60984-57-8

Basic information

• Product Name: N,N'-BIS(ACRYLOYL)CYSTAMINE
• Synonyms: CYSTAMINE-N,N'-BISACRYLAMIDE;BAC;BISACRYLOYLCYSTAMINE;BIS-ACRYLYLCYSTAMINE;2,2'-BISACRYLAMIDOETHYL DISULFIDE;2,2'-(BISACRYLAMINO)DIETHYL DISULFIDE;N N'-CYSTAMINE-BIS-ACRYLAMIDE;N,N'-DIACRYLOYLCYSTAMINE
• CAS NO: 60984-57-8
• Molecular Formula: C10H16N2O2S2
• Molecular Weight: 260.38
• EINECS: 262-546-8
• Mol File: 60984-57-8.mol
• Article Data: 23

Chemical Properties

• Melting Point: 121-125 °C
• Boiling Point: 538oC at 760 mmHg
• Flash Point: 279.2oC
• Appearance: /
• Density: 1.164g/cm3
• Storage Temp.: 2-8°C
• Solubility: acetic acid: 50 mg/mL
• PKA: 13.98±0.46(Predicted)
• Water Solubility: Soluble in acetic acid. Slightly soluble in water.
• Stability: Stable. Incompatible with strong oxidizing agents.
• CAS DataBase Reference: N,N'-BIS(ACRYLOYL)CYSTAMINE(CAS DataBase Reference)
• NIST Chemistry Reference: N,N'-BIS(ACRYLOYL)CYSTAMINE(60984-57-8)
• EPA Substance Registry System: N,N'-BIS(ACRYLOYL)CYSTAMINE(60984-57-8)

Safety Data

• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 26-36
• WGK Germany: 3
• F: 8
• Hazardous Substances Data: 60984-57-8(Hazardous Substances Data)

Usage

Description

N,N'-BIS(ACRYLOYL)CYSTAMINE is a white crystalline powder that is known for its versatile applications in various industries due to its unique chemical properties.

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

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

Relevant articles and documents

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.

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.

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.

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.

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 new strategy for hydrophobic drug delivery using a hydrophilic polymer equipped with stacking units

A highly hydrophilic polymer equipped with guanidinium groups was used to load aromatic ring-containing hydrophobic agent doxorubicin (DOX) via π-π interaction. The results have shown that the delivery system exhibited enhanced cellular uptake and antitumor efficiency compared with free drugs. This study opens new avenues for the application of hydrophilic polymers in drug delivery.

Fabrication of reduction-degradable micelle based on disulfide-linked graft copolymer-camptothecin conjugate for enhancing solubility and stability of camptothecin

This research is aimed to develop a reduction-degradable micelle delivery system based on polymer-camptothecin (CPT) conjugate in order to enhance the solubility and stability of CPT in aqueous media. Firstly, disulfide-linked poly(amido amine) (SS-PAA) containing alkyne groups was synthesized by Michael addition polymerization between propargyl amine and N,. N'-bis(acryloyl) cystamine (BAC). And then, azide-functionalized CPT derivatives were conjugated with SS-PAA by click cycloaddition. Further grafting of residual alkyne groups in SS-PAA with azide-terminated poly(ethylene glycol) methyl ether (mPEG) gave mPEG-. g-SS-PAA-CPT conjugate. At last, micelles with size of ca. 88 nm were fabricated from mPEG-. g-SS-PAA-CPT conjugate, suggesting their passive targeting potential to tumor tissue. It was worthy of note that the drug-loaded system of mPEG-. g-SS-PAA-CPT micelles improved the solubility and stability of CPT in aqueous media. Owing to the reduction degradability of disulfide linker in main chain of mPEG-. g-SS-PAA-CPT, the CPT sustainably release from micelles together with the gradual cleavage of polymer in the presence of dithiothreitol (DTT) at the concentration of simulating the intracellular condition while almost no change occurred at the level of DTT corresponding to extracellular condition. Furthermore, the cell viability results showed the essential decrease of cytotoxicity to L929 cell line. These results present a strategy in designing anti-tumor CPT-polymer conjugates for highly selective delivery to tumor cells.

Biotinylated disulfide containing PEI/avidin bioconjugate shows specific enhanced transfection efficiency in HepG2 cells

Targeting of non-viral gene vectors to liver cells could offer the opportunity to cure liver diseases. In this paper, disulfide-containing polyethylenimine (PEI-SS) was synthesized from low molecular weight branched PEI and cystamine bisacrylamide (CBA),

Stepwise dual pH and redox-responsive cross-linked polypeptide nanoparticles for enhanced cellular uptake and effective cancer therapy

The systemic toxicity, reduced cellular internalization, and uncontrollable intracellular drug release of smart nanoparticles (NPs) still need to be overcome for effective cancer therapy. Herein, a series of stepwise dual pH and redox responsive cross-linked polypeptides based on poly(l-lysine-co-N,N-bis(acryloyl)cystamine-co-γ-glutamic acid) (PLBG), were prepared for enhanced cellular uptake and effective cancer therapy. The prepared cross-linked PLBG nanoparticles (PLBG-NPs) exhibit negatively charged surfaces under physiological conditions, and the surface charge of the PLBG-NPs was observed to switch from negative to positive in a slightly acidic tumor extracellular environment at a pH level of ～6.5. Finally, the endosome escape of the PLBG-NPs was facilitated via a proton-sponge effect via protonation of the polymer chain in the endo/lysosome environment of the tumor cell at a pH level of ～5.0. Moreover, rapid drug release was triggered by a high concentration of reducing glutathione (GSH) in tumor cells via destruction of the disulfide linkages in the PLBG-NPs. Cytotoxicity assays demonstrated that no noticeable cytotoxicity was observed for the PLBG-NPs. However, DOX-loaded PLBG-NPs (PLBG-NPs-DOX) demonstrated remarkable tumor cell killing effects. In HeLa tumor-bearing mice, PLBG-NPs-DOX showed sustained tumor accumulation and enhanced inhibitory effects on tumor growth and angiogenesis. In conclusion, it is suggested that the as-designed novel charge-conversion PLBG-NPs with stepwise pH-responsivity and biodegradability could be used as a potential drug carrier for effective cancer therapy with less systemic toxicity.