592-95-0 Usage
Uses
Used in Pharmaceutical Industry:
Sulforaphene is used as an anti-inflammatory agent for its ability to reduce inflammation and alleviate symptoms associated with inflammatory conditions. It targets key inflammatory pathways, providing relief and potentially preventing the progression of chronic diseases.
Used in Anticancer Applications:
Sulforaphene is employed as an anti-cancer agent, particularly against various types of cancer. It modulates several oncological signaling pathways, leading to the inhibition of tumor growth and progression. Additionally, it demonstrates synergistic anticancer effects when combined with conventional chemotherapeutic drugs, enhancing chemo-sensitivity and efficacy in resistant cases.
Used in Drug Delivery Systems:
To overcome the limitations of Sulforaphene, novel drug delivery systems have been developed to enhance its applications and efficacy against cancer cells. Various organic and metallic nanoparticles have been employed as carriers for Sulforaphene delivery, aiming to improve its delivery, bioavailability, and therapeutic outcomes.
Pharmacological action
Sulforaphene, or raphanin, is the main sulfur component found in radish seeds of Raphanus sativus and is also found in broccoli and red cabbage. It was first described by G. Ivanovics and S. Horvath in 1947. Sulforaphene inhibits activity of viruses, some fungi and various bacteria including Staphylococcus, Streptococcus, Pneumococcus and Escherichia coli. The effect is stronger against Gram-positive than Gram-negative bacteria and against DNA than RNA viruses; it is suppressed by serum and by sulfur compounds such as hydrogen sulfide, mercaptoacetic acid, cystine and glutathione. The antibacterial, antifungal and antiviral effects from consuming radishes were recognized in traditional Chinese medicine. However, in the abstract to his 1947 paper, Ivanovics noted that because sulforaphene is highly toxic, it did not "hold the promise of a useful therapeutic agent".
Cancer Treatment
Sulforaphene may be a potential anti-triple negative breast cancer natural compound and its antiproliferation effects may be mediated by tumor suppressor Egr1; it has chemotherapeutic potential, it promotes Bax/Bcl2, MAPK-dependent human gastric cancer AGS cells apoptosis and inhibits migration via EGFR, p-ERK1/2 down-regulation; it enhances radiosensitivity of hepatocellular carcinoma through suppression of the NF-κB pathway. Sulforaphene has anti-proliferative and antibacterial properties. Sulforaphene also has herbicidal activity, the ED50 of it against velvetleaf seedlings was approximately 2×10-4 M.
Synthesis Reference(s)
Tetrahedron, 22, p. 2139, 1966 DOI: 10.1016/S0040-4020(01)82133-5
Check Digit Verification of cas no
The CAS Registry Mumber 592-95-0 includes 6 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 3 digits, 5,9 and 2 respectively; the second part has 2 digits, 9 and 5 respectively.
Calculate Digit Verification of CAS Registry Number 592-95:
(5*5)+(4*9)+(3*2)+(2*9)+(1*5)=90
90 % 10 = 0
So 592-95-0 is a valid CAS Registry Number.
InChI:InChI=1/C6H9NOS2/c1-10(8)5-3-2-4-7-6-9/h3,5H,2,4H2,1H3/b5-3+
592-95-0Relevant academic research and scientific papers
Cytotoxic and antioxidant activity of 4-methylthio-3-butenyl isothiocyanate from Raphanus sativus L. (Kaiware Daikon) sprouts
Papi, Alessio,Orlandi, Marina,Bartolini, Giovanna,Barillari, Jessica,Iori, Renato,Paolini, Moreno,Ferroni, Fiammetta,Fumo, Maria Grazia,Pedulli, Gian Franco,Valgimigli, Luca
experimental part, p. 875 - 883 (2009/05/08)
There is high current interest in the chemopreventive potential of Brassica vegetables (cruciferae), particularly due to their content in glucosinolates (GL), which upon myrosinase hydrolysis release the corresponding isythiocyanates (ITC). Some ITCs, such as sulforaphane (SFN) from broccoli (Brassica oleacea italica), have been found to possess anticancer activity through induction of apoptosis in selected cell lines, as well as indirect antioxidant activity through induction of phase II detoxifying enzymes. Japanese daikon (Raphanus sativus L.) is possibly the vegetable with the highest per capita consumption within the Brassicaceae family. Thanks to a recently improved gram scale production process, it was possible to prepare sufficient amounts of the GL glucoraphasatin (GRH) as well as the corresponding ITC 4-methylthio-3-butenyl isothiocyanate (GRH-ITC) from its sprouts. This paper reports a study on the cytotoxic and apoptotic activities of GRH-ITC compared with the oxidized counterpart 4-methylsulfinyl-3-butenyl isothiocyanate (GRE-ITC) on three human colon carcinoma cell lines (LoVo, HCT-116, and HT-29) together with a detailed kinetic investigation of the direct antioxidant/radical scavenging ability of GRH and GRH-ITC. Both GRH-ITC and GRE-ITC reduced cell proliferation in a dose-dependent manner and induced apoptosis in the three cancer cell lines. The compounds significantly (p -1 s-1, respectively (at 298 K in methanol), whereas the corresponding value measured here for the reference antioxidant α-tocopherol was 425 ± 40 M-1 s-1. GRH reacted with H2O2 and tert-butyl hydroperoxide in water (pH 7.4) at 37°C, with rate constants of 1.9 ± 0.3 × 10-2 and 9.5 ± 0.3 × 10-4 M -1 s-1 (paralleling recently developed synthetic antioxidants) being quantitatively (>97%) converted to GRE. It is demonstrated that GRH-ITC has interesting antioxidant/radical scavenging properties, associated with a selective cytotoxic/apoptotic activity toward three human colon carcinoma cell lines, and very limited toxicity on normal human T-lymphocytes.
