An enzyme-activatable and cell-permeable MnIII -porphyrin as a highly efficient T1 MRI contrast agent for cell labeling

Chemical Science
Inga HaedickeXiao-an Zhang

Abstract

Magnetic resonance imaging (MRI) is a preferred technique for noninvasively monitoring the fate of implanted cells, such as stem cells and immune cells in vivo. Cellular MRI requires contrast agents (CAs) to label the cells of interest. Despite promising progress made in this emerging field, highly sensitive, stable and biocompatible T1 CAs with high cell permeability and specificity remains an unmet challenge. To address this need, a novel MnIII-porphyrin, MnAMP was designed and synthesized based on the modification of MnIIItetra(carboxy-porphyrin) (MnTCP), a small and highly stable non-Gd extracellular CA with good biocompatibility and high T1 relaxivity (r1 = 7.9 mM-1 s-1) at clinical field of 3 Tesla (T). Cell permeability was achieved by masking the polar carboxylates of MnTCP with acetoxymethyl-ester (AM) groups, which are susceptible to hydrolysis by intracellular esterases. The enzymatic cleavage of AM groups led to disaggregation of the hydrophobic MnAMP, releasing activated MnTCP with significant increase in T1 relaxivity. Cell uptake of MnAMP is highly efficient as tested on two non-phagocytic human cell lines with no side effects observed on cell viability. MRI of labeled cells exhibited significant contrast enhance...Continue Reading

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Citations

Feb 19, 2019·Dalton Transactions : an International Journal of Inorganic Chemistry·Sara M A PintoCarlos F G C Geraldes
Jul 19, 2019·Contrast Media & Molecular Imaging·Inga E HaedickeHai-Ling Margaret Cheng
Dec 14, 2017·Journal of Materials Chemistry. B, Materials for Biology and Medicine·Lei WangRuiyuan Liu
Feb 28, 2021·Bioorganic & Medicinal Chemistry·Hui-Shan LuYuan-Yuan Lv
Oct 24, 2018·Chemical Reviews·Jessica WahsnerPeter Caravan

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Methods Mentioned

BETA
imaging techniques
column chromatography
NMR
Assay

Software Mentioned

Matlab

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