Dextran-conjugated tetrathiatriarylmethyl radicals as biocompatible spin probes for EPR spectroscopy and imaging.
Electron paramagnetic resonance
Spin probes
Trityl radicals
Journal
Bioorganic & medicinal chemistry letters
ISSN: 1464-3405
Titre abrégé: Bioorg Med Chem Lett
Pays: England
ID NLM: 9107377
Informations de publication
Date de publication:
15 07 2019
15 07 2019
Historique:
received:
19
04
2019
revised:
08
05
2019
accepted:
11
05
2019
pubmed:
28
5
2019
medline:
10
9
2020
entrez:
27
5
2019
Statut:
ppublish
Résumé
Tetrathiatriarylmethyl (TAM) radicals represent soluble paramagnetic probes for biomedical electron paramagnetic resonance (EPR)-based spectroscopy and imaging. There is an increasing demand in the development of multifunctional, biocompatible and targeted trityl probes hampered by the difficulties in derivatization of the TAM structure. We proposed a new straightforward synthetic strategy using click chemistry for the covalent conjugation of the TAM radical with a water-soluble biocompatible carrier exemplified here by dextran. A set of dextran-grafted probes varied in the degrees of Finland trityl radical loading and dextran modification by polyethelene glycol has been synthesized. The EPR spectrum of the optimized macromolecular probe exhibits a single narrow line with high sensitivity to oxygen and has advantages over the unbound Finland trityl of being insensitive to interactions with albumin. In vivo EPR imaging of tissue oxygenation performed in breast tumor-bearing mouse using dextran-grafted probe demonstrates its utility for preclinical oximetric applications.
Identifiants
pubmed: 31129052
pii: S0960-894X(19)30314-2
doi: 10.1016/j.bmcl.2019.05.017
pmc: PMC6557268
mid: NIHMS1033590
pii:
doi:
Substances chimiques
Dextrans
0
Trityl Compounds
0
Types de publication
Journal Article
Research Support, N.I.H., Extramural
Langues
eng
Sous-ensembles de citation
IM
Pagination
1756-1760Subventions
Organisme : NCI NIH HHS
ID : R01 CA194013
Pays : United States
Organisme : NIBIB NIH HHS
ID : R00 EB023990
Pays : United States
Organisme : NIBIB NIH HHS
ID : K99 EB023990
Pays : United States
Organisme : NIGMS NIH HHS
ID : U54 GM104942
Pays : United States
Organisme : NIBIB NIH HHS
ID : R01 EB023888
Pays : United States
Organisme : NCI NIH HHS
ID : R01 CA192064
Pays : United States
Organisme : NIBIB NIH HHS
ID : R21 EB022775
Pays : United States
Informations de copyright
Copyright © 2019 Elsevier Ltd. All rights reserved.
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