Alyssin
(Synonyms: 5-Methylsulfinylpentyl isothiocyanate, 5-Methylsulfinylpentyl ITC) 目录号 : GC46835
An isothiocyanate with diverse biological activities
Cas No.:646-23-1
Sample solution is provided at 25 µL, 10mM.
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Quality Control & SDS
- View current batch:
- Purity: >95.00%
- COA (Certificate Of Analysis)
- SDS (Safety Data Sheet)
- Datasheet
Alyssin is an isothiocyanate that has been found in W. japonica and has diverse biological activities, including antibacterial, fungicidal, CYP inhibitory, and antiproliferative properties.1,2,3 It is active against the bacteria B. subtilis, methicillin-sensitive S. aureus, methicillin-resistant S. aureus (MRSA), and E. coli, and the plant pathogenic fungus A. niger.1 Alyssin (0.5-2.5 µM) directly inhibits activity of the cytochrome P450 (CYP) isoforms CYP1A1 and CYP1A2 induced by the polycyclic aromatic hydrocarbons (PAHs) anthracene and dibenzo[a,h]anthracene in MCF-7 breast cancer cells.2 It inhibits proliferation of HCT116 colon cancer cells (IC50 = <4 µM).3 Alyssin also inhibits platelet aggregation induced by ADP or arachidonic acid (IC50s = 168 and 20 µM, respectively).4
1.Masuda, H., Harada, Y., Kishimoto, N., et al.Antimicrobial Activities of IsothiocyanatesAroma Active Compounds in Foods229-250(2001) 2.Skupinska, K., Misiewicz-Krzeminska, I., Lubelska, K., et al.The effect of isothiocyanates on CYP1A1 and CYP1A2 activities induced by polycyclic aromatic hydrocarbons in Mcf7 cellsToxicol. In Vitro23(5)763-771(2009) 3.Kim, M.J., Kim, S.H., and Lim, S.-J.Comparison of the apoptosis-inducing capability of sulforaphane analogues in human colon cancer cellsAnticancer Res.30(9)3611-3619(2010) 4.Morimitsu, Y., Hayashi, K., Nakagawa, Y., et al.Antiplatelet and anticancer isothiocyanates in Japanese domestic horseradish, WasabiMech. Ageing Dev.116(2-3)125-134(2000)
| Cas No. | 646-23-1 | SDF | |
| 别名 | 5-Methylsulfinylpentyl isothiocyanate, 5-Methylsulfinylpentyl ITC | ||
| Canonical SMILES | O=S(CCCCCN=C=S)C | ||
| 分子式 | C7H13NOS2 | 分子量 | 191.3 |
| 溶解度 | Chloroform: soluble,DMSO: soluble,Ethanol: soluble | 储存条件 | Store at -20°C |
| General tips | 请根据产品在不同溶剂中的溶解度选择合适的溶剂配制储备液；一旦配成溶液，请分装保存，避免反复冻融造成的产品失效。 储备液的保存方式和期限：-80°C 储存时，请在 6 个月内使用，-20°C 储存时，请在 1 个月内使用。 为了提高溶解度，请将管子加热至37℃，然后在超声波浴中震荡一段时间。 |
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| Shipping Condition | 评估样品解决方案：配备蓝冰进行发货。所有其他可用尺寸：配备RT，或根据请求配备蓝冰。 | ||
| 制备储备液 | |||
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1 mg | 5 mg | 10 mg |
| 1 mM | 5.2274 mL | 26.137 mL | 52.2739 mL |
| 5 mM | 1.0455 mL | 5.2274 mL | 10.4548 mL |
| 10 mM | 0.5227 mL | 2.6137 mL | 5.2274 mL |
| 第一步：请输入基本实验信息（考虑到实验过程中的损耗，建议多配一只动物的药量） | ||||||||||
| 给药剂量 | mg/kg |  |
动物平均体重 | g | |
每只动物给药体积 | ul | |
动物数量 | 只 |
| 第二步：请输入动物体内配方组成（配方适用于不溶于水的药物；不同批次药物配方比例不同，请联系GLPBIO为您提供正确的澄清溶液配方） | ||||||||||
| % DMSO % % Tween 80 % saline | ||||||||||
| 计算重置 | ||||||||||
计算结果:
工作液浓度： mg/ml；
DMSO母液配制方法： mg 药物溶于 μL DMSO溶液（母液浓度 mg/mL，
体内配方配制方法：取 μL DMSO母液，加入 μL PEG300，混匀澄清后加入μL Tween 80，混匀澄清后加入 μL saline，混匀澄清。
1. 首先保证母液是澄清的；
2.
一定要按照顺序依次将溶剂加入，进行下一步操作之前必须保证上一步操作得到的是澄清的溶液，可采用涡旋、超声或水浴加热等物理方法助溶。
3. 以上所有助溶剂都可在 GlpBio 网站选购。
Alyssin and Iberin in Cruciferous Vegetables Exert Anticancer Activity in HepG2 by Increasing Intracellular Reactive Oxygen Species and Tubulin Depolymerization
Biomol Ther (Seoul) 2019 Nov 1;27(6):540-552.PMID:31405267DOI:10.4062/biomolther.2019.027.
To determine the chemopreventive potential of Alyssin and iberin, the in vitro anticancer activities and molecular targets of isothiocyanates (ITCs) were measured and compared to sulforaphane in hepatocellular carcinoma cell HepG2. The SR-FTIR spectra observed a similar pattern vis-à-vis the biomolecular alteration amongst the ITCs-treated cells suggesting a similar mode of action. All of the ITCs in this study cause cancer cell death through both apoptosis and necrosis in concentration dependent manner (20-80 μM). We found no interactions of any of the ITCs studied with DNA. Notwithstanding, all of the ITCs studied increased intracellular reactive oxygen species (ROS) and suppressed tubulin polymerization, which led to cell-cycle arrest in the S and G2/M phase. Alyssin possessed the most potent anticancer ability; possibly due to its ability to increase intracellular ROS rather than tubulin depolymerization. Nevertheless, the structural influence of alkyl chain length on anticancer capabilities of ITCs remains inconclusive. The results of this study indicate an optional, potent ITC (viz., Alyssin) because of its underlying mechanisms against hepatic cancer. As a consequence, further selection and development of effective chemotherapeutic ITCs is recommended.
Differential response of human healthy lymphoblastoid and CCRF-SB leukemia cells to sulforaphane and its two analogues: 2-oxohexyl isothiocyanate and Alyssin
Pharmacol Rep 2007 Jan-Feb;59(1):80-7.PMID:17377210doi
The chemopreventive effect of sulforaphane and two of its analogues on human B-lymphocytes derived cells was evaluated in this study. Two cell lines used in the experiments were: human lymphoblastoid cells and human B-leukemia CCRF-SB. Both cell lines were treated with three structurally related isothiocyanates: sulforaphane, 2-oxohexyl isothiocyanate and Alyssin. The viability of cells, induction of a phase II enzyme-quinone reductase, apoptosis induction, GSH content and ROS formation were evaluated. The results indicate the differences between the chemopreventive properties and apoptosis-inducing activity of three isothiocyanates. The significant differences in response to these compounds were observed between healthy lymphoblastoid and leukemia CCRF-SB cells.
Induction of the Stringent Response Underlies the Antimicrobial Action of Aliphatic Isothiocyanates
Front Microbiol 2021 Jan 14;11:591802.PMID:33584562DOI:10.3389/fmicb.2020.591802.
Bacterial resistance to known antibiotics comprises a serious threat to public health. Propagation of multidrug-resistant pathogenic strains is a reason for undertaking a search for new therapeutic strategies, based on newly developed chemical compounds and the agents present in nature. Moreover, antibiotic treatment of infections caused by enterotoxin toxin-bearing strain-enterohemorrhagic Escherichia coli (EHEC) is considered hazardous and controversial due to the possibility of induction of bacteriophage-encoded toxin production by the antibiotic-mediated stress. The important source of potentially beneficial compounds are secondary plant metabolites, isothiocyanates (ITC), and phytoncides from the Brassicaceae family. We reported previously that sulforaphane and phenethyl isothiocyanate, already known for their chemopreventive and anticancer features, exhibit significant antibacterial effects against various pathogenic bacteria. The mechanism of their action is based on the induction of the stringent response and accumulation of its alarmones, the guanosine penta- and tetraphosphate. In this process, the amino acid starvation path is employed via the RelA protein, however, the precise mechanism of amino acid limitation in the presence of ITCs is yet unknown. In this work, we asked whether ITCs could act synergistically with each other to increase the antibacterial effect. A set of aliphatic ITCs, such as iberin, iberverin, Alyssin, erucin, sulforaphen, erysolin, and cheirolin was tested in combination with sulforaphane against E. coli. Our experiments show that all tested ITCs exhibit strong antimicrobial effect individually, and this effect involves the stringent response caused by induction of the amino acid starvation. Interestingly, excess of specific amino acids reversed the antimicrobial effects of ITCs, where the common amino acid for all tested compounds was glycine. The synergistic action observed for iberin, iberverin, and Alyssin also led to accumulation of (p)ppGpp, and the minimal inhibitory concentration necessary for the antibacterial effect was four- to eightfold lower than for individual ITCs. Moreover, the unique mode of ITC action is responsible for inhibition of prophage induction and toxin production, in addition to growth inhibition of EHEC strains. Thus, the antimicrobial effect of plant secondary metabolites by the stringent response induction could be employed in potential therapeutic strategies.
Isothiocyanate-drug interactions in the human adenocarcinoma cell line Caco-2
Mol Cell Biochem 2012 Aug;367(1-2):19-29.PMID:22527941DOI:10.1007/s11010-012-1314-y.
Isothiocyanates, among which Alyssin is counted, are the compounds that have proved chemopreventive properties and the ability to induce the 2 and the 3 detoxification phase by affecting the transcription factor nuclear erythroid 2-related factor (Nrf2). Having a positive effect on the human body, these compounds are used as dietary supplements. Because of the observed increase in the consumption of dietary supplements taken along with the drugs routinely used in medical practice, this study examined the possibility of interactions between Alyssin and drugs, which could have an impact on cell metabolism. We have determined the effects of the tested substances and their interactions on the expression and activity of the phase 2 genes, as well as on the drug transport, which could be influenced by affecting the expression of transport proteins that belong to the 3 phase of metabolism. It was also studied whether the transcription factor Nrf2 is responsible for the interactions that occurred. The results showed that the interactions between Alyssin and the tested drugs strengthen or weaken the effect of the drugs given separately depending on the concentration of Alyssin and the type of drug. Even though Nrf2 is involved in the interaction, it seems that it is not the only factor regulating the interactions between the tested medications.
Urease from Helicobacter pylori is inactivated by sulforaphane and other isothiocyanates
Biochem Biophys Res Commun 2013 May 24;435(1):1-7.PMID:23583386DOI:10.1016/j.bbrc.2013.03.126.
Infections by Helicobacter pylori are very common, causing gastroduodenal inflammation including peptic ulcers, and increasing the risk of gastric neoplasia. The isothiocyanate (ITC) sulforaphane [SF; 1-isothiocyanato-4-(methylsulfinyl)butane] derived from edible crucifers such as broccoli is potently bactericidal against Helicobacter, including antibiotic-resistant strains, suggesting a possible dietary therapy. Gastric H. pylori infections express high urease activity which generates ammonia, neutralizes gastric acidity, and promotes inflammation. The finding that SF inhibits (inactivates) urease (jack bean and Helicobacter) raised the issue of whether these properties might be functionally related. The rates of inactivation of urease activity depend on enzyme and SF concentrations and show first order kinetics. Treatment with SF results in time-dependent increases in the ultraviolet absorption of partially purified Helicobacter urease in the 260-320 nm region. This provides direct spectroscopic evidence for the formation of dithiocarbamates between the ITC group of SF and cysteine thiols of urease. The potencies of inactivation of Helicobacter urease by isothiocyanates structurally related to SF were surprisingly variable. Natural isothiocyanates closely related to SF, previously shown to be bactericidal (berteroin, hirsutin, phenethyl isothiocyanate, Alyssin, and erucin), did not inactivate urease activity. Furthermore, SF is bactericidal against both urease positive and negative H. pylori strains. In contrast, some isothiocyanates such as benzoyl-ITC, are very potent urease inactivators, but are not bactericidal. The bactericidal effects of SF and other ITC against Helicobacter are therefore not obligatorily linked to urease inactivation, but may reduce the inflammatory component of Helicobacter infections.