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Cyclodextrin‐Based Organic Radical Contrast Agents for in vivo Imaging of Gliomas
Author(s) -
Melone Lucio,
Bach Alice,
Lamura Gianrico,
Canepa Fabio,
Nivajärvi Riikka,
Olsson Venla,
Kettunen Mikko
Publication year - 2020
Publication title -
chempluschem
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.801
H-Index - 61
ISSN - 2192-6506
DOI - 10.1002/cplu.202000190
Subject(s) - chemistry , in vivo , intramolecular force , supramolecular chemistry , click chemistry , radical , molecule , combinatorial chemistry , stereochemistry , organic chemistry , microbiology and biotechnology , biology
Abstract Cyclodextrins (CDs), a class of cyclic oligosaccharides formed by α‐(1,4) linked glucopyranose units, were functionalized with (2,2,6,6‐tetramethylpiperidin‐1‐yl)oxyl (TEMPO) radicals to prepare water soluble supramolecular organic radical contrast agents (ORCAs) for the in vivo detection of glioma tumor in animal models. A first set of molecules ( CDn1 , n=6,7,8 is the number of both TEMPO and glucopyranose units) was studied by superconducting quantum interference devices (SQUID) magnetometry in order to define the role of the CD macrocycle on the effective magnetic moment (μ eff ). The μ eff value increased from 3.982 μ B ( CD61 ) to 4.522 μ B ( CD81 ) but was limited by intramolecular antiferromagnetic (AF) interactions. A set of water‐soluble ORCAs ( CDn8 , n=6,7,8) was prepared by a sequence of thiol‐ene and Cu(I)‐catalyzed alkyne–azide “click” reactions. Their 1 H water relaxivities r 1 of these ORCAs were between 0.739 mM −1 s −1 ( CD68 ) to 1.047 mM −1 s −1 ( CD88 ) in D 2 O/H 2 O 9 : 1 (v : v) at 300 K. One of them ( CD78 ) was tested on glioma‐bearing rats with reduced side effects and good relaxivity in vivo .