Synthesis and Stereochemical Assignment of Conioidine A: DNA- and HSA-Binding Studies of the Four Diastereomers
| Autor: | Ryan Shaktah, Lawrence A. Shaktah, Dupre Orr, Laura Vardanyan, Alexis Aleman, Thomas G. Minehan, Elroma David, Daniel Tamae |
|---|---|
| Rok vydání: | 2020 |
| Předmět: |
Pyrrolidines
Proline Stereochemistry Pharmaceutical Science Serum Albumin Human Calorimetry Binding Competitive Solanaceous Alkaloids Fluorescence spectroscopy Analytical Chemistry chemistry.chemical_compound Ethidium Drug Discovery medicine A-DNA Pharmacology Binding Sites Molecular Structure Circular Dichroism Organic Chemistry Diastereomer Absolute configuration Netropsin Stereoisomerism Isothermal titration calorimetry DNA Human serum albumin Molecular Docking Simulation Spectrometry Fluorescence Complementary and alternative medicine chemistry Molecular Medicine medicine.drug |
| Zdroj: | Journal of Natural Products. 83:3191-3198 |
| ISSN: | 1520-6025 0163-3864 |
| Popis: | Conioidine A (1), isolated in 1993 with unknown relative and absolute configuration, was suggested to be a DNA-binding compound by an indirect technique. Four stereoisomers of conioidine A have been synthesized from d- and l-proline, and the natural product has been identified as possessing (4R,6R) absolute configuration. Binding of the conioidine diastereomers to calf thymus DNA (CT DNA) and human serum albumin (HSA) has been investigated by fluorescence spectroscopy and isothermal titration calorimetry (ITC). All stereoisomers display at least an order of magnitude weaker binding to DNA than the control compound netropsin; however, a strong association with HSA was observed for the (4R,6S) stereoisomer. |
| Databáze: | OpenAIRE |
| Externí odkaz: |
|