The 8 year thicket of triazine dendrimers: strategies, targets and applications by Eric E. Simanek, Hanan Abdou, Sanjiv Lalwani, Jongdoo Lim, Meredith.

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Presentation transcript:

The 8 year thicket of triazine dendrimers: strategies, targets and applications by Eric E. Simanek, Hanan Abdou, Sanjiv Lalwani, Jongdoo Lim, Meredith Mintzer, Vincent J. Venditto, and Brandon Vittur Proceedings A Volume 466(2117): May 8, 2010 ©2010 by The Royal Society

Chemoselective reactivity of cyanuric chloride. Eric E. Simanek et al. Proc. R. Soc. A 2010;466: ©2010 by The Royal Society

Relative reactivity of a series of amines toward monochlorotriazines. Eric E. Simanek et al. Proc. R. Soc. A 2010;466: ©2010 by The Royal Society

A starting reference for the reactivity of amines with triazines as a function of temperature based on both experimental data and intuition. Eric E. Simanek et al. Proc. R. Soc. A 2010;466: ©2010 by The Royal Society

The first syntheses of triazine dendrimers. Eric E. Simanek et al. Proc. R. Soc. A 2010;466: ©2010 by The Royal Society

The fifth generation dendron. Eric E. Simanek et al. Proc. R. Soc. A 2010;466: ©2010 by The Royal Society

Convergent routes to growing trees relying on p-aminobenzylamine linkers. Eric E. Simanek et al. Proc. R. Soc. A 2010;466: ©2010 by The Royal Society

Dendrimers with piperazine and p-ABA linkers show different propensity for gelation in acidic chloroform. Eric E. Simanek et al. Proc. R. Soc. A 2010;466: ©2010 by The Royal Society

Exploring new linking diamines and chemoselective reactions. Eric E. Simanek et al. Proc. R. Soc. A 2010;466: ©2010 by The Royal Society

An orthogonally reactive dendrimer with 4 hydroxyl groups, 4 silyl ethers, 4 esters, 4 disulphides and 16 BOC-protected amines. Eric E. Simanek et al. Proc. R. Soc. A 2010;466: ©2010 by The Royal Society

A less diverse, generation 4 dendrimer with 16 BOC-protected amines, eight alcohols (four protected) and two monochlorotriazines. Eric E. Simanek et al. Proc. R. Soc. A 2010;466: ©2010 by The Royal Society

A generation 3 dendrimer comprising orthogonally protected amines derived from a generation 2 dendrons and a generation 1 ‘super’ core (dotted circle). Eric E. Simanek et al. Proc. R. Soc. A 2010;466: ©2010 by The Royal Society

A dendrimer with unique linking diamines and other conformational models. Eric E. Simanek et al. Proc. R. Soc. A 2010;466: ©2010 by The Royal Society

A host of guests derived convergently using piperazine linkers and a ‘common’ core. Eric E. Simanek et al. Proc. R. Soc. A 2010;466: ©2010 by The Royal Society

Targets for DNA conjugation. Eric E. Simanek et al. Proc. R. Soc. A 2010;466: ©2010 by The Royal Society

Multivalent displays for thiol-disulphide exchange with captopril or CLKKDDRA. Reproduced with permission from Umali & Simanek (2003). Eric E. Simanek et al. Proc. R. Soc. A 2010;466: ©2010 by The Royal Society

Targets for evaluating the kinetics of thiol-disulphide exchange using mass spectrometry. Eric E. Simanek et al. Proc. R. Soc. A 2010;466: ©2010 by The Royal Society

Triazine dendrimers cannot intercalate into the interstitial galleries of smectite clays. Eric E. Simanek et al. Proc. R. Soc. A 2010;466: ©2010 by The Royal Society

Triazine dendrons can be grown divergently (or attached after convergent synthesis) to inorganic supports. Eric E. Simanek et al. Proc. R. Soc. A 2010;466: ©2010 by The Royal Society

Evaluating the biological compatibility of third generation dendrimers with AB4 peripheral groups. Eric E. Simanek et al. Proc. R. Soc. A 2010;466: ©2010 by The Royal Society

A water soluble dendrimer displaying paclitaxel. Eric E. Simanek et al. Proc. R. Soc. A 2010;466: ©2010 by The Royal Society

A divergent route to diversity with a representative dichlorotriazine monomer that was added to the trispiperazinyltriazine core, capped with aminoethoxyethanol and elaborated. Eric E. Simanek et al. Proc. R. Soc. A 2010;466: ©2010 by The Royal Society

An iterative, divergent route to diversity. Eric E. Simanek et al. Proc. R. Soc. A 2010;466: ©2010 by The Royal Society

Generation 1–5 dendrimers can be accessed through the divergent approach described in scheme 14, but the generation 4 and 5 materials are not ‘single chemical entities’ but rather mixtures. Eric E. Simanek et al. Proc. R. Soc. A 2010;466: ©2010 by The Royal Society