121-68-6Relevant academic research and scientific papers
Thermally controlled wettability of a nanoporous membrane grafted with catechol-tethered poly(N-isopropylacrylamide)
Kim, Jee Seon,Kim, Taek Gyung,Kong, Won Ho,Park, Tae Gwan,Nam, Yoon Sung
, p. 9227 - 9229 (2012)
A nanoporous membrane is coated with catechol-tethered poly(N- isopropylacrylamide). The thermosensitive variation of surface wettability determines the hindered diffusivity of dextran (40 kDa) through the nanopores.
RAFT of sulfobetaine for modifying poly(glycidyl methacrylate) microspheres to reduce nonspecific protein adsorption
Koubková, Jana,MacKová, Hana,Proks, Vladimír,Trchová, Miroslava,Brus, Ji?í,Horák, Daniel
, p. 2273 - 2284 (2015)
The minimization of nonspecific protein adsorption is a crucial step in the development of bioseparation processes, immunoassays, and affinity diagnostics. Among the numerous biomaterials, polyzwitterions are known to effectively suppress protein and cell adhesion. This article describes the formation of monodisperse polymer microspheres coated with polysulfobetaine with the aim to limit nonspecific adsorption of bovine serum albumin (BSA) as a model protein. In this process, 2-μm poly(glycidyl methacrylate) (PGMA) microspheres were prepared by dispersion polymerization. To render the microspheres hydrophilic and biocompatible, [3-(methacryloylamino)propyl]dimethyl(3-sulfopropyl)ammonium hydroxide (MPDSAH) was grafted from the surface by reversible addition-fragmentation chain transfer (RAFT) polymerization. Elemental analysis of the modified microspheres revealed up to 20 wt % of poly{[3-(methacryloylamino)propyl]dimethyl(3-sulfopropyl)ammonimum hydroxide} (PMPDSAH). The microspheres were characterized in terms of particle size, morphology, and zeta potential. The amount of BSA nonspecifically adsorbed on the PMPDSAH-modified microspheres decreased to half of that captured on the unmodified PGMA microspheres.
Synthesis and characterization of well-defined optically active methacrylic diblock copolymers
Achilleos, Mariliz,Kafouris, Demetris,Holder, Simon J.,Krasia-Christoforou, Theodora
, p. 4215 - 4222 (2012)
A new, simple, and cost-effective approach toward the development of well-defined optically active diblock copolymers based on methacrylate monomers is described for the first time. Starting from the low-cost optically active (S)-(-)-2-methyl-1-butanol, a new optically active methacrylic monomer, namely, (S)-(+)-2-methyl-1-butyl methacrylate [(S)-(+)-MBuMA], was synthesized. Reversible addition fragmentation chain transfer polymerization was then used for preparing well-defined poly[(S)-(+)-MBuMA] homopolymers and water-soluble diblock copolymers based on [(S)-(+)-MBuMA] and the hydrophilic and ionizable monomer 2-(dimethyl amino)ethyl methacrylate (DMAEMA). The respective homopolymers and diblock copolymers were characterized in terms of their molecular weights, polydispersity indices, and compositions by size exclusion chromatography and 1H NMR spectroscopy. Polarimetry measurements were used to determine the specific optical rotations of these systems. The structural and compositional characteristics of micellar nanostructures possessing an optically active core generated by p((S)-(+)-MBuMA)-b-p(DMAEMA) chains characterized by predetermined molecular characteristics may be easily tuned to match biological constructs. Consequently, the aggregation behavior of the p[(S)-(+)-MBuMA]-b-p[DMAEMA] diblock copolymers was investigated in aqueous media by means of dynamic light scattering and atomic force microscopy, which revealed the formation of micelles in neutral and acidified aqueous solutions.
End-linked poly[2-(dimethylamino)ethyl methacrylate]-poly(methacrylic acid) polyampholyte conetworks: Synthesis by sequential RAFT polymerization and swelling and SANS characterization
Pafiti, Kyriaki S.,Philippou, Zelina,Loizou, Elena,Porcar, Lionel,Patrickios, Costas S.
, p. 5352 - 5362 (2011)
Four well-defined end-linked triblock polyampholyte conetworks composed of positively ionizable 2-(dimethylamino)ethyl methacrylate (DMAEMA) repeating units and negatively ionizable methacrylic acid (MAA) repeating units were synthesized using one-pot, sequential reversible addition-fragmentation chain transfer (RAFT) polymerization, by employing 1,4-bis[2-(thiobenzoylthio)prop-2- yl]benzene (1,4-BTBTPB) as the chain transfer agent, and ethylene glycol dimethacrylate (EGDMA) as the cross-linker. From the four end-linked conetworks, three were based on ABA triblock polyampholytes with polyDMAEMA midblocks with a constant degree of polymerization (DP) and polyMAA end-blocks of different DPs. The fourth end-linked polyampholytic conetwork was based on an equimolar BAB triblock polyampholyte with a polyMAA midblock. Furthermore, two polyampholyte networks were also prepared: one based on an end-linked equimolar statistical polyampholyte, and one with a randomly cross-linked, rather than an end-linked, architecture. Finally, the two homopolymer networks based on the DMAEMA and the MAA monomers were also synthesized. The MAA units were introduced in the (co)networks via the polymerization of 2-tetrahydropyranyl methacrylate (THPMA) followed by its acid hydrolysis after (co)network formation. The linear precursors to the (co)networks were found to have molecular weights and compositions close to the expected values, whereas the extractables from the (co)networks were determined to be lower than 30%. In water, the degrees of swelling (DS) of all the polyampholyte (co)networks presented a characteristic minimum at intermediate pH values, around the (co)network isoelectric point (pI), while they increased at acidic and basic pHs. The pI values of the ampholytic (co)networks were estimated as the midpoints of the regions of reduced swelling and ranged between 5.3 and 6.8, decreasing with the increase of the MAA content in the (co)networks. Finally, small-angle neutron scattering (SANS) studies of the polyampholyte (co)networks swollen in D2O provided SANS profiles without any peaks but broad shoulders whose location was consistent with the spacing of the cross-linking cores.
Thermal decomposition of cumyl dithiobenzoate
Liu, Yang,He, Junpo,Xu, Jiangtao,Fan, Deqin,Tang, Wei,Yang, Yuliang
, p. 10332 - 10335 (2005)
Thermal decomposition of cumyl dithiobenzoate (CDB), a reagent widely used in controlled polymerization of various monomers, was investigated. CDB was synthesized by flash chromatography followed by recrystallization and obtained as large purple crystals. A close analysis of the MS spectra revealed the presence of isopropylbenzene and cumyl thiobenzoate. Results show that the polymeric dithioesters, which are more stable than CDB, are formed after the initiation period, accounting for the fact that CDB-mediated RAFT polymerization of styrene works well at high temperature.
Synthesis and characterization of a naphthalimide-dye end-labeled copolymer by reversible addition-fragmentation chain transfer (RAFT) polymerization
Li, Binxin,Majonis, Daniel,Liu, Peng,Winnik, Mitchell A.
, p. 317 - 325 (2011)
We describe the synthesis of an end-functionalized copolymer of N-(2-hydroxypropyl)methacrylamide (HPMA) and N-hydroxysuccinimide methacrylate (NMS) by reversible addition-fragmentation chain transfer (RAFT) polymerization. To control the polymer composition, the faster reacting monomer (NMS) was added slowly to the reaction mixture beginning 30 min after initating the polymerization (ca. 16% HPMA conversion). One RAFT agent, based on azocyanopentanoic acid, introduced a-COOH group to the chain at one end. Use of a different RAFT agent containing a 4-amino-1,8-naphthalimide dye introduced a UV-vis absorbing and fluorescent group at this chain end. The polymers obtained had molecular weights of 30000 and 20000, respectively, and contained about 30 mol% NMS active ester groups.
Intracellular nitric oxide delivery from stable NO-polymeric nanoparticle carriers
Duong, Hien T. T.,Kamarudin, Zulkamal M.,Erlich, Rafael B.,Li, Yang,Jones, Mathew W.,Kavallaris, Maria,Boyer, Cyrille,Davis, Thomas P.
, p. 4190 - 4192 (2013)
The encapsulation of S-nitrosoglutathione into polymeric nanoparticles substantially improves NO stability in aqueous media without affecting the efficacy of intracellular delivery. The combination of nano-NO delivery and chemotherapy has been found to enhance antitumour activity of chemotherapeutics, as demonstrated using preliminary in vitro experiments with neuroblastoma cells.
Defect-free nanoporous thin films from ABC triblock copolymers
Bang, Joona,Kim, Seung Hyun,Drockenmuller, Eric,Misner, Matthew J.,Russell, Thomas P.,Hawker, Craig J.
, p. 7622 - 7629 (2006)
The self-assembly of triblock copolymers of poly(ethylene oxide-b-methyl methacrylate-b-styrene) (PEO-b-PMMA-b-PS), where PS is the major component and PMMA and PEO are minor components, provides a robust route to highly ordered, nanoporous arrays with cylindrical pores of 10-15 nm that show promise in block copolymer lithography. These ABC triblock copolymers were synthesized by controlled living radical polymerization, and after solvent annealing, thin films showing defect-free cylindrical microdomains were obtained. The key to the successful generation of highly regular, porous thin films is the use of PMMA as a photodegradable mid-block which leads to nanoporous structures with an unprecedented degree of lateral order. The power of using a triblock copolymer when compared to a traditional diblock copolymer is evidenced by the ability to exploit and combine the advantages of two separate diblock copolymer systems, the high degree of lateral ordering inherent in PS-b-PEO diblocks plus the facile degradability of PS-b-PMMA diblock copolymer systems, while negating the corresponding disadvantages, poor degradability in PS-b-PEO systems and no long-range order for PS-b-PMMA diblocks.
RAFT polymer end-group modification and chain coupling/conjugation Via disulfide bonds
Boyer, Cyrille,Liu, Jingquan,Bulmus, Volga,Davis, Thomas P.
, p. 830 - 847 (2009)
End-group modification of polymers prepared by reversible additionfragmentation chain transfer (RAFT) polymerization was accomplished by the conversion of trithiocarbonate or dithioester end-groups into a pyridyl disulfide (PDS) functionality. Several different polymers, such as poly(methyl methacrylate), polystyrene, poly(oligoethylene glycol-acrylate), poly(hydroxypropylacrylamide), and poly(N-isopropylacrylamide) were prepared by RAFT polymerization, and subjected to aminolysis in the presence of 2,2′-dithiodipyridine to yield thiol-terminated polymers with yields in the range 6590% dependent on the polymer structure. Furthermore, this PDS end-group was utilized to generate higher-order architectures, such as diblock copolymers with high yields and selectively. In addition, the PDS end-groups were used for the bioconjugation of different biomolecules, such as oligonucleotides, carbohydrates, and peptides. The successful modification of well-defined polymers was confirmed by a combination of UV-vis, NMR spectroscopy, and gel permeation chromatography.
Sequence-defined polypeptide-polymer conjugates utilizing reversible addition fragmentation transfer radical polymerization
Ten Cate, Mattijs G.J.,Rettig, Hartmut,Bernhardt, Kaj,Borner, Hans G.
, p. 10643 - 10649 (2005)
Straightforward solid-phase-supported synthesis routes were presented to obtain novel oligopeptide-based reversible addition fragmentation transfer (RAFT) agents. These approaches include the coupling of a functional RAFT agent to a resin-bound peptide and the functionality switch of an oligopeptide ATRP macroinitiator into an oligopeptide transfer agent. The solid-phase-supported methods allowed easy purification of the transfer agents, making difficult column purification steps unnecessary. Well-defined conjugates comprising sequence-defined peptides and synthetic polymers could be accessed by applying RAFT polymerization techniques in combination with the peptide macrotransfer agents. Polymerization reactions of n-butyl acrylate were performed in solution, yielding peptide-polymer conjugates with controllable molecular weight and low polydispersities of around 1.1. The peptide-polymer conjugates were characterized using 1H NMR spectroscopy and size exclusion chromatography (SEC), while the incorporation of the oligopeptide into the synthetic polymer and the preservation of the chirality were shown by circular dichroism (CD) spectroscopy.
