606130-90-9Relevant articles and documents
Synthesis of branched monodisperse oligoethylene glycols and 19f mri-traceable biomaterials through reductive dimerization of azides
Chen, Shizhen,Jiang, Zhong-Xing,Li, Yu,Yang, Hao,Yang, Zhigang,Yuan, Yuan,Zhang, Huaibin,Zhang, Jing,Zhou, Xin
, p. 6778 - 6787 (2020/06/08)
Multifunctionalized and branched M-OEGs represent valuable PEGylation agents, linkers, and scaffolds in biomedicine. However, the tedious synthesis limited their availability and application. We herein present an azide reductive dimerization method for the convenient synthesis of aza-M-OEGs and derivatives, which provides easy access to a variety of multifunctionalized and branched M-OEGs in one step. With this method, hexa-arm M-OEGs with 54 symmetrical fluorines were synthesized in two steps as a water-soluble, self-assemble, 19F MRI sensitive, and biocompatible dendritic biomaterial.
Tuneable Transient Thermogels Mediated by a pH- and Redox-Regulated Supramolecular Polymerization
Spitzer, Daniel,Rodrigues, Leona Lucas,Stra?burger, David,Mezger, Markus,Besenius, Pol
, p. 15461 - 15465 (2017/11/13)
A multistimuli-responsive transient supramolecular polymerization of β-sheet-encoded dendritic peptide monomers in water is presented. The amphiphiles, which contain glutamic acid and methionine, undergo a glucose oxidase catalyzed, glucose-fueled transient hydrogelation in response to an interplay of pH and oxidation stimuli, promoted by the production of reactive oxygen species (ROS). Adjusting the enzyme and glucose concentration allows tuning of the assembly and the disassembly rates of the supramolecular polymers, which dictate the stiffness and transient stability of the hydrogels. The incorporation of triethylene glycol chains introduces thermoresponsive properties to the materials. We further show that repair enzymes are able to reverse the oxidative damage in the methionine-based thioether side chains. Since ROS play an important role in signal transduction cascades, our strategy offers great potential for applications of these dynamic biomaterials in redox microenvironments.
N-monosubstituted methoxy-oligo(ethylene glycol) carbamate ester prodrugs of resveratrol
Mattarei, Andrea,Azzolini, Michele,Zoratti, Mario,Biasutto, Lucia,Paradisi, Cristina
, p. 16085 - 16102 (2015/12/01)
Resveratrol is a natural polyphenol with many interesting biological activities. Its pharmacological exploitation in vivo is, however, hindered by its rapid elimination via phase II conjugative metabolism at the intestinal and, most importantly, hepatic levels. One approach to bypass this problem relies on prodrugs. We report here the synthesis, characterization, hydrolysis, and in vivo pharmacokinetic behavior of resveratrol prodrugs in which the OH groups are engaged in an N-monosubstituted carbamate ester linkage. As promoiety, methoxy-oligo(ethylene glycol) groups (m-OEG) (CH3-[OCH2CH2]n-) of defined chain length (n = 3, 4, 6) were used. These are expected to modulate the chemico-physical properties of the resulting derivatives, much like longer poly(ethylene glycol) (PEG) chains, while retaining a relatively low MW and, thus, a favorable drug loading capacity. Intragastric administration to rats resulted in the appearance in the bloodstream of the prodrug and of the products of its partial hydrolysis, confirming protection from first-pass metabolism during absorption.
