Modulation of the Passive Permeability of Semipeptidic Macrocycles: N- and C-Methylations Fine-Tune Conformation and Properties
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Title
Modulation of the Passive Permeability of Semipeptidic Macrocycles: N- and C-Methylations Fine-Tune Conformation and Properties
Authors
Keywords
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Journal
JOURNAL OF MEDICINAL CHEMISTRY
Volume 64, Issue 9, Pages 5365-5383
Publisher
American Chemical Society (ACS)
Online
2021-03-23
DOI
10.1021/acs.jmedchem.0c02036
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Note: Only part of the references are listed.- Volume-scaled common nearest neighbor clustering algorithm with free-energy hierarchy
- (2021) R. Gregor Weiß et al. JOURNAL OF CHEMICAL PHYSICS
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- (2020) Emma Danelius et al. CHEMISTRY-A EUROPEAN JOURNAL
- SciPy 1.0: fundamental algorithms for scientific computing in Python
- (2020) Pauli Virtanen et al. NATURE METHODS
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- (2020) Antoine Le Roux et al. JOURNAL OF MEDICINAL CHEMISTRY
- Toward the elucidation of the mechanism for passive membrane permeability of cyclic peptides
- (2019) Sereina Riniker Future Medicinal Chemistry
- Free Ligand 1D NMR Conformational Signatures to Enhance Structure Based Drug Design of a Mcl-1 inhibitor (AZD5991) and other Synthetic Macrocycles
- (2019) Amber Y S Balazs et al. JOURNAL OF MEDICINAL CHEMISTRY
- Conformational Control of Macrocycles by Remote Structural Modification
- (2019) Solomon D. Appavoo et al. CHEMICAL REVIEWS
- Getting in: emerging methods and design principles for cell-penetrant peptides
- (2018) Leila Peraro et al. ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
- Improving oral bioavailability of cyclic peptides by N -methylation
- (2018) Andreas F.B. Räder et al. BIOORGANIC & MEDICINAL CHEMISTRY
- Impact of Dynamically Exposed Polarity on Permeability and Solubility of Chameleonic Drugs Beyond the Rule of 5
- (2018) Matteo Rossi Sebastiano et al. JOURNAL OF MEDICINAL CHEMISTRY
- Natural Cyclic Peptides as an Attractive Modality for Therapeutics: A Mini Review
- (2018) Muna Abdalla et al. MOLECULES
- Toward the Design of Molecular Chameleons: Flexible Shielding of an Amide Bond Enhances Macrocycle Cell Permeability
- (2018) Mohit Tyagi et al. ORGANIC LETTERS
- Rationalization of the Membrane Permeability Differences in a Series of Analogue Cyclic Decapeptides
- (2018) Jagna Witek et al. Journal of Chemical Information and Modeling
- Modulation of Oral Bioavailability and Metabolism for Closely Related Cyclic Hexapeptides
- (2017) Thomas Vorherr et al. International Journal of Peptide Research and Therapeutics
- Quantifying the chameleonic properties of macrocycles and other high-molecular-weight drugs
- (2016) Adrian Whitty et al. DRUG DISCOVERY TODAY
- Structural and conformational determinants of macrocycle cell permeability
- (2016) Björn Over et al. Nature Chemical Biology
- Small molecules, big targets: drug discovery faces the protein–protein interaction challenge
- (2016) Duncan E. Scott et al. NATURE REVIEWS DRUG DISCOVERY
- Systematic Targeting of Protein–Protein Interactions
- (2016) Ashley E. Modell et al. TRENDS IN PHARMACOLOGICAL SCIENCES
- MDTraj: A Modern Open Library for the Analysis of Molecular Dynamics Trajectories
- (2015) Robert T. McGibbon et al. BIOPHYSICAL JOURNAL
- Peptide therapeutics: current status and future directions
- (2015) Keld Fosgerau et al. DRUG DISCOVERY TODAY
- PyEMMA 2: A Software Package for Estimation, Validation, and Analysis of Markov Models
- (2015) Martin K. Scherer et al. Journal of Chemical Theory and Computation
- Going Out on a Limb: Delineating The Effects of β-Branching, N-Methylation, and Side Chain Size on the Passive Permeability, Solubility, and Flexibility of Sanguinamide A Analogues
- (2015) Andrew T. Bockus et al. JOURNAL OF MEDICINAL CHEMISTRY
- Effects of Thionation and Fluorination on Cis–Trans Isomerization in Tertiary Amides: An Investigation of N-Alkylglycine (Peptoid) Rotamers
- (2015) Jens Engel-Andreasen et al. JOURNAL OF ORGANIC CHEMISTRY
- Cell-Permeable Cyclic Peptides from Synthetic Libraries Inspired by Natural Products
- (2015) William M. Hewitt et al. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY
- Peptide to Peptoid Substitutions Increase Cell Permeability in Cyclic Hexapeptides
- (2015) Joshua Schwochert et al. ORGANIC LETTERS
- Improving on Nature: Making a Cyclic Heptapeptide Orally Bioavailable
- (2014) Daniel S. Nielsen et al. ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
- Rational design and synthesis of an orally bioavailable peptide guided by NMR amide temperature coefficients
- (2014) Conan K. Wang et al. PROCEEDINGS OF THE NATIONAL ACADEMY OF SCIENCES OF THE UNITED STATES OF AMERICA
- Macrocyclic Drugs and Clinical Candidates: What Can Medicinal Chemists Learn from Their Properties?
- (2013) Fabrizio Giordanetto et al. JOURNAL OF MEDICINAL CHEMISTRY
- Cis–Trans Amide Bond Rotamers in β-Peptoids and Peptoids: Evaluation of Stereoelectronic Effects in Backbone and Side Chains
- (2013) Jonas S. Laursen et al. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY
- Macrocycles in new drug discovery
- (2012) Jamie Mallinson et al. Future Medicinal Chemistry
- Conformer Generation with OMEGA: Learning from the Data Set and the Analysis of Failures
- (2012) Paul C. D. Hawkins et al. Journal of Chemical Information and Modeling
- Intestinal Permeability of Cyclic Peptides: Common Key Backbone Motifs Identified
- (2012) Johannes G. Beck et al. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY
- Architecture, implementation and parallelisation of the GROMOS software for biomolecular simulation
- (2011) Nathan Schmid et al. COMPUTER PHYSICS COMMUNICATIONS
- Definition and testing of the GROMOS force-field versions 54A7 and 54B7
- (2011) Nathan Schmid et al. EUROPEAN BIOPHYSICS JOURNAL WITH BIOPHYSICS LETTERS
- GROMOS++ Software for the Analysis of Biomolecular Simulation Trajectories
- (2011) Andreas P. Eichenberger et al. Journal of Chemical Theory and Computation
- Optimization of the Potency and Pharmacokinetic Properties of a Macrocyclic Ghrelin Receptor Agonist (Part I): Development of Ulimorelin (TZP-101) from Hit to Clinic
- (2011) Hamid R. Hoveyda et al. JOURNAL OF MEDICINAL CHEMISTRY
- Macrocycles Are Great Cycles: Applications, Opportunities, and Challenges of Synthetic Macrocycles in Drug Discovery
- (2011) Eric Marsault et al. JOURNAL OF MEDICINAL CHEMISTRY
- On-resin N-methylation of cyclic peptides for discovery of orally bioavailable scaffolds
- (2011) Tina R White et al. Nature Chemical Biology
- Intramolecular hydrogen bonding to improve membrane permeability and absorption in beyond rule of five chemical space
- (2011) Alexander Alex et al. MedChemComm
- Conformer Generation with OMEGA: Algorithm and Validation Using High Quality Structures from the Protein Databank and Cambridge Structural Database
- (2010) Paul C. D. Hawkins et al. Journal of Chemical Information and Modeling
- Comparing geometric and kinetic cluster algorithms for molecular simulation data
- (2010) Bettina Keller et al. JOURNAL OF CHEMICAL PHYSICS
- Solid-Phase Synthesis of N-Substituted Glycine Oligomers (α‑Peptoids) and Derivatives
- (2010) Adrian S. Culf et al. MOLECULES
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- (2008) Eric Biron et al. ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
- EASY ROESY: Reliable Cross-Peak Integration in Adiabatic Symmetrized ROESY
- (2008) Christina M. Thiele et al. CHEMISTRY-A EUROPEAN JOURNAL
- The exploration of macrocycles for drug discovery — an underexploited structural class
- (2008) Edward M. Driggers et al. NATURE REVIEWS DRUG DISCOVERY
- Protein–protein interaction and quaternary structure
- (2008) Joël Janin et al. QUARTERLY REVIEWS OF BIOPHYSICS
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