ArticleChembiochem : a European journal of chemical biology2018
Enhanced Permeability and Binding Activity of Isobutylene-Grafted Peptides.
Article in Chembiochem : a European journal of chemical biology, 2018. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 5 papers.
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Who cites it
5 citing papers in PubMed, 15 citations in OpenAlex.
- Selection of Nucleotide-Encoded Mass Libraries of Macrocyclic Peptides for Inaccessible Drug Targets.Chemical reviews · 2024Review
- Macrocyclization strategies for cyclic peptides and peptidomimetics.RSC medicinal chemistry · 2021Review
- A Physical Organic Approach to Tuning Reagents for Selective and Stable Methionine Bioconjugation.Journal of the American Chemical Society · 2019Article
- Radical-Mediated Thiol-Ene Strategy: Photoactivation of Thiol-Containing Drugs in Cancer Cells.Angewandte Chemie (International ed. in English) · 2018Article
- Enhanced Permeability and Binding Activity of Isobutylene-Grafted Peptides.Chembiochem : a European journal of chemical biology · 2018Article
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Authors and funding
7 authors at 3 institutions in 3 countries.
Funding
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Abstract
We present a new peptide-macrocyclization strategy with an isobutylene graft. The reaction is mild and proceeds rapidly and efficiently both for linear and cyclic peptides. The resulting isobutylene-grafted peptides possess improved passive membrane permeability due to the shielding of the polar backbone of the amides, as demonstrated by NMR spectroscopy and molecular dynamics simulations. The isobutylene-stapled structures are fully stable in human plasma and in the presence of glutathione. This strategy can be applied to bioactive cyclic peptides such as somatostatin. Importantly, we found that structural preorganization forced by the isobutylene graft leads to a significant improvement in binding. The combined advantages of directness, selectivity, and smallness could allow application to peptide macrocyclization based on this attachment of the isobutylene graft.
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