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 defining the role of the CD macrocycle on the effective magnetic moment (μeff). It increased from 3.982 μB(CD61) to 4.522 μB (CD81) but was limited by intra-molecular 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 1H water relaxivities r1 were between 0.739 mM-1 s-1 (CD68) to 1.047 mM-1 s-1 (CD88) in D2O/H2O 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.

Cyclodextrin‐Based Organic Radical Contrast Agents for In Vivo Imaging of Gliomas

Lucio Melone
;
2020

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 defining the role of the CD macrocycle on the effective magnetic moment (μeff). It increased from 3.982 μB(CD61) to 4.522 μB (CD81) but was limited by intra-molecular 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 1H water relaxivities r1 were between 0.739 mM-1 s-1 (CD68) to 1.047 mM-1 s-1 (CD88) in D2O/H2O 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.
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Utilizza questo identificativo per citare o creare un link a questo documento: http://hdl.handle.net/11389/30133
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