ArticleJournal of medicinal chemistry2012
Structure-activity relationships in human Toll-like receptor 2-specific monoacyl lipopeptides.
Article in Journal of medicinal chemistry, 2012. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 25 papers.
What it found
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The abstract states no effect estimate the extractor could read, or names no intervention and outcome on the map, so this paper lights no cell and moves no belief. It is still indexed, cited and linked below.
The trial behind it
Trials whose registry record cites this paper, or whose number appears in the abstract. A trial that started after this paper was published is citing it as background, not reporting it.
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Who cites it
25 citing papers in PubMed, 49 citations in OpenAlex.
- Mono-Palmitoyl-N-Alkylurea Ligands as Specific Activators of Human Toll-Like Receptor 2/6 Heterodimer.Chembiochem : a European journal of chemical biology · 2024Article
- Simplified scalable synthesis of a water-soluble toll-like receptor 2 agonistic lipopeptide adjuvant for use with protein-based viral vaccines.Bioorganic chemistry · 2024Article
- Toll-like receptors as a missing link in Notch signaling cascade during neurodevelopment.Frontiers in molecular neuroscience · 2024Article
- Stereoisomeric PamRSC medicinal chemistry · 2022Article
- Simplified Monopalmitoyl Toll-like Receptor 2 Ligand Mini-UPam for Self-Adjuvanting Neoantigen-Based Synthetic Cancer Vaccines.Chembiochem : a European journal of chemical biology · 2021Article
- Identification of Human Toll-like Receptor 2-Agonistic Activity in Dihydropyridine-Quinolone Carboxamides.ACS medicinal chemistry letters · 2019Article
- Diprovocims: A New and Exceptionally Potent Class of Toll-like Receptor Agonists.Journal of the American Chemical Society · 2018Article
- Transcriptomal signatures of vaccine adjuvants and accessory immunostimulation of sentinel cells by toll-like receptor 2/6 agonists.Human vaccines & immunotherapeutics · 2018Article
- Toll-like Receptor Agonist Conjugation: A Chemical Perspective.Bioconjugate chemistry · 2018Review
- An efficient and scalable synthesis of potent TLR2 agonistic PAMRSC advances · 2018Article
- TLR2 agonism reverses chemotherapy-induced neutropenia inBlood advances · 2017Article
- Peptide Lipidation - A Synthetic Strategy to Afford Peptide Based Therapeutics.Advances in experimental medicine and biology · 2017Review
- Strategies for designing synthetic immune agonists.Immunology · 2016Review
- Discovery and Structure-Activity Relationships of the Neoseptins: A New Class of Toll-like Receptor-4 (TLR4) Agonists.Journal of medicinal chemistry · 2016Article
- 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
- 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
- Directing the immune system with chemical compounds.ACS chemical biology · 2014Review
- Exquisite selectivity for human toll-like receptor 8 in substituted furo[2,3-c]quinolines.Journal of medicinal chemistry · 2013Article
Corrections and comments
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Authors and funding
7 authors at 1 institution in 1 country.
Funding
Abstract
Toll-like receptor 2-agonistic lipopeptides typified by S-[2,3-bis(palmitoyloxy)-(2RS)-propyl]-R-cysteinyl-S-serine (PAM(2)CS) compounds are potential vaccine adjuvants. We had previously determined that at least one acyl group of optimal length (C(16)) and an appropriately orientated ester carbonyl group is essential for TLR2-agonistic activity. We now show that these structurally simpler analogues display agonistic activities with human, but not murine, TLR2. SAR studies on the monoacyl derivatives show that the optimal acyl chain length is C(16), and aryl substituents are not tolerated. A variety of alkyl and acyl substituents on the cysteine amine were examined. All N-alkyl derivatives were inactive. In contradistinction, short-chain N-acyl analogues were found to be highly active, with a clear dependence on the chain length. A cysteine N-acetyl analogue was found to be the most potent (EC(50): 1 nM), followed by the N-butyryl analogue. The N-acetyl analogue is human TLR2-specific, with its potency comparable to that of PAM(2)CS.
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Registered trials
Read under generation 80e0d062 · epoch 390. Bibliography from PubMed, PubMed Central and OpenAlex; grants from NIH RePORTER; trial links from ClinicalTrials.gov; estimates, votes and beliefs from the OpenQuestion graph.