ArticlePharmaceutical research1996
The effect of conformation on membrane permeability of an acyloxyalkoxy-linked cyclic prodrug of a model hexapeptide.
Article in Pharmaceutical research, 1996. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 16 papers.
What it found
Each row is one number read from the abstract, on the scale the paper reported it, with its interval. Left of the dashed line favours the treatment, right favours the comparator. Under each row is the sentence it came from. New to these charts? A ten-minute tutorial.
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.
Neither the registry nor the abstract names a trial number. If this is a trial report, that itself is worth knowing.
Who cites it
16 citing papers in PubMed.
- Structure of a Cyclic Peptide as an Inhibitor ofPharmaceuticals (Basel, Switzerland) · 2024Article
- Lessons for Oral Bioavailability: How Conformationally Flexible Cyclic Peptides Enter and Cross Lipid Membranes.Journal of medicinal chemistry · 2023Article
- Polar/apolar interfaces modulate the conformational behavior of cyclic peptides with impact on their passive membrane permeability.RSC advances · 2022Article
- Pathways and progress in improving drug delivery through the intestinal mucosa and blood-brain barriers.Therapeutic delivery · 2014Review
- Modeling kinetics of subcellular disposition of chemicals.Chemical reviews · 2009Review
- A randomly coiled, high-molecular-weight polypeptide exhibits increased paracellular diffusion in vitro and in situ relative to the highly ordered alpha-helix conformer.Pharmaceutical research · 2005Article
- Characterization of the efflux transporter(s) responsible for restricting intestinal mucosa permeation of an acyloxyalkoxy-based cyclic prodrug of the opioid peptide DADLE.Pharmaceutical research · 2002Article
- Coumarinic acid-based cyclic prodrugs of opioid peptides that exhibit metabolic stability to peptidases and excellent cellular permeability.Pharmaceutical research · 1999Article
- Acyloxyalkoxy-based cyclic prodrugs of opioid peptides: evaluation of the chemical and enzymatic stability as well as their transport properties across Caco-2 cell monolayers.Pharmaceutical research · 1999Article
- Permeation of unfolded basic fibroblast growth factor (bFGF) across rabbit buccal mucosa--does unfolding of bFGF enhance transport?Pharmaceutical research · 1998Article
- The effect of beta-turn structure on the permeation of peptides across monolayers of bovine brain microvessel endothelial cells.Pharmaceutical research · 1997Article
- The effect of beta-turn structure on the passive diffusion of peptides across Caco-2 cell monolayers.Pharmaceutical research · 1997Article
- Prodrug and analog approaches to improving the intestinal absorption of a cyclic peptide, GPIIb/IIIa receptor antagonist.Pharmaceutical research · 1997Article
- Effect of restricted conformational flexibility on the permeation of model hexapeptides across Caco-2 cell monolayers.Pharmaceutical research · 1997Article
- Esterase-sensitive cyclic prodrugs of peptides: evaluation of a phenylpropionic acid promoiety in a model hexapeptide.Pharmaceutical research · 1997Article
- Esterase-sensitive cyclic prodrugs of peptides: evaluation of an acyloxyalkoxy promoiety in a model hexapeptide.Pharmaceutical research · 1996Article
Corrections and comments
PubMed lists nothing against this paper. Absence here is not a guarantee, only a check that was made.
Authors and funding
6 authors.
Funding
Abstract
purposeTo determine the different conformations of the acyloxyalkoxy-linked cyclic prodrug 1 of the model hexapeptide 2 in solution and to investigate the relationship between these solution conformations and the cellular permeability characteristics of this prodrug.
methodsTwo-dimensional Homonuclear Hartmann-Hahn spectroscopy, Rotating-Frame Overhouser effect spectroscopy, circular dichroism and molecular dynamics simulations were used to find the solution conformers of cyclic prodrug 1.
resultsOur spectroscopic findings suggest that cyclic prodrug 1 exhibits a major and a minor conformer in solution. The major conformer appears to have a well-defined secondary structure, which involves a beta-turn and 4-->1 intramolecular hydrogen bond, creating a compact structure with a reduced average hydrodynamic radius compared to the model hexapeptide 2.
conclusionsThe increased ability of cyclic prodrug 1 to permeate membranes compared to the model hexapeptide 2 could be due to reduction in the average hydrodynamic radius of the molecule facilitating paracellular flux and/or the reduction in the hydrogen bonding potential facilitating transcellular flux.
Indexed as
Identifiers
8956330What OpenQuestion holds
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.