4.6 Article

Methyl to trifluoromethyl substitution as a strategy to increase the membrane permeability of short peptides

Related references

Note: Only part of the references are listed.
Review Biochemistry & Molecular Biology

Fluorinated peptide biomaterials

Janna N. Sloand et al.

Summary: Fluorinated compounds are gaining importance in biomedical research, especially in peptide/protein engineering. Strategies utilizing the fluorous effect to direct peptide assembly can lead to the creation of bioactive materials for applications ranging from drug delivery to antibacterial coatings.

PEPTIDE SCIENCE (2021)

Article Chemistry, Multidisciplinary

Connecting Hydrophobic Surfaces in Cyclic Peptides Increases Membrane Permeability

Huy N. Hoang et al.

Summary: Research has shown that a single methyl group only increases membrane permeability when it connects or expands hydrophobic surface patches. Positional isomers with the same characteristics can have different permeabilities based on the size of the largest continuous hydrophobic surface patch, illuminating a key local molecular determinant of membrane permeability.

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION (2021)

Article Nanoscience & Nanotechnology

In Vivo Tracking of Fluorinated Polypeptide Gene Carriers by Positron Emission Tomography Imaging

Xinyu Wang et al.

ACS APPLIED MATERIALS & INTERFACES (2020)

Article Chemistry, Medicinal

N-Trifluoromethyl Amines and Azoles: An Underexplored Functional Group in the Medicinal Chemist's Toolbox

Stefan Schiesser et al.

JOURNAL OF MEDICINAL CHEMISTRY (2020)

Review Chemistry, Multidisciplinary

Macrocyclic Peptides as Drug Candidates: Recent Progress and Remaining Challenges

Alexander A. Vinogradov et al.

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY (2019)

Review Chemistry, Multidisciplinary

Approaches to Obtaining Fluorinated α-Amino Acids

Johann Moschner et al.

CHEMICAL REVIEWS (2019)

Article Chemistry, Multidisciplinary

Overcoming the Lack of Oral Availability of Cyclic Hexapeptides: Design of a Selective and Orally Available Ligand for the Integrin αvβ3

Michael Weinmueller et al.

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION (2017)

Article Chemistry, Medicinal

Applications of Fluorine in Medicinal Chemistry

Eric P. Gillis et al.

JOURNAL OF MEDICINAL CHEMISTRY (2015)

Article Chemistry, Organic

Fluorous Peptide Nucleic Acids: PNA Analogues with Fluorine in Backbone (γ-CF2-apg-PNA) Enhance Cellular Uptake

Satheesh Ellipilli et al.

JOURNAL OF ORGANIC CHEMISTRY (2015)

Article Multidisciplinary Sciences

Rational design and synthesis of an orally bioavailable peptide guided by NMR amide temperature coefficients

Conan K. Wang et al.

PROCEEDINGS OF THE NATIONAL ACADEMY OF SCIENCES OF THE UNITED STATES OF AMERICA (2014)

Article Chemistry, Inorganic & Nuclear

On the polarity of partially fluorinated methyl groups

Quentin A. Huchet et al.

JOURNAL OF FLUORINE CHEMISTRY (2013)

Article Chemistry, Multidisciplinary

Intestinal Permeability of Cyclic Peptides: Common Key Backbone Motifs Identified

Johannes G. Beck et al.

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY (2012)

Article Biochemistry & Molecular Biology

On-resin N-methylation of cyclic peptides for discovery of orally bioavailable scaffolds

Tina R. White et al.

NATURE CHEMICAL BIOLOGY (2011)

Article Chemistry, Physical

Fluorine in Protein Environments: A QM and MD Study

Sergey A. Samsonov et al.

JOURNAL OF PHYSICAL CHEMISTRY B (2009)

Article Chemistry, Multidisciplinary

Improving oral bioavailability of peptides by multiple N-methylation: Somatostatin analogues

Eric Biron et al.

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION (2008)

Review Chemistry, Multidisciplinary

Fluorine in medicinal chemistry

Sophie Purser et al.

CHEMICAL SOCIETY REVIEWS (2008)

Editorial Material Chemistry, Medicinal

The many roles for fluorine in medicinal chemistry

William K. Hagmann

JOURNAL OF MEDICINAL CHEMISTRY (2008)

Review Biochemistry & Molecular Biology

Synthesis of fluorinated amino acids

A Sutherland et al.

NATURAL PRODUCT REPORTS (2000)