ArticleJournal of medicinal chemistry2011
Structure-activity relationships in nucleotide oligomerization domain 1 (Nod1) agonistic γ-glutamyldiaminopimelic acid derivatives.
Article in Journal of medicinal chemistry, 2011. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 24 papers.
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Who cites it
24 citing papers in PubMed, 38 citations in OpenAlex.
- Conjugated NOD1-Centered Dual Agonists Exhibit Modest In Vitro Immunomodulation but Potent In Vivo Adjuvanticity.ACS bio & med chem Au · 2026Article
- Small molecule modulators of immune pattern recognition receptors.RSC chemical biology · 2023Review
- Immunogenic molecules associated with gut bacterial cell walls: chemical structures, immune-modulating functions, and mechanisms.Protein & cell · 2023Review
- Nucleotide-Binding Oligomerization Domain 1/Toll-Like Receptor 4 Co-Engagement Promotes Non-Specific Immune Response Against K562 Cancer Cells.Frontiers in pharmacology · 2022Article
- Synthesis of Conformationally Constrained d-Glu-Molecules (Basel, Switzerland) · 2020Article
- Peptidoglycan Metabolite Photoaffinity Reporters Reveal Direct Binding to Intracellular Pattern Recognition Receptors and Arf GTPases.ACS chemical biology · 2019Article
- Translation of peptidoglycan metabolites into immunotherapeutics.Clinical & translational immunology · 2019Review
- Transcriptomal signatures of vaccine adjuvants and accessory immunostimulation of sentinel cells by toll-like receptor 2/6 agonists.Human vaccines & immunotherapeutics · 2018Article
- Identification of Adjuvantic Activity of Amphotericin B in a Novel, Multiplexed, Poly-TLR/NLR High-Throughput Screen.PloS one · 2016Article
- Structure-Based Design of Human TLR8-Specific Agonists with Augmented Potency and Adjuvanticity.Journal of medicinal chemistry · 2015Article
- An intermolecular binding mechanism involving multiple LysM domains mediates carbohydrate recognition by an endopeptidase.Acta crystallographica. Section D, Biological crystallography · 2015Article
- Helical shape of Helicobacter pylori requires an atypical glutamine as a zinc ligand in the carboxypeptidase Csd4.The Journal of biological chemistry · 2015Article
- Review
- Determinants of activity at human Toll-like receptors 7 and 8: quantitative structure-activity relationship (QSAR) of diverse heterocyclic scaffolds.Journal of medicinal chemistry · 2014Article
- Human Toll-like receptor 8-selective agonistic activities in 1-alkyl-1H-benzimidazol-2-amines.Journal of medicinal chemistry · 2014Article
- Structure-based design of novel human Toll-like receptor 8 agonists.ChemMedChem · 2014Article
- A novel rapamycin-polymer conjugate based on a new poly(ethylene glycol) multiblock copolymer.Pharmaceutical research · 2014Article
- Exquisite selectivity for human toll-like receptor 8 in substituted furo[2,3-c]quinolines.Journal of medicinal chemistry · 2013Article
- Design and development of stable, water-soluble, human Toll-like receptor 2 specific monoacyl lipopeptides as candidate vaccine adjuvants.Journal of medicinal chemistry · 2013Article
- Anticonvulsant activity of 1,2,3,4,6-penta-O-galloyl-β-D-glucopyranose isolated from leaves of Mangifera indica.Naunyn-Schmiedeberg's archives of pharmacology · 2013Article
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Authors and funding
7 authors at 1 institution in 1 country.
Funding
Abstract
N-acyl-γ-glutamyldiaminopimelic acid is a prototype ligand for Nod1. We report a detailed SAR of C(12)-γ-D-Glu-DAP. Analogues with glutaric or γ-aminobutyric acid replacing the glutamic acid show greatly attenuated Nod1-agonistic activity. Substitution of the meso-diaminopimelic (DAP) acid component with monoaminopimelic acid, L- or D-lysine, or cadaverine also results in reduced activity. The free amine on DAP is crucial. However, the N-acyl group on the D-glutamyl residue can be substituted with N-alkyl groups with full preservation of activity. The free carboxylates on the DAP and Glu components can also be esterified, resulting in more lipophilic but active analogues. Transcriptomal profiling showed a dominant up-regulation of IL-19, IL-20, IL-22, and IL-24, which may explain the pronounced Th2-polarizing activity of these compounds and also implicate cell signaling mediated by TREM-1. These results may explain the hitherto unknown mechanism of synergy between Nod1 and TLR agonists and are likely to be useful in designing vaccine adjuvants.
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