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Nat Chem. 2010 Jan;2(1):54-60. doi: 10.1038/nchem.480. Epub 2009 Dec 17.

A biocompatible condensation reaction for controlled assembly of nanostructures in living cells.

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Molecular Imaging Program at Stanford, Department of Radiology, Stanford University, 1201 Welch Road, Stanford, California 94305-5484, USA.

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  • Nat Chem. 2010 Mar;2(3):239.


Through controlled synthesis and molecular assembly, biological systems are able to organize molecules into supramolecular structures that carry out sophisticated processes. Although chemists have reported a few examples of supramolecular assembly in water, the controlled covalent synthesis of large molecules and structures in vivo has remained challenging. Here we report a condensation reaction between 1,2-aminothiol and 2-cyanobenzothiazole that occurs in vitro and in living cells under the control of either pH, disulfide reduction or enzymatic cleavage. In vitro, the size and shape of the condensation products, and the nanostructures subsequently assembled, were different in each case and could thus be controlled by tuning the structure of the monomers. Direct imaging of the products obtained in the cells revealed their locations-near the Golgi bodies under enzymatic cleavage control-demonstrating the feasibility of a controlled and localized reaction in living cells. This intracellular condensation process enabled the imaging of the proteolytic activity of furin.

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