Constrictive binding

Several chemical compounds may cause inflammation or constriction of the blood vessel wall (vasoconstriction). Ergot alkaloids at high doses cause constriction and thickening of the vessel wall. Allylamine may also induce constriction of coronary arteries, thickening of their smooth muscle walls, and a disease state that corresponds to coronary heart disease. The culprit is a toxic reactive metabolite of allylamine, acrolein, that binds covalently to nucleophilic groups of proteins and nucleic acids in the cardiac myocytes. 

Most of the molecules introduced in this chapter are hydrophobic. Even those molecules that have been functionalized to improve water-solubility (for example, CCVJ and CCVJ triethyleneglycol ester 43, Fig. 14) contain large hydrophobic structures. In aqueous solutions that contain proteins or other macromolecules with hydrophobic regions, molecular rotors are attracted to these pockets and bind to the proteins. Noncovalent attraction to hydrophobic pockets is associated with restricted intramolecular rotation and consequently increased quantum yield. In this respect, molecular rotors are superior protein probes, because they do not only indicate the presence of proteins (similar to antibody-conjugated fluorescent markers), but they also report a constricted environment and can therefore be used to probe protein structure and assembly. 

K. N. Houk, K. Nakamura, C. Sheu, A. E. Keating, Gating as a Control Element in Constrictive Binding and Guest Release by Hemicarcerands , Science 1996, 273, 627-629. 

Keywords Constrictive Binding m Crown Ethers m Hemicarcerands a Host-Guest Chemistry a Noncovalent Interactions aRotaxanes a Self-Assembly a Slippage a Supramolecular Chemistry... 

D. J. Cram, J. M. Cram, Hemicarcerands and Constrictive Binding , In Container Molecules and Their Guests (Ed. J. F. Stoddart), The Royal Society of Chemistiy, Cambridge, 1994, pp. 149-169, and references cited therein. 

Wagner DA, Czajkowski C. 2001. Structure and dynamics of the GABA binding pocket a narrowing cleft that constricts during activation. J Neurosci 21 (1) 67. 

Compd. Slereochem. R Opioid receptor binding K, (nM) Mouse abdominal constriction... 

---