Porphyrin-containing polyaspartamide gadolinium complexes as potential magnetic resonance imaging contrast agents

Yan, Guoping; Li, Zhen; Xu, Wei; Zhou, Cheng-Kai; Yang, Lian; Zhang, Qiao; Li, Liang; Liu, Fan; Han, Lin; Ge, Yuan-Xing; Guo, Jiansheng

doi:10.1016/j.ijpharm.2011.01.036

Cited by 26 publications

(16 citation statements)

References 43 publications

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“…Gadolinium complexes (GdC) function as contrast agents for magnetic resonance imaging (MRI) [1][2][3][4][5][6][7][8], and solutions dissolving the GdC homogeneously at molecular level are available commercially. The GdC molecules flow fast in living bodies.…”

Section: Introductionmentioning

confidence: 99%

Preparation of Gd Complex-Immobilized Silica Particles and Their Application to MRI

Kobayashi

Morimoto

Nakagawa

et al. 2013

ISRN Nanotechnology

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A preparation method for Gd-ethylenediaminetetraacetic acid disodium salt dihydrate (ETDA) complex-immobilized silica particles (Gd-EDTA/SiO2) is proposed. Preparation of spherical silica particles was performed by a sol-gel method at 35°C using 0.2 M tetraethylorthosilicate, 25 M H2O, and 0.01 M NaOH in ethanol, which produced silica particles with an average size of nm. Immobilization of Gd-EDTA on the silica particles was conducted at 35°C by introducing amino groups on the silica particles with (3-aminopropyl)trimethoxysilane at pH 3 (NH2/SiO2) and then making Gd-EDTA act on the NH2/SiO2 particles at pH 5. The as-prepared Gd-EDTA/SiO2 particle colloid solution was concentrated up to a Gd concentration of 0.347 mM by centrifugation. The sphere structure of Gd-EDTA/SiO2 particles was undamaged, and the colloid solution was still colloidally stable, even after the concentrating process. The concentrated Gd-EDTA/SiO2 colloid solution revealed good MRI properties. A relaxivity value for T1-weighted imaging was as high as 5.15 mM−1 s−1, that was comparable to that for a commercial Gd complex contrast agent.

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Section: Introductionmentioning

confidence: 99%

Preparation of Gd Complex-Immobilized Silica Particles and Their Application to MRI

Kobayashi

Morimoto

Nakagawa

et al. 2013

ISRN Nanotechnology

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“…The relaxivity was calculated as the slope of the curves 1/T1 with respect to the gadolinium concentration. 7,24 The r1 of PDG was 12.963 mM −1 s −1 ( Figure 5B), which was about 1.7 times higher than Magnevist (about r1=4.9 mM…”

Section: In Vitro Mri and Relaxivity Measurementsmentioning

confidence: 83%

Design, synthesis, and evaluation of VEGFR-targeted macromolecular MRI contrast agent based on biotin–avidin-specific binding

Liu

Sun

et al. 2017

IJN

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Developing magnetic resonance imaging (MRI) contrast agents with high relaxivity and specificity was essential to increase MRI diagnostic sensitivity and accuracy. In this study, the MRI contrast agent, vascular endothelial growth factor receptor (VEGFR)-targeted poly ( l -lysine) (PLL)-diethylene triamine pentacetate acid (DTPA)-gadolinium (Gd) (VEGFR-targeted PLL-DTPA-Gd, VPDG), was designed and prepared to enhance the MRI diagnosis capacity of tumor. Biotin-PLL-DTPA-Gd was synthesized first, then, VEGFR antibody was linked to biotin-PLL-DTPA-Gd using biotin–avidin reaction. In vitro cytotoxicity study results showed that VPDG had low toxicity to MCF-7 cells and HepG2 cells at experimental concentrations. In cell uptake experiments, VPDG could significantly increase the internalization rates (61.75%±5.22%) in VEGFR-positive HepG2 cells compared to PLL-DTPA-Gd (PDG) (25.16%±4.71%, P <0.05). In MRI studies in vitro, significantly higher T1 relaxivity (14.184 mM −1 s −1 ) was observed compared to Magnevist ® (4.9 mM −1 s −1 ; P <0.01). Furthermore, in vivo MRI study results showed that VPDG could significantly enhance the tumor signal intensity and prolong the diagnostic time (from <1 h to 2.5 h). These results indicated that macromolecular VPDG was a promising MRI contrast agent and held great potential for molecular diagnosis of tumor.

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“…5,26,31 Water-soluble APTSPP and CTMIO were incorporated into PHEA to synthesize the tumor-targeting polyaspartamide isoindoline nitroxides containing porphyrin and CTMIO groups. 5,26,31 Water-soluble APTSPP and CTMIO were incorporated into PHEA to synthesize the tumor-targeting polyaspartamide isoindoline nitroxides containing porphyrin and CTMIO groups.…”

Section: Resultsmentioning

confidence: 99%

“…A series of porphyrin-bound isoindoline nitroxides linked to porphyrin ring have been made and evaluated by fluorescence spectroscopy and EPR as potential fluorescence-suppressed spin probes. 25–31…”

Section: Introductionmentioning

confidence: 99%

Polyaspartamide spin probes containing isoindoline nitroxide and porphyrin groups

Yan

Liu

et al. 2012

Journal of Bioactive and Compatible Polymers

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Water-soluble polyaspartamide isoindoline nitroxides 5-(4′-aminophenyl)-10,15,20-tris (4′-sulfonatophenyl) porphyrin, trisodium salt-poly[α,β-N-(2-hydroxyethyl)-l-aspartamide]-5-carboxy-1,1,3,3-tetramethylisoindolin-2-yloxyl were synthesized by the incorporation of 5-(4′-aminophenyl)-10,15,20-tris(4′-sulfonatophenyl) porphyrin, trisodium salt, as a tumortargeting group, and 5-carboxy-1,1,3,3-tetramethylisoindolin-2-yloxyl into poly[α,β-N-(2hydroxyethyl)-l-aspartamide]. These compounds were characterized, and the in vitro properties were evaluated. The polyaspartamide isoindoline nitroxides had higher relaxation effectiveness and had greater toxicity to HeLa cells than that of 5-carboxy-1,1,3,3-tetramethylisoindolin-2yloxyl. The polyaspartamide isoindoline nitroxides retained similar electrochemical properties and redox reaction mechanisms as the parent nitroxides. The electron paramagnetic resonance spectra of polyaspartamide isoindoline nitroxides exhibited characteristic hyperfine electron paramagnetic resonance spectra of tetramethyl isoindoline nitroxides, with typical nitroxide g-values and nitrogen isotropic hyperfine coupling constants. Therefore, the water-soluble 5-(4′-aminophenyl)-10,15,20-tris(4′-sulfonatophenyl) porphyrin, trisodium salt-poly[α,β-N-(2hydroxyethyl)-l-aspartamide]-5-carboxy-1,1,3,3-tetramethylisoindolin-2-yloxyl is considered to be a novel potential spin probe for electron paramagnetic resonance.Electron paramagnetic resonance (EPR) spectroscopy (or electron spin resonance (ESR)) is the most direct and powerful method for the detection and identification of free radicals and other species with unpaired electrons. Electron paramagnetic resonance imaging (EPRI) is an important new clinical tool for noninvasive three-dimensional spatial mapping of tissue oxygenation and potentially multidimensional imaging of the spatial distribution of paramagnetic species, such as free radicals in biological tissues, by using several combinations of magnetic field gradients. Moreover, EPRI can be used to study the tumor hypoxia, tissue heterogenicity with respect to oxygen and redox status, and vascular deficiencies in vivo. 1-3 However, the naturally occurring paramagnetic species amenable for EPRI in the body are below the detection limits and most possess a short half-life. It is normally necessary to introduce spin probes into the system by intravenous or intramuscular infusion of stable but slowly metabolizable nontoxic water-soluble paramagnetic materials or stable implantable particulate materials. 4,5 Due to their redox-and radical-trapping properties, nitroxides are extensively used as EPR spin labels for proteins, enzymes, nucleotides, and other biological systems. They can be used for large tissue samples or whole animals in vivo. Although the piperidine-and pyrrolidine-based nitroxides are more widely used, some isoindoline nitroxides possess advantages over current commercially available species. They have enhanced bioreductive stability, excellent thermal and chemical stability, and can gen...

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Porphyrin-containing polyaspartamide gadolinium complexes as potential magnetic resonance imaging contrast agents

Cited by 26 publications

References 43 publications

Preparation of Gd Complex-Immobilized Silica Particles and Their Application to MRI

Preparation of Gd Complex-Immobilized Silica Particles and Their Application to MRI

Design, synthesis, and evaluation of VEGFR-targeted macromolecular MRI contrast agent based on biotin–avidin-specific binding

Polyaspartamide spin probes containing isoindoline nitroxide and porphyrin groups

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Porphyrin-containing polyaspartamide gadolinium complexes as potential magnetic resonance imaging contrast agents

Cited by 26 publications

References 43 publications

Preparation of Gd Complex-Immobilized Silica Particles and Their Application to MRI

Preparation of Gd Complex-Immobilized Silica Particles and Their Application to MRI

Design, synthesis, and evaluation of VEGFR-targeted macromolecular MRI contrast agent based on biotin&ndash;avidin-specific binding

Polyaspartamide spin probes containing isoindoline nitroxide and porphyrin groups

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Product

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Design, synthesis, and evaluation of VEGFR-targeted macromolecular MRI contrast agent based on biotin–avidin-specific binding