Cyclosporin Structure and Permeability: From A to Z and Beyond

Interplay among Conformation, Intramolecular Hydrogen Bonds, and Chameleonicity in the Membrane Permeability and Cyclophilin A Binding of Macrocyclic Peptide Cyclosporin O Derivatives

(2021) Dongjae Lee et al.   JOURNAL OF MEDICINAL CHEMISTRY

Improving Membrane Permeation in the Beyond Rule-of-Five Space by Using Prodrugs to Mask Hydrogen Bond Donors

(2020) Nicholas Barlow et al.   ACS Chemical Biology

Drug‐like properties in macrocycles above MW 1000: Backbone rigidity vs. side‐chain lipophilicity

(2020) Akihiro Furukawa et al.   ANGEWANDTE CHEMIE-INTERNATIONAL EDITION

Comparison of cyclosporin variants B–E based on their structural properties and activity in mitochondrial membranes

(2020) S.V. Efimov et al.   BIOCHEMICAL AND BIOPHYSICAL RESEARCH COMMUNICATIONS

Gradient selected pure shift EASY-ROESY techniques facilitate the quantitative measurement of 1H,1H-distance restraints in congested spectral regions

(2020) Julian Ilgen et al.   JOURNAL OF MAGNETIC RESONANCE

Applications of Molecular Dynamics Simulation in Structure Prediction of Peptides and Proteins

(2019) Hao Geng et al.   Computational and Structural Biotechnology Journal

Conformational Flexibility Is a Determinant of Permeability for Cyclosporin

(2018) Conan K. Wang et al.   JOURNAL OF PHYSICAL CHEMISTRY B

Synthesis and biochemical evaluation of two novel N-hydroxyalkylated cyclosporin A analogs

(2018) Viktoria Kahlert et al.   ORGANIC & BIOMOLECULAR CHEMISTRY

Using 1H and 13C NMR chemical shifts to determine cyclic peptide conformations: a combined molecular dynamics and quantum mechanics approach

(2018) Q. Nhu N. Nguyen et al.   PHYSICAL CHEMISTRY CHEMICAL PHYSICS

Lipophilic Permeability Efficiency Reconciles the Opposing Roles of Lipophilicity in Membrane Permeability and Aqueous Solubility

(2018) Matthew R. Naylor et al.   JOURNAL OF MEDICINAL CHEMISTRY

Beyond the Rule of 5: Lessons Learned from AbbVie’s Drugs and Compound Collection

(2017) David A. DeGoey et al.   JOURNAL OF MEDICINAL CHEMISTRY

Structural Diversity and Biological Activities of Fungal Cyclic Peptides, Excluding Cyclodipeptides

(2017) Xiaohan Wang et al.   MOLECULES

Toward accurately modeling N-methylated cyclic peptides

(2017) Diana P. Slough et al.   PHYSICAL CHEMISTRY CHEMICAL PHYSICS

Diffusion of the small, very polar, drug piracetam through a lipid bilayer: an MD simulation study

(2017) Rui P. Ribeiro et al.   THEORETICAL CHEMISTRY ACCOUNTS

Cell permeability beyond the rule of 5

(2016) Pär Matsson et al.   ADVANCED DRUG DELIVERY REVIEWS

Quantifying the chameleonic properties of macrocycles and other high-molecular-weight drugs

(2016) Adrian Whitty et al.   DRUG DISCOVERY TODAY

Kinetic Models of Cyclosporin A in Polar and Apolar Environments Reveal Multiple Congruent Conformational States

(2016) Jagna Witek et al.   Journal of Chemical Information and Modeling

Accurate Structure Prediction and Conformational Analysis of Cyclic Peptides with Residue-Specific Force Fields

(2016) Hao Geng et al.   Journal of Physical Chemistry Letters

Hofmeister Ion-Induced Changes in Water Structure Correlate with Changes in Solvation of an Aggregated Protein Complex

(2016) Taylor P. Light et al.   LANGMUIR

Differential Effects of Cyclosporin A and Tacrolimus on Magnesium Influx in Caco2 Cells

(2016) Elodie Gouadon et al.   JOURNAL OF PHARMACY AND PHARMACEUTICAL SCIENCES

Conformational Heterogeneity of Cyclosporin A in Cyclophilin 18 Binding

(2016) Weilin Lin et al.   PLoS One

Beyond cyclosporine A: conformation-dependent passive membrane permeabilities of cyclic peptide natural products

(2015) Christopher L Ahlbach et al.   Future Medicinal Chemistry

Sub-terahertz spectroscopy reveals that proteins influence the properties of water at greater distances than previously detected

(2015) Oleksandr Sushko et al.   JOURNAL OF CHEMICAL PHYSICS

Cell-Permeable Cyclic Peptides from Synthetic Libraries Inspired by Natural Products

(2015) William M. Hewitt et al.   JOURNAL OF THE AMERICAN CHEMICAL SOCIETY

Toward Oral Delivery of Biopharmaceuticals: An Assessment of the Gastrointestinal Stability of 17 Peptide Drugs

(2015) Jie Wang et al.   MOLECULAR PHARMACEUTICS

Detection of conformation types of cyclosporin retaining intramolecular hydrogen bonds by mass spectrometry

(2014) Suk-Joon Hyung et al.   ANALYTICAL AND BIOANALYTICAL CHEMISTRY

Observation of Conformational Exchange in Cyclosporin in Media of Varying Polarity by NMR Spectroscopy

(2014) Sergey Efimov et al.   APPLIED MAGNETIC RESONANCE

Oral Druggable Space beyond the Rule of 5: Insights from Drugs and Clinical Candidates

(2014) Bradley Croy Doak et al.   CHEMISTRY & BIOLOGY

From Chemical Tools to Clinical Medicines: Nonimmunosuppressive Cyclophilin Inhibitors Derived from the Cyclosporin and Sanglifehrin Scaffolds

(2014) Zachary K. Sweeney et al.   JOURNAL OF MEDICINAL CHEMISTRY

Disordered Structural Ensembles of Vasopressin and Oxytocin and Their Mutants

(2014) Eugene Yedvabny et al.   JOURNAL OF PHYSICAL CHEMISTRY B

The Adaptive Biasing Force Method: Everything You Always Wanted To Know but Were Afraid To Ask

(2014) Jeffrey Comer et al.   JOURNAL OF PHYSICAL CHEMISTRY B

Anti-inflammatory Effects of Extracellular Cyclosporins Are Exclusively Mediated by CD147

(2013) Miroslav Malesevic et al.   JOURNAL OF MEDICINAL CHEMISTRY

Getting in Shape: Controlling Peptide Bioactivity and Bioavailability Using Conformational Constraints

(2012) Jonathan E. Bock et al.   ACS Chemical Biology

Practically Efficient and Robust Free Energy Calculations: Double-Integration Orthogonal Space Tempering

(2012) Lianqing Zheng et al.   Journal of Chemical Theory and Computation

Spatial structure of cyclosporin A and insight into its flexibility

(2012) S.V. Efimov et al.   JOURNAL OF MOLECULAR STRUCTURE

Cyclosporine metabolic side effects: association with the WNK4 system

(2011) Semyon Melnikov et al.   EUROPEAN JOURNAL OF CLINICAL INVESTIGATION

Intramolecular hydrogen bonding to improve membrane permeability and absorption in beyond rule of five chemical space

(2011) Alexander Alex et al.   MedChemComm

Umbrella sampling

(2011) Johannes Kästner   Wiley Interdisciplinary Reviews-Computational Molecular Science

Metadynamics

(2011) Alessandro Barducci et al.   Wiley Interdisciplinary Reviews-Computational Molecular Science

Crystallization of cyclosporin A in lyotropic reverse hexagonal liquid crystals

(2010) Dima Libster et al.   CRYSTENGCOMM

The Neutron Structure of the Formyl Peptide Receptor Antagonist Cyclosporin H (CsH) Unambiguously Determines the Solvent and Hydrogen-Bonding Structure for Crystal Form II

(2010) Anna S. Gardberg et al.   JOURNAL OF CHEMICAL CRYSTALLOGRAPHY

A Cell-Impermeable Cyclosporine A Derivative Reduces Pathology in a Mouse Model of Allergic Lung Inflammation

(2010) M. A. Balsley et al.   JOURNAL OF IMMUNOLOGY

A Cyclosporin Derivative Discriminates between Extracellular and Intracellular Cyclophilins

(2009) Miroslav Malešević et al.   ANGEWANDTE CHEMIE-INTERNATIONAL EDITION

Collective Dynamics of Protein Hydration Water by Brillouin Neutron Spectroscopy

(2009) Andrea Orecchini et al.   JOURNAL OF THE AMERICAN CHEMICAL SOCIETY

The role of dynamic conformational ensembles in biomolecular recognition

(2009) David D Boehr et al.   Nature Chemical Biology

Random walk in orthogonal space to achieve efficient free-energy simulation of complex systems

(2008) L. Zheng et al.   PROCEEDINGS OF THE NATIONAL ACADEMY OF SCIENCES OF THE UNITED STATES OF AMERICA

Selected-fit versus induced-fit protein binding: Kinetic differences and mutational analysis

(2008) Thomas R. Weikl et al.   PROTEINS-STRUCTURE FUNCTION AND BIOINFORMATICS

Solution Structures of Cyclosporin A and Its Complex with Dysprosium(III) in SDS Micelles:  NMR and Molecular Dynamics Studies

(2007) Francesca Bernardi et al.   JOURNAL OF PHYSICAL CHEMISTRY B