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C7602 Sigma

L-Cystine

from non-animal source, meets EP testing specifications, suitable for cell culture, 98.5-101.0%

Synonym: (R,R)-3,3′-Dithiobis(2-aminopropionicacid)

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Properties

Related Categories Amino Acid Derivatives, Amino Acid Library, Amino Acids, Amino Acids & Vitamins, Amino Acids and Vitamins,
biological source   from non-animal source
assay   98.5-101.0%
form   powder
impurities   endotoxin, tested
mp   >240 °C (dec.)(lit.)
solubility   1 M HCl: soluble100 mg/mL
suitability   meets EP testing specifications
  suitable for cell culture

Description

Packaging

10 mg in autosample vial

Other Notes

Tandem Mass Spectrometry data independently generated by Scripps Center for Metabolomics is available to view or download in PDF. C7602.pdf Tested metabolites are featured on Scripps Center for Metabolomics METLIN Metabolite Database. To learn more, visit sigma.com/metlin.

Price and Availability

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Metabolomic Pathways Chart

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Safety & Documentation

Safety Information

WGK Germany 
1
RTECS 
HA2690000

Protocols & Articles

Peer-Reviewed Papers

References

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Cys-pair reporters detect a constrained trigger loop in a paused RNA polymerase. Nayak D, Voss M, Windgassen T, et al. Mol. Cell. 50(6), 882-93, (2013)

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Cysteine/cystine redox signaling in cardiovascular disease. Go YM and Jones DP Free Radic. Biol. Med. 50(4), 495-509, (2011)

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Reduced renal function and benefits of treatment in cystinuria vs other forms of nephrolithiasis. Worcester EM, Coe FL, Evan AP, et al. BJU Int. 97(6), 1285-90, (2006)

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Detection of autosomal dominant polycystic kidney disease by NMR spectroscopic fingerprinting of urine. Gronwald W, Klein MS, Zeltner R, et al. Kidney Int. 79(11), 1244-53, (2011)

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Targeting of liver metastases of colorectal cancer with IgG, F(ab')2, and Fab' anti-carcinoembryonic antigen antibodies labeled with 99mTc: the role of metabolism and kinetics. Behr T, Becker W, Hannappel E, et al. Cancer Res. 55(23 Suppl), 5777s-5785s, (1995)

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Utilization of L-cystine as a source of carbon and nitrogen by various fungi. Kunert J Acta Univ. Palacki. Olomuc. Fac. Med. 123, 351-64, (1989)

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Transcription factor Nrf1 negatively regulates the cystine/glutamate transporter and lipid-metabolizing enzymes. Tsujita T, Peirce V, Baird L, et al. Mol. Cell. Biol. 34(20), 3800-16, (2014)

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Interactions of disulfide-deficient selenocysteine analogs of μ-conotoxin BuIIIB with the α-subunit of the voltage-gated sodium channel subtype 1.3. Green BR, Zhang MM, Chhabra S, et al. FEBS J. 281(13), 2885-98, (2014)

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Elevated levels of methylmalonate and homocysteine in Parkinson's disease, progressive supranuclear palsy and amyotrophic lateral sclerosis. Levin J, Bötzel K, Giese A, et al. Dement. Geriatr. Cogn. Disord. 29(6), 553-9, (2010)

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Metals and oxidative stress in patients with Parkinson's disease. Forte G, Alimonti A, Pino A, et al. Ann. Ist. Super. Sanita 41(2), 189-95, (2005)

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Screening for biochemical abnormalities in urolithiasis patients. Orakzai N, Hanbury DC, and Farrington K J. Ayub Med. Coll. Abbottabad 16(2), 60-3, (2004)

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Targeting allosteric disulphide bonds in cancer. Hogg PJ Nat. Rev. Cancer 13(6), 425-31, (2013)

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Alternative C-terminal helix orientation alters chemokine function: structure of the anti-angiogenic chemokine, CXCL4L1. Kuo JH, Chen YP, Liu JS, et al. J. Biol. Chem. 288(19), 13522-33, (2013)

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Ratio of 8-hydroxyguanine in intact DNA to free 8-hydroxyguanine is increased in Alzheimer disease ventricular cerebrospinal fluid. Lovell MA and Markesbery WR Arch. Neurol. 58(3), 392-6, (2001)

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Immunoregulation through membrane proteins modified by reducing conditions induced by immune reactions. Stegmann M, Metcalfe C, and Barclay AN Eur. J. Immunol. 43(1), 15-21, (2013)

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Mechanisms of oxidative glutamate toxicity: the glutamate/cystine antiporter system xc- as a neuroprotective drug target. Albrecht P, Lewerenz J, Dittmer S, et al. CNS Neurol. Disord. Drug Targets 9(3), 373-82, (2010)

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The consequences of methylmercury exposure on interactive functions between astrocytes and neurons. Allen JW, Shanker G, Tan KH, et al. Neurotoxicology 23(6), 755-9, (2002)

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Formation of insulin fragments by insulin-degrading enzyme: the role of zinc(II) and cystine bridges. Bellia F, Pietropaolo A, and Grasso G J. Mass Spectrom. 48(2), 135-40, (2013)

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In vitro reconstitution of complexes between pro-matrix metalloproteinase-9 and the proteoglycans serglycin and versican. Malla N, Berg E, Theocharis AD, et al. FEBS J. 280(12), 2870-87, (2013)

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NMR mapping of RANTES surfaces interacting with CCR5 using linked extracellular domains. Schnur E, Kessler N, Zherdev Y, et al. FEBS J. 280(9), 2068-84, (2013)

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Human β-defensin-3 structure motifs that are important in CXCR4 antagonism. Feng Z, Dubyak GR, Jia X, et al. FEBS J. 280(14), 3365-75, (2013)

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Synthesis of single- and multiple-stranded cystine-rich peptides. Moroder L, Musiol HJ, Götz M, et al. Biopolymers 80(2-3), 85-97, (2005)

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Remarkable increase in the concentration of 8-hydroxyguanosine in cerebrospinal fluid from patients with Alzheimer's disease. Abe T, Tohgi H, Isobe C, et al. J. Neurosci. Res. 70(3), 447-50, (2002)

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Tying the knot: the cystine signature and molecular-recognition processes of the vascular endothelial growth factor family of angiogenic cytokines. Iyer S and Acharya KR FEBS J. 278(22), 4304-22, (2011)

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Amino acids and biogenic amines in cerebrospinal fluid of patients with Parkinson's disease. Engelborghs S, Marescau B, and De Deyn PP Neurochem. Res. 28(8), 1145-50, (2003)

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Exome sequencing reveals a thrombopoietin ligand mutation in a Micronesian family with autosomal recessive aplastic anemia. Dasouki MJ, Rafi SK, Olm-Shipman AJ, et al. Blood 122(20), 3440-9, (2013)

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Pentosidine and N(epsilon)-(carboxymethyl)-lysine in Alzheimer's disease and vascular dementia. Bär KJ, Franke S, Wenda B, et al. Neurobiol. Aging 24(2), 333-8, (2003)

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Natural and artificial cystine knots for assembly of homo- and heterotrimeric collagen models. Boulègue C, Musiol HJ, Götz MG, et al. Antioxid. Redox Signal. 10(1), 113-25, (2008)

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Insulin analog with additional disulfide bond has increased stability and preserved activity. Vinther TN, Norrman M, Ribel U, et al. Protein Sci. 22(3), 296-305, (2013)

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Alteration of 8-hydroxyguanosine concentrations in the cerebrospinal fluid and serum from patients with Parkinson's disease. Abe T, Isobe C, Murata T, et al. Neurosci. Lett. 336(2), 105-8, (2003)

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Plasma and cerebrospinal fluid amino acids in epileptic patients. Rainesalo S, Keränen T, Palmio J, et al. Neurochem. Res. 29(1), 319-24, (2004)

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Endoplasmic reticulum stress-activated transcription factor ATF6α requires the disulfide isomerase PDIA5 to modulate chemoresistance. Higa A, Taouji S, Lhomond S, et al. Mol. Cell. Biol. 34(10), 1839-49, (2014)

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Evaluation of the taurine concentrations in dog plasma and aqueous humour: a pilot study. Rosolen SG, Neveux N, Sahel JA, et al. Adv. Exp. Med. Biol. 775, 145-54, (2013)

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The characteristics of the stone and urine composition in Chinese stone formers: primary report of a single-center results. Wu W, Yang D, Tiselius HG, et al. Urology 83(4), 732-7, (2014)

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Radiopacity and hounsfield attenuation of cystine urolithiasis: case series and review of the literature. Patel SR, Wagner LE, Lubner MG, et al. J. Endourol. 28(4), 472-5, (2014)

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Illusory spirals and loops in crystal growth. Shtukenberg AG, Zhu Z, An Z, et al. Proc. Natl. Acad. Sci. U. S. A. 110(43), 17195-8, (2013)

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Differential acetylcholine and choline concentrations in the cerebrospinal fluid of patients with Alzheimer's disease and vascular dementia. Jia JP, Jia JM, Zhou WD, et al. Chin. Med. J. 117(8), 1161-4, (2004)

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Molecular identification and cellular localization of a potential transport system involved in cystine/cysteine uptake in human lenses. Lim JC, Lam L, Li B, et al. Exp. Eye Res. 116, 219-26, (2013)

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Optical diagnosis of a metabolic disease: cystinosis. Cinotti E, Perrot JL, Labeille B, et al. J. Biomed. Opt. 18(4), 046013, (2013)

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Chemical synthesis and biotinylation of the thrombospondin domain TSR2. Tiefenbrunn TK Protein Sci. 18(5), 970-9, (2009)

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Nonmetal haptens induce ATP release from keratinocytes through opening of pannexin hemichannels by reactive oxygen species. Onami K, Kimura Y, Ito Y, et al. J. Invest. Dermatol. 134(7), 1951-60, (2014)

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Cysteine, cystine or N-acetylcysteine supplementation in parenterally fed neonates. Soghier LM and Brion LP Cochrane Database Syst. Rev. (4), CD004869, (2006)

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Chemical composition and binary mixture of human urinary stones using FT-Raman spectroscopy method. Selvaraju R, Raja A, and Thiruppathi G Spectrochim. Acta. A. Mol. Biomol. Spectrosc. 114, 650-7, (2013)

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Effect of fudosteine, a cysteine derivative, on airway hyperresponsiveness, inflammation, and remodeling in a murine model of asthma. Ueno-Iio T, Shibakura M, Iio K, et al. Life Sci. 92(20-21), 1015-23, (2013)

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Nitrite and malondialdehyde content in cerebrospinal fluid of patients with Parkinson's disease. Shukla R, Rajani M, Srivastava N, et al. Int. J. Neurosci. 116(12), 1391-402, (2006)

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Cystinosis as a cause of noncirrhotic portal hypertension. Rossi S, Herrine SK, and Navarro VJ Dig. Dis. Sci. 50(7), 1372-5, (2005)

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Swallowing dysfunction in 101 patients with nephropathic cystinosis: benefit of long-term cysteamine therapy. Sonies BC, Almajid P, Kleta R, et al. Medicine (Baltimore.) 84(3), 137-46, (2005)

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N-methyl-D-aspartate receptor-dependent denitrosylation of neuronal nitric oxide synthase increase the enzyme activity. Qu ZW, Miao WY, Hu SQ, et al. PLoS ONE 7(12), e52788, (2012)

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Cystine calculi: challenging group of stones. Ahmed K, Dasgupta P, and Khan MS Postgrad. Med. J. 82(974), 799-801, (2006)

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The formation of 3-hydroxy-4-methoxyphenylalanine and 3-hydroxy-4-methoxyphenethylamine in plasma during L-DOPA therapy in patients with Parkinson's disease. Ishimitsu T, Hirose S, Asahara K, et al. Chem. Pharm. Bull. 32(8), 3320-2, (1984)

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Type AII lantibiotic bovicin HJ50 with a rare disulfide bond: structure, structure-activity relationships and mode of action. Zhang J, Feng Y, Teng K, et al. Biochem. J. 461(3), 497-508, (2014)

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Effects of non-toxic cryoprotective agents on the viability of cord blood derived MNCs. Bissoyi A and Pramanik K Cryo. Letters 34(5), 453-65, (2013)

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Functional role of CD44v-xCT system in the development of spasmolytic polypeptide-expressing metaplasia. Wada T, Ishimoto T, Seishima R, et al. Cancer Sci. 104(10), 1323-9, (2013)

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Determination of urinary stone composition using dual-energy spectral CT: initial in vitro analysis. Li XH, Zhao R, Liu B, et al. Clin. Radiol. 68(7), e370-7, (2013)

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Developmental potential of prepubertal mouse oocytes is compromised due mainly to their impaired synthesis of glutathione. Jiao GZ, Cao XY, Cui W, et al. PLoS ONE 8(3), e58018, (2013)

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Merck 14,2782

Beil. 4,IV,3155

FT-IR 1 (1), 596:B / FT-IR 2 (1), 942:C / IR-Spectra (2), 314:H / IR-Spectra (3), 354:G / NMR-Reference 2 (1), 503:A / RegBook 1 (1), 675:H / Sigma FT-IR 1 (1), 123:C / Structure Index 1, 102:A:2

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