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Two Decades of Triazine Dendrimers molecules Review Two Decades of Triazine Dendrimers Eric E. Simanek Department of Chemistry & Biochemistry, Texas Christian University, Fort Worth, TX 76129, USA; [email protected]; Tel.: +1-817-257-5355 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. Keywords: dendrimer; triazine; drug delivery; gene delivery; RNA delivery; biological activity; theranostic; paclitaxel; MRI; physical organic chemistry; synthesis; membrane; separation; composite; nanoparticle; materials; atrazine; VOC Citation: Simanek, E.E. Two Decades of Triazine Dendrimers. Molecules 2021, 26, 4774. https://doi.org/ 10.3390/molecules26164774 1. Introduction For two decades, efforts in my laboratory focused on the exploration of triazine Academic Editors: Ashok Kakkar and dendrimers. When we entered the field in 2000, dendrimer science was a well-established Anne-Marie Caminade subdiscipline that occupied the interface between small molecule chemistry and polymer science. It was guided by individuals including Donald Tomalia, Bert Meijer, George Received: 29 March 2021 Newkome, Rene Roy, and Jean Frechet as well as the pair of Jean-Pierre Majoral and Anne- Accepted: 16 July 2021 Marie Caminade. All pioneered and/or advanced classes of dendrimers that proved to be Published: 6 August 2021 workhorses for the field including poly(ethyleneimine), poly(amidoamine), poly(esters), carbohydrates, poly(ethers), and the poly(phosphazines). Publisher’s Note: MDPI stays neutral with regard to jurisdictional claims in By virtue of the nature of the monomer and the chemistries employed, most den- published maps and institutional affil- drimers were homopolymers that could be derivatized, often statistically, on the periphery iations. to yield function. We envisioned that exploiting the stepwise substitution of the [1,3,5]- triazine nucleus of trichlorotriazine using diamine nucleophiles offered a chance to con- tribute to the discipline especially in terms of the compositional diversity that might be readily generated. Being a young, assistant professor—as well as being new to the field—Jean-Pierre Copyright: © 2021 by the author. Majoral, for whom this issue is dedicated, greeted me (as well as others in my cohort) with Licensee MDPI, Basel, Switzerland. This article is an open access article warmth and collegiality. He fully embodied the spirit of the community. He took extra distributed under the terms and efforts to make sure that we were included and heard, allowing us the opportunity to chair conditions of the Creative Commons conference sessions and participate in other activities. Attribution (CC BY) license (https:// His role is perhaps best portrayed by an event that occurred while he and Anne-Marie creativecommons.org/licenses/by/ Caminade hosted the Fifth International Dendrimers Symposium in Toulouse, France 4.0/). in 2007. As we watched a football match one evening after the conference proceedings Molecules 2021, 26, 4774. https://doi.org/10.3390/molecules26164774 https://www.mdpi.com/journal/molecules Molecules 2021, 26, x FOR PEER REVIEW 2 of 21 Molecules 2021, 26, x FOR PEER REVIEW 2 of 21 France in 2007. As we watched a football match one evening after the conference Molecules 2021, 26, 4774 France in 2007. As we watched a football match one evening after the conference2 of 19 proceedings had concluded, the crowds erupted in ‘Allez, allez, allez! Allez, Toulouse allez!’ The encouraging and energetic refrain of ‘Go! Go! Go!’ perfectly captured Jean- Pierre’s persona. Supportive. Enthusiastic. Optimistic. Words offered with the recognition had concluded, the crowds erupted in ‘Allez, allez, allez! Allez, Toulouse allez!’ The that there was still work to be done and that we were part of an international team to do encouraging and energetic refrain of ‘Go! Go! Go!’ perfectly captured Jean-Pierre’s persona. it. While my research interests have moved away from dendrimers, my appreciation for Supportive. Enthusiastic. Optimistic. Words offered with the recognition that there was Jean-Pierre’s guiding scientific contributions to the field and his personal dedication to still work to be done and that we were part of an international team to do it. While my the development of new faculty will remain with me always. Happy birthday, Jean-Pierre! research interests have moved away from dendrimers, my appreciation for Jean-Pierre’s GOAL!!! guiding scientific contributions to the field and his personal dedication to the development of new faculty will remain with me always. Happy birthday, Jean-Pierre! GOAL!!! 2. Results 2. ResultsThis mini-review is organized in sections to discuss synthesis (convergent and divergent, with solid-supported routes discussed later), the drivers for synthesis divergent,This mini-review with solid-supported is organized inroutes sections discussed to discuss later), synthesis the (convergentdrivers for andsynthesis diver- (evaluating solubility, studying structural hypotheses), examining host–guest chemistries (evaluatinggent, with solid-supported solubility, studying routes structural discussed hypotheses), later), the examining drivers for host–guest synthesis (evaluatingchemistries and biological activity, and, finally, the use of triazine dendrimers in materials science andsolubility, biological studying activity, structural and, finally, hypotheses), the use examining of triazine host–guest dendrimers chemistries in materials and science biolog- (composite materials comprising clays, silica and polymeric solid supports, and (compositeical activity, materials and, finally, comprising the use of triazineclays, silica dendrimers and polymeric in materials solid science supports, (composite and nanoparticles). nanoparticles).materials comprising clays, silica and polymeric solid supports, and nanoparticles). 2.1. Synthesis Synthesis Triazine trichloride is an inexpensive building block capable of undergoing three substitutionsubstitution reactions in a stepwise fashion with rates that can be influenced influenced by the choice of nucleophile, temperature, and solvent (Scheme 1 1).). Scheme 1. The stepwise substitution of trichlorotriazine (cyanuric chloride). Scheme 1. The stepwise substitution of trichlorotriazine (cyanuric chloride). Linking triazines triazines with with diamines diamines served served as as the the basis basis for for all all of of our our efforts efforts in in this this area. area. The discussion is subdivided into efforts th thatat explore convergent routes and those that explore divergentdivergent routes, routes, which which is an is organizational an organizational strategy strategy that also mirrorsthat also chronology. mirrors chronology.Depending onDepending the symmetry, on the symmetry, dendrimers dendrime are referredrs are to referred as ‘bowtie’ to as to‘bowtie’ convey to that convey the thatcentral thecore central has core two has branches two branches emanating, emanating, and they and are they indicated are indicated as such using as such the usingletter the ‘B’ letter(Scheme ‘B’ 2(Scheme). In the 2). absence In the absence of this designation, of this designation, triazine triazine dendrimers dendrimers typically typically offer three offer threebranches branches (indicated (indicated with a with ‘G’). a The ‘G’). word The ‘dendon’ word ‘dendon’ indicates indicates that the that focus the is focus still reactive is still reactiveand amenable and amenable for elaboration. for elaboration. Dendrons Dendrons are typically are typically the product the ofproduct convergent of convergent methods. methods.Such structures Such structures are designated are designated with a ‘D’. with The a word ‘D’. The ‘generation’ word ‘generation’ (indicated (indicated with a number with athat number follows that the follows designation the designation B, G, or D) refersB, G, or to theD) refers number to ofthe branching number triazinesof branching that triazinesseparate thethat core separate and periphery. the core and periphery. Scheme 2. BowtieBowtie (B), (B), dendrimer dendrimer (G), an andd dendron (D) architectures. Molecules 2021, 26, x FOR PEER REVIEW 3 of 21 Molecules 2021, 26, 4774 2.1.1. Convergent Methods 3 of 19 Table 1 summarizes our efforts in the convergent synthesis of dendrimers. Table 1. Synthetic efforts utilizing the convergent strategy. ‘B’ refers to a two-branched bowtie 2.1.1.
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