Preparation of thermoresponsive polymers bearing amino acid diamide derivatives via RAFT polymerization

Liu, Zhilei; Hu, Jiwen; Sun, Jianping; He, Guping; Li, Yinghui; Zhang, Ganwei

doi:10.1002/pola.24137

Cited by 35 publications

(27 citation statements)

References 63 publications

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“…[ 62 ] ITO nanocrystals were prepared using methods we have described in previous reports, [ 9 ] and stripped of their hydrophobic native ligands using Meerwein's salt according to our published procedures. [ 62 ] ITO nanocrystals were prepared using methods we have described in previous reports, [ 9 ] and stripped of their hydrophobic native ligands using Meerwein's salt according to our published procedures.…”

Section: Methodsmentioning

confidence: 99%

Dispersible Plasmonic Doped Metal Oxide Nanocrystal Sensors that Optically Track Redox Reactions in Aqueous Media with Single‐Electron Sensitivity

Mendelsberg

McBride

Duong

et al. 2015

Advanced Optical Materials

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chemical, biochemical, and even biological species ( Figure 1 ). Furthermore, their distinctive near-infrared (NIR) optical response can be quantitatively interpreted [ 14,15 ] so that these redox processes can be tracked with single-electron sensitivity. To demonstrate their exciting new properties in interrogating complex redox systems, we use them to quantify chemically driven charge transfer across the electrifi ed cell membranes of Shewanella oneidensis MR-1, requiring only a simple optical readout and absent any external electrodes. Results and DiscussionRecently, it was shown that the characteristic wavelength and intensity of the NIR plasmon resonance absorption of tin-doped indium oxide (ITO) nanocrystals bound to an electrode can be strongly modulated in a reversible manner using a directional voltage bias. [ 9,16 ] These changes arise from the dependence of the Electron transfer in complex aqueous systems can be observed remotely with single-electron sensitivity using locally dispersed nanostructures conferred with electronic charge concentration-dependent plasmonic properties. When introduced to a system out of redox equilibrium, tin-doped indium oxide nanocrystals undergo rapid multielectron transfer until redox equilibrium is reached; this modulates their free carrier concentration and plasmonic optical properties in the spectrally isolated near-infrared. This capability is harnessed here to noninvasively track, model, and quantify electron transfer events reversibly for organic, inorganic, biogenic, and even living cells.Adv. Optical Mater. 2015, 3, 1293-1300 www.MaterialsViews.com www.advopticalmat.de Figure 1. Plasmonic doped metal oxide nanocrystals reversibly exchange electrons with redox-active small molecules, biomacromolecules, and live bacteria. These multi-electron exchanges modulate their free-carrier concentration, thus changing their plasmonic optical properties. This redoxresponsive plasmon absorbance can be modeled to provide quantitative analysis of electron transfer in systems out of redox equilibrium. wileyonlinelibrary.com

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Section: Methodsmentioning

confidence: 99%

Dispersible Plasmonic Doped Metal Oxide Nanocrystal Sensors that Optically Track Redox Reactions in Aqueous Media with Single‐Electron Sensitivity

Mendelsberg

McBride

Duong

et al. 2015

Advanced Optical Materials

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“…Recently, Hu and co‐workers172 reported the synthesis of thermoresponsive and optically active polymers by RAFT polymerization of N ‐acryloyl‐ L ‐valine N ′‐methylamide (A‐Val‐MA) using 2‐dodecylsulfanylthiocarbonylsulfanyl‐2‐methyl‐propionic acid propargyl alcohol ester (CTA8) with a terminal alkyne group as CTA. The LCST of the poly(A‐Val‐MA) obtained by RAFT polymerization with CTA8 was less than 9 °C, whereas the polymer prepared by conventional free radical polymerization showed a LCST‐type soluble–insoluble transition at around 18 °C.…”

Section: Thermoresponsive and Dual Stimuli‐responsive Block Copolymentioning

confidence: 99%

Amino‐Acid‐Based Block Copolymers by RAFT Polymerization

Mori

Endō

2012

Macromol. Rapid Commun.

104

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This review summarizes recent advances in the design and synthesis of amino-acid-based block copolymers by reversible addition-fragmentation chain transfer (RAFT) polymerization of amino-acid-bearing monomers. We will mainly focus on stimuli-responsive block copolymers, such as pH-, thermo-, and dual-stimuli-responsive block copolymers, and self-assembled block copolymers, including amphiphilic and double-hydrophilic block copolymers having tunable chiroptical properties. We will also highlight recent results in RAFT synthesis of amino-acid-based copolymers having various properties, such as catalytic and optoelectronic properties, cross-linked block copolymer micelles, unimolecular micelles, and organic-inorganic hybrids.

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“…18–22 Previously, RAFT polymerizations have been reported with a variety of functional monomers including anionic, 23–25 zwitterionic, 26,27 and neutral 28–40 in both organic and aqueous media. 41–48 For example, our group conducted the initial controlled polymerization of the cationic methacrylamide monomer, N -[3-(dimethylamino)propyl]methacrylamide (DMAPMA), using aqueous media and 4-cyanopentanoic acid dithiobenzoate (CTP) as the chain transfer agent. 18 An acidic environment was necessary in order to obtain controlled molecular weight (M n ) and low M w /M n values.…”

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confidence: 99%

Guanidine-Containing Methacrylamide (Co)polymers via aRAFT: Toward a Cell-Penetrating Peptide Mimic

et al. 2011

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We report the synthesis and controlled radical homo- and block copolymerization of 3-guanidinopropyl methacrylamide (GPMA) utilizing aqueous reversible addition-fragmentation chain transfer (aRAFT) polymerization. The resulting homopolymer and block copolymer with N-(2-hydroxypropyl) methacrylamide (HPMA) were prepared to mimic the behavior of cell penetrating peptides (CPPs) and poly(arginine) (> 6 units) which have been shown to cross cell membranes. The homopolymerization mediated by 4-cyano-4-(ethylsulfanylthiocarbonylsulfanyl)pentanoic acid (CEP) in aqueous buffer exhibited pseudo-first-order kinetics and linear growth of molecular weight with conversion. Retention of the “living” thiocarbonylthio ω-end-group was demonstrated through successful chain extension of the GPMA macroCTA yielding GPMA37-b-GPMA61 (Mw/Mn =1.05). Block copolymers of GPMA with the non-immunogenic, biocompatible HPMA were synthesized yielding HPMA271-b-GPMA13 (Mw/Mn = 1.15). Notably, intracellular uptake was confirmed by fluorescence microscopy, confocal laser scanning microscopy, and flow cytometry experiments after 2.5 h incubation with KB cells at 4 °C and at 37 °C utilizing FITC-labeled, GPMA-containing copolymers. The observed facility of cellular uptake and the structural control afforded by aRAFT polymerization suggest significant potential for these synthetic (co)polymers as drug delivery vehicles in targeted therapies.

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Preparation of thermoresponsive polymers bearing amino acid diamide derivatives via RAFT polymerization

Cited by 35 publications

References 63 publications

Dispersible Plasmonic Doped Metal Oxide Nanocrystal Sensors that Optically Track Redox Reactions in Aqueous Media with Single‐Electron Sensitivity

Dispersible Plasmonic Doped Metal Oxide Nanocrystal Sensors that Optically Track Redox Reactions in Aqueous Media with Single‐Electron Sensitivity

Amino‐Acid‐Based Block Copolymers by RAFT Polymerization

Guanidine-Containing Methacrylamide (Co)polymers via aRAFT: Toward a Cell-Penetrating Peptide Mimic

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