ArticleChembiochem : a European journal of chemical biology2010
Incorporation of 2,3-diaminopropionic acid into linear cationic amphipathic peptides produces pH-sensitive vectors.
Article in Chembiochem : a European journal of chemical biology, 2010. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 14 papers.
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Who cites it
14 citing papers in PubMed, 38 citations in OpenAlex.
- Antibiofilm Activities of Tritrpticin Analogs Against PathogenicMolecules (Basel, Switzerland) · 2025Article
- Highly Efficient Transpeptidase-Catalyzed Isopeptide Ligation.Journal of the American Chemical Society · 2025Article
- Antimicrobial and Cell-Penetrating Peptides: Understanding Penetration for the Design of Novel Conjugate Antibiotics.Antibiotics (Basel, Switzerland) · 2022Review
- An efflux-susceptible antibiotic-adjuvant with systemic efficacy against mouse infections.Scientific reports · 2022Article
- Mutually stabilizing interactions between proto-peptides and RNA.Nature communications · 2020Article
- Selective incorporation of proteinaceous over nonproteinaceous cationic amino acids in model prebiotic oligomerization reactions.Proceedings of the National Academy of Sciences of the United States of America · 2019Article
- De Novo Designed Amphipathic α-Helical Antimicrobial Peptides Incorporating Dab and Dap Residues on the Polar Face To Treat the Gram-Negative Pathogen, Acinetobacter baumannii.Journal of medicinal chemistry · 2019Article
- Design of Novel Amphipathic α-Helical Antimicrobial Peptides with No Toxicity as Therapeutics against the Antibiotic-Resistant Gram-Negative Bacterial Pathogen,Journal of medicinal chemistry and drug design · 2019Article
- Trapping biosynthetic acyl-enzyme intermediates with encoded 2,3-diaminopropionic acid.Nature · 2019Article
- Mechanistic analysis of ghrelin-O-acyltransferase using substrate analogs.Bioorganic chemistry · 2015Article
- Formulation of pH responsive peptides as inhalable dry powders for pulmonary delivery of nucleic acids.European journal of pharmaceutics and biopharmaceutics : official journal of Arbeitsgemeinschaft fur Pharmazeutische Verfahrenstechnik e.V · 2014Article
- Manipulating the pH response of 2,3-diaminopropionic acid rich peptides to mediate highly effective gene silencing with low-toxicity.Journal of controlled release : official journal of the Controlled Release Society · 2013Article
- Control of pH responsive peptide self-association during endocytosis is required for effective gene transfer.Biochimica et biophysica acta · 2012Article
- Effective endogenous gene silencing mediated by pH responsive peptides proceeds via multiple pathways.Journal of controlled release : official journal of the Controlled Release Society · 2012Article
Corrections and comments
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Authors and funding
13 authors at 3 institutions in 2 countries.
Funding
Abstract
Nonviral vectors that harness the change in pH in endosomes, are increasingly being used to deliver cargoes, including nucleic acids, into mammalian cells. Here we present evidence that the pK(a) of the beta-NH(2) in 2,3-diaminopropionic acid (Dap) is sufficiently lowered, when Dap is incorporated into peptides, that its protonation state is sensitive to the pH changes that occur during endosomal acidification. The lowered pK(a) of around 6.3 is stabilized by the increased electron-withdrawing effect of the peptide bonds, by intermolecular hydrogen bonding and from contributions arising from the peptide conformation. These include mixed polar/apolar environments, Coulombic interactions and intermolecular hydrogen bonding. Changes in the charged state are therefore expected between pH 5 and 7, and large-scale conformational changes are observed in Dap-rich peptides, in contrast to analogues containing lysine or ornithine, when the pH is altered through this range. These physical properties confer a robust gene-delivery capability on designed cationic amphipathic peptides that incorporate Dap.
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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.