Chemoselective Ligation in the Functionalization of Polysaccharide-Based Particles Export

@article{citeulike:5402091, abstract = {Despite the promise of precisely targeted or otherwise functionalized polymeric particulate drug delivery vehicles, typical biocompatible particles are generally not amenable to facile and selective surface modification. Herein, we report the development of a simple, mild, and chemoselective strategy for the conjugation of biologically active molecules to the surface of dextran-based microparticles. Alkoxyamine-bearing reagents were used to form stable oxime conjugates with latent aldehyde functionality present in reducing carbohydrate chain ends. We demonstrate the functionalization of dextran-based microparticles with a fluorophore as well as a cell-penetrating peptide sequence, which facilitated the delivery of cargo to nonphagocytic cells leading to a 60-fold increase in the expression of a reporter gene when plasmid DNA-loaded particles were used.}, author = {Beaudette, Tristan T. and Cohen, Joel A. and Bachelder, Eric M. and Broaders, Kyle E. and Cohen, Jessica L. and Engleman, Edgar G. and Fréchet, Jean M. J.}, citeulike-article-id = {5402091}, citeulike-linkout-0 = {http://dx.doi.org/10.1021/ja903984s}, citeulike-linkout-1 = {http://pubs.acs.org/doi/abs/10.1021/ja903984s}, day = {5}, doi = {10.1021/ja903984s}, journal = {Journal of the American Chemical Society}, keywords = {chemoselective, functionalization, ligation, polysaccharide}, month = {August}, number = {30}, pages = {10360--10361}, posted-at = {2009-08-09 23:09:30}, priority = {2}, title = {Chemoselective Ligation in the Functionalization of Polysaccharide-Based Particles}, url = {http://dx.doi.org/10.1021/ja903984s}, volume = {131}, year = {2009} }

TY - JOUR ID - citeulike:5402091 L3 - citeulike-article-id:5402091 N2 - Despite the promise of precisely targeted or otherwise functionalized polymeric particulate drug delivery vehicles, typical biocompatible particles are generally not amenable to facile and selective surface modification. Herein, we report the development of a simple, mild, and chemoselective strategy for the conjugation of biologically active molecules to the surface of dextran-based microparticles. Alkoxyamine-bearing reagents were used to form stable oxime conjugates with latent aldehyde functionality present in reducing carbohydrate chain ends. We demonstrate the functionalization of dextran-based microparticles with a fluorophore as well as a cell-penetrating peptide sequence, which facilitated the delivery of cargo to nonphagocytic cells leading to a 60-fold increase in the expression of a reporter gene when plasmid DNA-loaded particles were used. IS - 30 JF - Journal of the American Chemical Society EP - 10361 TI - Chemoselective Ligation in the Functionalization of Polysaccharide-Based Particles VL - 131 SP - 10360 KW - chemoselective KW - functionalization KW - ligation KW - polysaccharide AU - Beaudette, Tristan AU - Cohen, Joel AU - Bachelder, Eric AU - Broaders, Kyle AU - Cohen, Jessica AU - Engleman, Edgar AU - Fréchet, Jean PY - 2009/08/05/ UR - http://dx.doi.org/10.1021/ja903984s ER -