Literature DB >> 20037678

A divergent route towards single-chemical entity triazine dendrimers with opportunities for structural diversity.

Hannah Crampton1, Emily Hollink, Lisa M Perez, Eric E Simanek.   

Abstract

This manuscript describes the successful synthesis and characterization of five generations of dendrimers based on melamine. Early generations of these materials appear to be single chemical entities: upon purification, no detectable impurities are observed using NMR spectroscopy, mass spectrometry, and HPLC and GPC analysis. The analysis of larger generation materials precludes an unambiguous statement of purity. The synthetic route to these targets is divergent, relying on dichlorotriazine monomers that react with a polyamine dendrimer core of generation n to produce a poly(monochlorotriazine) dendrimer of generation n + 1. Subsequently, the poly(monochlorotriazine) is derivatized through nucleophilic aromatic substitution before additional nucleophilic amines are unmasked and the process iterated.

Entities:  

Year:  2007        PMID: 20037678      PMCID: PMC2797734          DOI: 10.1039/b617875h

Source DB:  PubMed          Journal:  New J Chem        ISSN: 1144-0546            Impact factor:   3.591


  7 in total

1.  Synthesis and manipulation of orthogonally protected dendrimers: building blocks for library synthesis.

Authors:  Mackay B Steffensen; Eric E Simanek
Journal:  Angew Chem Int Ed Engl       Date:  2004-10-04       Impact factor: 15.336

2.  Chemistry. Dendrimers at work.

Authors:  Brett Helms; E W Meijer
Journal:  Science       Date:  2006-08-18       Impact factor: 47.728

3.  The selective reaction of primary amines with carbonyl imidazole containing compounds: selective amide and carbamate synthesis

Authors: 
Journal:  Org Lett       Date:  2000-07-13       Impact factor: 6.005

4.  Toward the next-generation drug delivery vehicle: synthesis of a dendrimer with four orthogonally reactive groups.

Authors:  Jongdoo Lim; Eric E Simanek
Journal:  Mol Pharm       Date:  2005 Jul-Aug       Impact factor: 4.939

5.  A divergent route to diversity in macromolecules.

Authors:  Emily Hollink; Eric E Simanek
Journal:  Org Lett       Date:  2006-05-25       Impact factor: 6.005

6.  Dendrimers Based on [1,3,5]-Triazines.

Authors:  Mackay B Steffensen; Emily Hollink; Frank Kuschel; Monika Bauer; Eric E Simanek
Journal:  J Polym Sci A Polym Chem       Date:  2006-06-01       Impact factor: 2.702

7.  Cytotoxicity, hemolysis, and acute in vivo toxicity of dendrimers based on melamine, candidate vehicles for drug delivery.

Authors:  Hui-Ting Chen; Michael F Neerman; Alan R Parrish; Eric E Simanek
Journal:  J Am Chem Soc       Date:  2004-08-18       Impact factor: 15.419

  7 in total
  8 in total

1.  Electrophoretic Behavior of Anionic Triazine and PAMAM Dendrimers: Methods for Improving Resolution and Assessing Purity Using Capillary Electrophoresis.

Authors:  Sanjiv Lalwani; Vincent J Venditto; Abdellatif Chouai; Gregory E Rivera; Sunil Shaunak; Eric E Simanek
Journal:  Macromolecules       Date:  2009-04-28       Impact factor: 5.985

2.  Synthesis of odd generation triazine dendrimers using a divergent, macromonomer approach.

Authors:  Jongdoo Lim; Meredith A Mintzer; Lisa M Perez; Eric E Simanek
Journal:  Org Lett       Date:  2010-03-19       Impact factor: 6.005

3.  Synthesis and characterization of a triazine dendrimer that sequesters iron(III) using 12 desferrioxamine B groups.

Authors:  Jongdoo Lim; Vincent J Venditto; Eric E Simanek
Journal:  Bioorg Med Chem       Date:  2010-05-20       Impact factor: 3.641

4.  Divergent synthesis of triazine dendrimers using a trimethylene-dipiperidine linker that increases efficiency, simplifies analysis, and improves product solubility.

Authors:  Meredith A Mintzer; Lisa M Perez; Eric E Simanek
Journal:  Tetrahedron Lett       Date:  2010-03-31       Impact factor: 2.415

5.  LARGE SCALE, GREEN SYNTHESIS OF A GENERATION-1 MELAMINE (TRIAZINE) DENDRIMER.

Authors:  Abdellatif Chouai; Vincent J Venditto; Eric E Simanek; Brian C Vanderplas; John A Ragan
Journal:  Organic Synth       Date:  2009-01-01

6.  Identification of Diamine Linkers with Differing Reactivity and their Application in the Synthesis of a Melamine Dendrimers.

Authors:  Karlos X Moreno; Eric E Simanek
Journal:  Tetrahedron Lett       Date:  2008-02-11       Impact factor: 2.415

7.  SYNTHESIS OF 2-[3,3'-DI-(TERT-BUTOXYCARBONYL)-AMINODIPROPYLAMINE]-4,6,-DICHLORO-1,3,5-TRIAZINE AS A MONOMER AND 1,3,5-[TRIS-PIPERAZINE]-TRIAZINE AS A CORE FOR THE LARGE SCALE SYNTHESIS OF MELAMINE (TRIAZINE) DENDRIMERS.

Authors:  Abdellatif Chouai; Vincent J Venditto; Eric E Simanek; Ruth E McDermott; John A Ragan
Journal:  Organic Synth       Date:  2009-01-01

8.  Dendrimers terminated with dichlorotriazine groups provide a route to compositional diversity.

Authors:  Subrata Patra; Brittany Kozura; Adela Y-T Huang; Alan E Enciso; Xiankai Sun; Jer-Tsong Hsieh; Chai-Lin Kao; Hui-Ting Chen; Eric E Simanek
Journal:  Org Lett       Date:  2013-07-19       Impact factor: 6.005

  8 in total

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