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23 pages, 8320 KiB

Open AccessReview

Investigation of Phosphorus Dendrons and Their Properties for the Functionalization of Materials

by Cédric-Olivier Turrin, Valérie Maraval and Anne-Marie Caminade

J. Compos. Sci. 2025, 9(8), 382; https://doi.org/10.3390/jcs9080382 - 22 Jul 2025

Viewed by 259

Dendrons, also named dendritic wedges, are a kind of molecular tree, having a branched structure linked to a functional core. The functional core can be used in particular for the functionalization of materials. Different types of dendrons are known, synthesized either by a [...] Read more.

Dendrons, also named dendritic wedges, are a kind of molecular tree, having a branched structure linked to a functional core. The functional core can be used in particular for the functionalization of materials. Different types of dendrons are known, synthesized either by a convergent process, from the external part to the core, or by a divergent process from the core to the external part. Polyphosphorhydrazone (PPH) dendrons are always synthesized by a divergent process, which enables a fine-tuning of both the core function and the external functions. They have been used for the functionalization of diverse materials such as silica, titanium dioxide, gold, graphene oxide, or different types of nanoparticles. Nanocomposites based on materials functionalized with PPH dendrons have been used in diverse fields such as catalysts, chemical sensors, for trapping pollutants, to support cell cultures, and against cancers, as will be emphasized in this review. Full article

(This article belongs to the Special Issue Functional Composites: Fabrication, Properties and Applications)

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22 pages, 11505 KiB

Open AccessReview

Interplay between Nanoparticles and Phosphorus Dendrimers, and Their Properties

by Anne-Marie Caminade

Molecules 2023, 28(15), 5739; https://doi.org/10.3390/molecules28155739 - 29 Jul 2023

Cited by 1 | Viewed by 2080

Abstract

This review presents the state of the art of interactions between two different families of nanoobjects: nanoparticles—mainly metal nanoparticles, and dendrimers—mainly phosphorhydrazone dendrimers (or dendrons). The review firstly presents the encapsulation/protection of existing nanoparticles (organic or metallic) by phosphorus-based dendrimers and dendrons. In [...] Read more.

This review presents the state of the art of interactions between two different families of nanoobjects: nanoparticles—mainly metal nanoparticles, and dendrimers—mainly phosphorhydrazone dendrimers (or dendrons). The review firstly presents the encapsulation/protection of existing nanoparticles (organic or metallic) by phosphorus-based dendrimers and dendrons. In the second part, several methods for the synthesis of metal nanoparticles, thanks to the dendrimer that acts as a template, are presented. The properties of the associations between dendrimers and nanoparticles are emphasized throughout the review. These properties mainly concern the elaboration of diverse types of hybrid materials, some of them being used as sensitive chemosensors or biosensors. Several examples concerning catalysis are also given, displaying in particular the efficient recovery and reuse of the catalytic entities. Full article

(This article belongs to the Special Issue Women in Nanochemistry)

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18 pages, 7005 KiB

Open AccessReview

Strategies for the Preparation of Phosphorus Janus Dendrimers and Their Properties

by Joel Cejas-Sánchez, Anna Kajetanowicz, Karol Grela, Anne-Marie Caminade and Rosa María Sebastián

Molecules 2023, 28(14), 5570; https://doi.org/10.3390/molecules28145570 - 21 Jul 2023

Cited by 5 | Viewed by 2095

Abstract

Dendrimers, being highly branched monodispersed macromolecules, predominantly exhibit identical terminal functionalities within their structural framework. Nonetheless, there are instances where the presence of two distinct surface functionalities becomes advantageous for the fulfilment of specific properties. To achieve this objective, one approach involves implementing [...] Read more.

Dendrimers, being highly branched monodispersed macromolecules, predominantly exhibit identical terminal functionalities within their structural framework. Nonetheless, there are instances where the presence of two distinct surface functionalities becomes advantageous for the fulfilment of specific properties. To achieve this objective, one approach involves implementing Janus dendrimers, consisting of two dendrimeric wedges terminated by dissimilar functionalities. The prevalent method for creating these structures involves the synthesis of dendrons that possess a core functionality that complements that of a second dendron, facilitating their coupling to generate the desired dendrimers. In this comprehensive review, various techniques employed in the fabrication of phosphorus-based Janus dendrimers are elucidated, displaying the different coupling methodologies employed between the two units. The advantages of phosphorus dendrimers over classic dendrimers will be shown, as the presence of at least one phosphorus atom in each generation allows for the easy monitoring of reactions and the confirmation of purity through a simple technique such as ³¹P NMR, as these structures typically exhibit easily interpretable patterns. Full article

(This article belongs to the Special Issue Recent Progress in Organophosphorus Chemistry)

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19 pages, 7116 KiB

Open AccessReview

Single-Component Physical Hydrogels of Dendritic Molecules

by Evgeny Apartsin and Anne-Marie Caminade

J. Compos. Sci. 2023, 7(1), 26; https://doi.org/10.3390/jcs7010026 - 10 Jan 2023

Cited by 4 | Viewed by 2332

Abstract

Hydrogels are hydrophilic, three-dimensional networks able to imprison large amounts of water and are largely used in pharmaceutical formulations. Hydrogels are frequently obtained from hydrophilic polymers, either natural, biohybrid, or synthetic. Owing to their peculiar structure, dendrimers can be considered prospective building blocks [...] Read more.

Hydrogels are hydrophilic, three-dimensional networks able to imprison large amounts of water and are largely used in pharmaceutical formulations. Hydrogels are frequently obtained from hydrophilic polymers, either natural, biohybrid, or synthetic. Owing to their peculiar structure, dendrimers can be considered prospective building blocks for hydrogel networks. This review gathers the use of different types of amphiphilic dendritic structures able to generate physical hydrogels alone. Such dendritic structures comprise dendrimers, Janus dendrimers, and dendrons. The first part concerns different types of positively charged phosphorus dendrimers used to generate hydrogels, which are also suitable to form fibers, and for encapsulating diverse substances, or forming complexes with genetic materials for their slow delivery. The second part concerns PAMAM dendrimers functionalized with collagen mimetics. The third part concerns amphiphilic Janus dendrimers, whereas the fourth part displays different types of amphiphilic dendrons and their use, in particular in the fields of materials and drug delivery. Full article

(This article belongs to the Special Issue Hydrogel and Biomaterials)

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13 pages, 3245 KiB

Open AccessArticle

Amphiphilic Triazine-Phosphorus Metallodendrons Possessing Anti-Cancer Stem Cell Activity

by Evgeny K. Apartsin, Nadezhda Knauer, Ulf Dietrich Kahlert and Anne-Marie Caminade

Pharmaceutics 2022, 14(2), 393; https://doi.org/10.3390/pharmaceutics14020393 - 10 Feb 2022

Cited by 12 | Viewed by 2555

Abstract

Dendritic molecules bearing metal complexes in their structure (metallodendrimers and metallodendrons) are considered prospective therapeutic entities. In particular, metallodendrons raise interest as antitumor agents for the treatment of poorly curable or drug-resistant tumors. Herein, we have synthesized amphiphilic triazine-phosphorus dendrons bearing multiple copper [...] Read more.

Dendritic molecules bearing metal complexes in their structure (metallodendrimers and metallodendrons) are considered prospective therapeutic entities. In particular, metallodendrons raise interest as antitumor agents for the treatment of poorly curable or drug-resistant tumors. Herein, we have synthesized amphiphilic triazine-phosphorus dendrons bearing multiple copper (II) or gold (III) complexes on the periphery and a branched hydrophobic fragment at the focal point. Due to their amphiphilic nature, metallodendrons formed single micelles (mean diameter ~9 nm) or multi-micellar aggregates (mean diameter ~60 nm) in a water solution. We have tested the antitumor activity of amphiphilic metallodendrons towards glioblastoma, a malignant brain tumor with a notoriously high level of therapy resistance, as a model disease. The metallodendrons exhibit higher cytotoxic activity towards glioblastoma stem cells (BTSC233, JHH520, NCH644, and SF188 cell lines) and U87 glioblastoma cells (IC50 was 3–6 µM for copper-containing dendron and 11–15 µM for gold-containing dendron) in comparison with temozolomide (IC50 >100 µM)—the clinical standard of care for glioblastoma. Our findings show the potential of metallodendron-based nanoformulations as antitumor entities. Full article

(This article belongs to the Section Nanomedicine and Nanotechnology)

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24 pages, 11501 KiB

Open AccessReview

AB₅ Derivatives of Cyclotriphosphazene for the Synthesis of Dendrons and Their Applications

by Artem Zibarov, Abdelouahd Oukhrib, Julien Aujard Catot, Cédric-Olivier Turrin and Anne-Marie Caminade

Molecules 2021, 26(13), 4017; https://doi.org/10.3390/molecules26134017 - 30 Jun 2021

Cited by 18 | Viewed by 3809

Abstract

AB₅ compounds issued from the reactivity of hexachlorocyclotriphosphazene are relatively easy to obtain using two ways: either first the reaction of one chloride with one reagent, followed by the reaction of the five remaining Cl with another reagent, or first the reaction [...] Read more.

AB₅ compounds issued from the reactivity of hexachlorocyclotriphosphazene are relatively easy to obtain using two ways: either first the reaction of one chloride with one reagent, followed by the reaction of the five remaining Cl with another reagent, or first the reaction of five chlorides with one reagent, followed by the reaction of the single remaining Cl with another reagent. This particular property led to the use of such compounds as core for the synthesis of dendrons (dendritic wedges), using the five functions for growing the dendritic branches. The single function can be used for the synthesis of diverse types of dendrimers (onion peel, dumbbell-shape, Janus), for covalent or non-covalent grafting to solid surfaces, providing nanomaterials, for grafting a fluorophore, especially for studying biological mechanisms, or for self-associations to get micelles. All these properties are reviewed in this paper. Full article

(This article belongs to the Special Issue Recent Advances in Phosphorus Chemistry)

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14 pages, 4231 KiB

Open AccessReview

First-in-Class Phosphorus Dendritic Framework, a Wide Surface Functional Group Palette Bringing Noteworthy Anti-Cancer and Anti-Tuberculosis Activities: What Lessons to Learn?

by Serge Mignani, Jérôme Bignon, Xiangyang Shi and Jean-Pierre Majoral

Molecules 2021, 26(12), 3708; https://doi.org/10.3390/molecules26123708 - 17 Jun 2021

Cited by 5 | Viewed by 2569

Abstract

Based on phenotypic screening, the major advantages of phosphorus dendrimers and dendrons as drugs allowed the discovery of new therapeutic applications, for instance, as anti-cancer and anti-tuberculosis agents. These biological activities depend on the nature of the chemical groups (neutral or cationic) on [...] Read more.

Based on phenotypic screening, the major advantages of phosphorus dendrimers and dendrons as drugs allowed the discovery of new therapeutic applications, for instance, as anti-cancer and anti-tuberculosis agents. These biological activities depend on the nature of the chemical groups (neutral or cationic) on their surface as well as their generation. As lessons to learn, in the oncology domain, the increase in the generation of metallo-dendrimers is in the same direction as the anti-proliferative activities, in contrast to the development of polycationic dendrimers, where the most potent anti-tuberculosis phosphorus dendrimer was observed to have the lowest generation (G0). The examples presented in this original analysis of phosphorus dendrimers and dendrons provide support for the lessons learned and for the development of new nanoparticles in nanomedicine. Full article

(This article belongs to the Special Issue Dendrimers in Medicine: Theme Issue Honoring Professor Jean-Pierre Majoral on His 80th Birthday)

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24 pages, 4082 KiB

Open AccessReview

Bifunctional Phosphorus Dendrimers and Their Properties

by Anne-Marie Caminade and Jean-Pierre Majoral

Molecules 2016, 21(4), 538; https://doi.org/10.3390/molecules21040538 - 23 Apr 2016

Cited by 34 | Viewed by 8402

Abstract

Dendrimers are hyperbranched and monodisperse macromolecules, generally considered as a special class of polymers, but synthesized step-by-step. Most dendrimers have a uniform structure, with a single type of terminal function. However, it is often desirable to have at least two different functional groups. [...] Read more.

Dendrimers are hyperbranched and monodisperse macromolecules, generally considered as a special class of polymers, but synthesized step-by-step. Most dendrimers have a uniform structure, with a single type of terminal function. However, it is often desirable to have at least two different functional groups. This review will discuss the case of bifunctional phosphorus-containing dendrimers, and the consequences for their properties. Besides the terminal functions, dendritic structures may have also a function at the core, or linked off-center to the core, or at the core of dendrons (dendritic wedges). Association of two dendrons having different terminal functions leads to Janus dendrimers (two faces). The internal structure can also possess functional groups on one layer, or linked to one layer, or on several layers. Finally, there are several ways to have two types of terminal functions, besides the case of Janus dendrimers: either each terminal function bears two functions sequentially, or two different functions are linked to each terminal branching point. Examples of each type of structure will be given in this review, as well as practical uses of such sophisticated structures in the fields of fluorescence, catalysis, nanomaterials and biology. Full article

(This article belongs to the Special Issue Functional Dendrimers)

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