Vinthionine

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

MedKoo CAT#: 597354

CAS#: 70858-14-9

Description: Vinthionine binds covalently to rat liver DNA, RNA and protein in vivo, but not in vitro. This amino acid is directly mutagenic in Salmonella typhimurium TA100 and TA1535; the mechanism of its metabolic activation in vivo in bacteria and liver is under study.


Price and Availability

Size Price Shipping out time Quantity
Inquire bulk and customized quantity

Pricing updated 2020-08-15. Prices are subject to change without notice.

Vinthionine is not in stock, may be available through custom synthesis. For cost-effective reason, minimum 1 gram order is requested. The product will be characterized by NMR, HPLC and MS analysis. Purity (HPLC) is usually >98%. CoA, QC data, MSDS will be provided when product is successfully made. The estimated lead time is 2-3 months. Please send email to sales@medkoo.com to inquire quote.


Chemical Structure

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Theoretical Analysis

MedKoo Cat#: 597354
Name: Vinthionine
CAS#: 70858-14-9
Chemical Formula: C6H11NO2S
Exact Mass: 161.051
Molecular Weight: 161.21
Elemental Analysis: C, 44.70; H, 6.88; N, 8.69; O, 19.85; S, 19.89


Synonym: Vinthionine; L-Vinthionine; S-Ethenyl-L-homocysteine;

IUPAC/Chemical Name: S-vinyl-L-homocysteine

InChi Key: ZDASADFVRGVYFK-YFKPBYRVSA-N

InChi Code: InChI=1S/C6H11NO2S/c1-2-10-4-3-5(7)6(8)9/h2,5H,1,3-4,7H2,(H,8,9)/t5-/m0/s1

SMILES Code: N[C@@H](CCSC=C)C(O)=O


Technical Data

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:
2934.99.03.00


References

1: Catcott KC, Yan J, Qu W, Wysocki VH, Zhou ZS. Identifying Unknown Enzyme-Substrate Pairs from the Cellular Milieu with Native Mass Spectrometry. Chembiochem. 2017 Apr 4;18(7):613-617. doi: 10.1002/cbic.201600634. Epub 2017 Mar 14. PubMed PMID: 28140508.

2: 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.

3: Qu W, Catcott KC, Zhang K, Liu S, Guo JJ, Ma J, Pablo M, Glick J, Xiu Y, Kenton N, Ma X, Duclos RI Jr, Zhou ZS. Capturing Unknown Substrates via in Situ Formation of Tightly Bound Bisubstrate Adducts: S-Adenosyl-vinthionine as a Functional Probe for AdoMet-Dependent Methyltransferases. J Am Chem Soc. 2016 Mar 9;138(9):2877-80. doi: 10.1021/jacs.5b05950. Epub 2016 Feb 29. PubMed PMID: 26901520.

4: Sohn YW, Lee GH, Liem A, Miller JA. Activation of H-ras oncogenes in male B6C3F1 mouse liver tumors induced by vinthionine or 2-chloroethyl-methyl sulfide. Carcinogenesis. 1996 Jun;17(6):1361-4. PubMed PMID: 8681456.

5: Kim HJ, Balcezak TJ, Nathin SJ, McMullen HF, Hansen DE. The use of a spectrophotometric assay to study the interaction of S-adenosylmethionine synthetase with methionine analogues. Anal Biochem. 1992 Nov 15;207(1):68-72. PubMed PMID: 1489102.

6: Koechel DA, Krejci ME, Ridgewell RE. The acute effects of S-(1,2-dichlorovinyl)-L-cysteine and related chemicals on renal function and ultrastructure in the pentobarbital-anesthetized dog: structure-activity relationships, biotransformation, and unique site-specific nephrotoxicity. Fundam Appl Toxicol. 1991 Jul;17(1):17-33. PubMed PMID: 1916074.

7: Leopold WR, Miller JA, Miller EC. Comparison of some carcinogenic, mutagenic, and biochemical properties of S-vinylhomocysteine and ethionine. Cancer Res. 1982 Nov;42(11):4364-74. PubMed PMID: 6290034.