Lanthionine | CAS#922-55-4 | thioether analogue of cystine

MedKoo Cat#: 597021 | Name: Lanthionine

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Description:

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

Lanthionine is a thioether analogue of cystine; a component of lantibiotics (BACTERIOCINS).

Chemical Structure

Lanthionine

CAS#922-55-4

Theoretical Analysis

MedKoo Cat#: 597021

Name: Lanthionine

CAS#: 922-55-4

Chemical Formula: C6H12N2O4S

Exact Mass: 208.0518

Molecular Weight: 208.23

Elemental Analysis: C, 34.61; H, 5.81; N, 13.45; O, 30.73; S, 15.40

Price and Availability

Size	Price	Availability	Quantity
100mg	USD 500.00	2 Weeks

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Related CAS #

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Synonym

Lanthionine; L-Lanthionine; NSC 83248; NSC-83248; NSC83248;

IUPAC/Chemical Name

(2R,2'R)-3,3'-thiobis(2-aminopropanoic acid)

InChi Key

DWPCPZJAHOETAG-IMJSIDKUSA-N

InChi Code

InChI=1S/C6H12N2O4S/c7-3(5(9)10)1-13-2-4(8)6(11)12/h3-4H,1-2,7-8H2,(H,9,10)(H,11,12)/t3-,4-/m0/s1

SMILES Code

N[C@@H](CSC[C@H](N)C(O)=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

>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:

Lanthionine (DL- and meso- mixture) is a cysteine derivative.

In vitro activity:

In pro-calcific culture conditions, lanthionine increased both the intracellular and extracellular calcium content and induced the expression of Bone Morphogenetic Protein 2 (BMP2) and RUNX Family Transcription Factor 2 (RUNX2). Reference: Biomedicines. 2022 Feb 14;10(2):444. https://pubmed.ncbi.nlm.nih.gov/35203651/

In vivo activity:

The corpus callosum (CC) and somatosensory cortex was examined by immunohistochemistry (IHC), electron microscopy and for mRNA expression changes in mice provided 5 weeks of CPZ (cuprizone) diet followed by 2 weeks of normal diet in the presence of LKE (lanthionine ketenimine ethyl ester) or vehicle. A significant increase in the number of myelinated axons, and increased myelin thickness was observed in the CC of LKE-treated groups compared to vehicle-treated groups. Reference: ASN Neuro. 2022 Jan-Dec;14:17590914221112352. https://pubmed.ncbi.nlm.nih.gov/35791633/

Preparing Stock Solutions

The following data is based on the product molecular weight 208.23 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.

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. Coppola A, Vigorito C, Lombari P, Martínez YG, Borriello M, Trepiccione F, Ingrosso D, Perna AF. Uremic Toxin Lanthionine Induces Endothelial Cell Mineralization In Vitro. Biomedicines. 2022 Feb 14;10(2):444. doi: 10.3390/biomedicines10020444. PMID: 35203651; PMCID: PMC8962276. 2. Vigorito C, Anishchenko E, Mele L, Capolongo G, Trepiccione F, Zacchia M, Lombari P, Capasso R, Ingrosso D, Perna AF. Uremic Toxin Lanthionine Interferes with the Transsulfuration Pathway, Angiogenetic Signaling and Increases Intracellular Calcium. Int J Mol Sci. 2019 May 8;20(9):2269. doi: 10.3390/ijms20092269. PMID: 31071929; PMCID: PMC6539355. 3. Dupree JL, Paez PM, Tiwari-Woodruff SK, Denton TT, Hensley K, Angeliu CG, Boullerne AI, Kalinin S, Egge S, Cheli VT, Denaroso G, Atkinson KC, Feri M, Feinstein DL. Lanthionine Ketimine Ethyl Ester Accelerates Remyelination in a Mouse Model of Multiple Sclerosis. ASN Neuro. 2022 Jan-Dec;14:17590914221112352. doi: 10.1177/17590914221112352. PMID: 35791633; PMCID: PMC9272172. 4. Yazawa A, Hensley K, Ohshima T. Effects of Lanthionine Ketimine-5-Ethyl Ester on the α-Synucleinopathy Mouse Model. Neurochem Res. 2022 Aug;47(8):2373-2382. doi: 10.1007/s11064-022-03626-9. Epub 2022 May 19. PMID: 35589915.

In vitro protocol:

In vivo protocol:

1. Dupree JL, Paez PM, Tiwari-Woodruff SK, Denton TT, Hensley K, Angeliu CG, Boullerne AI, Kalinin S, Egge S, Cheli VT, Denaroso G, Atkinson KC, Feri M, Feinstein DL. Lanthionine Ketimine Ethyl Ester Accelerates Remyelination in a Mouse Model of Multiple Sclerosis. ASN Neuro. 2022 Jan-Dec;14:17590914221112352. doi: 10.1177/17590914221112352. PMID: 35791633; PMCID: PMC9272172. 2. Yazawa A, Hensley K, Ohshima T. Effects of Lanthionine Ketimine-5-Ethyl Ester on the α-Synucleinopathy Mouse Model. Neurochem Res. 2022 Aug;47(8):2373-2382. doi: 10.1007/s11064-022-03626-9. Epub 2022 May 19. PMID: 35589915.

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PubMed PMID: 29749386; PubMed Central PMCID: PMC5945643. 5: Dhar I, Svingen GFT, Pedersen ER, DeRatt B, Ulvik A, Strand E, Ueland PM, Bønaa KH, Gregory JF, Nygård OK. Plasma cystathionine and risk of acute myocardial infarction among patients with coronary heart disease: Results from two independent cohorts. Int J Cardiol. 2018 Sep 1;266:24-30. doi: 10.1016/j.ijcard.2018.04.083. Epub 2018 Apr 21. PubMed PMID: 29728335. 6: Leber A, Hontecillas R, Zoccoli-Rodriguez V, Bassaganya-Riera J. Activation of LANCL2 by BT-11 Ameliorates IBD by Supporting Regulatory T Cell Stability Through Immunometabolic Mechanisms. Inflamm Bowel Dis. 2018 Apr 28. doi: 10.1093/ibd/izy167. [Epub ahead of print] PubMed PMID: 29718324. 7: Denoel T, Lemaire C, Luxen A. Progress in lanthionine and protected lanthionine synthesis. Chemistry. 2018 May 1. doi: 10.1002/chem.201801115. [Epub ahead of print] PubMed PMID: 29714402. 8: Perna AF, Anishchenko E, Vigorito C, Zacchia M, Trepiccione F, D'Aniello S, Ingrosso D. Zebrafish, a Novel Model System to Study Uremic Toxins: The Case for the Sulfur Amino Acid Lanthionine. Int J Mol Sci. 2018 Apr 29;19(5). pii: E1323. doi: 10.3390/ijms19051323. PubMed PMID: 29710830; PubMed Central PMCID: PMC5983689. 9: Li Q, Montalban-Lopez M, Kuipers OP. Increasing the Antimicrobial Activity of Nisin-Based Lantibiotics against Gram-Negative Pathogens. Appl Environ Microbiol. 2018 May 31;84(12). pii: e00052-18. doi: 10.1128/AEM.00052-18. Print 2018 Jun 15. PubMed PMID: 29625984; PubMed Central PMCID: PMC5981070. 10: Dolle AB, Jagadeesh N, Bhaumik S, Prakash S, Biswal HS, Gowd KH. Electron transfer dissociation of synthetic and natural peptides containing lanthionine/methyllanthionine bridges. Rapid Commun Mass Spectrom. 2018 Jun 15;32(11):831-843. doi: 10.1002/rcm.8108. PubMed PMID: 29520895. 11: Montalbán-López M, Deng J, van Heel AJ, Kuipers OP. Specificity and Application of the Lantibiotic Protease NisP. Front Microbiol. 2018 Feb 9;9:160. doi: 10.3389/fmicb.2018.00160. eCollection 2018. PubMed PMID: 29479343; PubMed Central PMCID: PMC5812297. 12: Koehler D, Shah ZA, Hensley K, Williams FE. Lanthionine ketimine-5-ethyl ester provides neuroprotection in a zebrafish model of okadaic acid-induced Alzheimer's disease. Neurochem Int. 2018 May;115:61-68. doi: 10.1016/j.neuint.2018.02.002. Epub 2018 Feb 21. PubMed PMID: 29475037; PubMed Central PMCID: PMC5865644. 13: Ogasawara Y, Dairi T. Peptide Epimerization Machineries Found in Microorganisms. Front Microbiol. 2018 Feb 6;9:156. doi: 10.3389/fmicb.2018.00156. eCollection 2018. Review. PubMed PMID: 29467749; PubMed Central PMCID: PMC5808125. 14: Kakkar N, Perez JG, Liu WR, Jewett MC, van der Donk WA. Incorporation of Nonproteinogenic Amino Acids in Class I and II Lantibiotics. ACS Chem Biol. 2018 Apr 20;13(4):951-957. doi: 10.1021/acschembio.7b01024. Epub 2018 Feb 21. PubMed PMID: 29439566; PubMed Central PMCID: PMC5910287. 15: Cichero E, Fresia C, Guida L, Booz V, Millo E, Scotti C, Iamele L, de Jonge H, Galante D, De Flora A, Sturla L, Vigliarolo T, Zocchi E, Fossa P. Identification of a high affinity binding site for abscisic acid on human lanthionine synthetase component C-like protein 2. Int J Biochem Cell Biol. 2018 Apr;97:52-61. doi: 10.1016/j.biocel.2018.02.003. Epub 2018 Feb 5. PubMed PMID: 29421190. 16: Wang J, Xiao Q, Chen X, Tong S, Sun J, Lv R, Wang S, Gou Y, Tan L, Xu J, Fan C, Ding G. LanCL1 protects prostate cancer cells from oxidative stress via suppression of JNK pathway. Cell Death Dis. 2018 Feb 7;9(2):197. doi: 10.1038/s41419-017-0207-0. PubMed PMID: 29416001; PubMed Central PMCID: PMC5833716. 17: Clemens R, Zaschke-Kriesche J, Khosa S, Smits SHJ. Insight into Two ABC Transporter Families Involved in Lantibiotic Resistance. Front Mol Biosci. 2018 Jan 22;4:91. doi: 10.3389/fmolb.2017.00091. eCollection 2017. Review. PubMed PMID: 29404338; PubMed Central PMCID: PMC5786555. 18: Shen D, Hensley K, Denton TT. Multiple-step, one-pot synthesis of 2-substituted-3-phosphono-1-thia-4-aza-2-cyclohexene-5-carboxylates and their corresponding ethyl esters. Bioorg Med Chem Lett. 2018 Feb 15;28(4):562-565. doi: 10.1016/j.bmcl.2018.01.052. Epub 2018 Feb 1. PubMed PMID: 29398540; PubMed Central PMCID: PMC5817002. 19: Both EB, Shao S, Xiang J, Jókai Z, Yin H, Liu Y, Magyar A, Dernovics M. Selenolanthionine is the major water-soluble selenium compound in the selenium tolerant plant Cardamine violifolia. Biochim Biophys Acta. 2018 Jan 10. pii: S0304-4165(18)30006-0. doi: 10.1016/j.bbagen.2018.01.006. [Epub ahead of print] PubMed PMID: 29331509. 20: Jeong JH, Ha SC. Crystal Structure of NisI in a Lipid-Free Form, the Nisin Immunity Protein, from Lactococcus lactis. Antimicrob Agents Chemother. 2018 Feb 23;62(3). pii: e01966-17. doi: 10.1128/AAC.01966-17. Print 2018 Mar. 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