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6-Methylsulfinylhexyl isothiocyanate

6-Methylsulfinylhexyl isothiocyanate (6-MSITC) is an isothiocyanate that has been found in wasabi (W. japonica) and has diverse biological activities.<sup class="referenceList">[1],[2],[3],[4],[5]</sup> It inhibits nitric oxide (NO) production in mouse peritoneal exudate macrophages when used at a concentration of 5 µM.<sup class="referenceList">[1]</sup> It inhibits aggregation of isolated human platelets induced by arachidonic acid.<sup class="referenceList">[2]</sup> 6-MSITC reduces cell survival in a panel of breast, brain, colon, lung, ovarian, renal, and prostate cancer cell lines (mean IC50 = 43.7 µM).<sup class="referenceList">[3]</sup> In vivo, 6-MSITC (5 mg/kg twice weekly) reduces apoptosis of substantia nigral dopaminergic neurons and motor dysfunction in a mouse model of Parkinson's disease induced by 6-OHDA.<sup class="referenceList">[4]</sup> 6-MSITC also reduces the number of lung metastases in a B16/F10 murine melanoma model.<sup class="referenceList">[5]</sup>
4430-35-7
Item No.
TX00DGBQ
CAS No.
4430-35-7
Molecular Formula
C8H15NOS2
Molecular Weight
205.3408
Pricing ＆ Availability
Pack Size Purity Price(USD) Availability Quantity
1mg ≥98% $28.00 in stock
5mg ≥98% $104.00 in stock
10mg ≥98% $157.00 in stock
25mg ≥98% $196.00 in stock
WARNING This product is for research use only. SDS
Technical Information
Item No.:
TX00DGBQ
Product Name:
6-Methylsulfinylhexyl isothiocyanate
Description:
Synonyms:
6-MSITC; 6-Methylsulfinylhexyl isothiocyanate; Hesperin
CAS Number:
4430-35-7
MDL:
MFCD03093720
Molecular Formula:
C8H15NOS2
Molecular Weight:
205.3408
SMILES:
S=C=NCCCCCCS(C)=O
Cell Assay:
Primary human umbilical vein endothelial cells (HUVECs) are cultured in collagen-coated tissue-culture dishes in an atmosphere containing 95 % air and 5 % CO2. Human monoblast U937 cells are grown in RPMI-1640 medium with 10 % fetal bovine serum, 10 U/mL Penicillin, and 10μg/mL Streptomycin. HUVECs are cultured in collagen-coated 96-well plates as confluent monolayers. Hesperin is added into wells at the indicated final concentrations (0-30 μg/mL) and then incubated for 24 h. Cell viability is measured by cell counting kits[2]. Method(s) not verified, for reference only.
Animal Administration:
Mice[1]A colony of wild-type and Nrf2-null mice are backcrossed with C57BL/6 mice for ten generations. All mice are housed in the same animal care facility controlled for temperature, humidity, and light. Seven-week-old male wild-typeand Nrf2-null mice (n=6-8/group) are divided into five groups fed the following diets: 1) a standard diet (AIN-93, containing 4% soybean oil) for 12 weeks and vehicle (1:10 solution of DMSO/PBS) injected intraperitoneally 4 times per week for the last four weeks (control group), 2) a high-fat diet (HFD) (containing 4% soybean oil and 31% lard) for 12 weeks and vehicle injected intraperitoneally 4 times per week for the last four weeks (HFD group),3) a HFD for 12 weeks and Hesperin (10mg/Kg/day; dissolved in 1:10 solution of DMSO/PBS) injected intraperitoneally 4 times per week for the last four weeks (HFD+ Hesperin), 4) a HFD for 6 weeks followed by a HFD containing 1% carbonyl iron for 6 weeks and vehicle injected intraperitoneally 4 times per week for the last four weeks(HFD+Iron), and 5) a HFD for 6 weeks followed by a HFD containing 1% carbonyl iron for 6 weeks and Hesperin (10mg/Kg/day) injected intraperitoneally 4 times per week for the last four weeks (HFD+Iron+Hesperin). After 12 weeks, blood samples are collected by cardiac puncture under anesthesia with sodium pentobarbital (50 mg/kg, ip) and livers are harvested and stored at -80°C until analysis[1]. Method(s) not verified, for reference only.
Solubility:
DMF: 50 mg/mL, DMSO: 30mg/mL, Ethanol: 50 mg/mL, PBS (pH 7.2): 10 mg/mL
Shipping Condition:
Room temperature in continental US; may vary elsewhere.
References & Citations:
[1]. 1.Morimitsu, Y., Hayashi, K., Nakagawa, Y., et al. Antiplatelet and anticancer isothiocyanates in Japanese domestic horseradish, Wasabi Mech. Ageing Dev. 116(2-3),125-134 (2000).
[2]. Morroni, F., Sita, G., Tarozzi, A., et al. Neuroprotection by 6-(methylsulfinyl)hexyl isothiocyanate in a 6-hydroxydopamine mouse model of Parkinson’s disease Brain Res. 1589,93-104 (2014).
[3]. Noshita, T., Kidachi, Y., Funayama, H., et al. Anti-nitric oxide production activity of isothiocyanates correlates with their polar surface area rather than their lipophilicity Eur. J. Med. Chem. 44(12),4931-4936 (2009).
[4]. Nomura, T., Shinoda, S., Yamori, T., et al. Selective sensitivity to wasabi-derived 6-(methylsulfinyl)hexyl isothiocyanate of human breast cancer and melanoma cell lines studied in vitro Cancer Detect. Prev. 29(2),155-160 (2005).
[5]. Fuke, Y., Shinoda, S., Nagata, I., et al. Preventive effect of oral administration of 6-(methylsulfinyl)hexyl isothiocyanate derived from wasabi (Wasabia japonica Matsum) against pulmonary metastasis of B16-BL6 mouse melanoma cells Cancer Detect. Prev. 30(2),174-179 (2006).