AI Article Synopsis
- Alexidine is commonly used as an oral and contact lens disinfectant and is a mixture of stereoisomers, with potential for higher biological activity from its individual chiral forms.
- A synthetic method for isolating the enantiomers of alexidine is highlighted as desirable due to the chiral nature of its biological targets.
- The study reports the first successful synthesis of both enantiomers in high purity and tests their effectiveness in disrupting the interaction between anti-apoptotic protein Bcl-xL and pro-apoptotic protein Bak.
Article Abstract
Alexidine is in everyday human use as oral disinfectant and contact lens disinfectant. It is used as a mixture of stereoisomers. Since all of alexidine's known biological targets are chiral, the biological activity of any of its chiral stereoisomers could be significantly higher than that of the mixture of stereoisomers. This makes a synthetic methodology for obtaining the individual enantiomers of the chiral diastereoisomer highly desirable. Here, we describe the first synthesis of both enantiomers of alexidine in high enantiomeric purity, and demonstrate their activity against the protein-protein interaction between the anti-apoptotic protein Bcl-xL and the pro-apoptotic protein Bak.
Download full-text PDF |
Source |
|---|---|
| http://dx.doi.org/10.1016/j.bmc.2013.09.057 | DOI Listing |
Publication Analysis
Top Keywords
Similar Publications
Recent Advances in Enantiorecognition and Enantioseparation Techniques of Chiral Molecules in the Pharmaceutical Field.
Biomed Chromatogr
February 2025
Department of Pharmaceutical Chemistry and Analysis, ISF College of Pharmacy, Moga, Punjab, India.
Enantioseparation and enantiorecognition are crucial in the pharmaceutical analysis of chiral substances, impacting safety, efficacy, and regulatory compliance. Enantioseparation refers to the process of separating enantiomers from a mixture, typically achieved through chromatography techniques like HPLC and SFC. In contrast, enantiorecognition involves the identification of enantiomers based on their interaction with a chiral selector without the need for separation.
View Article and Find Full Text PDFGoniodomic Acid, a Transient Oxirane Intermediate in the Conversion of the Macrolide Algal Toxin Goniodomin A to Seco Acids.
Chem Res Toxicol
December 2024
Department of Chemistry, Vanderbilt University, Nashville, Tennessee 37235, United States.
The algal macrolide goniodomin A (GDA) undergoes ring-cleavage under unusually mild, alkaline conditions to form mixtures of stereoisomers of seco acids GDA-sa and iso-GDA-sa. In the primary fragmentation pathway, opening of the macrolide ring occurs by displacement of the carboxyl group by a base-catalyzed attack of the C32 hemiketal hydroxy group on C31, yielding an oxirane-carboxylic acid, named goniodomic acid. The oxirane ring is unstable, undergoing solvolytic opening to form mainly GDA-sa.
View Article and Find Full Text PDFDeepNose: An Equivariant Convolutional Neural Network Predictive Of Human Olfactory Percepts.
ArXiv
December 2024
Department of Neuroscience, Cold Spring Harbor Laboratory, Cold Spring Harbor, USA.
The olfactory system employs responses of an ensemble of odorant receptors (ORs) to sense molecules and to generate olfactory percepts. Here we hypothesized that ORs can be viewed as 3D spatial filters that extract molecular features relevant to the olfactory system, similarly to the spatio-temporal filters found in other sensory modalities. To build these filters, we trained a convolutional neural network (CNN) to predict human olfactory percepts obtained from several semantic datasets.
View Article and Find Full Text PDFGeneration and Application of All Possible Conformations of Cyclic Tryptophan within and beyond Post-translational Modification.
J Org Chem
December 2024
Department of Organic and Medicinal Chemistry, Graduate School of Pharmaceutical Sciences, The University of Tokyo, 7-3-1 Hongo, Bunkyo-ku, Tokyo 113-0033, Japan.
Isoprenylation of the indole C3-position of tryptophan accompanied by cyclization (c-Trp) is one of the most attractive post-translational modifications because of C-C bond formation and drastic conformational alteration. As the modification generates two stereoisomers of the 6/5/5-fused ring system and consequently, a mixture of four possible conformations as considered in proline, it is expected to influence the biological activity in quorum sensing pheromone ComX containing the c-Trp residue. In this study, the simultaneous control of the amide equilibrium and pyrrolidine ring puckering was achieved by utilizing an N-carbamoylated and α-methylated 6/5/5-fused ring system.
View Article and Find Full Text PDFEfficient Method of ()-Nicotine Synthesis.
Molecules
December 2024
Faculty of Medicine, The John Paul II Catholic University of Lublin, Konstantynów 1J/4.03, 20-708 Lublin, Poland.
Improved methods for the synthesis of nicotine are of great importance due to the wide range of applications of synthetic nicotine, which is free from contamination with nitrosamines. Herein, we present a four-step chemical synthesis of ()-nicotine, involving the reduction in myosmine, enantiomeric separation of nornicotine, and subsequent methylation of the appropriate enantiomer of nornicotine obtained. The reduction in myosmine was investigated using both electrochemical and chemical approaches, achieving up to 90% yields of pure nornicotine.
View Article and Find Full Text PDFWant AI Summaries of new PubMed Abstracts delivered to your In-box?
Enter search terms and have AI summaries delivered each week - change queries or unsubscribe any time!