Applications of Pi Stacking
A powerful demonstration of stacking is found in the buckycatcher. This molecular tweezer is based on two concave buckybowls with a perfect fit for one convex fullerene molecule. Complexation takes place simply by evaporating a toluene solution containing both compounds. In solution an association constant of 8600 M−1 is measured based on changes in NMR chemical shifts.
Pi stacking is prevalent in protein crystal structures, and also contributes to the interactions between small-molecules and proteins. As a result, pi-pi and cation-pi interactions are important factors in rational drug design. One example is the FDA-approved acetylcholinesterase (AChE) inhibitor Tacrine which is used in the treatment of Alzheimer's disease. Tacrine is proposed to have a pi stacking interaction with the indolic ring of Trp84, and this interaction has been exploited in the rational design of novel AChE inhibitors.
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Famous quotes containing the word stacking:
“The Universal Soul, as it is called, has an interest in the stacking of hay, the foddering of cattle, and the draining of peat-meadows.”
—Henry David Thoreau (1817–1862)