Two Decades of Triazine Dendrimers

Abstract

For two decades, methods for the synthesis and characterization of dendrimers based on [1,3,5]-triazine have been advanced by the group. Motivated by the desire to generate structural complexity on the periphery, initial efforts focused on convergent syntheses, which yielded pure materials to generation three. To obtain larger generations of dendrimers, divergent strategies were pursued using iterative reactions of monomers, sequential additions of triazine and diamines, and ultimately, macromonomers. Strategies for the incorporation of bioactive molecules using non-covalent and covalent strategies have been explored. These bioactive materials included small molecule drugs, peptides, and genetic material. In some cases, these constructs were examined in both in vitro and in vivo models with a focus on targeting prostate tumor subtypes with paclitaxel conjugates. In the materials realm, the use of triazine dendrimers anchored on solid surfaces including smectite clay, silica, mesoporous alumina, polystyrene, and others was explored for the separation of volatile organics from gas streams or the sequestration of atrazine from solution. The combination of these organics with metal nanoparticles has been probed. The goal of this review is to summarize these efforts.

Dendrimer: An update on recent developments and future opportunities for the brain tumors diagnosis and treatment

“…A study was conducted recently on the siRNA transport ability of a series of “triazine dendrimers with different core structures, generation numbers and surface functions”. Dendrimers with inflexible structures and “arginine-like or hydrophobic terminals had the most efficient siRNA gene repression effects” on Hela cells in an experimental luciferase model ( Simanek, 2021 ). Triazine dendrimers are deemed suitable for various biomedical applications due to their liquid crystalline structure and non-linear optical properties.…”

A Model for the Rapid Assessment of Solution Structures for 24-Atom Macrocycles: The Impact of β-Branched Amino Acids on Conformation

“…The development of predictive models that confirm conservation of the molecular shape based on simple experiments�here, a 1D 1 H NMR spectrum and rOe pattern with a single resonance�can greatly accelerate these efforts. Our longstanding interest in triazine chemistry 24 and recent studies of hydrazine-substituted triazines 25,26 led us to explore macrocycles incorporating triazinyl hydrazones as molecular frameworks. 27,28 The ease of synthesis and the numerous sites available to explore functional variation make triazine-based macrocycles a versatile platform for pursuing structure− property relationships.…”

“…Our longstanding interest in triazine chemistry and recent studies of hydrazine-substituted triazines , led us to explore macrocycles incorporating triazinyl hydrazones as molecular frameworks. , The ease of synthesis and the numerous sites available to explore functional variation make triazine-based macrocycles a versatile platform for pursuing structure–property relationships. Zerkowski and coworkers showed earlier that static, covalent chemistry could yield similar triazine targets …”

Click Chemistry of Melamine Dendrimers: Comparison of “Click-and-Grow” and “Grow-Then-Click” Strategies Using a Divergent Route to Diversity

“…Dendrimers can also be modified by an introduction of various functional groups, which is a promising strategy for enabling their use in drug delivery vehicles and catalysis [4][5][6][7][8][9][10][11][12][13]. For example, triazine dendrimers are a class of dendrimers that offer notable advantages such as ease of synthesis, stability, welldefined spherical structure, multivalency, potential to achieve acceptable drug loadings, and low polydispersity [14,15]. Recently, Simanek et al, synthesized various triazine dendrimers with multiple functional groups such as hydroxy and amino groups at the end of the molecule, and modified each functional group to incorporate multiple functionalities into the triazine dendrimers [16][17][18].…”