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Dendrimers in Medicine: Theme Issue Honoring Professor Jean-Pierre Majoral on His 80th Birthday

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A special issue of Molecules (ISSN 1420-3049). This special issue belongs to the section "Nanochemistry".

Deadline for manuscript submissions: closed (31 March 2021) | Viewed by 42751

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Prof. Dr. Ashok Kakkar

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Department of Chemistry, McGill University, 801 Sherbrooke St. West, Montreal, QC H3A 0B8, Canada
Interests: nanostructures; soft nanoparticles; macromolecules; dendrimers; miktoarm polymers; telodendrimers; naked nanocarriers; metal nanoparticles; gold nanoshells; iron oxide nanoparticles; nanomedicine; drug delivery; diagnostics
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Dr. Anne-Marie Caminade

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Laboratoire de Chimie de Coordination, CNRS UPR-8241, Toulouse, France
Interests: dendrimer chemistry; organic and organophosphorus chemistry; macromolecules for catalysis; nanomedicine and materials
Special Issues, Collections and Topics in MDPI journals

Special Issue Information

Dear Colleagues,

Hyperbranched macromolecules with a unique build-up, the so-called dendrimers, have provided a fertile platform since the 1980s to explore their potential in a variety of areas including medicine. Parallel to the developments taking place in poly(amidoamine amine) (PAMAM, Donald A. Tomalia) and poly(aryl ether) (Jean M. J. Frechet) dendrimers, organo-phosphorus dendrimers developed by the group of Jean-Pierre Majoral and Anne-Marie Caminade were starting to take shape in streamlining their synthesis, and understanding their properties. Since then, phosphorus dendrimers have become increasingly popular in designing a diverse range of nanomaterials for applications in catalysis, nanomedicine and biology. With fascinating research contributed by numerous scientists, dendrimers with varied backbones continue to invoke great interest, particularly in addressing key issues in biomedical sciences.

Molecules is pleased to host a special issue entitled “Dendrimers in Medicine: Theme Issue Honoring Professor Jean-Pierre Majoral on his 80^th Birthday” to congratulate Professor Jean-Pierre Majoral at the occasion of his 80^th birthday in 2021, and celebrate his outstanding contributions to the area of dendrimers.

Dr. Jean-Pierre Majoral obtained his BSc, followed by a PhD, from the University of Paul Sabatier (UPS), Toulouse, France in 1973. He subsequently spent a year at University of East Anglia, Norwich (UK) as a Post-doctoral Fellow. He started his academic career at Laboratoire de Chimie Physique at the UPS, Toulouse (France), in 1972 as Attaché de Recherche, then moved to the Laboratoire de Chimie de Coordination, CNRS, Toulouse, France in 1988, and arose to the status of Directeur de Recherche Classe Exceptionnelle CNRS in 1997. He was appointed as Directeur de Recherche CNRS Emerite in 2006, and holds that position currently. He was the Vice-Director of Laboratoire de Chimie de Coordination, Toulouse, France from 1998–2002, and Editor-in-Chief of New Journal of Chemistry from 2005–2009. He is also the co-founder of two companies Dendris (2009), and Biodendrimer International (2011). He has received numerous awards including Award of the French Chemical Society, Coordination Chemistry Division (1990); Prix Jecker Award of the French Academy of Sciences (1993); Wittig Grignard Award of the German Chemical Society (1994); von Humboldt Foundation Award (1995); Catalan-Sabatier Award of the Spanish Royal Society of Chemistry (2002); Le Bel Award of the French Chemical Society (2003); Nanqiang Lecture Award (China, 2007); Doctor Honoris Causa University of Lodz, Poland 2014; Consulting Professor, Donghua University, Shanghai, China, 2018; and Universitatis Lodzensis Amico Medal, Poland, 2019. He is also a member of the European Academy of Sciences, Arts and Letters (1997); Academia Europeae (1999); Polish Academy of Sciences (2000); Akademie der Wissenchaften (German Academy of Sciences, 2005); Grand Prix Emile Jungfleisch, Academie des Sciences, France (2008), as well as a Fellow of the Royal Society of Chemistry (2004). Professor Majoral has published more than 660 papers with an h-index of 66, and has ever increasing 17000 citations of his work.

Professors Ashok Kakkar and Anne-Marie Caminade, and the Editors of Molecules, invite scientists to join us in celebrating Professor Jean-Pierre Majoral’s exceptional achievements by contributing original research articles as well as reviews.

Prof. Dr. Ashok Kakkar
Prof. Dr. Anne-Marie Caminade
Guest Editors

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Keywords

Dendrimers
Phosphorus dendrimers
Hyperbranched macromolecules
Dendrons
Telodendrimers
Nanomedicine
Dendrimers in drug and gene delivery
Biomedical applications of dendrimers
Dendrimers as sensors

Published Papers (14 papers)

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Research

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21 pages, 3718 KiB

Open AccessArticle

Use of Half-Generation PAMAM Dendrimers (G0.5–G3.5) with Carboxylate End-Groups to Improve the DACHPtCl₂ and 5-FU Efficacy as Anticancer Drugs

by Cláudia Camacho, Helena Tomás and João Rodrigues

Molecules 2021, 26(10), 2924; https://doi.org/10.3390/molecules26102924 - 14 May 2021

Cited by 11 | Viewed by 3022

Abstract

The DACHPtCl₂ compound (trans-(R,R)-1,2-diaminocyclohexanedichloroplatinum(II)) is a potent anticancer drug with a broad spectrum of activity and is less toxic than oxaliplatin (trans-l-diaminocyclohexane oxalate platinum II), with which it shares the active metal fragment DACHPt. Nevertheless, due to poor water solubility, its use as a chemotherapeutic drug is limited. Here, DACHPtCl₂ was conjugated, in a bidentate form, with half-generation PAMAM dendrimers (G0.5–G3.5) with carboxylate end-groups, and the resulting conjugates were evaluated against various types of cancer cell lines. In this way, we aimed at increasing the solubility and availability at the target site of DACHPt while potentially reducing the adverse side effects. DNA binding assays showed a hyperchromic effect compatible with DNA helix’s disruption upon the interaction of the metallodendrimers and/or the released active metallic fragments with DNA. Furthermore, the prepared DACHPt metallodendrimers presented cytotoxicity in a wide set of cancer cell lines used (the relative potency regarding oxaliplatin was in general high) and were not hemotoxic. Importantly, their selectivity for A2780 and CACO-2 cancer cells with respect to non-cancer cells was particularly high. Subsequently, the anticancer drug 5-FU was loaded in a selected metallodendrimer (the G2.5COO(DACHPt)₁₆) to investigate a possible synergistic effect between the two drugs carried by the same dendrimer scaffold and tested for cytotoxicity in A2780cisR and CACO-2 cancer cell lines. This combination resulted in IC₅₀ values much lower than the IC₅₀ for 5-FU but higher than those found for the metallodendrimers without 5-FU. It seems, thus, that the metallic fragment-induced cytotoxicity dominates over the cytotoxicity of 5-FU in the set of considered cell lines. 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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16 pages, 2993 KiB

Open AccessArticle

Design, Synthetic Strategies, and Therapeutic Applications of Heterofunctional Glycodendrimers

by Leila Mousavifar and René Roy

Molecules 2021, 26(9), 2428; https://doi.org/10.3390/molecules26092428 - 22 Apr 2021

Cited by 16 | Viewed by 2810

Abstract

Glycodendrimers have attracted considerable interest in the field of dendrimer sciences owing to their plethora of implications in biomedical applications. This is primarily due to the fact that cell surfaces expose a wide range of highly diversified glycan architectures varying by the nature of the sugars, their number, and their natural multiantennary structures. This particular situation has led to cancer cell metastasis, pathogen recognition and adhesion, and immune cell communications that are implicated in vaccine development. The diverse nature and complexity of multivalent carbohydrate–protein interactions have been the impetus toward the syntheses of glycodendrimers. Since their inception in 1993, chemical strategies toward glycodendrimers have constantly evolved into highly sophisticated methodologies. This review constitutes the first part of a series of papers dedicated to the design, synthesis, and biological applications of heterofunctional glycodendrimers. Herein, we highlight the most common synthetic approaches toward these complex molecular architectures and present modern applications in nanomolecular therapeutics and synthetic vaccines. 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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15 pages, 2207 KiB

Open AccessArticle

UV-Cured Antibacterial Hydrogels Based on PEG and Monodisperse Heterofunctional Bis-MPA Dendrimers

by Patrik Stenström, Yanmiao Fan, Yuning Zhang, Daniel Hutchinson, Sandra García-Gallego and Michael Malkoch

Molecules 2021, 26(8), 2364; https://doi.org/10.3390/molecules26082364 - 19 Apr 2021

Cited by 1 | Viewed by 2728

Abstract

Bacterial infections are one of the major threats to human health due to the raising crisis of antibiotic resistance. Herein, second generation antibacterial heterofunctional dendrimers based on 2,2-bis(methylol)propionic acid were synthesized. The dendrimers possessed six alkenes and 12 ammonium end-groups per molecule and were used to fabricate antibacterial hydrogels together with dithiol-functional polyethylene glycol (mol wt of 2, 6 and 10 kDa) as crosslinkers via thiol-ene chemistry. The network formation can be completed within 10 s upon UV-irradiation as determined by the stabilization of the storage modulus in a rheometer. The hydrogels swelled in aqueous media and could be functionalized with the N-hydroxysuccinimide ester of the dye disperse red 13, which allowed for visually studying the degradation of the hydrogels through the hydrolysis of the ester bonds of the dendritic component. The maximum swelling ratio of the gels was recorded within 4–8 h and the swelling ratios increased with higher molecular weight of the polyethylene glycol crosslinker. The gel formed with 10 kDa polyethylene glycol crosslinker showed the highest swelling ratio of 40 and good mechanical properties, with a storage modulus of 8 kPa. In addition, the hydrogels exhibited good biocompatibility towards both human fibroblasts and mouse monocytes, while showing strong antibacterial activity against both gram-positive and gram-negative bacteria. 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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18 pages, 4113 KiB

Open AccessFeature PaperArticle

Induction of Cytokines by Nucleic Acid Nanoparticles (NANPs) Depends on the Type of Delivery Carrier

by Yelixza I. Avila, Morgan Chandler, Edward Cedrone, Hannah S. Newton, Melina Richardson, Jie Xu, Jeffrey D. Clogston, Neill J. Liptrott, Kirill A. Afonin and Marina A. Dobrovolskaia

Molecules 2021, 26(3), 652; https://doi.org/10.3390/molecules26030652 - 27 Jan 2021

Cited by 23 | Viewed by 3760

Abstract

Recent insights into the immunostimulatory properties of nucleic acid nanoparticles (NANPs) have demonstrated that variations in the shape, size, and composition lead to distinct patterns in their immunostimulatory properties. While most of these studies have used a single lipid-based carrier to allow for NANPs’ intracellular delivery, it is now apparent that the platform for delivery, which has historically been a hurdle for therapeutic nucleic acids, is an additional means to tailoring NANP immunorecognition. Here, the use of dendrimers for the delivery of NANPs is compared to the lipid-based platform and the differences in resulting cytokine induction are presented. 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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19 pages, 3591 KiB

Open AccessArticle

Synthesis, Internalization and Visualization of N-(4-Carbomethoxy) Pyrrolidone Terminated PAMAM [G5:G3-TREN] Tecto(dendrimers) in Mammalian Cells

by Maciej Studzian, Paula Działak, Łukasz Pułaski, David M. Hedstrand, Donald A. Tomalia and Barbara Klajnert-Maculewicz

Molecules 2020, 25(19), 4406; https://doi.org/10.3390/molecules25194406 - 25 Sep 2020

Cited by 17 | Viewed by 2449

Abstract

Tecto(dendrimers) are well-defined, dendrimer cluster type covalent structures. In this article, we present the synthesis of such a PAMAM [G5:G3-(TREN)]-N-(4-carbomethoxy) pyrrolidone terminated tecto(dendrimer). This tecto(dendrimer) exhibits nontraditional intrinsic luminescence (NTIL; excitation 376 nm; emission 455 nm) that has been attributed to three fluorescent components characterized by different fluorescence lifetimes. Furthermore, it has been shown that this PAMAM [G5:G3-(TREN)]-N-(4-carbomethoxy) pyrrolidone terminated tecto(dendrimer) is able to form a polyplex with double stranded DNA, and is nontoxic for HeLa and HMEC-1 cells up to a concentration of 10 mg/mL, even though it accumulates in endosomal compartments as demonstrated by its unique NTIL emission properties. Many of the above features would portend the proposed use of this tecto(dendrimer) as an efficient transfection agent. Quite surprisingly, transfection activity could not be demonstrated in HeLa cells, and the possible reasons are discussed in the article. 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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19 pages, 1932 KiB

Open AccessFeature PaperReview

Two Decades of Triazine Dendrimers

by Eric E. Simanek

Molecules 2021, 26(16), 4774; https://doi.org/10.3390/molecules26164774 - 06 Aug 2021

Cited by 11 | Viewed by 2831

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. 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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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 1854

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 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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32 pages, 4045 KiB

Open AccessReview

Developments in Treatment Methodologies Using Dendrimers for Infectious Diseases

by Nina Filipczak, Satya Siva Kishan Yalamarty, Xiang Li, Farzana Parveen and Vladimir Torchilin

Molecules 2021, 26(11), 3304; https://doi.org/10.3390/molecules26113304 - 31 May 2021

Cited by 24 | Viewed by 3384

Abstract

Dendrimers comprise a specific group of macromolecules, which combine structural properties of both single molecules and long expanded polymers. The three-dimensional form of dendrimers and the extensive possibilities for use of additional substrates for their construction creates a multivalent potential and a wide possibility for medical, diagnostic and environmental purposes. Depending on their composition and structure, dendrimers have been of interest in many fields of science, ranging from chemistry, biotechnology to biochemical applications. These compounds have found wide application from the production of catalysts for their use as antibacterial, antifungal and antiviral agents. Of particular interest are peptide dendrimers as a medium for transport of therapeutic substances: synthetic vaccines against parasites, bacteria and viruses, contrast agents used in MRI, antibodies and genetic material. This review focuses on the description of the current classes of dendrimers, the methodology for their synthesis and briefly drawbacks of their properties and their use as potential therapies against infectious diseases. 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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12 pages, 2294 KiB

Open AccessFeature PaperReview

Grafting Dendrons onto Pillar[5]Arene Scaffolds

by Iwona Nierengarten, Michel Holler, Marine Rémy, Uwe Hahn, Aurélien Billot, Robert Deschenaux and Jean-François Nierengarten

Molecules 2021, 26(8), 2358; https://doi.org/10.3390/molecules26082358 - 18 Apr 2021

Cited by 4 | Viewed by 2837

Abstract

With their ten peripheral substituents, pillar[5]arenes are attractive compact scaffolds for the construction of nanomaterials with a controlled number of functional groups distributed around the macrocyclic core. This review paper is focused on the functionalization of pillar[5]arene derivatives with small dendrons to generate dendrimer-like nanomaterials and bioactive compounds. Examples include non-viral gene vectors, bioactive glycoclusters, and liquid-crystalline materials. 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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9 pages, 2225 KiB

Open AccessFeature PaperReview

Polyphosphorhydrazone-Based Radical Dendrimers

by Vega Lloveras and José Vidal-Gancedo

Molecules 2021, 26(5), 1230; https://doi.org/10.3390/molecules26051230 - 25 Feb 2021

Cited by 4 | Viewed by 1852

Abstract

The search for new biomedical applications of dendrimers has promoted the synthesis of new radical-based molecules. Specifically, obtaining radical dendrimers has opened the door to their use in various fields such as magnetic resonance imaging, as anti-tumor or antioxidant agents, or the possibility of developing new types of devices based on the paramagnetic properties of organic radicals. Herein, we present a mini review of radical dendrimers based on polyphosphorhydrazone, a new type of macromolecule with which, thanks to their versatility, new metal-free contrast agents are being obtained, among other possible applications. 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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26 pages, 2456 KiB

Open AccessFeature PaperReview

Dendrimers as Modulators of Brain Cells

by Dusica Maysinger, Qiaochu Zhang and Ashok Kakkar

Molecules 2020, 25(19), 4489; https://doi.org/10.3390/molecules25194489 - 30 Sep 2020

Cited by 9 | Viewed by 3447

Abstract

Nanostructured hyperbranched macromolecules have been extensively studied at the chemical, physical and morphological levels. The cellular structural and functional complexity of neural cells and their cross-talk have made it rather difficult to evaluate dendrimer effects in a mixed population of glial cells and neurons. Thus, we are at a relatively early stage of bench-to-bedside translation, and this is due mainly to the lack of data valuable for clinical investigations. It is only recently that techniques have become available that allow for analyses of biological processes inside the living cells, at the nanoscale, in real time. This review summarizes the essential properties of neural cells and dendrimers, and provides a cross-section of biological, pre-clinical and early clinical studies, where dendrimers were used as nanocarriers. It also highlights some examples of biological studies employing dendritic polyglycerol sulfates and their effects on glia and neurons. It is the aim of this review to encourage young scientists to advance mechanistic and technological approaches in dendrimer research so that these extremely versatile and attractive nanostructures gain even greater recognition in translational medicine. 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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32 pages, 4411 KiB

Open AccessFeature PaperReview

Telodendrimers: Promising Architectural Polymers for Drug Delivery

by Søren Mejlsøe and Ashok Kakkar

Molecules 2020, 25(17), 3995; https://doi.org/10.3390/molecules25173995 - 02 Sep 2020

Cited by 9 | Viewed by 4041

Abstract

Architectural complexity has played a key role in enhancing the efficacy of nanocarriers for a variety of applications, including those in the biomedical field. With the continued evolution in designing macromolecules-based nanoparticles for drug delivery, the combination approach of using important features of linear polymers with dendrimers has offered an advantageous and viable platform. Such nanostructures, which are commonly referred to as telodendrimers, are hybrids of linear polymers covalently linked with different dendrimer generations and backbones. There is considerable variety in selection from widely studied linear polymers and dendrimers, which can help tune the overall composition of the resulting hybrid structures. This review highlights the advances in articulating syntheses of these macromolecules, and the contributions these are making in facilitating therapeutic administration. Limited progress has been made in the design and synthesis of these hybrid macromolecules, and it is through an understanding of their physicochemical properties and aqueous self-assembly that one can expect to fully exploit their potential in drug delivery. 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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20 pages, 6284 KiB

Open AccessFeature PaperReview

Phosphorus Dendrimers as Nanotools against Cancers

by Anne-Marie Caminade

Molecules 2020, 25(15), 3333; https://doi.org/10.3390/molecules25153333 - 22 Jul 2020

Cited by 27 | Viewed by 3523

Abstract

This review concerns the use of dendrimers, especially of phosphorhydrazone dendrimers, against cancers. After the introduction, the review is organized in three main topics, depending on the role played by the phosphorus dendrimers against cancers: (i) as drugs by themselves; (ii) as carriers of drugs; and (iii) as indirect inducer of cancerous cell death. In the first part, two main types of phosphorus dendrimers are considered: those functionalized on the surface by diverse organic derivatives, including known drugs, and those functionalized by diverse metal complexes. The second part will display the role of dendrimers as carriers of anticancer “drugs”, which can be either small molecules or anticancer siRNAs, or the combination of both. In the third part are gathered a few examples of phosphorhydrazone dendrimers that are not cytotoxic by themselves, but which under certain circumstances induce a cytotoxic effect on cancerous cells. These examples include a positive influence on the human immune system and the combination of bioimaging with photodynamic therapy properties. 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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14 pages, 1999 KiB

Open AccessReview

High Preventive Effect of G2-S16 Anionic Carbosilane Dendrimer against Sexually Transmitted HSV-2 Infection

by Ignacio Rodriguez-Izquierdo, Samanta Gasco and Maria Angeles Muñoz-Fernández

Molecules 2020, 25(13), 2965; https://doi.org/10.3390/molecules25132965 - 28 Jun 2020

Cited by 8 | Viewed by 2373

Abstract

Anionic carbosilane dendrimers such as G2-S16 are very effective in preventing HSV-2 infection both in vitro and in vivo. We present the main achievements obtained for the G2-S16 dendrimer in vivo, especially related to its efficacy against HSV-2 infection. Moreover, we discuss the mechanisms by which the G2-S16 dendrimer applied vaginally as a topical microbicide has been demonstrated to be safe and harmless for the vaginal microbiome balance, as both conditions present an essential step that has to be overcome during microbicide development. This review points to the marked protective effect of the G2-S16 dendrimer against sexually transmitted HSV-2 infection, supporting its role as a possible microbicide against HSV-2 infection. 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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