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MedKoo Cat#: 584140 | Name: Cystamine
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Description:

WARNING: This product is for research use only, not for human or veterinary use.

Cystamine, also known as Aminoethyl-SS-ethylamine, is a cleavable PEG Linker and radiation-protective agent that interferes with sulfhydryl enzymes. It may also protect against carbon tetrachloride liver damage.

Chemical Structure

Cystamine
Cystamine
CAS#51-85-4 (free base)

Theoretical Analysis

MedKoo Cat#: 584140

Name: Cystamine

CAS#: 51-85-4 (free base)

Chemical Formula: C4H12N2S2

Exact Mass: 152.0442

Molecular Weight: 152.27

Elemental Analysis: C, 31.55; H, 7.94; N, 18.40; S, 42.11

Price and Availability

Size Price Availability Quantity
250mg USD 250.00 2 Weeks
1g USD 550.00 2 Weeks
2g USD 750.00 2 Weeks
5g USD 1,050.00 2 Weeks
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Related CAS #
51-85-4 (free base) 56-17-7 (2HCl)
Synonym
Cystamine; Aminoethyl-SS-ethylamine; Mercamine disulfide; Becaptan disulfure; 1591 L; 1591-L; 1591L; BRN 1736027; BRN-1736027; BRN1736027
IUPAC/Chemical Name
2,2'-Dithiobis(ethylamine)
InChi Key
APQPRKLAWCIJEK-UHFFFAOYSA-N
InChi Code
InChI=1S/C4H12N2S2/c5-1-3-7-8-4-2-6/h1-6H2
SMILES Code
NCCSSCCN
Appearance
Solid powder
Purity
>95% (or refer to the Certificate of Analysis)
Shipping Condition
Shipped under ambient temperature as non-hazardous chemical. This product is stable enough for a few weeks during ordinary shipping and time spent in Customs.
Storage Condition
Dry, dark and at 0 - 4 C for short term (days to weeks) or -20 C for long term (months to years).
Solubility
Soluble in DMSO
Shelf Life
>2 years if stored properly
Drug Formulation
This drug may be formulated in DMSO
Stock Solution Storage
0 - 4 C for short term (days to weeks), or -20 C for long term (months).
HS Tariff Code
2934.99.9001
More Info
Product Data
Product Data
Instruction
View handling instruction
Biological target:
Cystamine is an alkyl chain-based PROTAC linker that can be used in the synthesis of PROTACs.
In vitro activity:
Cystamine treatment resulted in a dose- and time-dependent cytotoxicity in the DU145 and HeLa cell lines but showed no effect in the MCF7 and A549 cell lines (Fig. 1a–d). Reference: Biochim Biophys Acta. 2015 Mar;1853(3):619-31. https://pubmed.ncbi.nlm.nih.gov/25549939/
In vivo activity:
Interestingly, cystamine co-treatment profoundly suppressed 2,5-HD-induced motor deficits. Compared with the rats in the 2,5-HD group, the cystamine co-treated animals were able to walk normally although they moved slowly than the rats in the control group. Reference: Toxicol Res (Camb). 2017 Mar 1; 6(2): 199–204. https://www.ncbi.nlm.nih.gov/pmc/articles/PMC6062339/
Solvent mg/mL mM
Solubility
DMSO 100.0 656.73
Note: There can be variations in solubility for the same chemical from different vendors or different batches from the same vendor. The following factors can affect the solubility of the same chemical: solvent used for crystallization, residual solvent content, polymorphism, salt versus free form, degree of hydration, solvent temperature. Please use the solubility data as a reference only. Warming and sonication will facilitate dissolving. Still have questions? Please contact our Technical Support scientists.

Preparing Stock Solutions

The following data is based on the product molecular weight 152.27 Batch specific molecular weights may vary from batch to batch due to the degree of hydration, which will affect the solvent volumes required to prepare stock solutions.

Recalculate based on batch purity %
Concentration / Solvent Volume / Mass 1 mg 5 mg 10 mg
1 mM 1.15 mL 5.76 mL 11.51 mL
5 mM 0.23 mL 1.15 mL 2.3 mL
10 mM 0.12 mL 0.58 mL 1.15 mL
50 mM 0.02 mL 0.12 mL 0.23 mL
Formulation protocol:
1. Cho SY, Lee JH, Ju MK, Jeong EM, Kim HJ, Lim J, Lee S, Cho NH, Park HH, Choi K, Jeon JH, Kim IG. Cystamine induces AIF-mediated apoptosis through glutathione depletion. Biochim Biophys Acta. 2015 Mar;1853(3):619-31. doi: 10.1016/j.bbamcr.2014.12.028. Epub 2014 Dec 27. PMID: 25549939. 2. Wang S, Li X, Li M, Jiang L, Yuan H, Han W, Wang X, Zeng T, Xie K. Cystamine attenuated behavioral deficiency via increasing the expression of BDNF and activating PI3K/Akt signaling in 2,5-hexanedione intoxicated rats. Toxicol Res (Camb). 2016 Dec 12;6(2):199-204. doi: 10.1039/c6tx00409a. PMID: 30090490; PMCID: PMC6062339. 3. Cisbani G, Drouin-Ouellet J, Gibrat C, Saint-Pierre M, Lagacé M, Badrinarayanan S, Lavallée-Bourget MH, Charest J, Chabrat A, Boivin L, Lebel M, Bousquet M, Lévesque M, Cicchetti F. Cystamine/cysteamine rescues the dopaminergic system and shows neurorestorative properties in an animal model of Parkinson's disease. Neurobiol Dis. 2015 Oct;82:430-444. doi: 10.1016/j.nbd.2015.07.012. Epub 2015 Jul 29. PMID: 26232588.
In vitro protocol:
1. Cho SY, Lee JH, Ju MK, Jeong EM, Kim HJ, Lim J, Lee S, Cho NH, Park HH, Choi K, Jeon JH, Kim IG. Cystamine induces AIF-mediated apoptosis through glutathione depletion. Biochim Biophys Acta. 2015 Mar;1853(3):619-31. doi: 10.1016/j.bbamcr.2014.12.028. Epub 2014 Dec 27. PMID: 25549939.
In vivo protocol:
1. Wang S, Li X, Li M, Jiang L, Yuan H, Han W, Wang X, Zeng T, Xie K. Cystamine attenuated behavioral deficiency via increasing the expression of BDNF and activating PI3K/Akt signaling in 2,5-hexanedione intoxicated rats. Toxicol Res (Camb). 2016 Dec 12;6(2):199-204. doi: 10.1039/c6tx00409a. PMID: 30090490; PMCID: PMC6062339. 2. Cisbani G, Drouin-Ouellet J, Gibrat C, Saint-Pierre M, Lagacé M, Badrinarayanan S, Lavallée-Bourget MH, Charest J, Chabrat A, Boivin L, Lebel M, Bousquet M, Lévesque M, Cicchetti F. Cystamine/cysteamine rescues the dopaminergic system and shows neurorestorative properties in an animal model of Parkinson's disease. Neurobiol Dis. 2015 Oct;82:430-444. doi: 10.1016/j.nbd.2015.07.012. Epub 2015 Jul 29. PMID: 26232588.
1: M GA, S AT, Ayyavu M, A S, Kandasamy R. Synthesis and characterization of cystamine conjugated chitosan-SS-mPEG based 5-Fluorouracil loaded polymeric nanoparticles for redox responsive drug release. Eur J Pharm Sci. 2017 Nov 1. pii: S0928-0987(17)30588-2. doi: 10.1016/j.ejps.2017.10.035. [Epub ahead of print] PubMed PMID: 29080854. 2: Fujita I, Nobunaga M, Seki T, Kurauchi Y, Hisatsune A, Katsuki H. Cystamine-mediated inhibition of protein disulfide isomerase triggers aggregation of misfolded orexin-A in the Golgi apparatus and prevents extracellular secretion of orexin-A. Biochem Biophys Res Commun. 2017 Jul 22;489(2):164-170. doi: 10.1016/j.bbrc.2017.05.118. Epub 2017 May 23. PubMed PMID: 28549585. 3: Vasin MV, Ushakov IB, Kovtun VY, Komarova SN, Semenova LA, Galkin AA, Afanas'ev RV, Bukhtiyarov IV. Pharmacological Analysis of the Therapeutic Effect of Radioprotectors Cystamine and Indralin in the Capacity of Radiomitigators. Bull Exp Biol Med. 2017 Feb;162(4):466-469. doi: 10.1007/s10517-017-3641-1. Epub 2017 Feb 27. PubMed PMID: 28239785. 4: Du AW, Lu H, Stenzel M. Stabilization of Paclitaxel-Conjugated Micelles by Cross-Linking with Cystamine Compromises the Antitumor Effects against Two- and Three-Dimensional Tumor Cellular Models. Mol Pharm. 2016 Nov 7;13(11):3648-3656. Epub 2016 Oct 5. PubMed PMID: 27654333. 5: Liu Y, Yang J, Wang X, Liu J, Wang Z, Liu H, Chen L. In vitro and in vivo evaluation of redox-responsive sorafenib carrier nanomicelles synthesized from poly (acryic acid) -cystamine hydrochloride-D-α-tocopherol succinate. J Biomater Sci Polym Ed. 2016 Dec;27(17):1729-1747. Epub 2016 Sep 27. PubMed PMID: 27632696. 6: Kwon K, Kim JC. Redox-responsive alginate microsphere containing cystamine. J Biomater Sci Polym Ed. 2016 Oct;27(15):1520-33. doi: 10.1080/09205063.2016.1215800. Epub 2016 Aug 8. PubMed PMID: 27484719. 7: Bockuviene A, Slavuckyte K, Vareikis A, Zigmantas S, Zaliauskiene L, Makuska R. Intracellular Delivery and Triggered Release of DNA Using Biodegradable Poly(2-hydroxypropylene imine)s Containing Cystamine Units. Macromol Biosci. 2016 Oct;16(10):1497-1505. doi: 10.1002/mabi.201600155. Epub 2016 Jul 14. PubMed PMID: 27412922. 8: Yan T, Li D, Li J, Cheng F, Cheng J, Huang Y, He J. Effective co-delivery of doxorubicin and curcumin using a glycyrrhetinic acid-modified chitosan-cystamine-poly(ε-caprolactone) copolymer micelle for combination cancer chemotherapy. Colloids Surf B Biointerfaces. 2016 Sep 1;145:526-538. doi: 10.1016/j.colsurfb.2016.05.070. Epub 2016 May 26. PubMed PMID: 27281238. 9: Zhang H, Zheng M, Wu M, Xu D, Nishimura T, Nishimura Y, Giffard R, Xiong X, Xu LJ, Clark JD, Sahbaie P, Dill DL, Peltz G. A Pharmacogenetic Discovery: Cystamine Protects Against Haloperidol-Induced Toxicity and Ischemic Brain Injury. Genetics. 2016 May;203(1):599-609. doi: 10.1534/genetics.115.184648. Epub 2016 Mar 18. PubMed PMID: 26993135; PubMed Central PMCID: PMC4858802. 10: Wang X, Zhang J, Cheng R, Meng F, Deng C, Zhong Z. Facile Synthesis of Reductively Degradable Biopolymers Using Cystamine Diisocyanate as a Coupling Agent. Biomacromolecules. 2016 Mar 14;17(3):882-90. doi: 10.1021/acs.biomac.5b01578. Epub 2016 Feb 8. PubMed PMID: 26810050. 11: Engholm M, Pinilla E, Mogensen S, Matchkov V, Hedegaard ER, Chen H, Mulvany MJ, Simonsen U. Involvement of transglutaminase 2 and voltage-gated potassium channels in cystamine vasodilatation in rat mesenteric small arteries. Br J Pharmacol. 2016 Mar;173(5):839-55. doi: 10.1111/bph.13393. Epub 2016 Jan 27. PubMed PMID: 26603619; PubMed Central PMCID: PMC4761098. 12: Oliveira AV, Marcelo A, da Costa AM, Silva GA. Evaluation of cystamine-modified hyaluronic acid/chitosan polyplex as retinal gene vector. Mater Sci Eng C Mater Biol Appl. 2016 Jan 1;58:264-72. doi: 10.1016/j.msec.2015.08.047. Epub 2015 Aug 28. PubMed PMID: 26478310. 13: Cisbani G, Drouin-Ouellet J, Gibrat C, Saint-Pierre M, Lagacé M, Badrinarayanan S, Lavallée-Bourget MH, Charest J, Chabrat A, Boivin L, Lebel M, Bousquet M, Lévesque M, Cicchetti F. Cystamine/cysteamine rescues the dopaminergic system and shows neurorestorative properties in an animal model of Parkinson's disease. Neurobiol Dis. 2015 Oct;82:430-444. doi: 10.1016/j.nbd.2015.07.012. Epub 2015 Jul 29. PubMed PMID: 26232588. 14: Eslami M, Hashemianzadeh SM, Bagherzadeh K, Seyed Sajadi SA. Molecular perception of interactions between bis(7)tacrine and cystamine-tacrine dimer with cholinesterases as the promising proposed agents for the treatment of Alzheimer's disease. J Biomol Struct Dyn. 2016;34(4):855-69. doi: 10.1080/07391102.2015.1057526. Epub 2015 Jul 8. PubMed PMID: 26043757. 15: Aleman MM, Holle LA, Stember KG, Devette CI, Monroe DM, Wolberg AS. Cystamine preparations exhibit anticoagulant activity. PLoS One. 2015 Apr 27;10(4):e0124448. doi: 10.1371/journal.pone.0124448. eCollection 2015. PubMed PMID: 25915545; PubMed Central PMCID: PMC4411037. 16: Nanda SS, An SS, Yi DK. Oxidative stress and antibacterial properties of a graphene oxide-cystamine nanohybrid. Int J Nanomedicine. 2015 Jan 12;10:549-56. doi: 10.2147/IJN.S75768. eCollection 2015. PubMed PMID: 25609960; PubMed Central PMCID: PMC4298342. 17: Cho SY, Lee JH, Ju MK, Jeong EM, Kim HJ, Lim J, Lee S, Cho NH, Park HH, Choi K, Jeon JH, Kim IG. Cystamine induces AIF-mediated apoptosis through glutathione depletion. Biochim Biophys Acta. 2015 Mar;1853(3):619-31. doi: 10.1016/j.bbamcr.2014.12.028. Epub 2014 Dec 27. PubMed PMID: 25549939. 18: Li PC, Jiao Y, Ding J, Chen YC, Cui Y, Qian C, Yang XY, Ju SH, Yao HH, Teng GJ. Cystamine improves functional recovery via axon remodeling and neuroprotection after stroke in mice. CNS Neurosci Ther. 2015 Mar;21(3):231-40. doi: 10.1111/cns.12343. Epub 2014 Nov 27. PubMed PMID: 25430473. 19: Wu J, Sandberg M, Weber SG. Integrated electroosmotic perfusion of tissue with online microfluidic analysis to track the metabolism of cystamine, pantethine, and coenzyme A. Anal Chem. 2013 Dec 17;85(24):12020-7. doi: 10.1021/ac403005z. Epub 2013 Nov 22. PubMed PMID: 24215585; PubMed Central PMCID: PMC3899583. 20: Ribeiro M, Silva AC, Rodrigues J, Naia L, Rego AC. Oxidizing effects of exogenous stressors in Huntington's disease knock-in striatal cells--protective effect of cystamine and creatine. Toxicol Sci. 2013 Dec;136(2):487-99. doi: 10.1093/toxsci/kft199. Epub 2013 Sep 5. PubMed PMID: 24008831.