A lipophilic heparin derivative protects elastin against degradation by leucocyte elastase

An oleolylated derivative (I) of partially N-desulphated heparin was prepared containing an average number of three oleoyl residues for one molecule of heparin. The inhibitory capacity of I (IC 50 = 0.55 μ m) for leucocyte elastase resembles that of heparin (IC 50 = 0.2 μ m). In contrast to heparin, I is also an inhibitor of porcine pancreatic elastase (IC 50 = 0.68 μ m) and it also has the capacity to protect elastin fibres against the degradation by leucocyte elastase. When insoluble elastin is pretreated with I its degradation by leucocyte elastase is inhibited by almost 90% while pretreatment of elastin with heparin exhibited only a moderate effect on elastolysis (10% inhibition).