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Dendrimers: A Themed Issue in Honor of Professor Donald A. Tomalia on the Occasion of His 80th Birthday

A special issue of Molecules (ISSN 1420-3049).

Deadline for manuscript submissions: closed (5 March 2018) | Viewed by 110409

Printed Edition Available!
A printed edition of this Special Issue is available here.

Special Issue Editor

Prof. Dr. Ashok Kakkar

E-Mail Website
Guest Editor
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
Special Issues, Collections and Topics in MDPI journals

Special Issue Information

Dear Colleagues,

Dr. Donald A. Tomalia, one of the pioneers in the development of monodisperse and highly branched macromolecules, who coined the term “Dendrimers” in 1985 in reference to their tree like structure, has played a key role in establishing their place in polymer chemistry, and provided continued inspiration to many in expanding the scope and potential of these well-defined architectures. The divergent synthetic methodology to dendrimers, coupled with the convergent approach developed by Dr. Jean Fréchet, provided access to and an insight into the unique properties offered by these spherical macromolecules, which sparked an explosive growth of the dendrimer field. With excellent contributions of several leaders that followed, dendrimers have demonstrated potential and find applications in numerous areas including medicine, catalysis, sensors, etc.

“Molecules” is highly pleased to host a Themed Issue honoring Dr. Donald A. Tomalia for his outstanding achievements in advancing the field of dendrimers on the occasion of his 80th birthday.

Dr. Donald Tomalia obtained his B.A. in Chemistry from University of Michigan, subsequently joined Dow Chemical, and while there, completed his PhD in physical-organic chemistry from Michigan State University under the direction of Professor Harold Hart. His initial studies on cationic polymerization were recognized by international industrial awards for creative research in 1978 and 1986, and followed by another similar award in 1991 for the discovery of dendrimers. He has received several other accolades including Leonardo da Vinci award (1996) and Society of Polymer Science Japan award (2003) for discovering dendritic polymers. He worked at Michigan Molecular Institute from 1990-1999 in the capacity as Professor and Director. He currently serves as Adjunct Professor in the Department of Chemistry at the University of Pennsylvania. He co-founded Dendritech in 1992, the first supplier of commercially available dendrimers, founded Dendritech Nanotechnologies in 2002 in collaboration with Starpharma, and is currently the founder and CEO of Nanosynthons. Dr. Tomalia has authored/co-authored more than 200 peer-reviewed publications including books on dendrimers, and holds more than 100 dendrimer-based patents in the USA. He is an Associate Editor of Journal of Nanoparticle Research (Springer), and on the Honorary Editorial Board of Nanomedicine: Nanotechnology, Biology and Medicine (Elsevier). He is a Faculty Member in Faculty 1000 Prime.

Molecules invites scientists to submit original contributions to “Dendrimers: A Themed Issue in Honor of Professor Donald A. Tomalia on the Occasion of his 80th Birthday”, and join us in collectively congratulating him for his outstanding accomplishments.

Prof. Dr. Ashok Kakkar
Guest Editor

Manuscript Submission Information

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Submitted manuscripts should not have been published previously, nor be under consideration for publication elsewhere (except conference proceedings papers). All manuscripts are thoroughly refereed through a single-blind peer-review process. A guide for authors and other relevant information for submission of manuscripts is available on the Instructions for Authors page. Molecules is an international peer-reviewed open access semimonthly journal published by MDPI.

Please visit the Instructions for Authors page before submitting a manuscript. The Article Processing Charge (APC) for publication in this open access journal is 2700 CHF (Swiss Francs). Submitted papers should be well formatted and use good English. Authors may use MDPI's English editing service prior to publication or during author revisions.

Keywords

  • Dendrimers
  • Dendrons
  • Hyperbranched macromolecules
  • Divergent and convergent methodologies
  • Dendrimer conjugates
  • Metallodendrimers
  • Dendrimers in biomedicine
  • Light harvesting dendrimers
  • Dendrimers-based catalysis
  • Supramolecular dendrimers
  • Dendrimers for drug and gene delivery
  • Dendrimer-based sensors
  • Dendrimers as blood substitutes

Published Papers (18 papers)

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Editorial

Jump to: Research, Review

2 pages, 130 KiB  
Editorial
A Serendipitous Journey Leading to My Love of Dendritic Patterns and Chemistry
by Donald A. Tomalia
Molecules 2018, 23(4), 824; https://doi.org/10.3390/molecules23040824 - 04 Apr 2018
Cited by 1 | Viewed by 3233
Abstract
As the oldest of four Midwestern boys who were offsprings of an accountant and a housewife, each with less than a formal high school degree, we were blessed to have such parents.[...] Full article
(This article belongs to the Special Issue Dendrimers: A Themed Issue in Honor of Professor Donald A. Tomalia on the Occasion of His 80th Birthday)

Research

Jump to: Editorial, Review

15 pages, 1736 KiB  
Article
Evaluation of Amino-Functional Polyester Dendrimers Based on Bis-MPA as Nonviral Vectors for siRNA Delivery
by Patrik Stenström, Dario Manzanares, Yuning Zhang, Valentin Ceña and Michael Malkoch
Molecules 2018, 23(8), 2028; https://doi.org/10.3390/molecules23082028 - 14 Aug 2018
Cited by 37 | Viewed by 5414
Abstract
Herein, we present the first evaluation of cationic dendrimers based on 2,2-bis(methylol)propionic acid (bis-MPA) as nonviral vectors for transfection of short interfering RNA (siRNA) in cell cultures. The study encompassed dendrimers of generation one to four (G1–G4), modified to bear 6–48 amino end-groups, [...] Read more.
Herein, we present the first evaluation of cationic dendrimers based on 2,2-bis(methylol)propionic acid (bis-MPA) as nonviral vectors for transfection of short interfering RNA (siRNA) in cell cultures. The study encompassed dendrimers of generation one to four (G1–G4), modified to bear 6–48 amino end-groups, where the G2–G4 proved to be capable of siRNA complexation and protection against RNase-mediated degradation. The dendrimers were nontoxic to astrocytes, glioma (C6), and glioblastoma (U87), while G3 and G4 exhibited concentration dependent toxicity towards primary neurons. The G2 showed no toxicity to primary neurons at any of the tested concentrations. Fluorescence microscopy experiments suggested that the dendrimers are highly efficient at endo-lysosomal escape since fluorescently labeled dendrimers were localized specifically in mitochondria, and diffuse cytosolic distribution of fluorescent siRNA complexed by dendrimers was observed. This is a desired feature for intracellular drug delivery, since the endocytic pathway otherwise transfers the drugs into lysosomes where they can be degraded without reaching their intended target. siRNA-transfection was successful in C6 and U87 cell lines using the G3 and G4 dendrimers followed by a decrease of approximately 20% of target protein p42-MAPK expression. Full article
(This article belongs to the Special Issue Dendrimers: A Themed Issue in Honor of Professor Donald A. Tomalia on the Occasion of His 80th Birthday)
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Graphical abstract

21 pages, 4384 KiB  
Article
Effect of Dendrimer Generation and Aglyconic Linkers on the Binding Properties of Mannosylated Dendrimers Prepared by a Combined Convergent and Onion Peel Approach
by Celia Sehad, Tze Chieh Shiao, Lamyaa M. Sallam, Abdelkrim Azzouz and René Roy
Molecules 2018, 23(8), 1890; https://doi.org/10.3390/molecules23081890 - 28 Jul 2018
Cited by 18 | Viewed by 4262
Abstract
An efficient study of carbohydrate-protein interactions was achieved using multivalent glycodendrimer library. Different dendrimers with varied peripheral sugar densities and linkers provided an arsenal of potential novel therapeutic agents that could be useful for better specific action and greater binding affinities against their [...] Read more.
An efficient study of carbohydrate-protein interactions was achieved using multivalent glycodendrimer library. Different dendrimers with varied peripheral sugar densities and linkers provided an arsenal of potential novel therapeutic agents that could be useful for better specific action and greater binding affinities against their cognate protein receptors. Highly effective click chemistry represents the basic method used for the synthesis of mannosylated dendrimers. To this end, we used propargylated scaffolds of varying sugar densities ranging from 2 to 18 for the attachment of azido mannopyranoside derivatives using copper catalyzed click cycloaddition. Mannopyranosides with short and pegylated aglycones were used to evaluate their effects on the kinetics of binding. The mannosylated dendrons were built using varied scaffolds toward the accelerated and combined “onion peel” strategy These carbohydrates have been designed to fight E. coli urinary infections, by inhibiting the formation of bacterial biofilms, thus neutralizing the adhesion of FimH type 1 lectin present at the tip of their fimbriae against the natural multiantennary oligomannosides of uroplakin 1a receptors expressed on uroepithelial tissues. Preliminary DLS studies of the mannosylated dendrimers to cross- link the leguminous lectin Con A used as a model showed their high potency as candidates to fight the E. coli adhesion and biofilm formation. Full article
(This article belongs to the Special Issue Dendrimers: A Themed Issue in Honor of Professor Donald A. Tomalia on the Occasion of His 80th Birthday)
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17 pages, 2556 KiB  
Article
Poly(alkylidenimine) Dendrimers Functionalized with the Organometallic Moiety [Ru(η5-C5H5)(PPh3)2]+ as Promising Drugs Against Cisplatin-Resistant Cancer Cells and Human Mesenchymal Stem Cells
by Marisol Gouveia, João Figueira, Manuel G. Jardim, Rita Castro, Helena Tomás, Kari Rissanen and João Rodrigues
Molecules 2018, 23(6), 1471; https://doi.org/10.3390/molecules23061471 - 17 Jun 2018
Cited by 32 | Viewed by 5467
Abstract
Here and for the first time, we show that the organometallic compound [Ru(η5-C5H5)(PPh3)2Cl] (RuCp) has potential to be used as a metallodrug in anticancer therapy, and further present a new approach for the [...] Read more.
Here and for the first time, we show that the organometallic compound [Ru(η5-C5H5)(PPh3)2Cl] (RuCp) has potential to be used as a metallodrug in anticancer therapy, and further present a new approach for the cellular delivery of the [Ru(η5-C5H5)(PPh3)2]+ fragment via coordination on the periphery of low-generation poly(alkylidenimine) dendrimers through nitrile terminal groups. Importantly, both the RuCp and the dendrimers functionalized with [Ru(η5-C5H5)(PPh3)2]+ fragments present remarkable toxicity towards a wide set of cancer cells (Caco-2, MCF-7, CAL-72, and A2780 cells), including cisplatin-resistant human ovarian carcinoma cell lines (A2780cisR cells). Also, RuCp and the prepared metallodendrimers are active against human mesenchymal stem cells (hMSCs), which are often found in the tumor microenvironment where they seem to play a role in tumor progression and drug resistance. Full article
(This article belongs to the Special Issue Dendrimers: A Themed Issue in Honor of Professor Donald A. Tomalia on the Occasion of His 80th Birthday)
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Graphical abstract

27 pages, 11608 KiB  
Article
Hyperbranched Polyglycerol Derivatives as Prospective Copper Nanotransporter Candidates
by Mohiuddin Quadir, Susanne Fehse, Gerhard Multhaup and Rainer Haag
Molecules 2018, 23(6), 1281; https://doi.org/10.3390/molecules23061281 - 26 May 2018
Cited by 8 | Viewed by 4250
Abstract
Hyperbranched polyglycerol (hPG) has been used as a multivalent scaffold to develop a series of nanocarriers capable of high-affinity encapsulation of copper (Cu). A rationally selected set of Cu-complexing motifs has been conjugated to hPG hydroxyl groups to render the constructs potentially usable [...] Read more.
Hyperbranched polyglycerol (hPG) has been used as a multivalent scaffold to develop a series of nanocarriers capable of high-affinity encapsulation of copper (Cu). A rationally selected set of Cu-complexing motifs has been conjugated to hPG hydroxyl groups to render the constructs potentially usable as exogenous sources of Cu for addressing different pathological conditions associated with Cu-deficiency. We have utilized a newly discovered route to attach Cu-binding domains exclusively within a hPG core by selective differentiation between the primary and secondary hydroxyl groups of the polyol. These hPG-derivatives were found to form a stable complex with Cu ions depending on the type of immobilized ligands and corresponding degree of functionalization. In addition, these Cu-bearing nano-complexes demonstrated moderately cationic surface charge resulting in adjustable protein-binding characteristics and low cellular toxicity profile. We envision that these Cu-loaded hPG nanocarriers can be used as a stable platform to transport the metal ion across the systemic circulation to supply bioavailable quantity of Cu in disease-afflicted tissues. Full article
(This article belongs to the Special Issue Dendrimers: A Themed Issue in Honor of Professor Donald A. Tomalia on the Occasion of His 80th Birthday)
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Graphical abstract

14 pages, 5447 KiB  
Article
Preferential and Increased Uptake of Hydroxyl-Terminated PAMAM Dendrimers by Activated Microglia in Rabbit Brain Mixed Glial Culture
by Yossef Alnasser, Siva P. Kambhampati, Elizabeth Nance, Labchan Rajbhandari, Shiva Shrestha, Arun Venkatesan, Rangaramanujam M. Kannan and Sujatha Kannan
Molecules 2018, 23(5), 1025; https://doi.org/10.3390/molecules23051025 - 27 Apr 2018
Cited by 29 | Viewed by 5591
Abstract
Polyamidoamine (PAMAM) dendrimers are multifunctional nanoparticles with tunable physicochemical features, making them promising candidates for targeted drug delivery in the central nervous system (CNS). Systemically administered dendrimers have been shown to localize in activated glial cells, which mediate neuroinflammation in the CNS. These [...] Read more.
Polyamidoamine (PAMAM) dendrimers are multifunctional nanoparticles with tunable physicochemical features, making them promising candidates for targeted drug delivery in the central nervous system (CNS). Systemically administered dendrimers have been shown to localize in activated glial cells, which mediate neuroinflammation in the CNS. These dendrimers delivered drugs specifically to activated microglia, producing significant neurological improvements in multiple brain injury models, including in a neonatal rabbit model of cerebral palsy. To gain further insight into the mechanism of dendrimer cell uptake, we utilized an in vitro model of primary glial cells isolated from newborn rabbits to assess the differences in hydroxyl-terminated generation 4 PAMAM dendrimer (D4-OH) uptake by activated and non-activated glial cells. We used fluorescently-labelled D4-OH (D-Cy5) as a tool for investigating the mechanism of dendrimer uptake. D4-OH PAMAM dendrimer uptake was determined by fluorescence quantification using confocal microscopy and flow cytometry. Our results indicate that although microglial cells in the mixed cell population demonstrate early uptake of dendrimers in this in vitro system, activated microglia take up more dendrimer compared to resting microglia. Astrocytes showed delayed and limited uptake. We also illustrated the differences in mechanism of uptake between resting and activated microglia using different pathway inhibitors. Both resting and activated microglia primarily employed endocytotic pathways, which are enhanced in activated microglial cells. Additionally, we demonstrated that hydroxyl terminated dendrimers are taken up by primary microglia using other mechanisms including pinocytosis, caveolae, and aquaporin channels for dendrimer uptake. Full article
(This article belongs to the Special Issue Dendrimers: A Themed Issue in Honor of Professor Donald A. Tomalia on the Occasion of His 80th Birthday)
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Graphical abstract

13 pages, 1193 KiB  
Article
Dendrimeric Antigens for Drug Allergy Diagnosis: A New Approach for Basophil Activation Tests
by Noemi Molina, Angela Martin-Serrano, Tahia D. Fernandez, Amene Tesfaye, Francisco Najera, María J. Torres, Cristobalina Mayorga, Yolanda Vida, Maria I. Montañez and Ezequiel Perez-Inestrosa
Molecules 2018, 23(5), 997; https://doi.org/10.3390/molecules23050997 - 24 Apr 2018
Cited by 16 | Viewed by 4498
Abstract
Dendrimeric Antigens (DeAns) consist of dendrimers decorated with multiple units of drug antigenic determinants. These conjugates have been shown to be a powerful tool for diagnosing penicillin allergy using in vitro immunoassays, in which they are recognized by specific IgE from allergic patients. [...] Read more.
Dendrimeric Antigens (DeAns) consist of dendrimers decorated with multiple units of drug antigenic determinants. These conjugates have been shown to be a powerful tool for diagnosing penicillin allergy using in vitro immunoassays, in which they are recognized by specific IgE from allergic patients. Here we propose a new diagnostic approach using DeAns in cellular tests, in which recognition occurs through IgE bound to the basophil surface. Both IgE molecular recognition and subsequent cell activation may be influenced by the tridimensional architecture and size of the immunogens. Structural features of benzylpenicilloyl-DeAn and amoxicilloyl-DeAn (G2 and G4 PAMAM) were studied by diffusion Nuclear Magnetic Resonance (NMR) experiments and are discussed in relation to molecular dynamics simulation (MDS) observations. IgE recognition was clinically evaluated using the basophil activation test (BAT) for allergic patients and tolerant subjects. Diffusion NMR experiments, MDS and cellular studies provide evidence that the size of the DeAn, its antigen composition and tridimensional distribution play key roles in IgE-antigen recognition at the effector cell surface. These results indicate that the fourth generation DeAns induce a higher level of basophil activation in allergic patients. This approach can be considered as a potential complementary diagnostic method for evaluating penicillin allergy. Full article
(This article belongs to the Special Issue Dendrimers: A Themed Issue in Honor of Professor Donald A. Tomalia on the Occasion of His 80th Birthday)
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Graphical abstract

9 pages, 5825 KiB  
Article
Dendrimers for Drug Delivery
by Abhay Singh Chauhan
Molecules 2018, 23(4), 938; https://doi.org/10.3390/molecules23040938 - 18 Apr 2018
Cited by 257 | Viewed by 15425
Abstract
Dendrimers have come a long way in the last 25 years since their inception. Originally created as a wonder molecule of chemistry, dendrimer is now in the fourth class of polymers. Dr. Donald Tomalia first published his seminal work on Poly(amidoamine) (PAMAM) dendrimers [...] Read more.
Dendrimers have come a long way in the last 25 years since their inception. Originally created as a wonder molecule of chemistry, dendrimer is now in the fourth class of polymers. Dr. Donald Tomalia first published his seminal work on Poly(amidoamine) (PAMAM) dendrimers in 1985. Application of dendrimers as a drug delivery system started in late 1990s. Dendrimers for drug delivery are employed using two approaches: (i) formulation and (ii) nanoconstruct. In the formulation approach, drugs are physically entrapped in a dendrimer using non-covalent interactions, whereas drugs are covalently coupled on dendrimers in the nanoconstruct approach. We have demonstrated the utility of PAMAM dendrimers for enhancing solubility, stability and oral bioavailability of various drugs. Drug entrapment and drug release from dendrimers can be controlled by modifying dendrimer surfaces and generations. PAMAM dendrimers are also shown to increase transdermal permeation and specific drug targeting. Dendrimer platforms can be engineered to attach targeting ligands and imaging molecules to create a nanodevice. Dendrimer nanotechnology, due to its multifunctional ability, has the potential to create next generation nanodevices. Full article
(This article belongs to the Special Issue Dendrimers: A Themed Issue in Honor of Professor Donald A. Tomalia on the Occasion of His 80th Birthday)
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10 pages, 4217 KiB  
Article
Fluorescent Dendritic Micro-Hydrogels: Synthesis, Analysis and Use in Single-Cell Detection
by Lisa Christadore, Mark W. Grinstaff and Scott E. Schaus
Molecules 2018, 23(4), 936; https://doi.org/10.3390/molecules23040936 - 18 Apr 2018
Cited by 2 | Viewed by 3653
Abstract
Hydrogels are of keen interest for a wide range of medical and biotechnological applications including as 3D substrate structures for the detection of proteins, nucleic acids, and cells. Hydrogel parameters such as polymer wt % and crosslink density are typically altered for a [...] Read more.
Hydrogels are of keen interest for a wide range of medical and biotechnological applications including as 3D substrate structures for the detection of proteins, nucleic acids, and cells. Hydrogel parameters such as polymer wt % and crosslink density are typically altered for a specific application; now, fluorescence can be incorporated into such criteria by specific macromonomer selection. Intrinsic fluorescence was observed at λmax 445 nm from hydrogels polymerized from lysine and aldehyde- terminated poly(ethylene glycol) macromonomers upon excitation with visible light. The hydrogel’s photochemical properties are consistent with formation of a nitrone functionality. Printed hydrogels of 150 μm were used to detect individual cell adherence via a decreased in fluorescence. The use of such intrinsically fluorescent hydrogels as a platform for cell sorting and detection expands the current repertoire of tools available. Full article
(This article belongs to the Special Issue Dendrimers: A Themed Issue in Honor of Professor Donald A. Tomalia on the Occasion of His 80th Birthday)
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Graphical abstract

13 pages, 37282 KiB  
Article
On-Demand Bioadhesive Dendrimers with Reduced Cytotoxicity
by Feng Gao, Ivan Djordjevic, Oleksandr Pokholenko, Haobo Zhang, Junying Zhang and Terry W. J. Steele
Molecules 2018, 23(4), 796; https://doi.org/10.3390/molecules23040796 - 30 Mar 2018
Cited by 22 | Viewed by 6178
Abstract
Tissue adhesives based on polyamidoamine (PAMAM) dendrimer, grafted with UV-sensitive aryldiazirine (PAMAM-g-diazirine) are promising new candidates for light active adhesion on soft tissues. Diazirine carbene precursors form interfacial and intermolecular covalent crosslinks with tissues after UV light activation that requires no premixing or [...] Read more.
Tissue adhesives based on polyamidoamine (PAMAM) dendrimer, grafted with UV-sensitive aryldiazirine (PAMAM-g-diazirine) are promising new candidates for light active adhesion on soft tissues. Diazirine carbene precursors form interfacial and intermolecular covalent crosslinks with tissues after UV light activation that requires no premixing or inclusion of free radical initiators. However, primary amines on the PAMAM dendrimer surface present a potential risk due to their cytotoxic and immunological effects. PAMAM-g-diazirine formulations with cationic pendant amines converted into neutral amide groups were evaluated. In vitro toxicity is reduced by an order of magnitude upon amine capping while retaining bioadhesive properties. The in vivo immunological response to PAMAM-g-diazirine formulations was found to be optimal in comparison to standard poly(lactic-co-glycolic acid) (PLGA) thin films. Full article
(This article belongs to the Special Issue Dendrimers: A Themed Issue in Honor of Professor Donald A. Tomalia on the Occasion of His 80th Birthday)
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7 pages, 1046 KiB  
Article
Epitaxially Grown Ultra-Flat Self-Assembling Monolayers with Dendrimers
by Takane Imaoka, Noriko Bukeo and Kimihisa Yamamoto
Molecules 2018, 23(2), 485; https://doi.org/10.3390/molecules23020485 - 23 Feb 2018
Viewed by 3360
Abstract
Mono-molecular films formed by physical adsorption and dendrimer self-assembly were prepared on various substrate surfaces. It was demonstrated that a uniform dendrimer-based monolayer on the subnanometer scale can be easily constructed via simple dip coating. Furthermore, it was shown that an epitaxially grown [...] Read more.
Mono-molecular films formed by physical adsorption and dendrimer self-assembly were prepared on various substrate surfaces. It was demonstrated that a uniform dendrimer-based monolayer on the subnanometer scale can be easily constructed via simple dip coating. Furthermore, it was shown that an epitaxially grown monolayer film reflecting the crystal structure of the substrate (highly ordered pyrolytic graphite (HOPG)) can also be formed by aligning specific conditions. Full article
(This article belongs to the Special Issue Dendrimers: A Themed Issue in Honor of Professor Donald A. Tomalia on the Occasion of His 80th Birthday)
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1697 KiB  
Article
Design and Synthesis of Dendrimers with Facile Surface Group Functionalization, and an Evaluation of Their Bactericidal Efficacy
by Elizabeth Ladd, Amir Sheikhi, Na Li, Theo G.M. Van de Ven and Ashok Kakkar
Molecules 2017, 22(6), 868; https://doi.org/10.3390/molecules22060868 - 24 May 2017
Cited by 20 | Viewed by 6953
Abstract
We report a versatile divergent methodology to construct dendrimers from a tetrafunctional core, utilizing the robust copper(I) catalyzed alkyne-azide cycloaddition (CuAAC, “click”) reaction for both dendrimer synthesis and post-synthesis functionalization. Dendrimers of generations 1–3 with 8–32 protected or free OH and acetylene surface [...] Read more.
We report a versatile divergent methodology to construct dendrimers from a tetrafunctional core, utilizing the robust copper(I) catalyzed alkyne-azide cycloaddition (CuAAC, “click”) reaction for both dendrimer synthesis and post-synthesis functionalization. Dendrimers of generations 1–3 with 8–32 protected or free OH and acetylene surface groups, were synthesized using building blocks that included acetylene- or azide-terminated molecules with carboxylic acid or diol end groups, respectively. The acetylene surface groups were subsequently used to covalently link cationic amino groups. A preliminary evaluation indicated that the generation one dendrimer with terminal NH3+ groups was the most effective bactericide, and it was more potent than several previously studied dendrimers. Our results suggest that size, functional end groups and hydrophilicity are important parameters to consider in designing efficient antimicrobial dendrimers. Full article
(This article belongs to the Special Issue Dendrimers: A Themed Issue in Honor of Professor Donald A. Tomalia on the Occasion of His 80th Birthday)
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1065 KiB  
Article
Cation, Anion and Ion-Pair Complexes with a G-3 Poly(ethylene imine) Dendrimer in Aqueous Solution
by Matteo Savastano, Carla Bazzicalupi, Claudia Giorgi, Paola Gratteri and Antonio Bianchi
Molecules 2017, 22(5), 816; https://doi.org/10.3390/molecules22050816 - 16 May 2017
Cited by 4 | Viewed by 4389
Abstract
The G-3 poly(ethylene imine) ligand L2 shows a multifaceted coordination ability, being able to bind metal cations, anions and ion-pairs. The equilibrium constants for the formation of metal (Cu2+, Zn2+), anion (SO42−) and ion-pair (Cu2+ [...] Read more.
The G-3 poly(ethylene imine) ligand L2 shows a multifaceted coordination ability, being able to bind metal cations, anions and ion-pairs. The equilibrium constants for the formation of metal (Cu2+, Zn2+), anion (SO42−) and ion-pair (Cu2+/SO42−) complexes were determined in 0.1 M Me4NCl aqueous solution at 298.1 ± 0.1 K by means of potentiometric titrations. Thanks to its dendrimeric nature, L2 can form highly nucleated metal complexes, such as Cu5L210+ and Zn4L28+, in successive and well-defined complexation steps. Protonated forms of L2 give rise to relatively weak anion complexes with SO42−, but the addition of Cu2+ significantly enhances the binding ability of the ligand toward this anion below pH 9. In more alkaline solutions, an opposite trend is observed. The coordination properties of L2 are discussed with the support of modelling calculations. According to results, L2 is a promising molecule for the preparation of solid supported materials for the recovery of cations and anions from aqueous media and/or for applications in heterogeneous catalysis. Full article
(This article belongs to the Special Issue Dendrimers: A Themed Issue in Honor of Professor Donald A. Tomalia on the Occasion of His 80th Birthday)
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Review

Jump to: Editorial, Research

27 pages, 3310 KiB  
Review
New Advances in General Biomedical Applications of PAMAM Dendrimers
by Renan Vinicius de Araújo, Soraya da Silva Santos, Elizabeth Igne Ferreira and Jeanine Giarolla
Molecules 2018, 23(11), 2849; https://doi.org/10.3390/molecules23112849 - 02 Nov 2018
Cited by 157 | Viewed by 9414
Abstract
Dendrimers are nanoscopic compounds, which are monodispersed, and they are generally considered as homogeneous. PAMAM (polyamidoamine) was introduced in 1985, by Donald A. Tomalia, as a new class of polymers, named ‘starburst polymers’. This important contribution of Professor Tomalia opened a new research [...] Read more.
Dendrimers are nanoscopic compounds, which are monodispersed, and they are generally considered as homogeneous. PAMAM (polyamidoamine) was introduced in 1985, by Donald A. Tomalia, as a new class of polymers, named ‘starburst polymers’. This important contribution of Professor Tomalia opened a new research field involving nanotechnological approaches. From then on, many groups have been using PAMAM for diverse applications in many areas, including biomedical applications. The possibility of either linking drugs and bioactive compounds, or entrapping them into the dendrimer frame can improve many relevant biological properties, such as bioavailability, solubility, and selectivity. Directing groups to reach selective delivery in a specific organ is one of the advanced applications of PAMAM. In this review, structural and safety aspects of PAMAM and its derivatives are discussed, and some relevant applications are briefly presented. Emphasis has been given to gene delivery and targeting drugs, as advanced delivery systems using PAMAM and an incentive for its use on neglected diseases are briefly mentioned. Full article
(This article belongs to the Special Issue Dendrimers: A Themed Issue in Honor of Professor Donald A. Tomalia on the Occasion of His 80th Birthday)
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26 pages, 6307 KiB  
Review
Drug Delivery Systems from Self-Assembly of Dendron-Polymer Conjugates †
by Burcu Sumer Bolu, Rana Sanyal and Amitav Sanyal
Molecules 2018, 23(7), 1570; https://doi.org/10.3390/molecules23071570 - 28 Jun 2018
Cited by 52 | Viewed by 9144
Abstract
This review highlights the utilization of dendron-polymer conjugates as building blocks for the fabrication of nanosized drug delivery vehicles. The examples given provide an overview of the evolution of these delivery platforms, from simple micellar containers to smart stimuli- responsive drug delivery systems [...] Read more.
This review highlights the utilization of dendron-polymer conjugates as building blocks for the fabrication of nanosized drug delivery vehicles. The examples given provide an overview of the evolution of these delivery platforms, from simple micellar containers to smart stimuli- responsive drug delivery systems through their design at the macromolecular level. Variations in chemical composition and connectivity of the dendritic and polymeric segments provide a variety of self-assembled micellar nanostructures that embody desirable attributes of viable drug delivery systems. Full article
(This article belongs to the Special Issue Dendrimers: A Themed Issue in Honor of Professor Donald A. Tomalia on the Occasion of His 80th Birthday)
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15 pages, 8741 KiB  
Review
Dentromers, a Family of Super Dendrimers with Specific Properties and Applications
by Didier Astruc, Christophe Deraedt, Rodrigue Djeda, Catia Ornelas, Xiang Liu, Amalia Rapakousiou, Jaime Ruiz, Yanlan Wang and Qi Wang
Molecules 2018, 23(4), 966; https://doi.org/10.3390/molecules23040966 - 20 Apr 2018
Cited by 20 | Viewed by 5921
Abstract
Dentromers (from dentro, δεντρο: tree in Greek), and meros (μεροσ, in greek: part) are introduced as a family of dendrimers constructed according to successive divergent 1 → 3 branching. The smaller dentromers have 27 terminal branches. With alcohol termini they were originally [...] Read more.
Dentromers (from dentro, δεντρο: tree in Greek), and meros (μεροσ, in greek: part) are introduced as a family of dendrimers constructed according to successive divergent 1 → 3 branching. The smaller dentromers have 27 terminal branches. With alcohol termini they were originally named arborols by Newkome, who pioneered 1 → 3 constructions of dendrimers and dendrons. Giant dentromers have been constructed and decorated in particular with ferrocene and other redox active groups. The synthesis, specific properties, and applications are examined in this mini review article dedicated to Don Tomalia, with an emphasis on dense peripheral packing favoring the functions of encapsulation, redox sensing, and micellar template for catalysis in water and aqueous solvents. Full article
(This article belongs to the Special Issue Dendrimers: A Themed Issue in Honor of Professor Donald A. Tomalia on the Occasion of His 80th Birthday)
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21 pages, 4930 KiB  
Review
Hyperbranched Macromolecules: From Synthesis to Applications
by In-Yup Jeon, Hyuk-Jun Noh and Jong-Beom Baek
Molecules 2018, 23(3), 657; https://doi.org/10.3390/molecules23030657 - 14 Mar 2018
Cited by 45 | Viewed by 7063
Abstract
Hyperbranched macromolecules (HMs, also called hyperbranched polymers) are highly branched three-dimensional (3D) structures in which all bonds converge to a focal point or core, and which have a multiplicity of reactive chain-ends. This review summarizes major types of synthetic strategies exploited to produce [...] Read more.
Hyperbranched macromolecules (HMs, also called hyperbranched polymers) are highly branched three-dimensional (3D) structures in which all bonds converge to a focal point or core, and which have a multiplicity of reactive chain-ends. This review summarizes major types of synthetic strategies exploited to produce HMs, including the step-growth polycondensation, the self-condensing vinyl polymerization and ring opening polymerization. Compared to linear analogues, the globular and dendritic architectures of HMs endow new characteristics, such as abundant functional groups, intramolecular cavities, low viscosity, and high solubility. After discussing the general concepts, synthesis, and properties, various applications of HMs are also covered. HMs continue being materials for topical interest, and thus this review offers both concise summary for those new to the topic and for those with more experience in the field of HMs. Full article
(This article belongs to the Special Issue Dendrimers: A Themed Issue in Honor of Professor Donald A. Tomalia on the Occasion of His 80th Birthday)
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12 pages, 1387 KiB  
Review
Which Dendrimer to Attain the Desired Properties? Focus on Phosphorhydrazone Dendrimers
by Anne-Marie Caminade and Jean-Pierre Majoral
Molecules 2018, 23(3), 622; https://doi.org/10.3390/molecules23030622 - 09 Mar 2018
Cited by 18 | Viewed by 4279
Abstract
Among the six Critical Nanoscale Design Parameters (CNDPs) proposed by Prof. Donald A. Tomalia, this review illustrates the influence of the sixth one, which concerns the elemental composition, on the properties of dendrimers. After a large introduction that summarizes different types of dendrimers [...] Read more.
Among the six Critical Nanoscale Design Parameters (CNDPs) proposed by Prof. Donald A. Tomalia, this review illustrates the influence of the sixth one, which concerns the elemental composition, on the properties of dendrimers. After a large introduction that summarizes different types of dendrimers that have been compared with PolyAMidoAMine (PAMAM) dendrimers, this review will focus on the properties of positively and negatively charged phosphorhydrazone (PPH) dendrimers, especially in the field of biology, compared with other types of dendrimers, in particular PAMAM dendrimers, as well as polypropyleneimine (PPI), carbosilane, and p-Lysine dendrimers. Full article
(This article belongs to the Special Issue Dendrimers: A Themed Issue in Honor of Professor Donald A. Tomalia on the Occasion of His 80th Birthday)
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