Adamantyl-based compounds are used clinically for the treatment of neurological conditions, as anti-viral agents and as agents against type 2 diabetes. The value of the adamantyl group in drug design is multidimensional. The hydrophobic substituent constant for the adamantyl group has been estimated from the calculated partition coefficients (clogP values) of 31 adamantyl-bearing compounds in the clinic or in development as πadamantyl=3.1, which indicates that the logP value of a compound with high water solubility (logP<<0) could be moved with an adamantyl-based modification to a region that is more clinically useful. The steric bulk of the adamantyl group can: (i) restrict or modulate intramolecular reactivity; and (ii) impede the access of hydrolytic enzymes, thereby increasing drug stability and plasma half life. The value of the adamantyl group in drug design has been recognized most recently in the design of agents to treat iron overload disease (in development), malaria (in clinical trials) and type 2 diabetes (in the clinic).
Download full-text PDF |
Source |
|---|---|
| http://dx.doi.org/10.1016/j.ejmech.2011.01.047 | DOI Listing |
Publication Analysis
Top Keywords
Similar Publications
Fluorescence enhancement of cyanine/hemicyanine dyes with adamantane as an auxochrome through host-guest inclusion with methylated cyclodextrin in water.
Spectrochim Acta A Mol Biomol Spectrosc
November 2024
College of Chemistry, Chemical Engineering and Material Science, Soochow University, 199 Ren'Ai Road, Suzhou 215123, China; Jiangsu Key Laboratory of Medical Optics, Suzhou Institute of Biomedical Engineering and Technology, Chinese Academy of Sciences, Suzhou 215163, China. Electronic address:
Fluorescence of cyanine dyes is often quenched in aqueous solution, limiting their application in water or biological system. In this work, a novel strategy of host-guest interaction based on cyanine derivatives containing auxochromes was proposed to enhance fluorescence in aqueous solution and cell imaging. By using the host (methylated β-cyclodextrin, M-β-CD) to inclusion and suppress the TICT effect of the dye, the fluorescence was significantly enhanced at lower host concentration.
View Article and Find Full Text PDFAmide cyclodextrin that recognises monophosphate anions in harmony with water molecules.
Chem Sci
December 2024
Institute of Pure and Applied Sciences, University of Tsukuba 1-1-1 Tennodai Tsukuba Ibaraki 305-8571 Japan
Article Synopsis
- Anion recognition in water is a complex challenge due to competing water molecules, but a new macrocycle has been developed that utilizes multipoint hydrogen bonding.
- The synthesized -methylpyridinium amide β-cyclodextrin derivative selectively encapsulates monophosphate anions while avoiding interactions with other anion types, showcasing its selectivity.
- Experimentation revealed that different monophosphate substituents interact uniquely with the macrocycle, with distinct mechanisms of inclusion driven by factors such as configurational entropy and hydrophobic effects.
Tunable supramolecular self-assemblies based on cyclodextrin polymer as a loading platform for water-soluble drugs.
Carbohydr Polym
January 2025
Ministry of Education (MOE) Key Laboratory of Macromolecular Synthesis and Functionalization Department of Polymer Science and Engineering, Zhejiang University, Hangzhou 310058, China. Electronic address:
Drug loading capacity is a crucial character of nano-scaled drug carriers to achieve high quality pharmaceutical preparations. However, efficient encapsulation of water-soluble small molecular drugs still faces large obstacles in many cases. Herein, we designed a novel supramolecular delivery system constructed by poly(β-cyclodextrin) containing benzoic acid groups (PCD-PA) and adamantyl terminated poly(ethylene glycol) (PEG-AD) to provide multiple intermolecular interactions for competent loading of water-soluble small-molecular drugs.
View Article and Find Full Text PDFBiocompatible Flash Chemiluminescent Assay Enabled by Sterically Hindered Spiro-Strained-Oxetanyl-1,2-Dioxetane.
Chemistry
December 2024
School of Chemistry, Raymond and Beverly Sackler Faculty of Exact Sciences, Tel Aviv University, Tel Aviv, 69978, Israel.
Chemiluminescence is the emission of light that occurs as a result of a chemical reaction. Depending on the rate of chemiexcitation, light emission can occur as a long-lasting, low-intensity, glow-type reaction or a rapid, highly intense flash-type reaction. Assays using a flash-type mode of action provide enhanced detection sensitivity compared to those using a glow-type mode.
View Article and Find Full Text PDFHeteroleptic Triazole-Bisoxazoline Iron Complexes Reveal Lability of the Iron-Carbene Bond Even Within a Chelating Scaffold.
Inorg Chem
September 2024
Department of Chemistry, Biochemistry and pharmaceutical sciences, University of Bern, Bern CH-3012, Switzerland.
N-Heterocyclic carbenes have proven to be excellent ligands for transition metals, with numerous applications in catalysis and beyond. However, they have also displayed lability with first row transition metals, largely due to the hard-soft mismatch of the metal-carbon bond. Chelation is often considered a suitable methodology for supporting the labile M-C bond through the introduction of a strongly coordinating donor site such as hard phenolates.
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!