Water-soluble dopamine-based polymers for photoacoustic imaging

Repenko, Tatjana; Fokong, Stanley; Laporte, Laura De; Go, Dennis; Kießling, Fabian; Lammers, Twan; Kuehne, Alexander J. C.

doi:10.1039/c5cc00039d

Cited by 50 publications

(43 citation statements)

References 31 publications

(40 reference statements)

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“…The PA signals were again overlaid on the US images. An exponential decline in the PA signal intensity with the increase of injection depth (d, mm) was observed, which is in accordance with the previously published data from Repenko et al 36 The ICG liposome signal was clearly resolved till the depth of 10 mm, which is the relevant depth for subcutaneous tumor xenografts in mice. 37 Such a signal depth is also appropriate for several clinical applications such as monitoring of drug delivery to superficial skin tumors 38 as well as endoscopic detection of gastrointestinal tumors, 8 but certainly is not the limit that can be achieved in vivo.…”

Section: Phantom Experimentssupporting

confidence: 92%

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Photoacoustic imaging of tumor targeting with riboflavin-functionalized theranostic nanocarriers

Beztsinna

Tsvetkova

Jose

et al. 2017

IJN

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Photoacoustic imaging is an emerging method in the molecular imaging field, providing high spatiotemporal resolution and sufficient imaging depths for many clinical applications. Therefore, the aim of this study was to use photoacoustic imaging as a tool to evaluate a riboflavin (RF)-based targeted nanoplatform. RF is internalized by the cells through a specific pathway, and its derivatives were recently shown as promising tumor-targeting vectors for the drug delivery systems. Here, the RF amphiphile synthesized from a PEGylated phospholipid was successfully inserted into a long-circulating liposome formulation labeled with the clinically approved photoacoustic contrast agent – indocyanine green (ICG). The obtained liposomes had a diameter of 124 nm (polydispersity index =0.17) and had a negative zeta potential of −26 mV. Studies in biological phantoms indicated a stable and concentration-dependent photoacoustic signal (Vevo ® LAZR) of the ICG-containing RF-functionalized liposomes. In A431 cells, a high uptake of RF-functionalized liposomes was found and could be blocked competitively. First, studies in mice revealed ~3 times higher photoacoustic signal in subcutaneous A431 tumor xenografts ( P <0.05) after injection of RF-functionalized liposomes compared to control particles. In this context, the application of a spectral unmixing protocol confirmed the initial quantitative data and improved the localization of liposomes in the tumor. In conclusion, the synthesized RF amphiphile leads to efficient liposomal tumor targeting and can be favorably detected by photoacoustic imaging with a perspective of theranostic applications.

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Section: Phantom Experimentssupporting

confidence: 92%

“…36 The Vevo LAZR system features peak energies of 45±5 mJ, with a pulse duration of 4-6 ns at adjustable wavelengths between 680 and 970 nm (2 nm step size). In combination with the PA signal, high-resolution US images were acquired at 21 MHz (central frequency).…”

Section: Pa Imagingmentioning

confidence: 99%

Photoacoustic imaging of tumor targeting with riboflavin-functionalized theranostic nanocarriers

Beztsinna

Tsvetkova

Jose

et al. 2017

IJN

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“…However, materials intended for biomedical applications must be biocompatible. Although both FND and PDA are highly biocompatible materials, [8c,15h] we evaluated the biocompatibility of FND and PEGylated FND@PDA as a function of the concentration and incubation time using the (2-(4-Iodophenyl)-3-(4-nitrophenyl)-5-(2,4-disulfophenyl)-2H-tetrazolium sodium salt (WST-1) cell viability assay with mouse bone marrow-derived dendritic cells (BMDCs) and HeLa cells. Dendritic cells are antigen presenting cells that capture, process, and present antigens, and trigger T-cell mediated immune responses.…”

Section: Resultsmentioning

confidence: 99%

“…[14] PDA, which is a major pigment in naturally occurring eumelanin, has attracted attention due to its properties including adhesion, free radical quenching, metal ion chelation, large photoacoustic cross-section, and biocompatibility. [15] In addition, the presence of catechol/quinone groups on the PDA shell permits further reactions with amine or thiol containing molecules via Schiff base formation or Michael addition, respectively. The PDA encapsulation approach therefore provides a versatile platform for surface modification with a variety of functional molecules.…”

Section: Introductionmentioning

confidence: 99%

Polydopamine Encapsulation of Fluorescent Nanodiamonds for Biomedical Applications

Jung¹,

Cho

Seol³

et al. 2018

Adv Funct Materials

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Fluorescent nanodiamonds (FNDs) are promising bio-imaging probes compared with other fluorescent nanomaterials such as quantum dots, dye-doped nanoparticles, and metallic nanoclusters, due to their remarkable optical properties and excellent biocompatibility. Nevertheless, they are prone to aggregation in physiological salt solutions, and modifying their surface to conjugate biologically active agents remains challenging. Here, inspired by the adhesive protein of marine mussels, we demonstrate encapsulation of FNDs within a polydopamine (PDA) shell. These PDA surfaces are readily modified via Michael addition or Schiff base reactions with molecules presenting thiol or nitrogen derivatives. We describe modification of PDA shells by thiol terminated poly(ethylene glycol) (PEG-SH) molecules to enhance colloidal stability and biocompatibility of FNDs. We demonstrate their use as fluorescent probes for cell imaging; we find that PEGylated FNDs are taken up by HeLa cells and mouse bone marrow-derived dendritic cells and exhibit reduced nonspecific membrane adhesion. Furthermore, we demonstrate functionalization with biotin-PEG-SH and perform long-term high-resolution single-molecule fluorescence based tracking measurements of FNDs tethered via streptavidin to individual biotinylated DNA molecules. Our robust polydopamine encapsulation and functionalization strategy presents a facile route to develop FNDs as multifunctional labels, drug delivery vehicles, and targeting agents for biomedical applications.

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“…Repenko et al have reported a synthesis method for linear polydopamine via Kumada coupling. The obtained product can be converted into water‐soluble melanin, showing a promising potential for photoacoustic imaging . In this synthesis, dopamine is first brominated to p ‐dibrominated dopamine; then functional hydroxyl and amine groups in p ‐dibrominated dopamine are protected using t Boc.…”

Section: The Modulation Of Melanin‐like Materialsmentioning

confidence: 99%

The modulation of melanin‐like materials: methods, characterization and applications

Jin

Fan

2016

Polymer International

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Water-soluble dopamine-based polymers for photoacoustic imaging

Abstract: Here we present a facile synthetic method yielding a linear form of polydopamine via Kumada-coupling, which can be converted into water-soluble melanin, generating high contrast in photoacoustic imaging.

Cited by 50 publications

References 31 publications

Photoacoustic imaging of tumor targeting with riboflavin-functionalized theranostic nanocarriers

Photoacoustic imaging of tumor targeting with riboflavin-functionalized theranostic nanocarriers

Polydopamine Encapsulation of Fluorescent Nanodiamonds for Biomedical Applications

The modulation of melanin‐like materials: methods, characterization and applications

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