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MedKoo Cat#: 463026 | Name: Procysteine
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Description:

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

Procysteine is a prodrug form of cysteine that is metabolized to cysteine intracellularly and has antioxidant activity. It reduces TNF-α-induced increases in the expression of IL-6 and chemokine ligand 2 in ARPE-19 human retinal pigment epithelial cells when used at a concentration of 0.5 mM.3 Procysteine also increases liver glutathione levels in fasted, but not fed, mice.1 It reduces the production of reactive oxygen species in bronchoalveolar lavage fluid and decreases plasma extravasation in the lungs, as well as reverses decreases in the levels of hypoxia-inducible factor in a mouse model of allergic asthma when administered at doses of 80 and 160 mg/kg.

Chemical Structure

Procysteine
Procysteine
CAS#19771-63-2

Theoretical Analysis

MedKoo Cat#: 463026

Name: Procysteine

CAS#: 19771-63-2

Chemical Formula: C4H5NO3S

Exact Mass: 146.9990

Molecular Weight: 147.15

Elemental Analysis: C, 32.65; H, 3.43; N, 9.52; O, 32.62; S, 21.79

Price and Availability

Size Price Availability Quantity
1g USD 220.00 2 Weeks
5g USD 390.00 2 Weeks
10g USD 630.00 2 Weeks
25g USD 1,040.00 2 Weeks
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Related CAS #
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Synonym
L-2-oxothiazolidine-4-carboxylic acid; L-2-oxothiazolidine-4-carboxylate; OTC;
IUPAC/Chemical Name
(R)-2-oxothiazolidine-4-carboxylic acid
InChi Key
BMLMGCPTLHPWPY-REOHCLBHSA-N
InChi Code
InChI=1S/C4H5NO3S/c6-3(7)2-1-9-4(8)5-2/h2H,1H2,(H,5,8)(H,6,7)/t2-/m0/s1
SMILES Code
[H]N1[C@@H](CSC1=O)C(O)=O
Appearance
Solid powder
Purity
>98% (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
>3 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:
Procysteine, an antioxidant, is a proagent of cysteine that is inert until metabolized to cysteine intracellulary, thus stimulating glutathione synthesis.
In vitro activity:
In transient transfection assays, Procysteine inhibited gene expression controlled by the HIV-1 promoter in activated Jurkat cells but not in resting Jurkat cells. Gel-shift assays showed that Procysteine inhibited NF-kappa B DNA binding activity in nuclear extracts. Thus, Procysteine inhibits HIV expression, HIV promoter activity, and NF-kappa B binding activity in vitro. Reference: J Acquir Immune Defic Syndr Hum Retrovirol. 1995 Feb 1;8(2):107-15. https://pubmed.ncbi.nlm.nih.gov/7834394/
In vivo activity:
This study’s goals were (i) to minimize the degree of oxidant stress and attenuate atrophy by supplementing the diets of alcohol-fed rats with the glutathione precursor, procysteine, and (ii) to identify the roles of IL-6 family members in alcoholic myopathy. Procysteine treatment attenuated plantaris atrophy, restored glutathione levels, and increased catalase, Cu/Zn-SOD1, and Mn-SOD2 mRNA expression, but did not reduce other markers of oxidant stress or levels of these catabolic factors. Instead, procysteine stimulated gene expression of anabolic factors such as insulin-like growth factor-1, ciliary neurotrophic factor, and cardiotrophin-1. Procysteine significantly attenuated, but did not completely abrogate, alcohol-induced oxidant stress or catabolic factors. Reference: Alcohol Clin Exp Res. 2009 Aug;33(8):1450-9. https://pubmed.ncbi.nlm.nih.gov/19426167/
Solvent mg/mL mM
Solubility
DMF 30.0 203.88
DMSO 140.0 951.42
PBS (pH 7.2) 5.0 33.98
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 147.15 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. Lederman MM, Georges D, Dando S, Schmelzer R, Averill L, Goldberg D. L-2-oxothiazolidine-4-carboxylic acid (procysteine) inhibits expression of the human immunodeficiency virus and expression of the interleukin-2 receptor alpha chain. J Acquir Immune Defic Syndr Hum Retrovirol. 1995 Feb 1;8(2):107-15. PMID: 7834394. 2. Saito K, Kimura S, Saga T, Misonoo Y, Yoshizawa S, Akasaka Y, Ishii T, Kuwano K, Yamaguchi K, Tateda K. Protective effect of procysteine on Acinetobacter pneumonia in hyperoxic conditions. J Antimicrob Chemother. 2013 Oct;68(10):2305-10. doi: 10.1093/jac/dkt192. Epub 2013 May 16. PMID: 23681269. 3. Otis JS, Guidot DM. Procysteine stimulates expression of key anabolic factors and reduces plantaris atrophy in alcohol-fed rats. Alcohol Clin Exp Res. 2009 Aug;33(8):1450-9. doi: 10.1111/j.1530-0277.2009.00975.x. Epub 2009 May 4. PMID: 19426167; PMCID: PMC2723178.
In vitro protocol:
1. Lederman MM, Georges D, Dando S, Schmelzer R, Averill L, Goldberg D. L-2-oxothiazolidine-4-carboxylic acid (procysteine) inhibits expression of the human immunodeficiency virus and expression of the interleukin-2 receptor alpha chain. J Acquir Immune Defic Syndr Hum Retrovirol. 1995 Feb 1;8(2):107-15. PMID: 7834394.
In vivo protocol:
1. Saito K, Kimura S, Saga T, Misonoo Y, Yoshizawa S, Akasaka Y, Ishii T, Kuwano K, Yamaguchi K, Tateda K. Protective effect of procysteine on Acinetobacter pneumonia in hyperoxic conditions. J Antimicrob Chemother. 2013 Oct;68(10):2305-10. doi: 10.1093/jac/dkt192. Epub 2013 May 16. PMID: 23681269. 2. Otis JS, Guidot DM. Procysteine stimulates expression of key anabolic factors and reduces plantaris atrophy in alcohol-fed rats. Alcohol Clin Exp Res. 2009 Aug;33(8):1450-9. doi: 10.1111/j.1530-0277.2009.00975.x. Epub 2009 May 4. PMID: 19426167; PMCID: PMC2723178.
1: Patel JJ, Bourne LE, Thakur S, Farrington K, Gorog DA, Orriss IR, Baydoun AR. 2-Oxothiazolidine-4-carboxylic acid inhibits vascular calcification via induction of glutathione synthesis. J Cell Physiol. 2020 Sep 12. doi: 10.1002/jcp.30036. Epub ahead of print. PMID: 32918744. 2: Morin G, Guiraut C, Perez Marcogliese M, Mohamed I, Lavoie JC. Glutathione Supplementation of Parenteral Nutrition Prevents Oxidative Stress and Sustains Protein Synthesis in Guinea Pig Model. Nutrients. 2019 Sep 3;11(9):2063. doi: 10.3390/nu11092063. PMID: 31484318; PMCID: PMC6770543. 3: Lewis SR, Pritchard MW, Thomas CM, Smith AF. Pharmacological agents for adults with acute respiratory distress syndrome. Cochrane Database Syst Rev. 2019 Jul 23;7(7):CD004477. doi: 10.1002/14651858.CD004477.pub3. PMID: 31334568; PMCID: PMC6646953. 4: Künstler A, Kátay G, Gullner G, Király L. Artificial elevation of glutathione contents in salicylic acid-deficient tobacco (Nicotiana tabacum cv. Xanthi NahG) reduces susceptibility to the powdery mildew pathogen Euoidium longipes. Plant Biol (Stuttg). 2020 Jan;22(1):70-80. doi: 10.1111/plb.13030. Epub 2019 Jul 31. PMID: 31283085. 5: Liu Y, Min JW, Feng S, Subedi K, Qiao F, Mammenga E, Callegari E, Wang H. Therapeutic Role of a Cysteine Precursor, OTC, in Ischemic Stroke Is Mediated by Improved Proteostasis in Mice. Transl Stroke Res. 2020 Feb;11(1):147-160. doi: 10.1007/s12975-019-00707-w. Epub 2019 May 2. PMID: 31049841; PMCID: PMC6824933. 6: Sosinska-Zawierucha P, Mackowiak B, Begier-Krasinska B, Hoppe K, Breborowicz A. L-2-oxothiazolidine-4-carboxylic acids slow down dialysate-induced senescence in human peritoneal mesothelial cells. J Physiol Pharmacol. 2018 Dec;69(6). doi: 10.26402/jpp.2018.6.08. Epub 2019 Feb 21. PMID: 30802216. 7: Giustarini D, Galvagni F, Dalle Donne I, Milzani A, Severi FM, Santucci A, Rossi R. N-acetylcysteine ethyl ester as GSH enhancer in human primary endothelial cells: A comparative study with other drugs. Free Radic Biol Med. 2018 Oct;126:202-209. doi: 10.1016/j.freeradbiomed.2018.08.013. Epub 2018 Aug 14. PMID: 30114478. 8: Jia XL, Chen YK, Xu XZ, Shen F, Zheng QB, Du Z, Wang Y, Wu T, Xu XF, Han ZH, Zhang XZ. miR156 switches on vegetative phase change under the regulation of redox signals in apple seedlings. Sci Rep. 2017 Oct 27;7(1):14223. doi: 10.1038/s41598-017-14671-8. PMID: 29079841; PMCID: PMC5660156. 9: Bolling AK, Solhaug A, Morisbak E, Holme JA, Samuelsen JT. The dental monomer hydroxyethyl methacrylate (HEMA) counteracts lipopolysaccharide-induced IL-1β release-Possible role of glutathione. Toxicol Lett. 2017 Mar 15;270:25-33. doi: 10.1016/j.toxlet.2017.02.007. Epub 2017 Feb 7. PMID: 28188892. 10: Terrill JR, Pinniger GJ, Graves JA, Grounds MD, Arthur PG. Increasing taurine intake and taurine synthesis improves skeletal muscle function in the mdx mouse model for Duchenne muscular dystrophy. J Physiol. 2016 Jun 1;594(11):3095-110. doi: 10.1113/JP271418. Epub 2016 Jan 18. PMID: 26659826; PMCID: PMC4887673. 11: Kirpichnikova KM, Petrov YP, Filatova NA, Gamaley IA. [CELLS FORM AND THEIR SENSITIVITY TO LYTIC ACTIVITY OF NATURAL KILLER CELLS UNDER THE ANTIOXIDANT ACTION]. Tsitologiia. 2015;57(8):578-83. Russian. PMID: 26591569. 12: Al-Kinani AA, Naughton DP, Calabrese G, Vangala A, Smith JR, Pierscionek BK, Alany RG. Analysis of 2-oxothiazolidine-4-carboxylic acid by hydrophilic interaction liquid chromatography: application for ocular delivery using chitosan nanoparticles. Anal Bioanal Chem. 2015 Mar;407(9):2645-50. doi: 10.1007/s00216-015-8494-8. Epub 2015 Feb 10. PMID: 25662935. 13: Deevska G, Sunkara M, Karakashian C, Peppers B, Morris AJ, Nikolova- Karakashian MN. Effect of procysteine on aging-associated changes in hepatic GSH and SMase: evidence for transcriptional regulation of smpd3. J Lipid Res. 2014 Oct;55(10):2041-52. doi: 10.1194/jlr.M048223. Epub 2014 Jul 21. PMID: 25047167; PMCID: PMC4173997. 14: Exil V, Ping L, Yu Y, Chakraborty S, Caito SW, Wells KS, Karki P, Lee E, Aschner M. Activation of MAPK and FoxO by manganese (Mn) in rat neonatal primary astrocyte cultures. PLoS One. 2014 May 2;9(5):e94753. doi: 10.1371/journal.pone.0094753. PMID: 24787138; PMCID: PMC4008430. 15: Promsote W, Veeranan-Karmegam R, Ananth S, Shen D, Chan CC, Lambert NA, Ganapathy V, Martin PM. L-2-oxothiazolidine-4-carboxylic acid attenuates oxidative stress and inflammation in retinal pigment epithelium. Mol Vis. 2014 Jan 7;20:73-88. PMID: 24426777; PMCID: PMC3888500. 16: Ho YC, Huang FM, Lee SS, Chang YC. The regulation of cytotoxicity and cyclooxygenase-2 expression by 2-hydroxy-ethyl methacrylate in human osteoblasts are related to intracellular glutathione levels. Int Endod J. 2014 Aug;47(8):784-90. doi: 10.1111/iej.12218. Epub 2013 Dec 11. PMID: 24245513. 17: Simet SM, Pavlik JA, Sisson JH. Dietary antioxidants prevent alcohol-induced ciliary dysfunction. Alcohol. 2013 Dec;47(8):629-35. doi: 10.1016/j.alcohol.2013.09.004. Epub 2013 Oct 11. PMID: 24169090; PMCID: PMC3850762. 18: Terrill JR, Boyatzis A, Grounds MD, Arthur PG. Treatment with the cysteine precursor l-2-oxothiazolidine-4-carboxylate (OTC) implicates taurine deficiency in severity of dystropathology in mdx mice. Int J Biochem Cell Biol. 2013 Sep;45(9):2097-108. doi: 10.1016/j.biocel.2013.07.009. Epub 2013 Jul 24. PMID: 23892094. 19: Saito K, Kimura S, Saga T, Misonoo Y, Yoshizawa S, Akasaka Y, Ishii T, Kuwano K, Yamaguchi K, Tateda K. Protective effect of procysteine on Acinetobacter pneumonia in hyperoxic conditions. J Antimicrob Chemother. 2013 Oct;68(10):2305-10. doi: 10.1093/jac/dkt192. Epub 2013 May 16. PMID: 23681269. 20: Choi J, Park KH, Kim SZ, Shin JH, Jang SI. The ameliorative effects of L-2-oxothiazolidine-4-carboxylate on acetaminophen-induced hepatotoxicity in mice. Molecules. 2013 Mar 18;18(3):3467-78. doi: 10.3390/molecules18033467. PMID: 23507776; PMCID: PMC6270228.