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Dendrimers in Biomedicine
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Dendrimers in Biomedicine

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

Deadline for manuscript submissions: closed (31 July 2020) | Viewed by 29664

Special Issue Editor

Dr. Jørn Bolstad Christensen

E-Mail Website1 Website2
Guest Editor
Department Chemistry, University of Copenhagen, Thorvaldsensvej 40, DK-1871 Copenhagen, Denmark
Interests: dendrimers; organic synthesis; protective group chemistry
Special Issues, Collections and Topics in MDPI journals

Special Issue Information

Dear Colleagues,

The field of dendrimers has evolved since the first report by Vögtle in 1978, from being mainly concerned with creating new structures to finding uses for them. The application of Dendrimers in Biomedicine is a field that is still under development, and although we have barely touched the surface, there are already examples of dendrimers being applied in transfection with DNA and siRNA in therapy or for cancer therapy, imaging, or as anti-inflammatory drugs, to name but a few. A lot of work is still required, and this Special Issue on “Dendrimers in Biomedicine” intends to collect results representing the entire field, in order to give a clear view of the present status. We welcome articles addressing synthesis, physical chemistry, molecular simulations, biological studies, thoughts on regulatory aspects, and other relevant aspects related to Dendrimers in Biomedicine.

Prof. Jørn Bolstad Christensen
Guest Editor

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Keywords

  • dendrimers
  • synthesis
  • biological properties
  • nanomedicine
  • analytical chemistry
  • in vitro
  • in vivo
  • molecular modeling
  • molecular simulation
  • scalability
  • reproducibility
  • regulatory issues

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Published Papers (7 papers)

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Research

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12 pages, 1462 KiB  
Article
First Class of Phosphorus Dendritic Compounds Containing β-Cyclodextrin Units in the Periphery Prepared by CuAAC
by Kendra Sorroza-Martínez, Israel González-Méndez, Mireille Vonlanthen, Kathleen I. Moineau-Chane Ching, Anne-Marie Caminade, Javier Illescas and Ernesto Rivera
Molecules 2020, 25(18), 4034; https://doi.org/10.3390/molecules25184034 - 4 Sep 2020
Cited by 6 | Viewed by 2490
Abstract
A new class of phosphorus dendritic compounds (PDCs) having a cyclotriphosphazene (P3N3) core and decorated with six β-cyclodextrin (βCD) units, named P3N3-[O-C6H4-O-(CH2)n-βCD]6, where n = [...] Read more.
A new class of phosphorus dendritic compounds (PDCs) having a cyclotriphosphazene (P3N3) core and decorated with six β-cyclodextrin (βCD) units, named P3N3-[O-C6H4-O-(CH2)n-βCD]6, where n = 3 or 4 was designed, and the synthesis was performed using copper (I) catalyzed alkyne-azide cycloaddition (CuAAC). To obtain the complete substitution of the P3N3, two linkers consisting of an aromatic ring and an aliphatic chain of two different lengths were assessed. We found that, with both linkers, the total modification of the periphery was achieved. The two new obtained dendritic compounds presented a considerably high water solubility (>1 g/mL). The compounds comprised in this new class of PDCs are potential drug carrier candidates, since the conjugation of the βCD units to the P3N3 core through the primary face will not only serve as surface cover but, also, provide them the faculty to encapsulate various drugs inside the βCDs cavities. Full article
(This article belongs to the Special Issue Dendrimers in Biomedicine)
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13 pages, 975 KiB  
Article
Synthesis and Antimicrobial Properties of a Ciprofloxacin and PAMAM-dendrimer Conjugate
by Søren Wedel Svenningsen, Rikki Franklin Frederiksen, Claire Counil, Mario Ficker, Jørgen J. Leisner and Jørn Bolstad Christensen
Molecules 2020, 25(6), 1389; https://doi.org/10.3390/molecules25061389 - 18 Mar 2020
Cited by 18 | Viewed by 4796
Abstract
Infections caused by bacteria resistant to antibiotics are an increasing problem. Multivalent antibiotics could be a solution. In the present study, a covalent conjugate between Ciprofloxacin and a G0-PAMAM dendrimer has been synthesized and tested against clinically relevant Gram-positive and Gram-negative bacteria. The [...] Read more.
Infections caused by bacteria resistant to antibiotics are an increasing problem. Multivalent antibiotics could be a solution. In the present study, a covalent conjugate between Ciprofloxacin and a G0-PAMAM dendrimer has been synthesized and tested against clinically relevant Gram-positive and Gram-negative bacteria. The conjugate has antimicrobial activity and there is a positive dendritic effect compared to Ciprofloxacin itself. Full article
(This article belongs to the Special Issue Dendrimers in Biomedicine)
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12 pages, 3425 KiB  
Article
Telodendrimer-Based Macromolecular Drug Design using 1,3-Dipolar Cycloaddition for Applications in Biology
by Hossein Yazdani, Esha Kaul, Ayoob Bazgir, Dusica Maysinger and Ashok Kakkar
Molecules 2020, 25(4), 857; https://doi.org/10.3390/molecules25040857 - 15 Feb 2020
Cited by 10 | Viewed by 3049
Abstract
An architectural polymer containing hydrophobic isoxazole-based dendron and hydrophilic polyethylene glycol linear tail is prepared by a combination of the robust ZnCl2 catalyzed alkyne-nitrile oxide 1,3-dipolar cycloaddition and esterification chemistry. This water soluble amphiphilic telodendrimer acts as a macromolecular biologically active agent [...] Read more.
An architectural polymer containing hydrophobic isoxazole-based dendron and hydrophilic polyethylene glycol linear tail is prepared by a combination of the robust ZnCl2 catalyzed alkyne-nitrile oxide 1,3-dipolar cycloaddition and esterification chemistry. This water soluble amphiphilic telodendrimer acts as a macromolecular biologically active agent and shows concentration dependent reduction of glioblastoma (U251) cell survival. Full article
(This article belongs to the Special Issue Dendrimers in Biomedicine)
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15 pages, 5205 KiB  
Article
New Ionic Carbosilane Dendrons Possessing Fluorinated Tails at Different Locations on the Skeleton
by Gabriel Mencia, Tania Lozano-Cruz, Mercedes Valiente, Javier de la Mata, Jesús Cano and Rafael Gómez
Molecules 2020, 25(4), 807; https://doi.org/10.3390/molecules25040807 - 13 Feb 2020
Cited by 8 | Viewed by 2432
Abstract
The fluorination of dendritic structures has attracted special attention in terms of self-assembly processes and biological applications. The presence of fluorine increases the hydrophobicity of the molecule, resulting in a better interaction with biological membranes and viability. In addition, the development of 19 [...] Read more.
The fluorination of dendritic structures has attracted special attention in terms of self-assembly processes and biological applications. The presence of fluorine increases the hydrophobicity of the molecule, resulting in a better interaction with biological membranes and viability. In addition, the development of 19F magnetic resonance imaging (19F-MRI) has greatly increased interest in the design of new fluorinated structures with specific properties. Here, we present the synthesis of new water-soluble fluorinated carbosilane dendrons containing fluorinated chains in different positions on the skeleton, focal point or surface, and their preliminary supramolecular aggregation studies. These new dendritic systems could be considered as potential systems to be employed in drug delivery or gene therapy and monitored by 19F-MRI. Full article
(This article belongs to the Special Issue Dendrimers in Biomedicine)
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20 pages, 6907 KiB  
Article
The Effect of Biotinylated PAMAM G3 Dendrimers Conjugated with COX-2 Inhibitor (celecoxib) and PPARγ Agonist (Fmoc-L-Leucine) on Human Normal Fibroblasts, Immortalized Keratinocytes and Glioma Cells in Vitro
by Łukasz Uram, Maria Misiorek, Monika Pichla, Aleksandra Filipowicz-Rachwał, Joanna Markowicz, Stanisław Wołowiec and Elżbieta Wałajtys-Rode
Molecules 2019, 24(20), 3801; https://doi.org/10.3390/molecules24203801 - 22 Oct 2019
Cited by 20 | Viewed by 3822
Abstract
Glioblastoma multiforme (GBM) is the most malignant type of central nervous system tumor that is resistant to all currently used forms of therapy. Thus, more effective GBM treatment strategies are being investigated, including combined therapies with drugs that may cross the blood brain [...] Read more.
Glioblastoma multiforme (GBM) is the most malignant type of central nervous system tumor that is resistant to all currently used forms of therapy. Thus, more effective GBM treatment strategies are being investigated, including combined therapies with drugs that may cross the blood brain barrier (BBB). Another important issue considers the decrease of deleterious side effects of therapy. It has been shown that nanocarrier conjugates with biotin can penetrate BBB. In this study, biotinylated PAMAM G3 dendrimers substituted with the recognized anticancer agents cyclooxygenase-2 (COX-2) inhibitor celecoxib and peroxisome proliferator-activated receptor γ (PPARγ) agonist Fmoc-L-Leucine (G3-BCL) were tested in vitro on human cell lines with different p53 status: glioblastoma (U-118 MG), normal fibroblasts (BJ) and immortalized keratinocytes (HaCaT). G3-BCL penetrated efficiently into the lysosomal and mitochondrial compartments of U-118 MG cells and induced death of U-118 MG cells via apoptosis and inhibited proliferation and migration at low IC50 = 1.25 µM concentration, considerably lower than either drug applied alone. Comparison of the effects of G3-BCL on expression of COX-2 and PPARγ protein and PGE2 production of three different investigated cell line phenotypes revealed that the anti-glioma effect of the conjugate was realized by other mechanisms other than influencing PPAR-γ expression and regardless of p53 cell status, it was dependent on COX-2 protein level and high PGE2 production. Similar G3-BCL cytotoxicity was seen in normal fibroblasts (IC50 = 1.29 µM) and higher resistance in HaCaT cells (IC50 = 4.49 µM). Thus, G3-BCL might be a good candidate for the targeted, local glioma therapy with limited site effects. Full article
(This article belongs to the Special Issue Dendrimers in Biomedicine)
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Review

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41 pages, 6917 KiB  
Review
Applications and Limitations of Dendrimers in Biomedicine
by Adriana Aurelia Chis, Carmen Dobrea, Claudiu Morgovan, Anca Maria Arseniu, Luca Liviu Rus, Anca Butuca, Anca Maria Juncan, Maria Totan, Andreea Loredana Vonica-Tincu, Gabriela Cormos, Andrei Catalin Muntean, Maria Lucia Muresan, Felicia Gabriela Gligor and Adina Frum
Molecules 2020, 25(17), 3982; https://doi.org/10.3390/molecules25173982 - 1 Sep 2020
Cited by 204 | Viewed by 9732
Abstract
Biomedicine represents one of the main study areas for dendrimers, which have proven to be valuable both in diagnostics and therapy, due to their capacity for improving solubility, absorption, bioavailability and targeted distribution. Molecular cytotoxicity constitutes a limiting characteristic, especially for cationic and [...] Read more.
Biomedicine represents one of the main study areas for dendrimers, which have proven to be valuable both in diagnostics and therapy, due to their capacity for improving solubility, absorption, bioavailability and targeted distribution. Molecular cytotoxicity constitutes a limiting characteristic, especially for cationic and higher-generation dendrimers. Antineoplastic research of dendrimers has been widely developed, and several types of poly(amidoamine) and poly(propylene imine) dendrimer complexes with doxorubicin, paclitaxel, imatinib, sunitinib, cisplatin, melphalan and methotrexate have shown an improvement in comparison with the drug molecule alone. The anti-inflammatory therapy focused on dendrimer complexes of ibuprofen, indomethacin, piroxicam, ketoprofen and diflunisal. In the context of the development of antibiotic-resistant bacterial strains, dendrimer complexes of fluoroquinolones, macrolides, beta-lactamines and aminoglycosides have shown promising effects. Regarding antiviral therapy, studies have been performed to develop dendrimer conjugates with tenofovir, maraviroc, zidovudine, oseltamivir and acyclovir, among others. Furthermore, cardiovascular therapy has strongly addressed dendrimers. Employed in imaging diagnostics, dendrimers reduce the dosage required to obtain images, thus improving the efficiency of radioisotopes. Dendrimers are macromolecular structures with multiple advantages that can suffer modifications depending on the chemical nature of the drug that has to be transported. The results obtained so far encourage the pursuit of new studies. Full article
(This article belongs to the Special Issue Dendrimers in Biomedicine)
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16 pages, 3365 KiB  
Review
Perceptions and Misconceptions in Molecular Recognition: Key Factors in Self-Assembling Multivalent (SAMul) Ligands/Polyanions Selectivity
by Domenico Marson, Erik Laurini, Suzana Aulic, Maurizio Fermeglia and Sabrina Pricl
Molecules 2020, 25(4), 1003; https://doi.org/10.3390/molecules25041003 - 24 Feb 2020
Cited by 1 | Viewed by 2605
Abstract
Biology is dominated by polyanions (cell membranes, nucleic acids, and polysaccharides just to name a few), and achieving selective recognition between biological polyanions and synthetic systems currently constitutes a major challenge in many biomedical applications, nanovectors-assisted gene delivery being a prime example. This [...] Read more.
Biology is dominated by polyanions (cell membranes, nucleic acids, and polysaccharides just to name a few), and achieving selective recognition between biological polyanions and synthetic systems currently constitutes a major challenge in many biomedical applications, nanovectors-assisted gene delivery being a prime example. This review work summarizes some of our recent efforts in this field; in particular, by using a combined experimental/computation approach, we investigated in detail some critical aspects in self-assembled nanomicelles and two major polyanions—DNA and heparin. Full article
(This article belongs to the Special Issue Dendrimers in Biomedicine)
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