):1796-804.

Figures

Dose responses of HEK-Blue™ hNOD1 (panel a) and HEK-Blue™ mNOD1 (panel b) reporter cells stimulated with 0.1 ng/ml to 10 μg/ml of NOD1 agonists: iE-DAP (dark green), C12-iE-DAP (light green), Tri-DAP (blue) and C14-Tri-LAN-Gly (red). After overnight incubation, the NF-κB response was determined using QUANTI‑Blue™, a SEAP detection reagent, and by reading the optical density (OD) at 630 nm.

Specifications

Specificity: NOD1 agonist

Source: Synthetic

Working concentration: 1 ng - 1 μg/ml

Solubility: 2 mg/ml in water

Synonym: Myristic-Alanine-D-iso-Glutamine-ε-meso-Lanthionine- Glycine

Formula: C₃₀H₅₃N₅O₁₀S

CAS: 1863978-69-1

Molecular weight: 675.84

Quality control:

• Purity: ≥95% (UHPLC)
• The biological activity has been validated using HEK‑Blue™ NOD1 cells.
• The absence of bacterial contamination (e.g. lipoproteins and endotoxins) has been confirmed using HEK-Blue™ TLR2 and HEK‑Blue™ TLR4 cells.

Contents

C14-Tri-LAN-Gly is provided lyophilized.

• 1 mg C14-Tri-LAN-Gly
• 1.5 ml sterile endotoxin-free water

C14-Tri-LAN-Gly is shipped at room temperature.

Upon receipt, store at -20 °C.
Upon resuspension, prepare aliquots of C14-Tri-LAN-Gly and store at -20 °C.

Resuspended product is stable for 6 months at -20 °C when properly stored.

Avoid repeated freeze-thaw cycles.