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A Biocompatible Condensation Reaction for Controlled Assembly of Nanostructures in Living Cells

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Journal Nat Chem
Specialty Chemistry
Date 2010 Dec 3
PMID 21124381
Citations 124
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Abstract

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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References
1.
Kolb H, Finn M, Sharpless K . Click Chemistry: Diverse Chemical Function from a Few Good Reactions. Angew Chem Int Ed Engl. 2001; 40(11):2004-2021. DOI: 10.1002/1521-3773(20010601)40:11<2004::AID-ANIE2004>3.0.CO;2-5. View

2.
Cheng M, Watson P, Paterson J, Seidah N, Chretien M, Shiu R . Pro-protein convertase gene expression in human breast cancer. Int J Cancer. 1997; 71(6):966-71. DOI: 10.1002/(sici)1097-0215(19970611)71:6<966::aid-ijc10>3.0.co;2-4. View

3.
Punna S, Kuzelka J, Wang Q, Finn M . Head-to-tail peptide cyclodimerization by copper-catalyzed azide-alkyne cycloaddition. Angew Chem Int Ed Engl. 2005; 44(15):2215-20. DOI: 10.1002/anie.200461656. View

4.
Shapiro J, Sciaky N, Lee J, Bosshart H, Angeletti R, Bonifacino J . Localization of endogenous furin in cultured cell lines. J Histochem Cytochem. 1997; 45(1):3-12. DOI: 10.1177/002215549704500102. View

5.
Yan S, Sameni M, Sloane B . Cathepsin B and human tumor progression. Biol Chem. 1998; 379(2):113-23. View