Synthesis and characterization of a cell-permeable bimodal contrast agent targeting β-galactosidase

Keliris, A; Ziegler, Thomas; Mishra, Ritu; Pohmann, R; Sauer, Martin; Uğurbil, Kâmil; Engelmann, J

doi:10.1016/j.bmc.2011.03.023

Cited by 44 publications

(41 citation statements)

References 51 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

“…The ability to noninvasively image cells in vivo is essential for applications that include fate mapping transplanted cells, 1–3 cancer detection, 4 tracking gene expression, 5–7 and detecting disease markers. 8–10 Modalities for in vivo imaging include optical techniques, ultrasound, positron emission tomography (PET), single-photon emission computed tomography (SPECT), computed tomography (CT), and magnetic resonance imaging (MRI).…”

Section: Introductionmentioning

confidence: 99%

Nanodiscs as a Modular Platform for Multimodal MR-Optical Imaging

et al. 2015

View full text Add to dashboard Cite

Nanodiscs are monodisperse, self-assembled discoidal particles that consist of a lipid bilayer encircled by membrane scaffold proteins (MSP). Nanodiscs have been used to solubilize membrane proteins for structural and functional studies and deliver therapeutic phospholipids. Herein, we report on tetramethylrhodamine (TMR) tagged nanodiscs that solubilize lipophilic MR contrast agents for generation of multimodal nanoparticles for cellular imaging. We incorporate both multimeric and monomeric Gd(III)-based contrast agents into nanodiscs and show that particles containing the monomeric agent (ND2) label cells with high efficiency and generate significant image contrast at 7 T compared to nanodiscs containing the multimeric agent (ND1) and Prohance, a clinically approved contrast agent.

show abstract

Section: Introductionmentioning

confidence: 99%

Nanodiscs as a Modular Platform for Multimodal MR-Optical Imaging

et al. 2015

View full text Add to dashboard Cite

show abstract

“…The integration of optical and MR imaging is therefore an appealing approach to facilitate applications such as fate mapping transplanted stem cells, 7–9 early detection of cancer, 10 tracking gene expression, 11 and importantly, histological validation of MR signal.…”

mentioning

confidence: 99%

A multimeric MR-optical contrast agent for multimodal imaging

et al. 2014

View full text Add to dashboard Cite

We describe the design, synthesis and in vitro evaluation of a multimodal and multimeric contrast agent. The agent consists of three macrocyclic Gd(III) chelates conjugated to a fluorophore and possesses high relaxivity, water solubility, and is nontoxic. The modular synthesis is amenable for the incorporation of a variety of fluorophores to generate molecular constructs for a number of applications.

show abstract

“…35 This technique has also been applied to luminescent metal complexes 36 and dual imaging agents. 37 Additional approaches to increase cellular accumulation include coupling complexes to moieties that facilitate interactions with cellular membrane receptors, 38 transporters, 39 or special groups such as exofacial thiols. 40 The translation of these approaches to the luminescent macrocyclic polyaminocarboxylate complexes described herein is being further investigated by our group.…”

Section: Resultsmentioning

confidence: 99%

Effect of Lanthanide Complex Structure on Cell Viability and Association

et al. 2014

View full text Add to dashboard Cite

A systematic study of the effect of hydrophobicity and charge on the cell viability and cell association of lanthanide metal complexes is presented. The terbium luminescent probes feature a macrocyclic polyaminocarboxylate ligand (DOTA) in which the hydrophobicity of the antenna and that of the carboxyamide pendant arms are independently varied. Three sensitizing antennas were investigated in terms of their function in vitro: 2-methoxyisophthalamide (IAM(OMe)), 2-hydroxyisophthalamide (IAM), and 6-methylphenanthridine (Phen). Of these complexes, Tb-DOTA-IAM exhibited the highest quantum yield, although the higher cell viability and more facile synthesis of the structurally related Tb-DOTA-IAM(OMe) platform renders it more attractive. Further modification of this latter core structure with carboxyamide arms featuring hydrophobic benzyl, hexyl, and trifluoro groups as well as hydrophilic amino acid based moieties generated a family of complexes that exhibit high cell viability (ED50 > 300 μM) regardless of the lipophilicity or the overall complex charge. Only the hexyl-substituted complex reduced cell viability to 60% in the presence of 100 μM complex. Additionally, cellular association was investigated by ICP-MS and fluorescence microscopy. Surprisingly, the hydrophobic moieties did not increase cell association in comparison to the hydrophilic amino acid derivatives. It is thus postulated that the hydrophilic nature of the 2-methoxyisophthalamide antenna (IAM(OMe)) disfavors the cellular association of these complexes. As such, responsive luminescent probes based on this scaffold would be appropriate for the detection of extracellular species.

show abstract

Synthesis and characterization of a cell-permeable bimodal contrast agent targeting β-galactosidase

Cited by 44 publications

References 51 publications

Nanodiscs as a Modular Platform for Multimodal MR-Optical Imaging

Nanodiscs as a Modular Platform for Multimodal MR-Optical Imaging

A multimeric MR-optical contrast agent for multimodal imaging

Effect of Lanthanide Complex Structure on Cell Viability and Association

Contact Info

Product

Resources

About