Synthesis and characterization of a stable and inert Mn^II-based Zn^II responsive MRI probe for molecular imaging of glucose stimulated zinc secretion (GSZS)

Abstract

A new potential Zn(II) responsive Mn(II)-based MRI CA candidate derived form pyclen-3,9-diacetate (3,9-PC2A) has been synthesized possessing a di-(2-picolyl)amine (DPA) moiety as an active arm. The PC2A-DPA ligand was found...

Bioimaging agents based on redox-active transition metal complexes

“…The increase can be visualized by MRI experiments in vitro , and in vivo tests confirmed that GSZS could be observed in the prostate of a healthy mouse. 31 Jasanoff's group developed a Mn-based MRI CA (43, Fig. 2 ) as a sensor for intracellular calcium ions (Ca 2+ ).…”

“…7,20,[28][29][30] The application of the metals essential for life can avoid the introduction of exogenous metals and the problems of biotoxicity and metabolism. 31,32 In recent years, a series of metal complexes-based probes have been developed with OI and MRI modalities, which can overcome the shortages of organic molecular probes and avoid the metabolic difficulty and biotoxicity of nano-sized probes. 9,16,19 More importantly, metal complexes-based probes have the potential to be used as bioimaging agents in clinic.…”

Recent progress in the chemistry of 12-membered pyridine-containing tetraazamacrocycles: from synthesis to catalysis

“…of the macrocycle. 41 A relatively long synthetic sequence was required in this case. Thus, the primary amine of pytren was protected as phthalimide to facilitate the introduction of tertbutyl acetate groups by alkylation.…”

“…More recently, Tircsó's group reported the synthesis of a new ligand L35 decorated with a tridentate arm at position 6 of the macrocycle. 41 A relatively long synthetic sequence was required in this case. Thus, the primary amine of pytren was protected as phthalimide to facilitate the introduction of tert -butyl acetate groups by alkylation.…”

A New Oxygen Containing Pyclen-Type Ligand as a Manganese(II) Binder for MRI and 52Mn PET Applications: Equilibrium, Kinetic, Relaxometric, Structural and Radiochemical Studies

“…However, its inertness requires further improvement as [Mn(3,9-PC2A)] is readily protonated, favoring an efficient dissociation via the proton-assisted mechanism (as confirmed by the calculation of the electrostatic potential using DFT methods). However, for the H 2 3,9-PC2A derivatives recently proposed as smart imaging probes (SCAs) for detecting tissue pH sensing Zn(II) ions or for angiographic imaging (H 2 3,9-PC2A-EA, H 2 3,9-PC2A-BP and H 2 3,9-PC2A-DPA, respectively, Scheme S1) the required inertness is achieved by the attachment of ethylamine (possessing picolyl moieties for Zn(II) sensing) or biphenyl moieties; herein, we intend to eradicate the most basic protonation site of the ligand [17][18][19]. It is achieved by the replacement of one amine nitrogen in the macrocycle for an etheric oxygen atom.…”