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MedKoo Cat#: 596496 | Name: Ethionine
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Description:

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

Ethionine is an antimetabolite and methionine antagonist that interferes with amino acid incorporation into proteins and with cellular ATP utilization. It also produces liver neoplasms.

Chemical Structure

Ethionine
Ethionine
CAS#13073-35-3

Theoretical Analysis

MedKoo Cat#: 596496

Name: Ethionine

CAS#: 13073-35-3

Chemical Formula: C6H13NO2S

Exact Mass: 163.0667

Molecular Weight: 163.23

Elemental Analysis: C, 44.15; H, 8.03; N, 8.58; O, 19.60; S, 19.64

Price and Availability

Size Price Availability Quantity
100mg USD 350.00 2 Weeks
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Related CAS #
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Synonym
Ethionine; L-Ethionine; ETH; NSC 82393; NSC-82393; NSC82393;
IUPAC/Chemical Name
S-ethylhomocysteine
InChi Key
GGLZPLKKBSSKCX-UHFFFAOYSA-N
InChi Code
InChI=1S/C6H13NO2S/c1-2-10-4-3-5(7)6(8)9/h5H,2-4,7H2,1H3,(H,8,9)
SMILES Code
O=C(O)C(N)CCSCC
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
>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:
TBD
In vitro activity:
In this study, to assess whether ethionine may regulate cell motile activity through LPA receptors, rat liver epithelial (WB-F344) cells were treated with ethionine for 48 h. In cell motility assay with a cell culture insert, the treatment of ethionine at 1.0 and 10 μM enhanced significantly high cell motile activity, compared with untreated cells. Reference: Mol Cell Biochem. 2013 Nov;383(1-2):173-7. https://pubmed.ncbi.nlm.nih.gov/23867992/
In vivo activity:
The results showed that with increased dose of ethionine, the rate of embryonic resorption and growth retardation was also increased. At 700 mg/kg ethionine, all embryos were resorbed, while at 500 mg/kg, the incidence of NTDs was at highest rate (54.8%) with a lower embryonic resorption rate (8.2%). Reference: Front Neurol. 2020; 11: 242. https://www.ncbi.nlm.nih.gov/pmc/articles/PMC7154092/

Preparing Stock Solutions

The following data is based on the product molecular weight 163.23 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. Zhang L, Dong Y, Wang W, Zhao T, Huang T, Khan A, Wang L, Liu Z, Xie J, Niu B. Ethionine Suppresses Mitochondria Autophagy and Induces Apoptosis via Activation of Reactive Oxygen Species in Neural Tube Defects. Front Neurol. 2020 Apr 7;11:242. doi: 10.3389/fneur.2020.00242. PMID: 32318018; PMCID: PMC7154092. 2. Inoue S, Tanabe E, Shibata A, Hirane M, Araki M, Dong Y, Fukushima N, Tsujiuchi T. Ethionine regulates cell motile activity through LPA receptor-3 in liver epithelial WB-F344 cells. Mol Cell Biochem. 2013 Nov;383(1-2):173-7. doi: 10.1007/s11010-013-1765-9. Epub 2013 Jul 19. PMID: 23867992.
In vitro protocol:
1. Zhang L, Dong Y, Wang W, Zhao T, Huang T, Khan A, Wang L, Liu Z, Xie J, Niu B. Ethionine Suppresses Mitochondria Autophagy and Induces Apoptosis via Activation of Reactive Oxygen Species in Neural Tube Defects. Front Neurol. 2020 Apr 7;11:242. doi: 10.3389/fneur.2020.00242. PMID: 32318018; PMCID: PMC7154092. 2. Inoue S, Tanabe E, Shibata A, Hirane M, Araki M, Dong Y, Fukushima N, Tsujiuchi T. Ethionine regulates cell motile activity through LPA receptor-3 in liver epithelial WB-F344 cells. Mol Cell Biochem. 2013 Nov;383(1-2):173-7. doi: 10.1007/s11010-013-1765-9. Epub 2013 Jul 19. PMID: 23867992.
In vivo protocol:
1. Zhang L, Dong Y, Wang W, Zhao T, Huang T, Khan A, Wang L, Liu Z, Xie J, Niu B. Ethionine Suppresses Mitochondria Autophagy and Induces Apoptosis via Activation of Reactive Oxygen Species in Neural Tube Defects. Front Neurol. 2020 Apr 7;11:242. doi: 10.3389/fneur.2020.00242. PMID: 32318018; PMCID: PMC7154092.
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An immune-modulating formula comprising whey peptides and fermented milk improves inflammation-related remote organ injuries in diet-induced acute pancreatitis in mice. Biosci Microbiota Food Health. 2018;37(1):1-8. doi: 10.12938/bmfh.17-011. Epub 2017 Aug 25. PubMed PMID: 29387516; PubMed Central PMCID: PMC5787410. 5: Tajul Arifin K, Sulaiman S, Md Saad S, Ahmad Damanhuri H, Wan Ngah WZ, Mohd Yusof YA. Elevation of tumour markers TGF-β, M(2)-PK, OV-6 and AFP in hepatocellular carcinoma (HCC)-induced rats and their suppression by microalgae Chlorella vulgaris. BMC Cancer. 2017 Dec 21;17(1):879. doi: 10.1186/s12885-017-3883-3. PubMed PMID: 29268718; PubMed Central PMCID: PMC5740965. 6: Gogoi-Tiwari J, Köhn-Gaone J, Giles C, Schmidt-Arras D, Gratte FD, Elsegood CL, McCaughan GW, Ramm GA, Olynyk JK, Tirnitz-Parker JEE. The Murine Choline-Deficient, Ethionine-Supplemented (CDE) Diet Model of Chronic Liver Injury. J Vis Exp. 2017 Oct 21;(128). doi: 10.3791/56138. PubMed PMID: 29155718. 7: Biczo G, Vegh ET, Shalbueva N, Mareninova OA, Elperin J, Lotshaw E, Gretler S, Lugea A, Malla SR, Dawson D, Ruchala P, Whitelegge J, French SW, Wen L, Husain SZ, Gorelick FS, Hegyi P, Rakonczay Z Jr., Gukovsky I, Gukovskaya AS. Mitochondrial Dysfunction, Through Impaired Autophagy, Leads to Endoplasmic Reticulum Stress, Deregulated Lipid Metabolism, and Pancreatitis in Animal Models. Gastroenterology. 2018 Feb;154(3):689-703. doi: 10.1053/j.gastro.2017.10.012. Epub 2017 Oct 23. PubMed PMID: 29074451. 8: Wang S, Lee C, Kim J, Hyun J, Lim M, Cha HJ, Oh SH, Choi YH, Jung Y. Tumor necrosis factor-inducible gene 6 protein ameliorates chronic liver damage by promoting autophagy formation in mice. Exp Mol Med. 2017 Sep 22;49(9):e380. doi: 10.1038/emm.2017.140. PubMed PMID: 28935975; PubMed Central PMCID: PMC5628276. 9: Choi SB, Bae GS, Jo IJ, Song HJ, Park SJ. Effects of Berberine on Acute Necrotizing Pancreatitis and Associated Lung Injury. Pancreas. 2017 Sep;46(8):1046-1055. doi: 10.1097/MPA.0000000000000877. PubMed PMID: 28797013. 10: Cai H, Hauser M, Naider F, Becker JM. Halo Assay for Toxic Peptides and Other Compounds in Microorganisms. Bio Protoc. 2016 Nov 20;6(22). pii: e2025. doi: 10.21769/BioProtoc.2025. PubMed PMID: 28573166; PubMed Central PMCID: PMC5448412. 11: Douglas SM, Chubiz LM, Harcombe WR, Marx CJ. Identification of the potentiating mutations and synergistic epistasis that enabled the evolution of inter-species cooperation. PLoS One. 2017 May 11;12(5):e0174345. doi: 10.1371/journal.pone.0174345. eCollection 2017. PubMed PMID: 28493869; PubMed Central PMCID: PMC5426591. 12: Zhou M, Mok MT, Sun H, Chan AW, Huang Y, Cheng AS, Xu G. The anti-diabetic drug exenatide, a glucagon-like peptide-1 receptor agonist, counteracts hepatocarcinogenesis through cAMP-PKA-EGFR-STAT3 axis. Oncogene. 2017 Jul 20;36(29):4135-4149. doi: 10.1038/onc.2017.38. Epub 2017 Mar 20. PubMed PMID: 28319060. 13: Bae NS, Seberg AP, Carroll LP, Swanson MJ. Identification of Genes in Saccharomyces cerevisiae that Are Haploinsufficient for Overcoming Amino Acid Starvation. G3 (Bethesda). 2017 Apr 3;7(4):1061-1084. doi: 10.1534/g3.116.037416. PubMed PMID: 28209762; PubMed Central PMCID: PMC5386856. 14: Iyer S, Park MJ, Moons D, Kwan R, Liao J, Liu L, Omary MB. Clusterin and Pycr1 alterations associate with strain and model differences in susceptibility to experimental pancreatitis. Biochem Biophys Res Commun. 2017 Jan 22;482(4):1346-1352. doi: 10.1016/j.bbrc.2016.12.039. Epub 2016 Dec 7. PubMed PMID: 27939882; PubMed Central PMCID: PMC5240812. 15: Rókusz A, Bugyik E, Szabó V, Szücs A, Paku S, Nagy P, Dezső K. Imatinib accelerates progenitor cell-mediated liver regeneration in choline-deficient ethionine-supplemented diet-fed mice. Int J Exp Pathol. 2016 Oct;97(5):389-396. doi: 10.1111/iep.12209. Epub 2016 Dec 5. PubMed PMID: 27918111; PubMed Central PMCID: PMC5206818. 16: Ruiter S, Sippel J, Bouwmeester MC, Lommelaars T, Beekhof P, Hodemaekers HM, Bakker F, van den Brandhof EJ, Pennings JL, van der Ven LT. Programmed Effects in Neurobehavior and Antioxidative Physiology in Zebrafish Embryonically Exposed to Cadmium: Observations and Hypothesized Adverse Outcome Pathway Framework. Int J Mol Sci. 2016 Nov 2;17(11). pii: E1830. PubMed PMID: 27827847; PubMed Central PMCID: PMC5133831. 17: Nagao S, Taguchi K, Sakai H, Yamasaki K, Watanabe H, Otagiri M, Maruyama T. Carbon monoxide-bound hemoglobin vesicles ameliorate multiorgan injuries induced by severe acute pancreatitis in mice by their anti-inflammatory and antioxidant properties. Int J Nanomedicine. 2016 Oct 27;11:5611-5620. eCollection 2016. PubMed PMID: 27822039; PubMed Central PMCID: PMC5089833. 18: Huang JF, Liu ZQ, Jin LQ, Tang XL, Shen ZY, Yin HH, Zheng YG. Metabolic engineering of Escherichia coli for microbial production of L-methionine. Biotechnol Bioeng. 2017 Apr;114(4):843-851. doi: 10.1002/bit.26198. Epub 2016 Oct 21. PubMed PMID: 27723097. 19: Vaughan MD, Su Z, Daub E, Honek JF. Intriguing cellular processing of a fluorinated amino acid during protein biosynthesis in Escherichia coli. Org Biomol Chem. 2016 Sep 26;14(38):8942-8946. PubMed PMID: 27722405. 20: Kanai M, Kawata T, Yoshida Y, Kita Y, Ogawa T, Mizunuma M, Watanabe D, Shimoi H, Mizuno A, Yamada O, Fujii T, Iefuji H. Sake yeast YHR032W/ERC1 haplotype contributes to high S-adenosylmethionine accumulation in sake yeast strains. J Biosci Bioeng. 2017 Jan;123(1):8-14. doi: 10.1016/j.jbiosc.2016.07.007. Epub 2016 Aug 24. PubMed PMID: 27567046.