GdDOTAGA(C<sub>18</sub>)<sub>2</sub>: an efficient amphiphilic Gd(<scp>iii</scp>) chelate for the preparation of self-assembled high relaxivity MRI nanoprobes

Filippi, Miriam; Remotti, Davide; Botta, Maurizio; Terreno, Enzo

doi:10.1039/c5cc06032j

Cited by 26 publications

(28 citation statements)

References 26 publications

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“…Secondly, the degree to which the relaxation of water protons changes is due to the multimeric effect which stems from the increased, localised contrast agent concentration . Many derivatives of Dotarem have been used for this purpose, including DOTAGA, monoamido‐DO3A (DOTMA) and DO3A –…”

Section: Introductionmentioning

confidence: 99%

Polyfunctionalised Nanoparticles Bearing Robust Gadolinium Surface Units for High Relaxivity Performance in MRI

Chabloz

Wenzel

Perry

et al. 2019

Chemistry A European J

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The first example of an octadentate gadolinium unit based on DO3A (hydration number q=1) with a dithiocarbamate tether has been designed and attached to the surface of gold nanoparticles (around 4.4 nm in diameter). In addition to the superior robustness of this attachment, the restricted rotation of the Gd complex on the nanoparticle surface leads to a dramatic increase in relaxivity (r1) from 4.0 mm−1 s−1 in unbound form to 34.3 mm−1 s−1 (at 10 MHz, 37 °C) and 22±2 mm−1 s−1 (at 63.87 MHz, 25 °C) when immobilised on the surface. The one‐pot synthetic route provides a straightforward and versatile way of preparing a range of multifunctional gold nanoparticles. The incorporation of additional surface units for biocompatibility (PEG and thioglucose units) and targeting (folic acid) leads to little detrimental effect on the high relaxivity observed for these non‐toxic multifunctional materials. In addition to the passive targeting attributed to gold nanoparticles, the inclusion of a unit capable of targeting the folate receptors overexpressed by cancer cells, such as HeLa cells, illustrates the potential of these assemblies.

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Section: Introductionmentioning

confidence: 99%

Polyfunctionalised Nanoparticles Bearing Robust Gadolinium Surface Units for High Relaxivity Performance in MRI

Chabloz

Wenzel

Perry

et al. 2019

Chemistry A European J

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“…liposome derivatized with P6.1 for her-2-overexpressing tumor cells 30,31 Representative images of the abdominal region of mice acquired before and at 15 and 30 min after the injection of liposomes are shown in Figure 7 (lower panel). The increase in signal intensity due to the presence of Gd is clearly detectable in blood, liver, and kidneys.…”

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confidence: 99%

Liposomes derivatized with multimeric copies of KCCYSL peptide as targeting agents for HER-2-overexpressing tumor cells

Ringhieri¹,

Mannucci²,

Conti³

et al. 2017

IJN

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Mixed liposomes, obtained by coaggregation of 1,2-dioleoyl-sn-glycero-3-phosphocholine and of the synthetic monomer containing a gadolinium complex ([C18]2DTPA[Gd]) have been prepared. Liposomes externally decorated with KCCYSL (P6.1 peptide) sequence in its monomeric, dimeric, and tetrameric forms are studied as target-selective delivery systems toward cancer cells overexpressing human epidermal growth factor receptor-2 (HER-2) receptors. Derivatization of liposomal surface with targeting peptides is achieved using the postmodification method: the alkyne-peptide derivative Pra-KCCYSL reacts, through click chemistry procedures, with a synthetic surfactant modified with 1, 2, or 4 azido moieties previously inserted in liposome formulation. Preliminary in vitro data on MDA-MB-231 and BT-474 cells indicated that liposomes functionalized with P6.1 peptide in its tetrameric form had better binding to and uptake into BT-474 cells compared to liposomes decorated with monomeric or dimeric versions of the P6.1 peptide. BT-474 cells treated with liposomes functionalized with the tetrameric form of P6.1 showed high degree of liposome uptake, which was comparable with the uptake of anti-HER-2 antibodies such as Herceptin. Moreover, magnetic MRI experiments have demonstrated the potential of liposomes to act as MRI contrast agents

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“…Notably, the relaxivity of Gd-DTPA, which reflects how the relaxation rates of a solution change as a function of concentration, was significantly increased after liposomal encapsulation, because DPPE-DTPA(Gd) embedding in the liposome bilayer confined Gd complexes in the bilayer and slowed down its tumbling motions, leading to a higher molecular relaxivity than Gd-DTPA alone. 27,28 Third, ligand-conjugated nanomedicines can significantly improve the therapeutic efficacy of chemotherapeutics, nucleic acid drugs, and diagnostic agents, and diagnosis of cancer. 39 In this study, the presence of mannose was critical to maintain the targeting activity of M-Gd-NL toward macrophages.…”

Section: Discussionmentioning

confidence: 99%

“…Such an increase in r1 of Gd-loaded liposomes was a consequence of the embedding of DPPE-DTPA (Gd) into the bilayer of liposomes, which slowed down the tumbling motion of Gd complexes and achieved high relaxivity. 27,28,34 The corresponding T 1 mapping image is shown in Figure S2A.…”

Section: Characterization Of Liposomesmentioning

confidence: 99%

“…Recently, liposomes have emerged as effective nanocarriers of imaging agents, as they increase the circulation time of loaded drugs and the relaxivity of imaging agents, and are of easy preparation and large-scale production. 27,28 Based on these findings, we hypothesized that mannosylated liposomes could be used in early detection of AP by targeting macrophages and improving MRI. After incorporation of mannosylated lipids into Gd-DTPA-loaded liposomes, these liposomes (named thereafter M-Gd-NL) could preferably target macrophages in AP, resulting in early detection of AP by improving MRI and discriminating between mild and severe AP.…”

Section: Introductionmentioning

confidence: 99%

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Mannose-coated gadolinium liposomes for improved magnetic resonance imaging in acute pancreatitis

Tian¹,

Liu²,

Chen³

et al. 2017

IJN

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Background Acute pancreatitis (AP) is an acute inflammatory condition of the pancreas. The symptoms, treatment, and prognosis of mild and severe AP are different, and severe AP is a potentially life-threatening disease with a high incidence of complications and high mortality rate. Thus, it is urgent to develop an effective approach to reliably discriminate between mild and severe AP. Methods We have developed novel gadolinium-diethylenetriaminepentaacetic (Gd-DTPA)-loaded mannosylated liposomes (named thereafter M-Gd-NL) that preferably target macrophages in AP. The targeting ability of M-Gd-NL toward macrophages in AP and its ability to discriminate between mild and severe AP were evaluated. Results The liposomes were of desired particle size (~100 nm), Gd-DTPA encapsulation efficiency (~85%), and stability. M-Gd-NL and non-targeted Gd-DTPA-loaded liposomes (Gd-NL) exhibited increased relaxivity compared with Gd-DTPA. Compared with Gd-NL and Gd-DTPA, M-Gd-NL showed increased uptake in macrophages, resulting in increased T 1 imaging ability both in vitro (macrophage cell line) and in vivo (severe AP model). Importantly, M-Gd-NL had the ability to discriminate between mild and severe AP, as reflected by a significantly higher T 1 magnetic resonance imaging signal in severe AP than in mild AP. M-Gd-NL did not show severe organ toxicity in rats. Conclusion Our data suggest that M-Gd-NL had enhanced magnetic resonance imaging ability by targeting macrophages in AP and good ability to discriminate between mild and severe AP. We believe that M-Gd-NL could shed new light on the diagnosis of AP in the near future.

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GdDOTAGA(C₁₈)₂: an efficient amphiphilic Gd(iii) chelate for the preparation of self-assembled high relaxivity MRI nanoprobes

Abstract: MRI-nanoprobes endowed with improved relaxivity, incorporation stability and in vivo MRI efficiency were prepared using a newly synthesized amphiphilic GdDOTA-like complex.

Cited by 26 publications

References 26 publications

Polyfunctionalised Nanoparticles Bearing Robust Gadolinium Surface Units for High Relaxivity Performance in MRI

Polyfunctionalised Nanoparticles Bearing Robust Gadolinium Surface Units for High Relaxivity Performance in MRI

Liposomes derivatized with multimeric copies of KCCYSL peptide as targeting agents for HER-2-overexpressing tumor cells

Mannose-coated gadolinium liposomes for improved magnetic resonance imaging in acute pancreatitis

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GdDOTAGA(C18)2: an efficient amphiphilic Gd(iii) chelate for the preparation of self-assembled high relaxivity MRI nanoprobes

Abstract: MRI-nanoprobes endowed with improved relaxivity, incorporation stability and in vivo MRI efficiency were prepared using a newly synthesized amphiphilic GdDOTA-like complex.

Cited by 26 publications

References 26 publications

Polyfunctionalised Nanoparticles Bearing Robust Gadolinium Surface Units for High Relaxivity Performance in MRI

Polyfunctionalised Nanoparticles Bearing Robust Gadolinium Surface Units for High Relaxivity Performance in MRI

Liposomes derivatized with multimeric copies of KCCYSL peptide as targeting agents for HER-2-overexpressing tumor cells

Mannose-coated gadolinium liposomes for improved magnetic resonance imaging in acute pancreatitis

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GdDOTAGA(C₁₈)₂: an efficient amphiphilic Gd(iii) chelate for the preparation of self-assembled high relaxivity MRI nanoprobes