ArticleBioconjugate chemistry2016
Engineering an Affinity-Enhanced Peptide through Optimization of Cyclization Chemistry.
Article in Bioconjugate chemistry, 2016. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 18 papers.
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Who cites it
18 citing papers in PubMed, 39 citations in OpenAlex.
- Integrative Peptide Drug Development: Chemical Engineering, AI-Driven Design, and Cell-Penetrating Peptides.Pharmaceutics · 2026Review
- Natural Bioactive Peptides from Tree Peony Flowers: Multifunctional Effects on Skin Antioxidation, Wrinkle Reduction, Moisturization, and Melanin Inhibition.Antioxidants (Basel, Switzerland) · 2026Article
- A helical peptide antagonist of the human growth hormone receptor.Endocrinology · 2026Article
- Design and Preliminary Immunogenicity Evaluation of Nipah Virus Glycoprotein G Epitope-Based Peptide Vaccine in Mice.Vaccines · 2025Article
- Peptide Design for Enhanced Anti-Melanogenesis: Optimizing Molecular Weight, Polarity, and Cyclization.Drug design, development and therapy · 2025Review
- Insight into the Functional Dynamics and Challenges of Exosomes in Pharmaceutical Innovation and Precision Medicine.Pharmaceutics · 2024Review
- Review
- Identification of Inhibitors of the Disease-Associated Protein Phosphatase Scp1 Using Antibody Mimetic Molecules.International journal of molecular sciences · 2024Article
- Genetically encoded discovery of perfluoroaryl macrocycles that bind to albumin and exhibit extended circulation in vivo.Nature communications · 2023Article
- Tumor-Associated Macrophage Subsets: Shaping Polarization and Targeting.International journal of molecular sciences · 2023Review
- Macrocyclization strategies for cyclic peptides and peptidomimetics.RSC medicinal chemistry · 2021Review
- Review
- Tumor Associated Macrophages: Origin, Recruitment, Phenotypic Diversity, and Targeting.Frontiers in oncology · 2021Review
- Targeting Ligands Deliver Model Drug Cargo into the Central Nervous System along Autonomic Neurons.ACS nano · 2019Article
- Arylation Chemistry for Bioconjugation.Angewandte Chemie (International ed. in English) · 2019Review
- Multivalent polymers displaying M2 macrophage-targeting peptides improve target binding avidity and serum stability.ACS biomaterials science & engineering · 2017Article
- Progress in tumor-associated macrophage (TAM)-targeted therapeutics.Advanced drug delivery reviews · 2017Review
- Optimized serum stability and specificity of an αvβ6 integrin-binding peptide for tumor targeting.The Journal of biological chemistryArticle
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Authors and funding
3 authors at 1 institution in 1 country.
Funding
Abstract
Peptide cyclization is a strategy used to improve stability and activity of peptides. The most commonly used cyclization method is disulfide bridge formation of cysteine-containing peptides, as is typically found in nature. Over the years, an increasing number of alternative chemistries for peptide cyclization with improved efficiency, kinetics, orthogonality, and stability have been reported. However, there has been less appreciation for the opportunity to fine-tune peptide activity via the diverse chemical entities introduced at the site of linkage by different cyclization strategies. Here, we demonstrate how cyclization optimization of an M2 "anti-inflammatory" macrophage-binding peptide (M2pep) resulted in a significant increase in binding affinity of the optimized analog to M2 macrophages while maintaining binding selectivity compared to M1 "pro-inflammatory" macrophages. In this study, we report synthesis and evaluation of four cyclic M2pep(RY) analogs with diverse cyclization strategies: (1) Asp-[amide]-Lys, (2) azido-Lys-[triazole(copper(I)-catalyzed alkyne-azide cycloaddition (CuAAC))]-propargyl-Gly, (3) Cys-[decafluorobiphenyl (DFBP)]-Cys, and (4) Cys-[decafluorobiphenyl sulfone (DFS)]-Cys, whereby the chemical entity or linker at the linkage site is shown in the square bracket and is between the residues involved in cyclization. These peptides are compared to a disulfide-cyclized M2pep(RY) that we previously reported as a serum-stable, affinity-enhanced analog to the original linear M2pep. DFBP-cyclized M2pep(RY) exhibits the highest binding activity to M2 macrophages with apparent dissociation constant (K
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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.