Post-modification of helical dipeptido polyisocyanides using the ‘click’ reaction

Kitto, Heather J.; Schwartz, Eduard; Nijemeisland, Marlies; Koepf, Matthieu; Cornelissen, Jeroen J. L. M.; Rowan, Alan E.; Nolte, Roeland J. M.

doi:10.1039/b811002f

Cited by 46 publications

(39 citation statements)

References 33 publications

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“…Colloidal silica SNOWTEX XS (SNTXS, 4–6 nm, 20wt% suspension in H 2 O), SNOWTEX 20 L (SNT20L, 40–50 nm, 20wt% suspension in H 2 O) and SNOWTEX ZL (SNTZL, 71 nm, 40wt% suspension in H 2 O) were gifts from Nissan Chemical Industries, Ltd. (Pasadena, TX). 1-azido-2-(2-(2-(2-methoxyethoxy)ethoxy) ethoxyethane (N34PEG) was synthesized according to a literature procedure (Kitto et al, 2008). Dialysis membranes (Spectra/Por ® Biotech Cellulose ester, molecular weight cut off (MWCO): 300 K, 12–14 K) were purchased from Spectrum Laboratories Inc. (Rancho Dominguez, CA).…”

Section: Methodsmentioning

confidence: 99%

Induced T cell cytokine production is enhanced by engineered nanoparticles

Chen

Zhang²,

Kaplan

et al. 2013

Nanotoxicology

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Engineered nanoparticles are widely used in commercial products, and yet due to the paucity of safety information, there are concerns surrounding potential adverse health effects, especially from inhaled nanoparticles and their putative contribution to allergic airway disease. The objective of this study was to investigate whether size or surface chemistry of engineered nanoparticles can influence the immune enhancing properties of these agents on antigen-specific T cell responses. Ovalbumin (OVA)-derived peptides were presented to T cells by either spleen-derived endogenous antigen presenting cells or a mouse dendritic cell (DC) line, DC2.4. In all models, interferon (IFN)-γ and interleukin (IL)-2 production by CD8+ or CD4+ T cells in response to peptide OVA257–264 or OVA323–339, respectively, was measured by flow cytometry. To address the study objective, silica nanoparticles (SNPs) were modified with alkyne-terminated surfaces and appended with polyethylene glycol chains via “click” chemistry. These modified SNPs were resistant to agglomerate in in vitro culture media, suggesting that their modulation of T cell responses is the result of true nanoscale-mediated effects. Under conditions of suboptimal T-cell activation, modified SNPs (up to 10 μg/ml) enhanced the proportion of CD8+, but not CD4+, T cells producing IFN-γ and IL-2. Various functional groups (–COOH, –NH2 and –OH) on modified SNPs enhanced IFN-γ and IL-2 production to different levels, with –COOH SNPs being the most effective. Furthermore, 51 nm –COOH SNPs exhibited a greater enhancing effect on the CD8+ T cell response than other sized particles. Collectively, our results show that modified SNPs can enhance antigen-specific CD8+ T cell responses, suggesting that certain modified SNPs exhibit potential adjuvant-like properties.

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Section: Methodsmentioning

confidence: 99%

Induced T cell cytokine production is enhanced by engineered nanoparticles

Chen

Zhang²,

Kaplan

et al. 2013

Nanotoxicology

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“…[2][3][4][5] The particular batch used in these experiments had a mean molecular weight of 9 × 10 5 g/mol, corresponding to an inferred mean chain length of around 180 nm. Regioregular poly(3-hexylthiophene) (P3HT) was purchased from Plextronics ("Plexcore HP", lot #05-10192).…”

Section: Experimental Procedures and Background Theorymentioning

confidence: 99%

“…[2,32] comparison. η and I are semi-empirical constants related to the optical cross-section of the sample and the pump beam intensity respectively.…”

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confidence: 99%

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Photophysical studies of poly-isocyanopeptide based photovoltaic blends

Finlayson¹,

Whitney²

2010

J. Phys. D: Appl. Phys.

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We report a photophysical study of photovoltaic blends containing perylene-substituted polyisocyanide (pery-PIC) materials, using time-correlated single photon counting (TCSPC) and photo-induced absorption spectroscopy, and compare the key characteristics to analogous perylene-diimide (PDI) monomer blends with polythiophene-and polyfluorene-based conjugated polymers. Pery-PIC consists of semiconducting perylene units, which self-stack in a regular fashion around a rigid helical poly-isocyanopeptide backbone. In particular, the charged state lifetimes in pery-PIC blends are found to be of order 10s of μs; this being typically less than half those of the perylene-anion in the corresponding PDI blends. We consider the influence of photophysical factors on the superior photovoltaic device performance of the pery-PIC blends, relative to the corresponding PDI-based devices, in addition to the morphological effects described in earlier studies.

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“…This precise architectural definition has been utilised in their application in electronic applications 7 . We found that a family of water-soluble thermoresponsive oligo(ethylene glycol) functionalized PICs is able to gel water with an extraordinary high efficiency [8][9][10] . Such hydrogel materials are very attractive in, for instance, the fields of drug delivery 11 , regenerative surgery 12 and advanced stimuli-responsive systems 13,14 .…”

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confidence: 99%

Responsive biomimetic networks from polyisocyanopeptide hydrogels

Kouwer

Koepf

Sage

et al. 2013

Nature

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483

561

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Responsive hydrogels applied in the biomedical area show great potential as synthetic extracellular matrix mimics and as host medium for cell growth. The hydrogels often lack the characteristic mechanical properties that are typically seen for natural gels. Here, we demonstrate the unique responsive and mechanical properties of hydrogels based on oligo(ethylene glycol) functionalized polyisocyanopeptides. These stiff helical polymers form gels upon warming at concentrations as low as 0.006 %-wt polymer, with materials properties almost identical to those of their intermediate filaments, a class of cytoskeletal proteins. Using a combination of macroscopic rheology and molecular force microscopy the hierarchical relationship between the macroscopic behaviour of theses peptide mimics has been correlated with the molecular parameters.

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Post-modification of helical dipeptido polyisocyanides using the ‘click’ reaction

Cited by 46 publications

References 33 publications

Induced T cell cytokine production is enhanced by engineered nanoparticles

Induced T cell cytokine production is enhanced by engineered nanoparticles

Photophysical studies of poly-isocyanopeptide based photovoltaic blends

Responsive biomimetic networks from polyisocyanopeptide hydrogels

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