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Special Issue "Functional Dendrimers"

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

Deadline for manuscript submissions: closed (20 February 2016).

Special Issue Editor

Prof. Dr. Ashok Kakkar
Website
Guest Editor
Department of Chemistry, McGill University, 801 Sherbrooke St. West, Montreal, Quebec, 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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Special Issue Information

Dear Colleagues,

Hyperbranched and monodisperse macromolecules that are commonly referred to as dendrimers have captivated the imagination of macromolecular chemists, and now occupy center stage in developing nanomaterials for a variety of applications. Our ability to synthetically articulate their architecture and introduce functional groups at the core, within their backbone and at the periphery, have enabled us to design well-defined scaffolds targeted for a specific purpose. Functional dendrimers have opened doors to fine tune their properties based on given event requirements. The elegance of synthetic methodologies has provided strong impetus to envision bringing these fascinating macromolecules to the realm of biomedical, industrial and polymer science applications.

This Special Issue on “Functional Dendrimers” is aimed at bringing inspiring efforts devoted in designing, construction and evaluating the potential of mono- to multivalent dendritic frameworks. It will solidify the notion that once considered an academic curiosity, these macromolecules provide an ideal platform to assemble cost-effective made-to-order synthetic architectures for biology, physics, medicine, etc. It will showcase important achievements in constructing functional dendrimers and highlight their significance in designing complex architectures.

Prof. Dr. Ashok Kakkar
Guest Editor

Manuscript Submission Information

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Please visit the Instructions for Authors page before submitting a manuscript. The Article Processing Charge (APC) for publication in this open access journal is 2000 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
  • hyperbranched
  • functional dendrimers
  • synthesis
  • biofriendly
  • tailored
  • functionalized nanostructures
  • nanotechnology
  • multifunctional dendrimers
  • multivalent dendrimers
  • multi-tasking nanostructures
  • amphiphilic dendrimers
  • surface functionalization
  • internal modification
  • dendritic macromolecules
  • dendronized polymers
  • dendrimer-polymer conjugates
  • arborescent polymers
  • functional materials
  • synthetic methodologies to dendrimers
  • drug delivery
  • theranostics
  • scale inhibition
  • energy storage and conversion
  • supramolecular dendrimers

Published Papers (11 papers)

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Open AccessEditorial
Special Issue: “Functional Dendrimers”
1 Department of Chemistry, University of Pennsylvania, Philadelphia, PA 19104, USA
2 Department of Physics, Virginia Commonwealth University, Richmond, VA 23284, USA
3 National Dendrimer & Nanotechnology Center, NanoSynthons LLC, 1200 N. Fancher Avenue, Mt. Pleasant, MI 48858, USA
Molecules 2016, 21(8), 1035; https://doi.org/10.3390/molecules21081035 - 09 Aug 2016
Cited by 8
Abstract
This special issue entitled “Functional Dendrimers” focuses on the manipulation of at least six “critical nanoscale design parameters” (CNDPs) of dendrimers including: size, shape, surface chemistry, flexibility/rigidity, architecture and elemental composition. These CNDPs collectively define properties of all “functional dendrimers”. This special issue [...] Read more.
This special issue entitled “Functional Dendrimers” focuses on the manipulation of at least six “critical nanoscale design parameters” (CNDPs) of dendrimers including: size, shape, surface chemistry, flexibility/rigidity, architecture and elemental composition. These CNDPs collectively define properties of all “functional dendrimers”. This special issue contains many interesting examples describing the manipulation of certain dendrimer CNDPs to create new emerging properties and, in some cases, predictive nanoperiodic property patterns (i.e., dendritic effects). The systematic engineering of CNDPs provides a valuable strategy for optimizing functional dendrimer properties for use in specific applications. Full article
(This article belongs to the Special Issue Functional Dendrimers)
Open AccessArticle
On Topological Indices of Certain Families of Nanostar Dendrimers
1 School of Informatics and Applied Mathematics, University Malaysia Terengganu, Kuala Terengganu, Terengganu 21030, Malaysia
2 Department of Mathematics, College of Computer Sciences and Mathematics, Tikrit University, Tikrit 34001, Iraq
3 Department of Mathematics, School of Natural Sciences, National University of Sciences and Technology, Sector H-12, Islamabad 44000, Pakistan
Molecules 2016, 21(7), 821; https://doi.org/10.3390/molecules21070821 - 24 Jun 2016
Cited by 6
Abstract
A topological index of graph G is a numerical parameter related to G which characterizes its molecular topology and is usually graph invariant. In the field of quantitative structure-activity (QSAR)/quantitative structure-activity structure-property (QSPR) research, theoretical properties of the chemical compounds and their molecular [...] Read more.
A topological index of graph G is a numerical parameter related to G which characterizes its molecular topology and is usually graph invariant. In the field of quantitative structure-activity (QSAR)/quantitative structure-activity structure-property (QSPR) research, theoretical properties of the chemical compounds and their molecular topological indices such as the Randić connectivity index, atom-bond connectivity (ABC) index and geometric-arithmetic (GA) index are used to predict the bioactivity of different chemical compounds. A dendrimer is an artificially manufactured or synthesized molecule built up from the branched units called monomers. In this paper, the fourth version of ABC index and the fifth version of GA index of certain families of nanostar dendrimers are investigated. We derive the analytical closed formulas for these families of nanostar dendrimers. The obtained results can be of use in molecular data mining, particularly in researching the uniqueness of tested (hyper-branched) molecular graphs. Full article
(This article belongs to the Special Issue Functional Dendrimers)
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Open AccessReview
Dendrimer Prodrugs
Laboratory of Design and Synthesis of Chemotherapeutics Potentially Active in Neglected Diseases (LAPEN), Department of Pharmacy, Faculty of Pharmaceutical Sciences, University of São Paulo—USP, Avenue Professor Lineu Prestes, 580–Building 13, São Paulo SP, 05508-900, Brazil
Molecules 2016, 21(6), 686; https://doi.org/10.3390/molecules21060686 - 31 May 2016
Cited by 15
Abstract
The main objective of this review is to describe the importance of dendrimer prodrugs in the design of new drugs, presenting numerous applications of these nanocomposites in the pharmaceutical field. Therefore, the use of dendrimer prodrugs as carrier for drug delivery, to improve [...] Read more.
The main objective of this review is to describe the importance of dendrimer prodrugs in the design of new drugs, presenting numerous applications of these nanocomposites in the pharmaceutical field. Therefore, the use of dendrimer prodrugs as carrier for drug delivery, to improve pharmacokinetic properties of prototype, to promote drug sustained-release, to increase selectivity and, consequently, to decrease toxicity, are just some examples of topics that have been extensively reported in the literature, especially in the last decade. The examples discussed here give a panel of the growing interest dendrimer prodrugs have been evoking in the scientific community. Full article
(This article belongs to the Special Issue Functional Dendrimers)
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Open AccessArticle
Thermoregulated Coacervation, Metal-Encapsulation and Nanoparticle Synthesis in Novel Triazine Dendrimers
1 Centro de Ciencias Aplicadas y Desarrollo Tecnológico, Universidad Nacional Autónoma de México, Cd. Universitaria, A.P. 70–186, C.P., Cd. Mx. 04510, Mexico
2 Department of Chemistry & Biochemistry, Texas Christian University, Fort Worth, TX 76129, USA
Molecules 2016, 21(5), 599; https://doi.org/10.3390/molecules21050599 - 11 May 2016
Cited by 5
Abstract
The synthesis and solubility behaviors of four generation five (G5) triazine dendrimers are studied. While the underivatized cationic dendrimer is soluble in water, the acetylated and propanoylated derivatives undergo coacervation in water upon increasing temperature. Occurring around room temperature, this behavior is related [...] Read more.
The synthesis and solubility behaviors of four generation five (G5) triazine dendrimers are studied. While the underivatized cationic dendrimer is soluble in water, the acetylated and propanoylated derivatives undergo coacervation in water upon increasing temperature. Occurring around room temperature, this behavior is related to a liquid-liquid phase transition with a lower critical solution temperature (LCST) and is explained by differences in composition, notably, the hydrophobic nature of the terminal groups. Interestingly, the water solubility of the acetylated dendrimer is affected by the addition of selected metal ions. Titrating solutions of acetylated dendrimer at temperatures below the LCST with gold or palladium ions promoted precipitation, but platinum, iridium, and copper did not. Gold nanoparticles having diameters of 2.5 ± 0.8 nm can be obtained from solutions of the acetylated dendrimer at concentrations of gold less than that required to induce precipitation by treating the solution with sodium borohydride. Full article
(This article belongs to the Special Issue Functional Dendrimers)
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Open AccessReview
Bifunctional Phosphorus Dendrimers and Their Properties
1 Laboratoire de Chimie de Coordination (LCC), CNRS, 205 Route de Narbonne, BP 44099, F-31077 Toulouse Cedex 4, France
2 UPS, INPT, Université de Toulouse, F-31077 Toulouse Cedex 4, France
Molecules 2016, 21(4), 538; https://doi.org/10.3390/molecules21040538 - 23 Apr 2016
Cited by 14
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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Open AccessReview
Dendrimers and Dendrons as Versatile Building Blocks for the Fabrication of Functional Hydrogels
1 Department of Chemistry, Bogazici University, Istanbul 34342, Turkey
2 Department of Polymer Engineering, Yalova University, Yalova 77100, Turkey
3 Center for Life Sciences and Technologies, Bogazici University, Istanbul, 34342, Turkey
Molecules 2016, 21(4), 497; https://doi.org/10.3390/molecules21040497 - 15 Apr 2016
Cited by 13
Abstract
Hydrogels have emerged as a versatile class of polymeric materials with a wide range of applications in biomedical sciences. The judicious choice of hydrogel precursors allows one to introduce the necessary attributes to these materials that dictate their performance towards intended applications. Traditionally, [...] Read more.
Hydrogels have emerged as a versatile class of polymeric materials with a wide range of applications in biomedical sciences. The judicious choice of hydrogel precursors allows one to introduce the necessary attributes to these materials that dictate their performance towards intended applications. Traditionally, hydrogels were fabricated using either polymerization of monomers or through crosslinking of polymers. In recent years, dendrimers and dendrons have been employed as well-defined building blocks in these materials. The multivalent and multifunctional nature of dendritic constructs offers advantages in either formulation or the physical and chemical properties of the obtained hydrogels. This review highlights various approaches utilized for the fabrication of hydrogels using well-defined dendrimers, dendrons and their polymeric conjugates. Examples from recent literature are chosen to illustrate the wide variety of hydrogels that have been designed using dendrimer- and dendron-based building blocks for applications, such as sensing, drug delivery and tissue engineering. Full article
(This article belongs to the Special Issue Functional Dendrimers)
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Open AccessArticle
Synthesis of Dense and Chiral Dendritic Polyols Using Glyconanosynthon Scaffolds
1 Pharmaqam and Nanoqam, Department of Chemistry, University of Québec a Montréal, P.O. Box 8888, Succ. Centre-Ville, Montréal, QC H3C 3P8, Canada
2 Department of Innovative Technologies, University of Applied Sciences and Arts of Southern Switzerland, Galleria 2, Manno CH-6928, Switzerland
Molecules 2016, 21(4), 448; https://doi.org/10.3390/molecules21040448 - 04 Apr 2016
Cited by 7
Abstract
Most classical dendrimers are frequently built-up from identical repeating units of low valency (usually AB2 monomers). This strategy necessitates several generations to achieve a large number of surface functionalities. In addition, these typical monomers are achiral. We propose herein the use of sugar [...] Read more.
Most classical dendrimers are frequently built-up from identical repeating units of low valency (usually AB2 monomers). This strategy necessitates several generations to achieve a large number of surface functionalities. In addition, these typical monomers are achiral. We propose herein the use of sugar derivatives consisting of several and varied functionalities with their own individual intrinsic chirality as both scaffolds/core as well as repeating units. This approach allows the construction of chiral, dense dendrimers with a large number of surface groups at low dendrimer generations. Perpropargylated β-D-glucopyranoside, serving as an A5 core, together with various derivatives, such as 2-azidoethyl tetra-O-allyl-β-D-glucopyranoside, serving as an AB4 repeating moiety, were utilized to construct chiral dendrimers using “click chemistry” (CuAAC reaction). These were further modified by thiol-ene and thiol-yne click reactions with alcohols to provide dendritic polyols. Molecular dynamic simulation supported the assumption that the resulting polyols have a dense structure. Full article
(This article belongs to the Special Issue Functional Dendrimers)
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Open AccessArticle
Nanoparticle Effects on Human Platelets in Vitro: A Comparison between PAMAM and Triazine Dendrimers
1 Department of Chemistry & Biochemistry, Texas Christian University, Fort Worth, TX 76129, USA
2 Nanotechnology Characterization Lab, Frederick National Laboratory for Cancer Research, Frederick, MD 21702, USA
3 Department of Molecular and Medical Genetics & Institute of Cancer Research, University of North Texas Health Science Center, Fort Worth, TX 76109, USA
Molecules 2016, 21(4), 428; https://doi.org/10.3390/molecules21040428 - 29 Mar 2016
Cited by 19
Abstract
Triazine and PAMAM dendrimers of similar size and number of cationic surface groups were compared for their ability to promote platelet aggregation. Triazine dendrimers (G3, G5 and G7) varied in molecular weight from 8 kDa–130 kDa and in surface groups 16–256. PAMAM dendrimers [...] Read more.
Triazine and PAMAM dendrimers of similar size and number of cationic surface groups were compared for their ability to promote platelet aggregation. Triazine dendrimers (G3, G5 and G7) varied in molecular weight from 8 kDa–130 kDa and in surface groups 16–256. PAMAM dendrimers selected for comparison included G3 (7 kDa, 32 surface groups) and G6 (58 kDa, 256 surface groups). The treatment of human platelet-rich plasma (PRP) with low generation triazine dendrimers (0.01–1 µM) did not show any significant effect in human platelet aggregation in vitro; however, the treatment of PRP with larger generations promotes an effective aggregation. These results are in agreement with studies performed with PAMAM dendrimers, where large generations promote aggregation. Triazine dendrimers promote aggregation less aggressively than PAMAM dendrimers, a factor attributed to differences in cationic charge or the formation of supramolecular assemblies of dendrimers. Full article
(This article belongs to the Special Issue Functional Dendrimers)
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Open AccessArticle
Fluoride-Promoted Esterification (FPE) Chemistry: A Robust Route to Bis-MPA Dendrons and Their Postfunctionalization
Department of Fibre and Polymer Technology, KTH Royal Institute of Technology, 10044 Stockholm, Sweden
Molecules 2016, 21(3), 366; https://doi.org/10.3390/molecules21030366 - 17 Mar 2016
Cited by 8
Abstract
Bifunctional dendrons based on 2,2-bis(methylol)propionic acid (bis-MPA) are highly desirable scaffolds for biomedical applications. This is due to their flawless nature and large and exact number of functional groups as well as being biodegradable and biocompatible. Herein, we describe a facile divergent growth [...] Read more.
Bifunctional dendrons based on 2,2-bis(methylol)propionic acid (bis-MPA) are highly desirable scaffolds for biomedical applications. This is due to their flawless nature and large and exact number of functional groups as well as being biodegradable and biocompatible. Herein, we describe a facile divergent growth approach to their synthesis from monobenzylated tetraethylene glycol and post functionalization utilizing fluoride-promoted esterification (FPE) chemistry protocols. The scaffolds, presenting selectively deprotectable hydroxyls in the periphery and at the focal point, were isolated on a multigram scale with excellent purity up to the fourth generation dendron with a molecular weight of 2346 Da in seven reactions with a total yield of 50%. The third generation dendron was used as a model compound to demonstrate its functionalizability. Selective deprotection of the dendron’s focal point was achieved with an outstanding yield of 94%, and biotin as well as azido functionalities were introduced to its focal point and periphery, respectively, through FPE chemistry. Bulky disperse red dyes were clicked through CuAAC to the dendron’s azido groups, giving a biotinylated dendron with multivalent dyes with a molecular weight of 6252 Da in a total yield of 37% in five reactions with an average yield of 82% starting from the third generation focally and peripherally protected dendron. FPE chemistry proved to be a superb improvement over previous protocols towards bis-MPA dendrons as high purity and yields were obtained with less toxic solvents and greatly improved monomer utilization. Full article
(This article belongs to the Special Issue Functional Dendrimers)
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Open AccessArticle
Functionalization of a Triazine Dendrimer Presenting Four Maleimides on the Periphery and a DOTA Group at the Core
Department of Chemistry and Biochemistry, Texas Christian University, Fort Worth, TX 76129, USA
Molecules 2016, 21(3), 335; https://doi.org/10.3390/molecules21030335 - 10 Mar 2016
Cited by 5
Abstract
A readily and rapidly accessible triazine dendrimer was manipulated in four steps with 23% overall yield to give a construct displaying four maleimide groups and DOTA. The maleimide groups of the dendrimer are sensitive to hydrolysis under basic conditions. The addition of up [...] Read more.
A readily and rapidly accessible triazine dendrimer was manipulated in four steps with 23% overall yield to give a construct displaying four maleimide groups and DOTA. The maleimide groups of the dendrimer are sensitive to hydrolysis under basic conditions. The addition of up to four molecules of water can be observed via mass spectrometry and HPLC. The evolution in the alkene region of the 1H-NMR—the transformation of the maleimide singlet to the appearance of two doublets—is consistent with imide hydrolysis and not the Michael addition. The hydrolysis events that proceeded over hours are sufficiently slower than the desired thiol addition reactions that occur in minutes. The addition of thiols to maleimides can be accomplished in a variety of solvents. The thiols examined derived from cysteine and include the protected amino acid, a protected dipeptide, and native oligopeptides containing either 9 or 18 amino acids. The addition reactions were monitored with HPLC and mass spectrometry in most cases. Complete substitution was observed for small molecule reactants. The model peptides containing nine or eighteen amino acids provided a mixture of products averaging between 3 and 4 substitutions/dendrimer. The functionalization of the chelate group with gadolinium was also accomplished easily. Full article
(This article belongs to the Special Issue Functional Dendrimers)
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Open AccessArticle
Comparison of Properties among Dendritic and Hyperbranched Poly(ether ether ketone)s and Linear Poly(ether ketone)s
Department Biomolecular Functional Engineering, Ibaraki University, 4-12-1, Nakanarusawa, Hitachi, Ibaraki 316-8511, Japan
Molecules 2016, 21(2), 219; https://doi.org/10.3390/molecules21020219 - 16 Feb 2016
Cited by 8
Abstract
Poly(ether ether ketone) dendrimers and hyperbranched polymers were prepared from 3,5-dimethoxy-4′-(4-fluorobenzoyl)diphenyl ether and 3,5-dihydroxy-4′-(4-fluorobenzoyl)diphenyl ether through aromatic nucleophilic substitution reactions. 1-(tert-Butyldimethylsiloxy)-3,5-bis(4-fluorobenzoyl)benzene was polycondensed with bisphenols, followed by cleavage of the protective group to form linear poly(ether ketone)s having the same hydroxyl [...] Read more.
Poly(ether ether ketone) dendrimers and hyperbranched polymers were prepared from 3,5-dimethoxy-4′-(4-fluorobenzoyl)diphenyl ether and 3,5-dihydroxy-4′-(4-fluorobenzoyl)diphenyl ether through aromatic nucleophilic substitution reactions. 1-(tert-Butyldimethylsiloxy)-3,5-bis(4-fluorobenzoyl)benzene was polycondensed with bisphenols, followed by cleavage of the protective group to form linear poly(ether ketone)s having the same hydroxyl groups in the side chains as the chain ends of the dendrimer and hyperbranched polymers. Their properties, such as solubilities, reduced viscosities, and thermal properties, were compared with one another. Similar comparisons were also carried out among the corresponding methoxy group polymers, and the size of the molecules was shown to affect the properties. Full article
(This article belongs to the Special Issue Functional Dendrimers)
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