We report the simple synthesis and full investigation
of a novel
heparin binding dye, mallard blue, an arginine-functionalized thionine.
This dye binds heparin in highly competitive media, including water
with high levels of competitive electrolyte, buffered aqueous solution
and human serum. The dye reports on heparin levels by a significant
change in its UV–vis spectroscopic profile. Molecular dynamics
modeling provides detailed insight into the binding mode. Heparin
binding is shown to be selective over other glycosaminoglycans, such
as hyaluronic acid and chondroitin sulfate. Importantly, we
demonstrate that, in the most competitive conditions, mallard blue
outperforms standard dyes used for heparin sensing such as azure A.