L-Cystine dimethyl ester dihydrochloride
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L-Cystine dimethyl ester dihydrochloride

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L-Cystine dimethyl ester dihydrochloride serves as an efficacious antioxidant, exhibiting commendable immunomodulatory, metabolic and cytoprotective potential. Its application is extended towards abating oxidative stress, addressing cardiovascular complications, and counteracting hepatic insult instigated by noxious agents. In essence, this compound offers a multifaceted therapeutic approach to sustain homeostatic balance in cellular milieu.

Category
L-Amino Acids
Catalog number
BAT-015046
CAS number
32854-09-4
Molecular Formula
C8H18Cl2N2O4S2
Molecular Weight
341.28
L-Cystine dimethyl ester dihydrochloride
Size Price Stock Quantity
100 g $199 In stock
IUPAC Name
methyl (2R)-2-amino-3-[[(2R)-2-amino-3-methoxy-3-oxopropyl]disulfanyl]propanoate;dihydrochloride
Synonyms
Dimethyl L-cystinate dihydrochloride; (2R,2'R)-Dimethyl 3,3'-disulfanediylbis(2-aminopropanoate) dihydrochloride; Dimethyl 3,3'-disulfanediyl(2R,2'R)-bis(2-aminopropanoate) dihydrochloride; NSC 161614; L-cysteine methyl ester (1->1')-disulfide compound with L-cysteine methyl ester hydrochloride
Related CAS
1069-29-0 (free base)
Appearance
White Solid
Purity
>95%
Melting Point
180-185°C
Boiling Point
375.5°C at 760 mmHg
Storage
Store at RT
Solubility
Soluble in DMSO, Methanol, Water
InChI
InChI=1S/C8H16N2O4S2.2ClH/c1-13-7(11)5(9)3-15-16-4-6(10)8(12)14-2;;/h5-6H,3-4,9-10H2,1-2H3;2*1H/t5-,6-;;/m0../s1
InChI Key
QKWGUPFPCRKKMQ-USPAICOZSA-N
Canonical SMILES
COC(=O)C(CSSCC(C(=O)OC)N)N.Cl.Cl

L-Cystine dimethyl ester dihydrochloride, a chemical compound with diverse applications in bioscience and medical research, offers a multitude of benefits. Here are four key applications:

Cell Culture Media: Often integrated as a supplement in cell culture media, L-Cystine dimethyl ester dihydrochloride plays a pivotal role in supporting the growth and maintenance of various cell lines. Providing an essential sulfur amino acid, it fosters enhanced cell viability and proliferation, proving invaluable in both academic research and industrial bioprocessing applications.

Antioxidant Research: Serving as a precursor to vital antioxidants like L-cystine and glutathione within the cell, this compound is a cornerstone in studying oxidative stress mechanisms and developing interventions to combat oxidative damage in diseases such as neurodegeneration and cancer. By offering a controlled source of cystine, L-Cystine dimethyl ester dihydrochloride aids in unraveling the intricate antioxidant pathways.

Biochemical Assays: Widely utilized in various biochemical assays, L-Cystine dimethyl ester dihydrochloride is instrumental in exploring the role of cystine in metabolic pathways and protein synthesis. Its frequent involvement in studies pertaining to the cystine-glutamate antiporter system, crucial for maintaining cellular amino acid balance, makes it particularly relevant in cancer research, where cystine transport is often deregulated.

Pharmaceutical Development: In the realm of drug development, L-Cystine dimethyl ester dihydrochloride plays a crucial role in producing cystine-rich peptides and proteins with heightened stability. Its ability to stabilize protein structures makes it a valuable component in formulating drugs with enhanced efficacy and extended shelf life. Additionally, it functions as a fundamental building block for prodrugs engineered to release cystine in a controlled manner, ensuring targeted therapeutic effects with precision.

1. Amino Acid Based Hydrogels with Dual Responsiveness for Oral Drug Delivery
Shiqi Wang, Xiaoxue Liu, Ignacio J Villar-Garcia, Rongjun Chen Macromol Biosci. 2016 Sep;16(9):1258-64. doi: 10.1002/mabi.201600078. Epub 2016 May 6.
This study reports a series of novel amino acid based dual-responsive hydrogels. Prepared by a facile one-pot 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide (EDC) coupling reaction, the solid content, structure, and mechanical behavior of hydrogels could be easily adjusted by changing the concentrations of the polymers and the crosslinkers. With pH-responsive anionic pseudo-peptides as backbones and disulfide-containing l-cystine dimethyl ester as crosslinkers, these hydrogels are able to collapse and form relatively compact structure at an acidic pH, while swelled and partly dissociated at a neutral pH. Further addition of dithiothreitol (DTT) facilitated complete degradation of hydrogels. The high loading efficiency, rapid but complete triggered-release, and good biocompatibility make these hydrogels promising candidates for oral delivery.
2. A pH-Responsive Amphiphilic Hydrogel Based on Pseudopeptides and Poly(ethylene glycol) for Oral Delivery of Hydrophobic Drugs
Shiqi Wang, Reva Attah, Jiali Li, Yitong Chen, Rongjun Chen ACS Biomater Sci Eng. 2018 Dec 10;4(12):4236-4243. doi: 10.1021/acsbiomaterials.8b01040. Epub 2018 Oct 10.
Oral administration is a noninvasive and convenient drug delivery route most preferred by patients. However, poor stability in the gastrointestinal tract and low bioavailability of hydrophobic drugs has greatly limited their oral administration. To address this problem, we report a pH-responsive, amphiphilic hydrogel drug carrier based on a pseudopeptide poly(l-lysine isophthalamide) (PLP) and poly(ethylene glycol) (PEG). The hydrogels were prepared by a simple N-(3-(dimethylamino)propyl)-N'-ethyl carbodiimide hydrochloride (EDC)/N-hydroxysuccinimide (NHS) coupling reaction, and the cross-linking was confirmed by infrared spectroscopy and differential scanning calorimetry analyses. Because of the pH-responsive conformational alteration of PLP, the hydrogels were relatively hydrophobic and collapsed at acidic pH, but became hydrophilic and swollen at neutral pH. The amphiphilicity enabled the hydrogels to well retain and protect hydrophobic model drugs in the simulated gastric fluid, but efficiently release them in the simulated intestinal fluid. These results suggested that the pH-responsive amphiphilic hydrogels are promising candidates for oral delivery of hydrophobic drugs.
3. A dual pH and redox-responsive Ag/AgO/carboxymethyl chitosan composite hydrogel for controlled dual drug delivery
Yanqin Xu, Jie Liu, Shumin Guan, Yuan Cao, Changguo Chen, Dan Wang J Biomater Sci Polym Ed. 2020 Sep;31(13):1706-1721. doi: 10.1080/09205063.2020.1774118. Epub 2020 Jul 2.
A pH and redox dual-responsive composite hydrogel was developed, which was formed from triblock copolymer PEG-SS-PCL-SS-PEG and Ag/AgO/carboxymethyl chitosan (CMCS) hydrogel inclusion complexes. Dithiodipropionic acid and poly(ethylene glycol) (PEG) were esterified to synthesize a hydrophilic segment PEG-SS-COOH polymer containing a disulfide bond, and ε-caprolactone is ring-opened in Ar atmosphere to obtain a hydrophobic segment HO-PCL-OH homopolymer. The PEG-SS-PCL-SS-PEG triblock polymers were prepared by reacting the two in a certain ratio, and spontaneously assembled into micelles in an aqueous solution. Ag/AgO/CMCS composite hydrogels with a pH and redox dual-responsive were prepared by dispersing aspirin-loaded micelles into an Ag/AgO/CMCS hydrogel network loaded with another hydrophilic drug ciprofloxacin hydrochloride (CIP). The results showed that the micelles had redox sensitivity due to the insertion of disulfide bonds, and had certain stability within 24 h without reducing substances. In vitro simulated drug release test of composite hydrogel showed that the hydrogel network swelled or degraded, the micelles were lysed, and the release of the drug was triggered when the composite hydrogels were exposed to the micro-environment with high pH or high DTT concentration. Therefore, this composite hydrogel could potentially be one of the candidate materials for the dual drug delivery system.
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