Development of novel nutrapharmaceuticals combining the anti-oxidant and anti-inflammatory properties of n-3 fatty acids with a nitric oxide donor - a potential new preventative strategy for heart disease.
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Atherosclerosis is a cardiovascular disease which forms plaques which narrow the arteries, restricting blood flow and thus increasing blood pressure. As this can lead to more serious conditions, such as myocardial infarction, it is important that atherosclerosis is treated to prevent dangerous levels of atherosclerotic plaques forming. The aim of this project was to create a library of novel PUFA-NO conjugates which would contain the combined beneficial cardioprotective and anti-inflammatory qualities of both groups. Synthesis of aliphatic-aminothiol conjugates has been achieved using both acid chloride (N-decanoyl cysteamine (Compound 1), N-decanoyl L-cysteine ethyl ester (compound 3)) and peptide coupling based reactions, and full characterisation has been achieved. The nitration stage of synthesis was achieved using tert-butyl nitrite and 'fuming' NO as the nitrating agents. Successful nitration was determined by MS analysis and by use of the Griess reaction as a colourimetric test to determine the ability of the synthesised compounds (S-nitroso N-decanoyl cysteamine (compound 7), S-nitroso N-oleoyl cysteamine (compound 8)) to release nitric oxide.