532424-75-2Relevant academic research and scientific papers
Organocatalytic synthesis and postpolymerization functionalization of allyl-functional poly(carbonate)s
Tempelaar, Sarah,Mespouille, Laetitia,Dubois, Philippe,Dove, Andrew P.
, p. 2084 - 2091 (2011)
Well-defined allyl-functional poly(carbonate)s were synthesized via the organocatalytic ring-opening polymerization of 5-methyl-5-allyloxycarbonyl-1,3- dioxan-2-one using the dual 1-(3,5-bis(trifluoromethyl)phenyl)-3- cyclohexylthiourea and (-)-sparteine catalyst system. The resulting allyl-functional poly(carbonate)s obtained showed low polydispersities and high end-group fidelity, with the versatility of the system being demonstrated by the synthesis of block copolymers and telechelic polymers. Further functionalization of homopolymers with degrees of polymerization of 11 and 100 were realized via the radical addition of thiols to the pendant allyl functional groups, resulting in a range of functional aliphatic poly(carbonate)s.
Leveraging a polycationic polymer to direct tunable loading of an anticancer agent and photosensitizer with opposite charges for chemo-photodynamic therapy
Zhao, Mingying,Wan, Shiyu,Peng, Xinyu,Zhang, Boya,Pan, Qingqing,Li, Sai,He, Bin,Pu, Yuji
, p. 1235 - 1244 (2020)
Herein, we reported a primary amine containing polycationic polymer to load an oppositely charged anticancer drug (doxorubicin, DOX) and a photosensitizer (chlorin e6, Ce6) for combinational chemo-photodynamic therapy. The electrostatic interactions as well as other multiple interactions between the polymer and payloads endowed the drug-loaded nanoparticles with excellent stability. Moreover, the electrostatic attraction between the cationic polymer and anionic Ce6 dictated that Ce6 had higher loading efficiency than DOX. DOX showed pH-responsive drug release owing to the increased solubility of protonated DOX and reduced interaction with the partially protonated polymer under acidic conditions. In contrast, Ce6 showed pH-insensitive release because of the smaller change in solubility and the intense interactions between Ce6 and the polymer. Synergistic chemo/photodynamic therapy of 4T1 cancer cells was achieved by light-triggered reactive oxygen species (ROS)-mediated enhanced cellular uptake and effective endo/lysosomal escape of drug-loaded nanoparticles. Our study demonstrated that the polycationic polymer could act as a robust carrier for differential loading and release of oppositely charged cargos for combinational therapy.
Facile synthesis of dopa-functional polycarbonates via thiol-Ene-coupling chemistry towards self-healing gels
Olofsson, Kristina,Malkoch, Michael,Hult, Anders
, p. 2370 - 2378 (2016)
Since extraction of the naturally occurring mussel-foot proteins is expensive and time-consuming, routes towards synthetic analogues are continuously being explored. Often, these methods involve several protection and deprotection steps, making the synthe
Lactic acid- and carbonate-based crosslinked polymeric micelles for drug delivery
Danquah, Michael,Fujiwara, Tomoko,Mahato, Ram I.
, p. 347 - 362 (2013/02/23)
Our objective was to synthesize and evaluate lactic acid- and carbonate-based biodegradable core- and core-corona crosslinkable copolymers for anticancer drug delivery. Methoxy poly(ethylene glycol)-b-poly(carbonate-co- lactide-co-5-methyl-5-allyloxycarbo
A simple and efficient synthesis of functionalized cyclic carbonate monomers using a versatile pentafluorophenyl ester intermediate
Sanders, Daniel P.,Fukushima, Kazuki,Coady, Daniel J.,Nelson, Alshakim,Fujiwara, Masaki,Yasumoto, Manabu,Hedrick, James L.
supporting information; experimental part, p. 14724 - 14726 (2010/12/24)
An improved two-step synthetic route to functionalized cyclic carbonate monomers that features a novel cyclic carbonate intermediate with an active pentafluorophenyl ester group (MTC-OPhF5) has been developed. The versatile pentafluorophenyl ester intermediate can be synthesized on the gram to kilogram scale in one high-yielding step and is easy to store and handle on the benchtop. The active pentafluorophenyl ester of MTC-OPhF5 is amenable to further substitution with suitable nucleophiles such as alcohols and amines to generate functionalized cyclic carbonates in high yields. The substitution reaction is tolerant of a wide variety of functionalities, including various hydrophobic and hydrophilic groups, reactive functionalities (via thiol-ene click chemistry or alkyl halides), and protected acids, alcohols, thiols, and amines. In view of the ever-increasing need for biodegradable and biocompatible polymers, this new methodology provides a simple and versatile platform for the synthesis of new and innovative materials.
POLYMERS BEARING PENDANT PENTAFLUOROPHENYL ESTER GROUPS, AND METHODS OF SYNTHESIS AND FUNCTIONALIZATION THEREOF
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Page/Page column 12, (2010/12/29)
A one pot method of preparing cyclic carbonyl compounds comprising an active pendant pentafluorophenyl ester group is disclosed. The cyclic carbonyl compounds can be polymerized by ring opening methods to form ROP polymers comprising repeat units comprising a side chain pentafluorophenyl ester group. Using a suitable nucleophile, the pendant pentafluorophenyl ester group can be selectively transformed into a variety of other functional groups before or after the ring opening polymerization.
