1.Identification of 2-nonynoic acid, a cosmetic component, as a potential trigger of primary biliary cirrhosis.
Rieger R1, Leung PS, Jeddeloh MR, Kurth MJ, Nantz MH, Lam KS, Barsky D, Ansari AA, Coppel RL, Mackay IR, Gershwin ME. J Autoimmun. 2006 Aug;27(1):7-16. Epub 2006 Jul 28.
Antimitochondrial antibodies (AMA) are unique among autoimmune serologic reactants because of their extremely high association with the index disease primary biliary cirrhosis (PBC). This autoantibody response is specifically directed only to the lipoyl domain of the mitochondrial 2-oxo-acid dehydrogenase complexes, which prompted us to search for environmental mimotopes in the form of xenobiotics and led to our identification of 2-octynoic acid as a high-affinity reactant for AMA. To focus on the chemical characteristics requisite for binding of AMA to the xenobiotic-modified self-peptide, quantitative structure-activity relationship (QSAR) studies were performed using a panel of alkynoic compounds, including examination of the length of the carbon chain and the location of the triple bond in the identified mimotope. Analyses of octynamides that varied in the position of the triple bond demonstrated that only the 2-octynamide reacted strongly with PBC sera.
2.Allergic contact dermatitis from methyl heptine and methyl octine carbonates.
English JS1, Rycroft RJ. Contact Dermatitis. 1988 Mar;18(3):174-5.