| Revision as of 11:09, 24 January 2011 editBeetstra (talk | contribs)Edit filter managers, Administrators172,071 edits Script assisted update of identifiers from ChemSpider, CommonChemistry and FDA for the Chem/Drugbox validation project - Updated: ChEMBL.← Previous edit |
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{{distinguish|cysteamine}} |
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{{Orphan|date=February 2009}} |
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{{chembox |
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{{Chembox |
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| verifiedrevid = 401032824 |
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| reference = <ref>''Merck Index'', 12th Edition, '''2846'''.</ref> |
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| verifiedrevid = 409739949 |
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| ImageFile = cystamine.svg |
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| ImageFile = cystamine.svg |
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| ImageSize = 200px |
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| ImageSize = 230 |
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| ImageAlt = Skeletal formula of cystamine |
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| IUPACName = 2,2'-Dithiobis(ethylamine) |
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| ImageFile1 = Cystamine 3D ball.png |
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| ImageSize1 = 230 |
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| ImageAlt1 = Ball-and-stick model of the cystamine molecule |
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| PIN = 2,2′-Disulfanediyldi(ethan-1-amine) |
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| OtherNames = 2,2'-Dithiobisethanamine<br>2-Aminoethyl disulfide<br>Decarboxycystine |
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| OtherNames = 2,2'-Dithiobisethanamine<br>2-Aminoethyl disulfide<br>Decarboxycystine |
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| Section1 = {{Chembox Identifiers |
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|Section1={{Chembox Identifiers |
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| Abbreviations = AED |
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| Abbreviations = AED |
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| UNII_Ref = {{fdacite|correct|FDA}} |
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| UNII_Ref = {{fdacite|correct|FDA}} |
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| UNII = R110LV8L02 |
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| UNII = R110LV8L02 |
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| InChIKey = APQPRKLAWCIJEK-UHFFFAOYAQ |
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| InChIKey = APQPRKLAWCIJEK-UHFFFAOYAQ |
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| ChEBI_Ref = {{ebicite|changed|EBI}} |
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| ChEBI = 78757 |
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| ChEMBL_Ref = {{ebicite|correct|EBI}} |
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| ChEMBL = 61350 |
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| ChEMBL = 61350 |
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| StdInChI_Ref = {{stdinchicite|correct|chemspider}} |
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| StdInChI_Ref = {{stdinchicite|correct|chemspider}} |
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| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}} |
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| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}} |
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| ChemSpiderID = 2812 |
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| ChemSpiderID = 2812 |
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| EINECS = |
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| EINECS = |
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| PubChem = 2915 |
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| PubChem = 2915 |
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| SMILES = S(SCCN)CCN |
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| SMILES = S(SCCN)CCN |
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| RTECS = |
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| MeSHName = |
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| ChEBI = |
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| KEGG_Ref = {{keggcite|correct|kegg}} |
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| KEGG_Ref = {{keggcite|correct|kegg}} |
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| KEGG = |
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}} |
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| ATCCode_prefix = |
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|Section2={{Chembox Properties |
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| ATCCode_suffix = |
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| ATC_Supplemental =}} |
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| Section2 = {{Chembox Properties |
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| Formula = C<sub>4</sub>H<sub>12</sub>N<sub>2</sub>S<sub>2</sub> |
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| Formula = C<sub>4</sub>H<sub>12</sub>N<sub>2</sub>S<sub>2</sub> |
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| MolarMass = 152.28 g/mol |
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| MolarMass = 152.28 g/mol<ref>''Merck Index'', 12th Edition, '''2846'''.</ref> |
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| Appearance = Viscous oil |
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| Appearance = colorless oil |
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| Density = |
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| Density = 1.1156 g/cm<sup>3</sup> |
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| MeltingPt = |
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| MeltingPtC = 135-6 |
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| Melting_notes = |
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| MeltingPt_notes = |
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| BoilingPt = Decomposes |
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| BoilingPt = 105-6 |
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| BoilingPt_notes = 5 torr |
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| Boiling_notes = |
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| Solubility = Miscible |
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| Solubility = Miscible |
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| SolubleOther = Soluble |
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| SolubleOther = Soluble |
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| Solvent = ] |
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| Solvent = ] |
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| pKa = |
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| pKa = |
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| pKb = }} |
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}} |
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| Section7 = {{Chembox Hazards |
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|Section7={{Chembox Hazards |
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| EUClass = |
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| MainHazards = |
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| EUIndex = |
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| NFPA-H = |
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| NFPA-R = |
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| NFPA-S = |
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| FlashPt = |
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| NFPA-O = |
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| AutoignitionPt = |
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| RPhrases = |
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| RSPhrases = |
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| FlashPt = |
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| PEL = }} |
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{{distinguish|cysteamine}} |
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'''Cystamine''' is an organic ]. It is formed when ] is heated, the result of ]. Cystamine is an unstable liquid and is generally handled as the dihydrochloride salt, C<sub>4</sub>H<sub>12</sub>N<sub>2</sub>S<sub>2</sub>{{unicode|·}}2HCl, which is stable to 203-214 °C at which point it decomposes. Cystamine is toxic if swallowed or inhaled and potentially harmful by contact. |
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'''Cystamine''' ('''2,2'-dithiobisethanamine''') is an organic ]. It is formed when ] is heated, the result of ]. Cystamine is an unstable liquid and is generally handled as the dihydrochloride salt, C<sub>4</sub>H<sub>12</sub>N<sub>2</sub>S<sub>2</sub>·2HCl, which is stable to 203-214 °C at which point it decomposes. Cystamine is toxic if swallowed{{Citation needed|reason=I could not find a primary reference for this claim|date=September 2021}} or inhaled and potentially harmful by contact. |
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== Structure and synthesis == |
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Cystamine is an organic disulfide which is formed when Cystine is heated as a result of decarboxylation. It is often used as sulfhydryl reagent, enzyme inhibitor and radiation-protective agent.<ref name=":0">{{Cite web |url=https://web.stanford.edu/group/hopes/cgi-bin/hopes_test/cystamine/ |title=Cystamine – HOPES |website=web.stanford.edu |language=en-US |access-date=2017-03-17}}</ref> ]s can be synthesized to disulfides like cystamine through chemical oxidation with various oxidizing agents (molecular oxygen, metal ion, metal oxide, DMSO, nitric oxide, halogen and sodium perborate), through electrochemical oxidation and through borohydride exchange resin (BER)-transition metal salts systems (like BER-CuSo4).<ref name=":1">{{Cite journal |last=Sharma |first=Rashmi |year=1995 |title=The uptake and metabolism of cystamine and taurine by isolated perfused rat and rabbit lungs |journal=The International Journal of Biochemistry & Cell Biology |volume=27 |issue=7 |pages=655–664 |doi=10.1016/1357-2725(95)00038-Q|pmid=7648421 }}</ref> |
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==Uses== |
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Cystamine dihydrochloride is a useful reagent to derivatize various polymer monoliths for hydrophilic interaction liquid chromatography, as a crosslinking agent in the development of polymer hydrogels, and as a functional group in nanoparticles developed for siRNA and DNA delivery. |
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It has also been studied as a potential ] agent.<ref name=":2">{{Cite journal |last=Kuna |first=Pavel |year=2004 |title=Acute toxicity and radioprotective effects of amifostine (WR-2721) or cystamine in single whole body fission neutrons irradiated rats |url=http://jab.zsf.jcu.cz/2_1/kunaamino.pdf |journal=Journal of Applied Biomedicine |volume=2 |pages=43–49 |doi=10.32725/jab.2004.005 |doi-access=free }}</ref><ref name="ElksGanellin1990">{{cite book |last1=Elks |first1=J. |title=Dictionary of Drugs |last2=Ganellin |first2=C. R. |year=1990 |doi=10.1007/978-1-4757-2085-3 |isbn=978-1-4757-2087-7}}</ref> It is found in the Soviet AI-2 "Aptechka" CBRN first-aid kit given to civilians.<ref>{{cite web |last1=Shertz |first1=Mike |title=USSR Civil Defense CBRN Kits "Aptechka" |url=https://www.crisis-medicine.com/ussr-civil-defense-cbrn-kits-aptechka/ |website=Crisis Medicine |date=5 November 2021}}</ref> |
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Cystamine has also been studied as a potential medicinal compound in the case of ],<ref name=":0" /> ],<ref>{{Cite journal |last1=Minarini |first1=A. |last2=Milelli |first2=A. |last3=Tumiatti |first3=V. |last4=Rosini |first4=M. |last5=Simoni |first5=E. |last6=Bolognesi |first6=M. L. |last7=Andrisano |first7=V. |last8=Bartolini |first8=M. |last9=Motori |first9=E. |date=2012-02-01 |title=Cystamine-tacrine dimer: A new multi-target-directed ligand as potential therapeutic agent for Alzheimer's disease treatment |journal=Neuropharmacology |series=Post-Traumatic Stress Disorder |volume=62 |issue=2 |pages=997–1003 |doi=10.1016/j.neuropharm.2011.10.007 |pmid=22032870|s2cid=27734077 }}</ref> ] liver damage,<ref>{{Cite journal |last1=de Toranzo |first1=E.G.D. |last2=Marzi |first2=A. |last3=Castro |first3=J.A. |title=Effects of cysteine and cystamine on the carbon tetrachloride induced decrease in arachidonic acid content of rat liver microsomal phospholipids |journal=Toxicology |volume=19 |issue=1 |pages=77–82 |doi=10.1016/0300-483x(81)90067-6 |pmid=7222059 |year=1981}}</ref> and inhibition of ]<ref>{{Cite journal |last1=Hassan |first1=W. |title=Inhibition of erythrocyte sickling by cystamine, a thiol reagent |journal=Proceedings of the National Academy of Sciences of the United States of America |volume=9 |issue=73 |pages=3288–3292 |doi=10.1073/pnas.73.9.3288 |pmid=135260 |year=1976|pmc=431012 }}</ref> |
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== Interactions == |
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Cystamine has been shown to bind reversibly with purified ] ''in vitro'', and imparts a radiation-protective effect to treated DNA.<ref>{{Cite journal |last1=Corry |first1=P. M. |last2=Cole |first2=A. |year=1968 |title=Radiation-Induced Double-Strand Scission of the DNA of Mammalian Metaphase Chromosomes |doi=10.2307/3572586 |journal=Radiation Research |volume=36 |issue=3 |pages=528–543 | pmid= 17387884 }}</ref> However, ''in vitro'' cell culture experiments on mammalian cells treated with cystamine failed to show a radiation-protective effect, whereas treatment with ] did.<ref>{{Cite journal |last1=Sawada |first1=S. |last2=Okada |first2=S. |year=1970 |title=Cysteamine, Cystamine, and Single-Strand Breaks of DNA in Cultured Mammalian Cells |journal=Radiation Research |volume=44 |issue=1 |pages=116–132|pmid=5528819 |doi=10.2307/3573177 }}</ref> |
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Furthermore, cystamine is also able to bind to ]s. The nucleic acids that form from binding to DNA are more stable then unbound nucleic acids. Binding of cystamine to nucleoproteins makes them precipitate. The disulfides than binds to DNA and precipitate nucleoproteins have an analogous interaction like ] and ] with DNA. The affinity of cystamine to DNA plays a role in the toxicity and radioprotecting properties of cystamine.{{Citation needed|reason=petrov does not show any nucleoprotein interaction and does not mention DNA, thus the reference is erroneous at best|date=September 2021}} <ref>{{Cite journal |last1=Petrov |first1=Alexander I. |last2=Dergachev |first2=Ilya D. |last3=Golovnev |first3=Nicolay N. |date=2016-03-03 |title=Coordination model, stability constant, and kinetics study of cystamine and l-cystine with 2− in hydrochloric aqueous solutions |journal=Journal of Coordination Chemistry |volume=69 |issue=5 |pages=748–762 |doi=10.1080/00958972.2016.1139095|s2cid=101591456 }}</ref> |
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Cystamine has also been shown to interact with the production of ] assemblies in bovine brain tissue. The interaction of cystamine interferes with the formation of microtubules, thus acting as an anti-microtubule at low concentrations. At high concentrations cystamine induces an abnormal ] polymerization. Five cystamine molecules can bind covalently to tubulin, this will cause mediated aggregation of tubulins.<ref>{{Cite journal |last=Banerjee |first=Asok |year=1987 |title=The interaction of cystamine with bovine brain tubulin |doi=10.1111/j.1432-1033.1987.tb11458.x |journal=European Journal of Biochemistry |volume=165 |issue=2 |pages=443–448|pmid=3595597 |doi-access=free }}</ref> |
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== Toxicity == |
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Multiple factors of potential cystamine toxicity have been described relating to hepatoxicity,<ref>{{Cite journal |last=Nicotera |first=Pierluigi |year=1996 |title=Cystamine induces toxicity in Hepatocytes through the elevation of cytosolic Ca2+ and the stimulation of nonlysosomal proteolytic system. |url=http://www.jbc.org/content/261/31/14628.full.pdf |journal=Journal of Biological Chemistry |volume=261 |issue=31 |pages=14628–14635 |doi=10.1016/S0021-9258(18)66917-0 |doi-access=free }}</ref> anti-coagulant activity<ref>{{Cite journal |last1=Aleman |first1=Maria M. |last2=Holle |first2=Lori A. |last3=Stember |first3=Katherine G. |last4=Devette |first4=Christa I. |last5=Monroe |first5=Dougald M. |last6=Wolberg |first6=Alisa S. |date=2015-04-27 |title=Cystamine Preparations Exhibit Anticoagulant Activity |journal=PLOS ONE |volume=10 |issue=4 |pages=e0124448 |doi=10.1371/journal.pone.0124448 |issn=1932-6203 |pmid=25915545 |pmc=4411037|bibcode=2015PLoSO..1024448A |doi-access=free }}</ref> and skin sensitisation.<ref>{{Cite journal |last1=Langton |first1=Kate |last2=Patlewicz |first2=Grace Y. |last3=Long |first3=Anthony |last4=Marchant |first4=Carol A. |last5=Basketter |first5=David A. |date=2006-12-01 |title=Structure–activity relationships for skin sensitization: recent improvements to Derek for Windows |journal=Contact Dermatitis |volume=55 |issue=6 |pages=342–347 |doi=10.1111/j.1600-0536.2006.00969.x|pmid=17101009 |s2cid=23728470 }}</ref> LD50/48H values after intravenous administration have been described for rats (97 mg/kg of body weight) and mice (155.93 mg/kg of body weight).<ref name=":2" /> |
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Cystamine inhibits coagulation factor XIa and thrombin, Therefore, exhibiting anti-coagulant behavior. Furthermore, cystamine can cause liver damage by elevating cytosolic Ca<sup>2+</sup> levels and subsequently activating a cytosolic proteolytic system. Skin sensitisation is a predicted effect of cystamine being a thiol. |
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== Metabolism == |
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Cystamine in the body is reduced into ] and RS-cysteamine mixed disulfide by thiol-disulfide exchange. This is done by consumption of intracellular glutathione. Cysteamine is then oxidized to hypotaurine, this is done by the enzyme dioxygenase. The now formed hypotaurine is finally oxidized to taurine by hypotaurine dehydrogenase and the reduction of NAD+. Taurine is excreted out of the body or used in the body.<ref name=":1" /> |
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==References== |
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==References== |
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