Isothiocyanate
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Isothiocyanate is the chemical group -N=C=S, formed by substituting sulfur for oxygen in the isocyanate group. Allyl isothiocyanate is a chemical compound found in mustard oil that is responsible for its pungency. It is used for amino acid sequencing in Edman degradation.
Reactions
Isothiocyanates generally act as electrophiles with the carbon atom as the electrophilic center.
Biological Activity
Isothiocyanates, such as phenethyl isothiocyanate (PEITC) and sulforaphane, have been shown to inhibit carcinogenesis and tumorigensis and as such are useful chemopreventive agents against the development and proliferation of cancers. They work on a variety of levels. Most notably, they have been shown to inhibit carcinogenesis through inhibition of cytochrome P450 enzymes, which oxidise compounds such as benzo[a]pyrene and other polycyclic aromatic hydrocarbons (PAHs)into more polar epoxy-diols which can then cause mutation and induce cancer development. Phenethyl isothiocyanate (PEITC) has been shown to induce apoptosis in certain cancer cell lines, and in some cases, is even able to induce apoptosis in cells that are resistant to some currently used chemotherapeutic drugs. For example, in drug resistant leukemia cells which produce the powerful apoptosis inhibitor protein BCl-2.
See also
References
de:Isothiocyanat sv:Isotiocyanat
Acknowledgement and Attribution Regarding Sources of Content
Some of the initial content on this page may be incorporated in part from copyleft sources in the public domain including wikis such as Wikipedia and AskDrWiki. Drug information for patients came from the The National Library of Medicine. Infectious disease information may have come from the Centers for Disease Control (CDC). Differential Diagnoses are drawn from clinicians as well as an amalgamation of 3 sources: 1.The Disease Database; 2. Kahan, Scott, Smith, Ellen G. In A Page: Signs and Symptoms. Malden, Massachusetts: Blackwell Publishing, 2004:3; 3. Sailer, Christian, Wasner, Susanne. Differential Diagnosis Pocket. Hermosa Beach, CA: Borm Bruckmeir Publishing LLC, 2002:7 .
