60984-57-8

Usage

Uses

Used in Biochemistry:
N,N'-BIS(ACRYLOYL)CYSTAMINE is used as a reversible cross-linker for polyacrylamide gels, which is essential in the process of DNA purification. This application allows for the efficient separation and analysis of DNA fragments in various research and diagnostic applications.
Used in Chemical Synthesis:
In the field of chemical synthesis, N,N'-BIS(ACRYLOYL)CYSTAMINE finds its use in the Suzuki reaction, a widely employed method for the formation of carbon-carbon bonds, particularly in the synthesis of complex organic molecules.
Used in Material Science:
N,N'-BIS(ACRYLOYL)CYSTAMINE is utilized in the fabrication of hydrogel-modified plasmonic crystals. These materials have potential applications in the development of advanced optical and sensing devices due to their unique optical properties.

Upstream product

• 56-17-7 cystamine dihydrochioride 
• 814-68-6 acryloyl chloride 
• 51-85-4 2,2'-dithio-bis[ethylamine] 
• 1072-22-6 cystamine hydrochloride 
• 156-57-0 2-mercaptoethylamine hydrochloride 

Relevant academic research and scientific papers

Fabrication and evaluation of reduction-sensitive supramolecular hydrogel based on cyclodextrin/polymer inclusion for injectable drug-carrier application

Supramolecular hydrogels based on cyclodextrin/polymer inclusion are an emerging injectable biomaterial for drug controlled-release and cell capsulation. Although the pH- and temperature-sensitivity has been focused on contributing to intelligence, the system sensitive to physiological reduction condition caused by glutathione tripepetide (GSH) has not been reported so far. In this work, novel reduction-sensitive supramolecular hydrogels were, for the first time, fabricated by the inclusion of [poly(ethylene glycol) monomethyl ether]-graft-[disulfide-linked poly(amido amine)] (mPEG-g-SS-PAA) with α-cyclodextrin (α-CD) in aqueous solution. The reduction-sensitivity was ascribed to the disulfide linker in the SS-PAA main chain while various physical conjugations contributed to a reversible gel-sol transition under shearing as a key of injectable function. The drug release from such a supramolecular hydrogel showed a prominent sustained release profile, and the release rate could further be regulated depending upon the reduction condition. It is worth noting that incorporating a low loading-level of reducing agent did not inhibit the formation of hydrogel. As a result, it became possible to use the reduction-sensitivity to regulate the drug release profile in extracellular milieus and normal tissue. Combined with acceptable cytotoxicity, this kind of reduction-sensitive supramolecular hydrogel based on cyclodextrin/polymer inclusion showed a great potential as an injectable smart biomaterial for the application of drug controlled-release.

Property and application of BACy-based functional hydrogels

Conventional polyacrylamide hydrogels prepared from the free radical polymerization between acrylamide and N,N-methylenebisacrylamide (NMBA) have been frequently used in the biochemical technique like the sodium dodecyl sulfate polyacrylamide gel electrophoresis (SDS-PAGE) to resolve protein mixtures. In this study, we have prepared an alternative polyacrylamide hydrogel from the cross-linking of acrylamide and N,N-bisacrylylcystamine (BACy). In addition, we have compared the BACy-based hydrogel with the NMBA-based polyacrylamide hydrogel for their physical properties such as swelling ratio, shear modulus, crosslink density and morphology. Moreover, we further determined whether BACy-based polyacrylamide hydrogel could be applied to SDS-PAGE and proteomics research. The results showed that this type of hydrogel is capable of separating proteins and facilitates further in-gel protein digestion and the following protein identifications by mass spectrometry. In summary, our study provides a basis for the putative application of BACy-based hydrogels.

Disulfide-functional poly(amido amine)s with tunable degradability for gene delivery

Controlled degradability in response to the local environment is one of the most effective strategies to achieve spatiotemporal release of genes from a polymeric carrier. Exploiting the differences in reduction potential between the extracellular and intracellular environment, disulfides are frequently incorporated into the backbone of polymeric drug delivery agents to ensure efficient intracellular release of the payload. However, although to a lesser extent, reduction of disulfides may also occur in the extracellular environment and should be prevented to avoid premature release. Accurate control over the stability of disulfide linkages enables the optimization of polymeric carriers for efficient drug delivery. Bioreducible poly(amido amine)s (PAAs) with varying degrees of steric hindrance adjacent to the disulfide bonds (0, 2 or 4 methyl groups) were prepared in order to obtain carriers with controlled stability. The degradation behavior of these PAA-polymers was evaluated under different reducing conditions and their in vitro toxicities and transfection efficiencies were assessed. Degradation of the PAA-based polyplexes consistently required higher reducing strengths as the steric hindrance near the disulfide bonds increased. Polyplexes based on 2-methyl cystamine disulfide based PAA polymer (PAA2m) remained stable under extracellular glutathione concentrations (0.001–0.01?mM), while degrading within 1?h under reducing conditions similar to those in the intracellular environment (1–10?mM glutathione). This polymer exhibited excellent transfection capabilities, with efficiencies up to 90% of transfected cells. PAA0m showed slightly reduced transfection properties compared to PAA2m, likely due to premature degradation. The severely hindered PAA4m, however, displayed increased toxicity, accompanied by reduced transfection efficiency, as a result of its exceptional stability. These results demonstrate the feasibility of introducing steric hindrance near the disulfide moiety to tune polyplex stability against bioreduction, and show that PAA2m is a promising polymer to be further developed for gene therapy.

Smart GSH/pH dual-bioresponsive degradable nanosponges based on β-CD-appended hyper-cross-linked polymer for triggered intracellular anticancer drug delivery

Efficient accumulation and on-demand intracellular drug release in the desired site are a crucial issue in developing ideal drug delivery systems (DDSs). Glutathione (GSH)/pH dual-bioresponsive degradable Nanosponges were developed based on β-CD-appended hyper-cross-linked polymer by one-pot polymerization of acryloyl-6- ethylenediamine-6-deoxy-β-Cyclodextrin (β-CD-NH-ACy), acrylic acid (AA) and N,N-bis(acryloyl)- cystamine (BACy) as cross-linker to deliver doxorubcin (DOX) and investigated for GSH/pH triggered DOX release, in which the massive carboxyl and amino groups, and disulfide bonds were used as pH and GSH bioresponsive fragments, respectively. In the proposed DDSs, DOX was readily incorporated into the three dimensional networks of the Nanosponges either as inclusion complexes or as non-inclusion complexes, with a high drug loading capacity of 22.6%. In vitro release studies suggested that the Nanosponges exhibited GSH/pH triggered disintegration and drug release performance, in which DOX release was significantly accelerated in acidic (pH5.0) and cytosolic reduction (10 mM GSH) conditions, with ~77.0% of DOX release. The morphology changes of DOX@Nanosponges in releasing media (pH5.0, 10 mM GSH) were further studied by TEM. Confocal microscopy observation demonstrated that DOX was delivered and released into cytoplasm and nucleus of A549 cells in 7 h incubation with DOX@Nanosponges. MTT assays manifested that the Nanosponges exhibited low cytotoxicity up to a concentration of 1000 μg/mL and DOX@Nanosponges had high anti-tumor activity. These findings demonstrated that the dual-bioresponsive Nanosponges may function as a promising platform for targeted delivery and intracellular drug controlled release in tumor therapy.

Redox-responsive chemosensitive polyspermine delivers ursolic acid targeting to human breast tumor cells: The depletion of intracellular GSH contents arouses chemosensitizing effects

Antitumor efficacy of ursolic acid (UA) is seriously limited due to its low hydrophilicity and needy bioavailability. To overcome these obstacles, chemosensitive polyspermine (CPSP) conjugated with UA and folic acid (FA) as a novel targeted prodrug was designed and successfully synthesized in this investigation. This prodrug not only showed high aqueous solubility, GSH-triggered degradation and good biocompatibility, but also exhibited better inhibition effect on the tumor cells proliferation in comparison with free UA. FA-CPSP-UA could down-regulate the generation of GSH and manifest excellent ability in enhancing antitumor efficacy. In addition, FA-CPSP-UA could inhibit the expression of MMP-9, which led to restricting MCF-7 cells migration. Taken together, the results indicated that FA-CPSP-UA, as a carrier, can efficiently deliver UA to folate receptor positive cancer cells and improve tumor therapy of UA by Chemosensitive effect.

Fluorescent mannose-functionalized hyperbranched poly(amido amine)s: Synthesis and interaction with E. coli

A water-soluble, biodegradable and fluorescent hyperbranched poly(amidoamine) with mannose groups on their surface (M-HPAMAM) has been successfully prepared, and the synthetic strategy includes Michael addition polymerization of diacrylamide with 1-(2-aminoethyl)piperazine and, subsequently, surface modification with mannosamine. The photoluminescence of M-HPAMAM was enhanced significantly due to the surface mannose groups. Incubation of E. coli with M-HPAMAMs yielded brightly fluorescent bacteria clusters, but the fluorescent intensity of the aqueous solution lowered. This indicates that the M-HPAMAMs have strong affinity with bacteria due to their polyvalent interactions. Based on the size and the amount of bacteria clusters formed, the bacteria with the concentrations higher than 102 cfu/mL can be detected.

Synthesis and qualitative analysis of BACy and Its self-polymer

Many synthetic strategies of a reversible cross-linker N,N'-bis(acryloyl) cystamine (BACy) involve the typical condensation between the amino group of cystamine and the acyl group of acryloyl chloride in the mixed-phase solvent system. In this study, the synthesis of BACy was performed in pure organic phase during the whole process. The yield and purity of synthesized BACy were comparable to those from aqueous/ organic phase procedures. In addition, polymerization of BACy was also carried out by free radical reaction to prepare the self-polymer and hydrogel which were characterized with FT-IR, DSC and UV/ VIS spectrophotometer. Notably, the BACy and its self-polymer were both cleavable when exposed to the reducing agents, i.e. 1,4-dithiothreitol (DTT) and 2-mercaptoethanol (-ME). Interestingly, the reduced product of BACy contains vinyl and thiol groups, which could be further applied to the co-polymerization with other monomeric units. On the other hand, carefully controlled reduction of BACy self-polymer may be used to create the modified polymers with available thiol-end groups for further chemistry. Together, our study provides modified procedure for BACy synthesis and characteristics of BACy self-polymer and hydrogel. Further application of BACy and its self-polymer in developing polymers with additional functionality is anticipated.

Albumin nanoparticles for glutathione-responsive release of cisplatin: New opportunities for medulloblastoma

Redox-responsive nanoparticles were synthesized by desolvation of bovine serum albumin followed by disulfide-bond crosslinking with N, N?-Bis (acryloyl) cystamine. Dynamic light scattering and transmission electron microscopy studies revealed spherical na

Bioreducible and acid-labile polydiethylenetriamines with sequential degradability for efficient transgelin-2 siRNA delivery

The transgelin-2 (TAGLN2) protein plays an important role in multidrug resistance in human breast cancer. siRNA mediated gene silencing of TAGLN2 is a promising strategy for paclitaxel resistance reversal in breast cancer. In this study, a series of bioreducible and acid-labile polydiethylenetriamines (PDs) with different proportions of cross-linkers were synthesized. TAGLN2 siRNA was condensed by PDs to form dual-responsive nanocomplexes, and these nanocomplexes were hypothesized to partially degrade in the acidic environment of endosomes, and then completely degrade in the reducing environment of the cytoplasm to release siRNA. It was found that PDs have good water solubility, acid-base buffering capacity, suitable degradability and high biocompatibility. Moreover, PDCKM can deliver TAGLN2 siRNA into MCF-7/PTX cells and inhibit the expression of TAGLN2 even better than PEI 25k. Besides, paclitaxel showed higher cytotoxicity in cells incubated with PDCKM/TAGLN2 siRNA nanocomplexes. These results suggested that PDs have great potential for safe and efficient siRNA delivery to reverse paclitaxel resistance in breast cancer.

A copolymer capsule with a magnetic core for hydrophilic or hydrophobic drug delivery via thermo-responsive stimuli or carrier biodegradation

In this work, we report the successful preparation of a dual-responsive polymer microcapsule carrier with a magnetic core, Fe3O4@capsule nanoparticles, by cross-linked polymerization of N-isopropylacrylamide and acrylamide in the presence of N,N′-bis(acryloyl)cystamine as a crosslinker. These novel drug carriers can undergo volume phase transition upon changing the environmental temperature or biodegradation of the polymer capsule by cleavage of the predesigned disulfide bonds within the crosslinker in the presence of glutathione (GSH) for hydrophilic or hydrophobic drug release. Herein, we take doxorubicin hydrochloride (DOX) as a hydrophilic drug model and curcumin as a hydrophobic drug model for investigating thermal responsiveness and biodegradation of magnetic polymer capsule carriers. Results indicate that DOX is released rapidly with thermal treatment and the release rate of DOX at PBS 5 is much faster than that at PBS 7.4. In addition, the release of water-insoluble drug curcumin is much faster with the assistance of GSH than without.