An isothiocyanate derivative and an active metabolite of sulforaphane
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S-(N-Methylsulfinylbutylthiocarbamoyl)-L-cysteine

Item No. 39555

Product Insert (PDF)Safety Data Sheet (SDS) (PDF)
Technical Information
Formal Name
S-[[[4-(methylsulfinyl)butyl]amino]thioxomethyl]-L-cysteine
CAS Number
364083-21-6
Synonyms
  • SFN-Cys
  • D,L-Sulforaphane-L-cysteine
Molecular Formula
C9H18N2O3S3
Formula Weight
298.4
Purity
≥95%
Formulation (Request formulation change)
A solid
Solubility(Learn about Variance in Solubility)
Methanol: Slightly solubleWater: Slightly soluble
SMILES
O=C(O)[C@@H](N)CSC(NCCCCS(C)=O)=S
InChi Code
InChI=1S/C9H18N2O3S3/c1-17(14)5-3-2-4-11-9(15)16-6-7(10)8(12)13/h7H,2-6,10H2,1H3,(H,11,15)(H,12,13)/t7-,17?/m0/s1
InChi Key
PUPMSTCTVNEOCX-ISJKBYAMSA-N
Origin
Synthetic
Shipping & Storage Information
Storage
-20°C
Shipping
Room temperature in continental US; may vary elsewhere
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    5 mg

    $318

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    Product Description

    S-(N-Methylsulfinylbutylthiocarbamoyl)-L-cysteine (SFN-Cys) is a isothiocyanate derivative and an active metabolite of the class I and II histone deacetylase (HDAC) inhibitor and anticancer agent sulforaphane (Item Nos. 10496 | 14797).1 It is formed from sulforaphane via DL-sulforaphane glutathione (Item No. 34731) and sulforaphane cysteinylglycine intermediates by mercapturic acid pathway enzymes. SFN-Cys (20 µM) reduces invasion and migration by U87MG and U373 MG glioblastoma cells in wound healing and chamber assays, respectively.2 It decreases levels of α-tubulin, βIII-tubulin, stathmin 1, and X-linked inhibitor of apoptosis (XIAP) in, as well as reduces cell density of, paclitaxel-resistant A549 lung cancer cells (A549/T) when used at a concentration of 45 µM.3 SFN-Cys (30 µM) induces apoptosis and cell cycle arrest at the G2/M phase in U87MG and U373 MG cells.4

    WARNING This product is not for human or veterinary use.

    References & Product Citations
    Product Description References

    1. Al Janobi, A.A., Mithen, R.F., Gasper, A.V., et al. Quantitative measurement of sulforaphane, iberin and their mercapturic acid pathway metabolites in human plasma and urine using liquid chromatography-tandem electrospray ionisation mass spectrometry. J. Chromatogr. B. Analyt. Technol. Biomed. Life Sci. 844(2), 223-234 (2006).

    2. Zhou, Y., Wang, Y., Wu, S., et al. Sulforaphane-cysteine inhibited migration and invasion via enhancing mitophagosome fusion to lysosome in human glioblastoma cells. Cell. Death. Dis. 11(9), 819 (2020).

    3. Wang, Y., Zhou, Y., Zheng, Z., et al. Sulforaphane metabolites reduce resistance to paclitaxel via microtubule disruption. Cell Death Dis. 9(11), 1134 (2018).

    4. Li, J., Zhou, Y., Yan, Y., et al. Sulforaphane-cysteine downregulates CDK4 /CDK6 and inhibits tubulin polymerization contributing to cell cycle arrest and apoptosis in human glioblastoma cells. Aging (Albany N.Y.) 12(17), 16837-16851 (2020).