Synthesis, Stability and Relaxivity of TEEPO-Met: An Organic Radical as a Potential Tumour Targeting Contrast Agent for Magnetic Resonance Imaging

Autor: Marjut Timonen, Maiju Soikkeli, Jari Kavakka, Jani O. Moilanen, Sami Heikkinen, Kaisa Horkka
Přispěvatelé: Department of Chemistry, University of Helsinki, Sauli Savolainen / Principal Investigator, Department of Diagnostics and Therapeutics, Clinicum, HUS Medical Imaging Center
Jazyk: angličtina
Rok vydání: 2018
Předmět:
116 Chemical sciences
Pharmaceutical Science
Contrast Media
01 natural sciences
Analytical Chemistry
law.invention
GLUCOSE
Nuclear magnetic resonance
Piperidines
law
Heterocyclic Compounds
Neoplasms
Drug Discovery
Moiety
magneettitutkimus
Spin label
Electron paramagnetic resonance
ta116
orgaaniset yhdisteet
medicine.diagnostic_test
Molecular Structure
Chemistry
Phantoms
Imaging
Relaxation (NMR)
radicals
Magnetic Resonance Imaging
3. Good health
Chemistry (miscellaneous)
Molecular Medicine
MRI
Radical
010402 general chemistry
vapaat radikaalit
Imaging phantom
Article
Cyclic N-Oxides
varjoainetutkimus
nitroxides
medicine
Animals
Humans
contrast agents
typpiyhdisteet
Physical and Theoretical Chemistry
methionine
010405 organic chemistry
Organic Chemistry
Electron Spin Resonance Spectroscopy
Magnetic resonance imaging
IN-VITRO
3126 Surgery
anesthesiology
intensive care
radiology
NMR
EPR
In vitro
TRANSPORT
0104 chemical sciences
REDUCTION
SPIN-LABEL
1182 Biochemistry
cell and molecular biology
Zdroj: Molecules; Volume 23; Issue 5; Pages: 1034
Molecules : A Journal of Synthetic Chemistry and Natural Product Chemistry
ISSN: 1420-3049
DOI: 10.3390/molecules23051034
Popis: Cancer is a widespread and life-threatening disease and its early-stage diagnosis is vital. One of the most effective, non-invasive tools in medical diagnostics is magnetic resonance imaging (MRI) with the aid of contrast agents. Contrast agents that are currently in clinical use contain metals, causing some restrictions in their use. Also, these contrast agents are mainly non-specific without any tissue targeting capabilities. Subsequently, the interest has notably increased in the research of organic, metal-free contrast agents. This study presents a new, stable organic radical, TEEPO-Met, where a radical moiety 2,2,6,6-tetraethylpiperidinoxide (TEEPO) is attached to an amino acid, methionine (Met), as a potentially tumour-targeting moiety. We describe the synthesis, stability assessment with electron paramagnetic resonance (EPR) spectroscopy and relaxation enhancement abilities by an in vitro nuclear magnetic resonance (NMR) and phantom MRI studies of TEEPO-Met. The new compound proved to be stable notably longer than the average imaging time in conditions mimicking a biological matrix. Also, it significantly reduced the relaxation times of water, making it a promising candidate as a novel tumour targeting contrast agent for MRI.
Databáze: OpenAIRE
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