Synthesis and characterization of carnitine nitro-derivatives

Nitric oxide (NO) acts as an autacoid molecule that diffuses from its endothelial production site to the neighboring muscular cells. NO-donors are often used to mimic the physiological effects of NO in biological systems. Organic nitrates are commonly used as NO-donors; the most popular, glycerol trinitrate (GTN), has been used in therapy for more than a century. Carnitine nitrates have been synthesized using an endogenous non-toxic molecule: (L)-carnitine. The biotransformation of carnitine nitro-derivatives in biological fluids (saliva and blood plasma) and in red blood cells (RBC) has been monitored by an electrochemical assay and the interaction of carnitine nitrates with the plasma membrane carnitine transporter has been investigated. Differences in the way carnitine nitro-derivatives are metabolized in biological fluids and cells and transported by OCTN2 transporter are modulated by the chemical structures and by the length of the acyl template which carries the nitro-group. (C) 2007 Elsevier Ltd. All rights reserved.