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Rational Alteration of Pharmacokinetics of Chiral Fluorinated and Deuterated Derivatives of Emixustat for Retinal Therapy

Journal Article · · Journal of Medicinal Chemistry

Research Organization:
Brookhaven National Lab. (BNL), Upton, NY (United States)
Sponsoring Organization:
~OTHER
DOE Contract Number:
SC0012704
OSTI ID:
1817347
Report Number(s):
BNL-222059-2021-JACI
Journal Information:
Journal of Medicinal Chemistry, Vol. 64, Issue 12
Country of Publication:
United States
Language:
English

References (57)

Diseases Caused by Defects in the Visual Cycle: Retinoids as Potential Therapeutic Agents journal February 2007
Shedding new light on the generation of the visual chromophore journal August 2020
The bisretinoids of retinal pigment epithelium journal March 2012
Positively charged retinoids are potent and selective inhibitors of the trans-cis isomerization in the retinoid (visual) cycle journal May 2005
Randomised study evaluating the pharmacodynamics of emixustat hydrochloride in subjects with macular atrophy secondary to Stargardt disease journal November 2020
Effects of emixustat hydrochloride in patients with proliferative diabetic retinopathy: a randomized, placebo-controlled phase 2 study journal August 2020
Pharmacotherapy for metabolic and cellular stress in degenerative retinal diseases journal February 2020
Emixustat Reduces Metabolic Demand of Dark Activity in the Retina journal November 2019
Emixustat Hydrochloride for Geographic Atrophy Secondary to Age-Related Macular Degeneration journal October 2018
Visual Cycle Modulation as an Approach toward Preservation of Retinal Integrity journal May 2015
Phase ii, Randomized, Placebo-Controlled, 90-Day Study of Emixustat Hydrochloride in Geographic Atrophy Associated with dry Age-Related Macular Degeneration journal January 2015
Phase 1, Dose-Ranging Study of Emixustat Hydrochloride (Acu-4429), a Novel Visual Cycle Modulator, in Healthy Volunteers journal January 2014
Oxidative Deamination of Emixustat by Human Vascular Adhesion Protein-1/Semicarbazide-Sensitive Amine Oxidase journal February 2019
Validation and reproducibility of an LC–MS/MS method for emixustat and its three deaminated metabolites in human plasma journal November 2018
Disposition, profiling and identification of emixustat and its metabolites in humans journal July 2017
Bioanalysis of emixustat (ACU-4429) in whole blood collected with volumetric absorptive microsampling by LC–MS/MS journal September 2015
Molecular pharmacodynamics of emixustat in protection against retinal degeneration journal June 2015
Primary amines protect against retinal degeneration in mouse models of retinopathies journal December 2011
Fluorine in Pharmaceuticals: Looking Beyond Intuition journal September 2007
Applications of Fluorine in Medicinal Chemistry journal July 2015
Using Deuterium in Drug Discovery: Leaving the Label in the Drug journal December 2013
The first example of a crystallization-induced asymmetric transformation (CIAT) in the Mannich reaction journal January 2010
Stereoselective Synthesis of syn-γ-Hydroxynorvaline and Related α-Amino Acids journal October 2019
Stereoselective Mannich Reaction Driven by Crystallization journal September 2020
Efficient large scale microwave assisted Mannich reactions using substituted acetophenones journal January 2003
Asymmetric Hydrogenation of β-Secondary Amino Ketones Catalyzed by a Ruthenocenyl Phosphino-oxazoline-ruthenium Complex (RuPHOX-Ru): the Synthesis of γ-Secondary Amino Alcohols journal October 2015
New Synthesis of Chiral 1,3-Oxazinan-2-ones from Carbohydrate Derivatives journal January 2005
Asymmetric total synthesis of sperabillins B and D via lithium amide conjugate addition journal January 2004
Catalytic mechanism of a retinoid isomerase essential for vertebrate vision journal April 2015
Rational Tuning of Visual Cycle Modulator Pharmacodynamics journal May 2017
Three types of stereospecificity and the kinetic deuterium isotope effect in the oxidative deamination of dopamine as catalyzed by different amine oxidases journal August 1988
Sponge Transgenic Mouse Model Reveals Important Roles for the MicroRNA-183 (miR-183)/96/182 Cluster in Postmitotic Photoreceptors of the Retina journal September 2011
Structure of RPE65 isomerase in a lipidic matrix reveals roles for phospholipids and iron in catalysis journal September 2012
Importance of Membrane Structural Integrity for RPE65 Retinoid Isomerization Activity journal January 2010
The Structure of a Retinal-Forming Carotenoid Oxygenase journal April 2005
Cl-π interactions in protein-ligand complexes journal July 2008
An evaluation of substituent effects on aromatic edge-to-face interactions and CF–π versus CH–π interactions using an imino torsion balance model journal January 2013
Stabilizing Fluorine–π Interactions journal May 2017
An efficient and near linear scaling pair natural orbital based local coupled cluster method journal January 2013
Natural triple excitations in local coupled cluster calculations with pair natural orbitals journal October 2013
Decomposition of Intermolecular Interaction Energies within the Local Pair Natural Orbital Coupled Cluster Framework journal September 2016
Revealing Noncovalent Interactions journal May 2010
Natural orbitals for chemical valence as descriptors of chemical bonding in transition metal complexes journal September 2006
Long-Range Corrected Hybrid Density Functionals with Improved Dispersion Corrections journal November 2012
Effect of the damping function in dispersion corrected density functional theory journal March 2011
The role of amine oxidases in xenobiotic metabolism journal July 2006
Biotransformation of xenobiotics by amine oxidases journal April 2001
Reaction of Vascular Adhesion Protein-1 (VAP-1) with Primary Amines journal August 2011
Multiple Isotope Effects on Enzyme-Catalyzed Reactions journal June 1989
The Expression of Isotope Effects on Enzyme-Catalyzed Reactions journal June 1981
The Use of Isotope Effects to Elucidate Enzyme Mechanisms journal December 1981
An Expedient Synthesis of CMF-019: (S)-5-Methyl-3-{1-(pentan-3-yl)-2- (thiophen-2-ylmethyl)-1H-benzo[d]imidazole-5-carboxamido}hexanoic Acid, a Potent Apelin Receptor (APJ) Agonist journal October 2018
Integration, scaling, space-group assignment and post-refinement journal January 2010
REFMAC 5 for the refinement of macromolecular crystal structures journal March 2011
Features and development of Coot journal March 2010
MolProbity: More and better reference data for improved all-atom structure validation: PROTEIN SCIENCE.ORG journal November 2017
A New Generation of Crystallographic Validation Tools for the Protein Data Bank journal October 2011