Procysteine
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MedKoo CAT#: 463026

CAS#: 19771-63-2

Description: 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

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Procysteine
CAS# 19771-63-2
Product data Instruction

Theoretical Analysis

MedKoo Cat#: 463026
Name: Procysteine
CAS#: 19771-63-2
Chemical Formula: C4H5NO3S
Exact Mass: 147.00
Molecular Weight: 147.148
Elemental Analysis: C, 32.65; H, 3.43; N, 9.52; O, 32.62; S, 21.79

Price and Availability

Size Price Availability Quantity
50mg USD -2 2 Weeks
100mg USD -2 2 Weeks
200mg USD -2 2 Weeks
500mg USD -2 2 Weeks
2g USD -2 2 Weeks
1g USD 220 2 Weeks
5g USD 390 2 Weeks
10g USD 630 2 Weeks
25g USD 1040 2 Weeks
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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/

Solubility Data

Solvent Max Conc. mg/mL Max Conc. mM
Solubility
DMF 30.0 203.88
DMSO 140.0 951.42
PBS (pH 7.2) 5.0 33.98

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.

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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.