1355342-67-4Relevant articles and documents
Oxidation-responsive poly(amino ester)s containing arylboronic ester and self-immolative motif: Synthesis and degradation study
Song, Cheng-Cheng,Ji, Ran,Du, Fu-Sheng,Li, Zi-Chen
, p. 8416 - 8425 (2013)
We report the synthesis of a new type of amphiphilic poly(amino ester)s which can be completely degraded in aqueous media via H2O2 oxidation. The polymers were prepared by the controlled Michael-type addition polymerization of a phenylboronic pinacol ester-containing diacrylate and N-aminoethylpiperazine, followed by postmodification with mPEG5K-succinimide ester. Upon oxidation, the side chain phenylboronic esters will be transformed into phenol groups which can trigger the sequential self-immolative process to degrade the polymer main chain. Meanwhile, the amino groups on the polymer main chain are capable of trapping the highly active quinone methides generated in situ during the oxidative degradation of the polymers. Based on the detailed oxidation kinetics and products of several model compounds, the H 2O2-triggered degradation of nanoparticles of these copolymers was investigated by NMR spectroscopy, GPC, and Nile red fluorescence probe. The results demonstrate that the poly(amino ester) backbones were completely degraded by H2O2, resulting in the dissociation of nanoparticles. Oxidative degradation rates of the nanoparticles could be accelerated by increasing the concentration of H2O2, the PEGylation degree, or the pH of the buffer. Interestingly, the in situ formed quinone methides could be captured by secondary amines due to their higher nucleophilicity than H2O. Of potential importance, these amphiphilic oxidation-responsive copolymers are sensitive to stimulation of 200 μM H 2O2; therefore, they may find application in the field of intelligent drug/gene delivery systems.
H2O2-Responsive amphiphilic polymer with aggregation-induced emission (AIE) for DOX delivery and tumor therapy
Liang, Ya-Xuan,Sun, Xue-Yi,Xu, De-Zhong,Huang, Jun-Ru,Tang, Quan,Lu, Zhong-Lin,Liu, Rui
, (2021/12/27)
Stimuli-responsive drug delivery systems (DDSs) based on amphiphilic polymers have attracted much attention. In this study, we reported an innovative H2O2-responsive amphiphilic polymer (TBP), bearing a H2O2-sen
ROS-responsive and multifunctional anti-Alzheimer prodrugs: Tacrine-ibuprofen hybrids via a phenyl boronate linker
Liu, Zhikun,Zhang, Bin,Xia, Shengjin,Fang, Lei,Gou, Shaohua
, (2020/11/20)
Current drugs available in clinic for Alzheimer's disease (AD) treatment can only alleviate disease symptoms without clearly curing or delaying the process of AD. And some AD drugs failed in Phase III clinical trials are only focused on targeting amyloid-
Multifunctional prodrug and derivative thereof, preparation method, pharmaceutical composition and application
-
, (2021/01/24)
The invention discloses a multifunctional prodrug and a derivative thereof, a preparation method, a pharmaceutical composition and application thereof. The chemical structure of the multifunctional prodrug is shown as a formula I, and the derivative of th
Lectin-Triggered Aggregation of Glyco-Gold Nanoprobes for Activity-based Sensing of Hydrogen Peroxide by the Naked Eye
Yeh, Che-Ming,Chen, Ming-Chun,Wu, Tzu-Chien,Chen, Jyun-Wei,Lai, Chian-Hui
, p. 3462 - 3468 (2021/09/16)
The purpose of this study was to develop a colorimetric assay for detecting hydrogen peroxide (H2O2) through a combination of using an aryl boronate (AB) derivative and gold nanoparticles (AuNPs). The unique optical property of AuNPs is applied to design a detection probe. The aggregation of AuNPs could be directly observed as a color change by the naked eye. A mannoside-boronate-sulfide (MBS) ligand was designed that contains an arylboronate (AB), a mannoside, and a thiol group. The thiol group bonds covalently with the surface of AuNPs to obtain MBS@AuNPs. The mannoside moiety recognizes concanavalin A (Con A), a lectin with four carbohydrate recognition sites that can specifically recognize the non-reducing end of an α-D-mannoside or α-D-glucoside structure. The AB structure on MBS first reacts with H2O2 and then inserts an oxygen atom in the B?H bond, which triggers intramolecular electron rearrangement to cleave the covalent bond, resulting in a MBSt mixture. The MBS or MBSt is then modified to citrate-coated AuNPs (c-AuNPs) to have MBS@AuNPs or MBSt@AuNPs. When the MBS@AuNPs are incubated with Con A, the Con A recognizes multiple mannosides on the surface of the MBS@AuNPs. Subsequently, the MBS@AuNPs aggregate and the solution's color changes from red to purple, but this color change does not occur in the case of MBSt@AuNPs. The phenomenon can be observed by the naked eye.
Oxidation-triggered aggregation of gold nanoparticles for naked-eye detection of hydrogen peroxide
Wu, Shaojue,Tan, Si Yu,Ang, Chung Yen,Luo, Zhong,Zhao, Yanli
, p. 3508 - 3511 (2016/03/04)
Naked-eye detection of H2O2 was realized based on the color change of gold nanoparticles upon aggregation. The removal of polyethylene glycol chains from the nanoparticle surface under H2O2 treatment let to the exposure of inner hydrophobic ligands, causing the nanoparticle aggregation in aqueous medium. This detection system shows a wide dynamic range in the μM scale and a distinguishable limit of 10 μM.
BIOCOMPATIBLE POLYMERIC NANOPARTICLES DEGRADE AND RELEASE CARGO IN RESPONSE TO BIOLOGICALLY RELEVANT LEVELS OF HYDROGEN PEROXIDE
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, (2014/09/29)
Disclosed are compositions and synthesis methods that pertain to biocompatible polymeric capsules capable of undergoing backbone degradation and cargo release upon exposure to biologically relevant concentrations of hydrogen peroxide (50-100 μM of H2
Biocompatible polymeric nanoparticles degrade and release cargo in response to biologically relevant levels of hydrogen peroxide
De Gracia Lux, Caroline,Joshi-Barr, Shivanjali,Nguyen, Trung,Mahmoud, Enas,Schopf, Eric,Fomina, Nadezda,Almutairi, Adah
, p. 15758 - 15764 (2012/11/13)
Oxidative stress is caused predominantly by accumulation of hydrogen peroxide and distinguishes inflamed tissue from healthy tissue. Hydrogen peroxide could potentially be useful as a stimulus for targeted drug delivery to diseased tissue. However, curren
A simple FRET-based modular design for diagnostic probes
Redy, Orit,Kisin-Finfer, Einat,Sella, Eran,Shabat, Doron
supporting information; experimental part, p. 710 - 715 (2012/02/05)
In recent years, there has been a massive effort to develop molecular probes with optical modes of action. Probes generally produce detectable signals based on changes in fluorescence properties. Here, we demonstrate the potential of self-immolative molecular adaptors as a platform for Turn-On probes based on the FRET technique. The probe is equipped with identical fluorophore pairs or a fluorophore/quencher FRET pair and a triggering substrate. Upon reaction of the analyte of interest with the triggering substrate, the self-immolative adaptor spontaneously releases the two dye molecules to break off the FRET effect. As a result, a new measurable fluorescent signal is generated. The fluorescence obtained can be used to quantify the analyte. The modular structure of the probe design will allow the preparation of various chemical probes based on the FRET activation technique.
