Design of Degradable Click Delivery Systems

Such, Georgina K.; Gunawan, Sylvia T.; Liang, Kang; Caruso, Frank

doi:10.1002/marc.201300093

Cited by 13 publications

(11 citation statements)

References 62 publications

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“…To date, the "click" approach has been exploited for the synthesis of various architectures [32]. In particular, the classical "click reaction" (CuAAC) [33], has been used to assemble a range of LbL films, and to functionalize the resulting films to tune their surface properties [34]. In contrast to films constructed using disulfide chemistry, films with CuAAC linkages are stable under different redox environments.…”

Section: Introductionmentioning

confidence: 99%

Multilayered polymer capsules with switchable permeability

Kempe

Noi

et al. 2014

Polymer

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a b s t r a c tThe preparation of layer-by-layer (LbL) polymer capsules stabilized by a combination of copper-catalyzed azide-alkyne cycloaddition (CuAAC, "click chemistry") and disulfide cross-linking is reported. The capsules obtained possess gated permeability due to the reversible nature of the disulfide cross-linking. Poly(methacrylic acid) (PMA) was modified with different ratios of alkyne and protected thiol functionalities (PMA Alk,SH ). Exploiting hydrogen bonding interactions, multilayered films were prepared by the alternate deposition of PMA Alk,SH (hydrogen bonding donor) and poly(N-vinylpyrrolidone) (PVPON; hydrogen bonding acceptor), yielding stable PMA Alk,SH capsules. Capsule pH responsive behavior and permeability, using a series of different size and labeled dextrans, were investigated in both the "closed" state (disulfide cross-linking intact) and "open" state (free thiol groups). To demonstrate the potential of these gateable systems, post-loading studies with fluorescent 45-base pair (bp) linear double-stranded (ds) DNA were performed. Fluorescence studies revealed the potential of these capsules to reversibly encapsulate cargo: cleavage and reformation of the disulfide groups resulted in reversible permeability to the DNA.

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Section: Introductionmentioning

confidence: 99%

Multilayered polymer capsules with switchable permeability

Kempe

Noi

et al. 2014

Polymer

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“…peptide conjugated cPPE 49 - b -PLLA 44 cSCKs (F3 scr. cPPE), in comparison to the previously described 6, 14 5 % crosslinked poly(acrylamidoethylamine)- block -poly(DL-lactide) (PAEA- b -PLA) A488 labeled cSCKs (A488 PAEA) (Figure S.1). TEM image analysis (assuming contrast is sufficient) provides a good indication of intrinsic, non-hydrated, fully collapsed particle size.…”

Section: Resultsmentioning

confidence: 84%

“…1–3 Recent development of such platforms has shifted from the use of non-degradable polymeric materials towards biodegradable polymer components, 2, 4–6 including poly(glucose carbonates), 7–10 polyphosphoesters 11–13 and poly(lactic acid). 14–16 However, with this shift comes an intrinsic complexity to the preparation, characterization and utilization of degradable materials that must be considered with rigorous experimental investigation.…”

Section: Introductionmentioning

confidence: 99%

Holistic Assessment of Covalently Labeled Core–Shell Polymeric Nanoparticles with Fluorescent Contrast Agents for Theranostic Applications

et al. 2014

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The successful development of degradable polymeric nanostructures as optical probes for use in nanotheranostic applications requires the intelligent design of materials such that their surface response, degradation, drug delivery and imaging properties are all optimized. In the case of imaging, optimization must result in materials that allow differentiation between unbound optical contrast agents and labeled polymeric materials as they undergo degradation. In this study, we have shown that use of traditional electrophoretic gel-plate assays for determination of the purity of dye-conjugated degradable nanoparticles is limited, due to polymer degradation characteristics. To overcome these limitations, we have outlined a holistic approach to evaluating dye-and peptide-polymer nanoparticle conjugation by utilizing steady-state fluorescence, anisotropy, and emission and anisotropy life-time decay profiles, through which nanoparticle-dye binding can be assessed independent of perturbations, such as those presented during the execution of electrolyte gel-based assays. This approach has been demonstrated to provide an overall understanding of the spectral signature-structure-function relationship, ascertaining key information on interactions between the fluorophore, polymer and solvent components that have a direct and measurable impact on the emissive properties of the optical probe. The use of these powerful techniques provides feedback that can be utilized to improve nanotheranostics by evaluating dye emissivity in degradable nanotheranostic systems, which has become increasingly important as modern platforms transition to architectures intentionally reliant on degradation and built-in environmental responses.

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“…59 Since the inception of the "click" cycloaddition reaction in the field of drug discovery in 2001 by Sharpless and coworkers, it has been used by numerous researchers to prepare nanosized particles including polymeric micelles and nanoparticles, liposomes and polymersomes, capsules, metal and silica nanoparticles, carbon nanotubes and fullerenes, or bionanoparticles for tumor diagnostic and drug delivery applications. [146][147][148][149][150][151][152][153][154][155][156][157][158][159][160] In addition, significant growth and interest is seen in developing new processes for the "click" reaction to achieve high reaction kinetics, excellent biocompatibility, selective labeling of specific targets, easily accessible reactive tags, and long shelf-life 146 . In the future, it can be expected that a majority of the nanosystems for tumor theranostics will utilize the "click" reaction.…”

Section: Polymer-core and Fluorophore Nanoparticlesmentioning

confidence: 99%

Mini-review: fluorescence imaging in cancer cells using dye-doped nanoparticles

2016

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Fluorescence imaging has gained increased attention over the past two decades as a viable means to detect a variety of cancers. Fluorescence imaging has the potential to provide physicians with high resolution images with enhanced contrast, which will allow them to be able to better diagnose and treat patients with cancer. Early detection and treatment are key to erradicating cancer in a patient, and fluorescence imaging has the ability to identify non-advanced, even pre-cancerous, tumors where imaging based on white light or radiation overlooked them. Several fluorescent dyes have been identified as possible fluorophores for enhanced fluorescence imaging, such as cyanine, squaraine, porphyrin, phthalocyanine, and borondipyrromethane dyes. These dyes have high fluorescence quantum yields, which provides a high target to background ratio; however, these dyes are often plagued by low water solubility. This low solubility can be ameliorated by conjugating or covalently attaching these dyes to polymeric crosslinked micelles, polymersomes, or polymer-core nanoparticles. These particle & dye systems then can become platforms on which secondary components can be attached to enhance the systems functionality. For example, dyes attached to these nanocarriers can target tumors through passive targeting; however, active targeting can be achieved by further modifying these nanocarriers with ligands that have a binding affinity for receptors overexpressed in tumor cells, cell surface receptors located on the tumor cell membrane, or endothelium. Fluorescence activation of the probes is another promising technology for the early detection of cancer. Activation requires that there be a change in fluorescence, whether it be an emission wavelength change or a fluorescence "on/off" signal when in the presence of some external stimuli. Activation increase the target to background ratio and enhances the contrast of the obtained image. This review serves to highlight the recent developments of (1) improved fluorescent dyes for the detection of cancer, with a specific focus on dyes that are being coupled to nanocarriers; (2) dye & nanocarrier systems that target, both actively and passively, tumors, and (3) fluorescence activation of these fluorophore systems for better image quality.

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Design of Degradable Click Delivery Systems

Cited by 13 publications

References 62 publications

Multilayered polymer capsules with switchable permeability

Multilayered polymer capsules with switchable permeability

Holistic Assessment of Covalently Labeled Core–Shell Polymeric Nanoparticles with Fluorescent Contrast Agents for Theranostic Applications

Mini-review: fluorescence imaging in cancer cells using dye-doped nanoparticles

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