» Articles » PMID: 21391687

Design, Synthesis, and Evaluation of Coumarin-based Molecular Probes for Imaging of Myelination

Overview
Journal J Med Chem
Specialty Chemistry
Date 2011 Mar 12
PMID 21391687
Citations 17
Authors
Affiliations
Soon will be listed here.
Abstract

Myelination represents one of the most fundamental biological processes in the vertebrate nervous system. Abnormalities and changes in myelination in the central nervous system (CNS) are seen in many neurodegenerative disorders, such as multiple sclerosis (MS). A long-standing goal has been to directly detect and quantify myelin content in order to facilitate diagnosis and therapeutic treatments of myelin-related diseases. In the course of our studies, we have developed a series of small-molecule probes (SMP) as myelin-imaging agents. Among them are coumarin derivatives, which exhibit promising brain permeability and myelin-binding properties. Herein we report a full account of the design and synthesis of coumarin-based SMPs as myelin-imaging agents. Systematic evaluation of these SMPs in both the CNS and peripheral nervous system (PNS) allowed us to identify some lead agents for potential use as fluorescent dyes for intraoperative nerve mapping in surgical operations or as radiotracers for positron emission tomography (PET) imaging of myelination.

Citing Articles

Shining a Light on Venom-Peptide Receptors: Venom Peptides as Targeted Agents for In Vivo Molecular Imaging.

Chow C, King G Toxins (Basel). 2024; 16(7).

PMID: 39057947 PMC: 11281729. DOI: 10.3390/toxins16070307.


Synthesis, DFT studies on a series of tunable quinoline derivatives.

Chavan N, Vijayakumar V RSC Adv. 2024; 14(29):21089-21101.

PMID: 38966815 PMC: 11223029. DOI: 10.1039/d4ra03961k.


Advances in optical molecular imaging for neural visualization.

Wei J, Liu C, Liang W, Yang X, Han S Front Bioeng Biotechnol. 2023; 11:1250594.

PMID: 37671191 PMC: 10475611. DOI: 10.3389/fbioe.2023.1250594.


3-Phenylcoumarins as a Privileged Scaffold in Medicinal Chemistry: The Landmarks of the Past Decade.

Matos M, Uriarte E, Santana L Molecules. 2021; 26(21).

PMID: 34771164 PMC: 8587835. DOI: 10.3390/molecules26216755.


Positron emission tomography in multiple sclerosis - straight to the target.

Bodini B, Tonietto M, Airas L, Stankoff B Nat Rev Neurol. 2021; 17(11):663-675.

PMID: 34545219 DOI: 10.1038/s41582-021-00537-1.


References
1.
Wu C, Wei J, Tian D, Feng Y, Miller R, Wang Y . Molecular probes for imaging myelinated white matter in CNS. J Med Chem. 2008; 51(21):6682-8. PMC: 2717170. DOI: 10.1021/jm8003637. View

2.
Franklin R, Hinks G . Understanding CNS remyelination: clues from developmental and regeneration biology. J Neurosci Res. 1999; 58(2):207-13. View

3.
Wang C, Wu C, Popescu D, Zhu J, Macklin W, Miller R . Longitudinal near-infrared imaging of myelination. J Neurosci. 2011; 31(7):2382-90. PMC: 3044505. DOI: 10.1523/JNEUROSCI.2698-10.2011. View

4.
Mozafari S, Sherafat M, Javan M, Mirnajafi-Zadeh J, Tiraihi T . Visual evoked potentials and MBP gene expression imply endogenous myelin repair in adult rat optic nerve and chiasm following local lysolecithin induced demyelination. Brain Res. 2010; 1351:50-56. DOI: 10.1016/j.brainres.2010.07.026. View

5.
Wu C, Tian D, Feng Y, Polak P, Wei J, Sharp A . A novel fluorescent probe that is brain permeable and selectively binds to myelin. J Histochem Cytochem. 2006; 54(9):997-1004. PMC: 3150784. DOI: 10.1369/jhc.5A6901.2006. View