4856-87-5Relevant articles and documents
Redox-Responsive Degradable PEG Cryogels as Potential Cell Scaffolds in Tissue Engineering
Dispinar, Tugba,Van Camp, Wim,De Cock, Liesbeth J.,De Geest, Bruno G.,Du Prez, Filip E.
, p. 383 - 394 (2012)
A Michael addition strategy involving the reaction between a maleimide double bond and amine groups is investigated for the synthesis of cryogels at subzero temperature. Low-molecular-weight PEG-based building blocks with amine end groups and disulfide-containing building blocks with maleimide end groups are combined to synthesize redox-responsive PEG cryogels. The cryogels exhibit an interconnected macroporous morphology, a high compressive modulus and gelation yields of around 95%. While the cryogels are stable under physiological conditions, complete dissolution of the cryogels into water-soluble products is obtained in the presence of a reducing agent (glutathione) in the medium. Cell seeding experiments and toxicologic analysis demonstrate their potential as scaffolds in tissue engineering.
Controlling a polymer adhesive using light and a molecular switch
Asadirad, Amir Mahmoud,Boutault, Stephanie,Erno, Zach,Branda, Neil R.
, p. 3024 - 3027 (2014)
A thermally remendable polymer was synthesized by the Diels-Alder reaction between dithienylfuran and maleimide monomers to generate a photoresponsive diarylethene. UV light (312 nm) and visible light (>435 nm) "gate" the reversibility of the Diels-Alder reaction and turn the self-healing properties of the polymer "off" and "on", respectively. After exposure to UV light, the strength of the polymer as an adhesive is enhanced. Visible light weakens the adhesive.
Polymersomes prepared from thermoresponsive fluorescent protein-polymer bioconjugates: Capture of and report on drug and protein payloads
Wong, Chin Ken,Laos, Alistair J.,Soeriyadi, Alexander H.,Wiedenmann, J?rg,Curmi, Paul M. G.,Gooding, J. Justin,Marquis, Christopher P.,Stenzel, Martina H.,Thordarson, Pall
, p. 5317 - 5322 (2015)
Polymersomes provide a good platform for targeted drug delivery and the creation of complex (bio)catalytically active systems for research in synthetic biology. To realize these applications requires both spatial control over the encapsulation components in these polymersomes and a means to report where the components are in the polymersomes. To address these twin challenges, we synthesized the protein-polymer bioconjugate PNIPAM-b-amilFP497 composed of thermoresponsive poly(N-isopropylacrylamide) (PNIPAM) and a green-fluorescent protein variant (amilFP497). Above 37 °C, this bioconjugate forms polymersomes that can (co-)encapsulate the fluorescent drug doxorubicin and the fluorescent light-harvesting protein phycoerythrin 545 (PE545). Using fluorescence lifetime imaging microscopy and F?rster resonance energy transfer (FLIM-FRET), we can distinguish the co-encapsulated PE545 protein inside the polymersome membrane while doxorubicin is found both in the polymersome core and membrane.
Novel cyclopeptide bolaamphiphile for constructing supramolecular nanotubes
Qin, Siyong,Wang, Qingrong,Pei, Yi,Peng, Mengyun,Zhuo, Renxi,Zhang, Xianzheng
, p. 22 - 26 (2014)
A novel dicyclopeptide-based bolaamphiphile was synthesized. The hydrophilic cyclopeptide fragments were linked to an alkyl chain 1,6-bis(maleimido)hexane, which acted as a hydrophobic spacer. The transmission electron microscopy (TEM) observation indicated that the cyclopeptide bolaamphiphile (CPB) self-assembled into the nanotubes with a thickness of about 3 nm. Based on the optimized molecular conformation obtained via MM2 method, the length of CPB was demonstrated to be around 4 nm, implying that the nanotubes were single-walled. Fourier transform infrared spectroscopy (FT-IR) and circular dichroism (CD) analysis showed that the cyclopeptides in CPB mainly acted as the hydrophilic headgroups, rather than providing the well-ordered hydrogen bonding interaction responsible for β-sheet conformation. To investigate the special self-assembly behavior of CPB, the single cyclopeptide (CP) without the connection of the linker was synthesized. Further investigation indicated that the CP molecules can not form tubular structures but nanofibers. Copyright
Design, synthesis and biochemical evaluation of novel ethanoanthracenes and related compounds to target burkitt’s lymphoma
Byrne, Andrew J.,Bright, Sandra A.,McKeown, James P.,O’brien, John E.,Twamley, Brendan,Fayne, Darren,Williams, D. Clive,Meegan, Mary J.
, (2020/01/31)
Lymphomas (cancers of the lymphatic system) account for 12% of malignant diseases worldwide. Burkitt’s lymphoma (BL) is a rare form of non-Hodgkin’s lymphoma in which the cancer starts in the immune B-cells. We report the synthesis and preliminary studies on the antiproliferative activity of a library of 9,10-dihydro-9,10-ethanoanthracene based compounds structurally related to the antidepressant drug maprotiline against BL cell lines MUTU-1 and DG- 75. Structural modifications were achieved by Diels-Alder reaction of the core 9-(2- nitrovinyl)anthracene with number of dienophiles including maleic anhydride, maleimides, acrylonitrile and benzyne. The antiproliferative activity of these compounds was evaluated in BL cell lines EBV? MUTU-1 and EBV+ DG-75 (chemoresistant). The most potent compounds 13j, 15, 16a, 16b, 16c, 16d and 19a displayed IC50 values in the range 0.17–0.38 μM against the BL cell line EBV? MUTU-1 and IC50 values in the range 0.45–0.78 μM against the chemoresistant BL cell line EBV+ DG- 75. Compounds 15, 16b and 16c demonstrated potent ROS dependent apoptotic effects on the BL cell lines which were superior to the control drug taxol and showed minimal cytotoxicity to peripheral blood mononuclear cells (PBMCs). The results suggest that this class of compounds merits further investigation as antiproliferative agents for BL.
Controlled Formation of a Main Chain Supramolecular Polymer Based on Metal–Ligand Interactions and a Thiol-Ene Click Reaction
Chen, Feiyi,Tian, Yu-Kui,Chen, Yulan
supporting information, p. 3169 - 3172 (2018/10/24)
Supramolecular polymers with multiple functionalities and hierarchical structures have received considerable attention and become a hot research topic over the past years. Herein, a main-chain supramolecular polymer has been successfully fabricated by using metal–ligand interactions and a thiol-ene click reaction. 1H NMR, UV/Vis, DOSY, and viscosity measurements were carried out to investigate the molecular recognition and the process of supramolecular polymerization. From the study, the orthogonality between thiol-ene click reactions and the terpyridine–metal ions complexation behavior was testified, and supramolecular polymeric assemblies could be constructed by a one pot method. In the meantime, due to the incorporation of metal-ligand interactions, the supramolecular polymer shows stimuli-responsive properties toward chemical stimuli. Hence, this work could provide a methodology for developing supramolecular polymers as smart materials.
A 26-membered macrocycle obtained by a double diels-alder cycloaddition between two 2H-pyran-2-one rings and two 1, 1′-(hexane-1, 6-diyl)bis (1H-pyrrole-2, 5-dione)s
Turek, Bor Lucijan,Ko?evar, Marijan,Kranjc, Kri?tof,Perdih, Franc
, p. 737 - 746 (2018/01/17)
With the application of a double dienophile 1, 1'-(hexane-1, 6-diyl)bis(1H-pyrrole-2, 5-dione) for a [4+2] cycloaddition with a substituted 2H-pyran-2-one a novel 26-membered tetraaza heteromacrocyclic system 3 was prepared via a direct method under solvent-free conditions with microwave irradiation. The macrocycle prepared is composed of two units of the dienophile and two of the diene. The structure of the macrocycle was characterized on the basis of IR, 1H and 13C NMR and mass spectroscopy, as well as by the elemental analysis and melting point determination. With X-ray diffraction of a single crystal of the macrocycle we have determined that the two acetyl groups (attached to the bridging double bond of the bicyclo[2.2.2]octene fragments) are oriented towards each other (and also towards the inside of the cavity of the macrocycle), therefore, mostly filling it completely.
Two alternative approaches to the Diels-Alder polymerization of tung oil
Lacerda, Talita M.,Carvalho, Antonio J. F.,Gandini, Alessandro
, p. 26829 - 26837 (2014/07/21)
Novel linear and crosslinked polymers from non-modified and modified tung oil are reported. These materials are based on the exploitation of the Diels-Alder reaction using, on the one hand, the dienic character of the three conjugated double bonds of tung oil and their susceptibility to react with a dienophile, and, on the other hand, the bulk reaction of furfuryl amine at the ester moieties of tung oil to produce three fatty acid furan amides, still bearing the three conjugated double bonds, and their linear polymerization with bismaleimides. This journal is the Partner Organisations 2014.
An efficient reverse Diels-Alder approach for the synthesis of N-alkyl bismaleimides
Rao, Venkataramanarao,Navath, Suryakiran,Kottur, Mohankumar,McElhanon, James R.,McGrath, Dominic V.
, p. 5011 - 5013 (2013/09/02)
Bismaleimides are useful precursors for Diels-Alder reactions, Michael additions, and thiol-maleimide based conjugation for the synthesis of materials and polymers. Use of bismaleimide cross linkers for generating polymers, bioconjugate molecules, and useful imaging molecules is an active area of research. An efficient and practical synthetic protocol for N-alkyl bis-maleimide cross linkers starting from furan protected maleimide employing a reverse Diels-Alder reaction is reported.
A Diels-Alder crosslinkable host polymer for improved PLED performance: The impact on solution processed doped device and multilayer device performance
Patel, Dinesh G.,Graham, Kenneth R.,Reynolds, John R.
experimental part, p. 3004 - 3014 (2012/05/20)
We report on the synthesis of a polyfluorene derivative, PFO(X), with furan pendant groups capable of Diels-Alder crosslinking with a maleimide containing small molecule passive crosslinker (PC) and a maleimide containing red emitting donor-acceptor-donor dopant molecule, bE-BTD(X). It was initially intended that a blend of these three components would afford a system where the dopant concentration could be increased to the point where complete energy transfer from the host polymer to the emissive dopant would be achieved. Because such systems often suffer from quenching and shifts in emission maxima indicative of emitter aggregation, it was hypothesized that crosslinking the emissive dopant with the host polymer would lead to de-aggregation of the dopant emitter. In thin films of PFO(X) and bE-BTD(X), a 16 nm bathochromic shift is observed in the emission maximum when the dopant concentration is increased from 1% to 8%, suggesting that the dopant is aggregating. In similar films where PC is included and the film is heated to affect crosslinking, a comparable 16 nm shift in the emission maximum is observed indicating that aggregation is still occurring and not affected by the heating step. Similar decreases in luminance are observed independent of whether the heating step is included. Not unexpectedly, however, crosslinking does afford an insoluble network that allows for the subsequent solution deposition of additional layers. When an electron transport layer (ETL) is used in PFO(X)/PC devices, increases of 190% and 490% are observed in luminance and luminous efficiency, respectively, relative to devices without an ETL indicating that this Diels-Alder crosslinkable system is amenable to multilayer deposition by solution methods. When bE-BTD(X) is included as the dopant emitter, similar increases in luminance and luminous efficiency are observed with the ETL included compared to devices where this layer is omitted.
