Dendrimers: synthesis, applications, and properties
© Abbasi et al.; licensee Springer. 2014
Received: 3 March 2014
Accepted: 3 May 2014
Published: 21 May 2014
Dendrimers are nano-sized, radially symmetric molecules with well-defined, homogeneous, and monodisperse structure that has a typically symmetric core, an inner shell, and an outer shell. Their three traditional macromolecular architectural classes are broadly recognized to generate rather polydisperse products of different molecular weights. A variety of dendrimers exist, and each has biological properties such as polyvalency, self-assembling, electrostatic interactions, chemical stability, low cytotoxicity, and solubility. These varied characteristics make dendrimers a good choice in the medical field, and this review covers their diverse applications.
KeywordsDendrimer Pseudorotaxane Nanoscale PAMAM
Structure and chemistry
Dendrimers are just in between molecular chemistry and polymer chemistry. They relate to the molecular chemistry world by virtue of their step-by-step controlled synthesis, and they relate to the polymer world because of their repetitive structure made of monomers [32–35]. The three traditional macromolecular architectural classes (i.e., linear, cross-linked, and branched) are broadly recognized to generate rather polydisperse products of different molecular weights. In contrast, the synthesis of dendrimers offers the chance to generate monodisperse, structure-controlled macromolecular architectures similar to those observed in biological systems [36, 37]. Dendrimers are generally prepared using either a divergent method or a convergent one . In the different methods, dendrimer grows outward from a multifunctional core molecule. The core molecule reacts with monomer molecules containing one reactive and two dormant groups, giving the first-generation dendrimer. Then, the new periphery of the molecule is activated for reactions with more monomers.
Cascade reactions are the foundation of dendrimer synthesis
The synthesis of dendrimers follows either a divergent or convergent approach
Properties of dendrimers
When comparing dendrimers with other nanoscale synthetic structures (e.g., traditional polymers, buck balls, or carbon nanotubes), these are either highly non-defined or have limited structural diversity.
Pharmacokinetic properties are one of the most significant aspects that need to be considered for the successful biomedical application of dendrimers, for instance, drug delivery, imaging, photodynamic therapy, and neutron capture therapy. The diversity of potential applications of dendrimers in medicine results in increasing interest in this area. For example, there are several modifications of dendrimers' peripheral groups which enable to obtain antibody-dendrimer, peptide-dendrimer conjugates or dendritic boxes that encapsulate guest molecules .
Covalent conjugation strategies
Polyvalency is useful as it provides for versatile functionalization; it is also extremely important to produce multiple interactions with biological receptor sites, for example, in the design of antiviral therapeutic agents.
Molecular recognition events at dendrimer surfaces are distinguished by the large number of often identical end-groups presented by the dendritic host. When these groups are charged, the surface may have as a polyelectrolyte and is likely to electrostatically attract oppositely charged molecules . One example of electrostatic interactions between polyelectrolyte dendrimers and charged species include the aggregation of methylene blue on the dendrimer surface and the binding of EPR probes such as copper complexes and nitroxide cation radicals [54, 55].
Today, dendrimers have several medicinal and practical applications.
Dendrimers in biomedical field
Dendritic polymers have advantage in biomedical applications. These dendritic polymers are analogous to protein, enzymes, and viruses, and are easily functionalized. Dendrimers and other molecules can either be attached to the periphery or can be encapsulated in their interior voids . Modern medicine uses a variety of this material as potential blood substitutes, e.g., polyamidoamine dendrimers .
Perhaps the most promising potential of dendrimers is in their possibility to perform controlled and specified drug delivery, which regards the topic of nanomedicine. One of the most fundamental problems that are set toward modern medicine is to improve pharmacokinetic properties of drugs for cancer . Drugs conjugated with polymers are characterized by lengthened half-life, higher stability, water solubility, decreased immunogenicity, and antigenicity . Unique pathophysiological traits of tumors such as extensive angiogenesis resulting in hypervascularization, the increased permeability of tumor vasculature, and limited lymphatic drainage enable passive targeting, and as a result, selective accumulation of macromolecules in tumor tissue. This phenomenon is known as ‘enhanced permeation and retention’ (EPR) [58, 60]. The drug-dendrimer conjugates show high solubility, reduced systemic toxicity, and selective accumulation in solid tumors. Different strategies have been proposed to enclose within the dendrimer structure drug molecules, genetic materials, targeting agents, and dyes either by encapsulation, complexation, or conjugation.
Dendrimers in drug delivery
In 1982, Maciejewski proposed, for the first time, the utilization of these highly branched molecules as molecular containers . Host-guest properties of dendritic polymers are currently under scientific investigation and have gained crucial position in the field of supramolecular chemistry. Host-guest chemistry is based on the reaction of binding of a substrate molecule (guest) to a receptor molecule (host) .
Transdermal drug delivery
Clinical use of NSAIDs is limited due to adverse reactions such as GI side effects and renal side effects when given orally. Transdermal drug delivery overcomes these bad effects and also maintains therapeutic blood level for longer period of time. Transdermal delivery suffers poor rates of transcutaneous delivery due to barrier function of the skin. Dendrimers have found applications in transdermal drug delivery systems. Generally, in bioactive drugs having hydrophobic moieties in their structure and low water solubility, dendrimers are a good choice in the field of efficient delivery system .
The primary promise that the combination of understanding molecular pathways of disease and the complete human genome sequence would yield safer and more efficient medicines and revolutionize the way we treat patients has not been fulfilled to date. However, there is little doubt that genetic therapies will make a significant contribution to our therapeutic armamentarium once some of the key challenges, such as specific and efficient delivery, have been solved . The ability to deliver pieces of DNA to the required parts of a cell includes many challenges. Current research is being performed to find ways to use dendrimers to traffic genes into cells without damaging or deactivating the DNA. To maintain the activity of DNA during dehydration, the dendrimer/DNA complexes were encapsulated in a water soluble polymer and then deposited on or sandwiched in functional polymer films with a fast degradation rate to mediate gene transfection. Based on this method, PAMAM dendrimer/DNA complexes were used to encapsulate functional biodegradable polymer films for substrate-mediated gene delivery. Research has shown that the fast-degrading functional polymer has great potential for localized transfection [65–67].
Dendrimers as magnetic resonance imaging contrast agents
Dendrimer-based metal chelates act as magnetic resonance imaging contrast agents. Dendrimers are extremely appropriate and used as image contrast media because of their properties .
Dendrimers used for enhancing solubility
PAMAM dendrimers are expected to have potential applications in enhancing solubility for drug delivery systems. Dendrimers have hydrophilic exteriors and interiors, which are responsible for its unimolecular micelle nature. Dendrimer-based carriers offer the opportunity to enhance the oral bioavailability of problematic drugs. Thus, dendrimer nano carriers offer the potential to enhance the bioavailability of drugs that are poorly soluble and/or substrates for efflux transporters [70, 71].
Photodynamic therapy (PDT) relies on the activation of a photosensitizing agent with visible or near-infrared (NIR) light. Upon excitation, a highly energetic state is formed which, upon reaction with oxygen, affords a highly reactive singlet oxygen capable of inducing necrosis and apoptosis in tumor cells. Dendritic delivery of PDT agents has been investigated within the last few years in order to improve upon tumor selectivity, retention, and pharmacokinetics [72–75].
Miscellaneous dendrimer applications
Clearly, there are many other areas of biological chemistry where application of dendrimer systems may be helpful. Cellular delivery using carrier dendritic polymers is used in the purification of water dendrimer-based product in cosmetics contaminated by toxic metal ion and inorganic solute, and dendrimer-based commercial products organic solutes . Furthermore, highly sensitive analytical devices [77, 78], MRI contrast agents , prion research , burn treatment , and EPR imaging with spin-labeled dendrimers [82–106] are some of the diverse areas of fascinating ongoing dendrimer research that are beyond the scope of this article.
Dendrimers are characterized by individual features that make them hopeful candidates for a lot of applications. Dendrimers are highly defined artificial macromolecules, which are characterized by a combination of a high number of functional groups and a compact molecular structure. A rapid increase of importance in the chemistry of dendrimers has been observed since the first dendrimers were prepared. Work was established to determine the methods of preparing and investigating the properties of the novel class of macro and micromolecules. In spite of the two decades since the finding of dendrimers, the multi-step synthesis still requires great effort.
The authors thank the Department of Medical Nanotechnology, Faculty of Advanced Medical Sciences of Tabriz University of Medical Sciences for all the support provided. This work is funded by Grant 2011-0014246 of the National Research Foundation of Korea.
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