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Dendrimers in Nanomedical Applications: Update and Future Directions

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A special issue of Pharmaceutics (ISSN 1999-4923).

Deadline for manuscript submissions: closed (30 October 2018) | Viewed by 61967

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Special Issue Editors

Prof. Dr. Xiangyang Shi

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Guest Editor

State Key Laboratory for Modification of Chemical Fibers and Polymer Materials, College of Chemistry, Chemical Engineering and Biotechnology, Donghua University, Shanghai, China
Interests: dendrimers; gold nanoparticles; magnetic nanoparticles; imaging; drug delivery; gene delivery; theranostics; tumors
Special Issues, Collections and Topics in MDPI journals

Prof. Jean-Pierre Majoral

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Laboratoire de Chimie de Coordination, Centre National de la Recherche Scientifique, Toulouse, France
Interests: dendrimers; nanomedicine; drug delivery; hybrid organic inorganic materials; diagnosis; nanotechnology

Prof. Dr. Serge Mignani

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Guest Editor

1. Laboratoire de Chimie et de Biochimie Pharmacologiques et Toxicologique, Université Paris Descartes, PRES Sorbonne Paris Cité, CNRS UMR 860, 45, rue des Saints Peres, 75006 Paris, France
2. CQM-Centro de Química da Madeira, MMRG, Universidade da Madeira, Campus da Penteada, 9020-105 Funchal, Portugal
Interests: medicinal chemistry; drug discovery; drug development; nanotechnology, drug delivery
Special Issues, Collections and Topics in MDPI journals

Special Issue Information

Dear Colleagues,

Advances in nanoscience and nanotechnology enable the development of nanomedicine that can improve our quality of life. Dendrimers intended for medical use have been widely used as nano-carriers in biological and medical applications, particularly the diagnosis or therapeutics in the oncology domain. Current research on functionalized dendrimer-based theranostics has been growing owing to the nanometer-scale dimensions and unique physiochemical properties of dendrimers. Dendrimers are ideal carrier systems that can incorporate various imaging elements, therapeutic drugs or specific genes to address the medical needs and application potentials. Functionalized dendrimers can be used to build up various nanoplatforms for multimodal diagnostics (optical, magnetic, thermal, radionuclide imaging, etc.) and combined therapeutics (e.g., chemotherapy, photothermal therapy, radiotherapy, gene delivery, etc.) in a simultaneous, comprehensive and effective manner.

This Special Issue will address advanced design and new developments in the area of dendrimer-based nanomaterials, including their production, synthesis, surface modification, characterization, and potential applications and future prospects as nanomedicine.

Original research papers or review articles on any of these aspects are welcomed for this Special Issue of Pharmaceutics on “Dendrimers in Nanomedical Applications: Update and Future Directions”.

Prof. Xiangyang Shi
Prof. Jean-Pierre Majoral
Prof. Serge Mignani
Guest Editors

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Keywords

dendrimers
diagnosis
therapy
drug delivery
gene delivery
targeted delivery
theranostics
combination therapy
nanomaterials
tumor treatment

Published Papers (13 papers)

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Research

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14 pages, 8955 KiB

Open AccessArticle

Chlorambucil Conjugated Ugi Dendrimers with PAMAM-NH₂ Core and Evaluation of Their Anticancer Activity

by Nalin Seixas, Bruno B. Ravanello, Ibrahim Morgan, Goran N. Kaluđerović and Ludger A. Wessjohann

Pharmaceutics 2019, 11(2), 59; https://doi.org/10.3390/pharmaceutics11020059 - 01 Feb 2019

Cited by 12 | Viewed by 4283

Abstract

Herein, a new Ugi multicomponent reaction strategy is described to enhance activity and solubility of the chemotherapeutic drug chlorambucil through its conjugation to poly(amidoamine) (PAMAM-NH₂) dendrimers with the simultaneous introduction of lipidic (i-Pr) and cationic (–NH₂) or anionic (–COOH) groups. Standard viability assays were used to evaluate the anticancer potential of the water-soluble dendrimers against PC-3 prostate and HT-29 colon cancer cell lines, as well as non-cancerous mouse NIH3T3 fibroblasts. It could be demonstrated that the anticancer activity against PC-3 cells was considerably improved when both chlorambucil and –NH₂ (cationic) groups were present on the dendrimer surface (1b). Additionally, this dendrimer showed activity only against the prostate cancer cells (PC-3), while it did not affect colon cancer cells and fibroblasts significantly. The cationic chlorambucil-dendrimer 1b blocks PC-3 cells in the G2/M phase and induces caspase independent apoptosis. Full article

(This article belongs to the Special Issue Dendrimers in Nanomedical Applications: Update and Future Directions)

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15 pages, 2689 KiB

Open AccessArticle

Complexes of Pro-Apoptotic siRNAs and Carbosilane Dendrimers: Formation and Effect on Cancer Cells

by Olga A. Krasheninina, Evgeny K. Apartsin, Elena Fuentes, Aleksandra Szulc, Maksim Ionov, Alya G. Venyaminova, Dzmitry Shcharbin, F. Javier De la Mata, Maria Bryszewska and Rafael Gόmez

Pharmaceutics 2019, 11(1), 25; https://doi.org/10.3390/pharmaceutics11010025 - 10 Jan 2019

Cited by 24 | Viewed by 3596

Abstract

This paper examines the complexation of anti-cancer small interfering RNAs (siRNAs) by cationic carbosilane dendrimers, and the interaction of the formed complexes with HeLa and HL-60 cancer cells. Stepwise formation of the complexes accompanied by the evolution of their properties has been observed through the increase of the charge ratio (dendrimer/siRNA). The complexes decrease the viability of both “easy-to-transfect” cells (HeLa) and “hard-to transfect” ones (HL-60), indicating a high potential of the cationic carbosilane dendrimers for siRNA delivery into tumor cells. Full article

(This article belongs to the Special Issue Dendrimers in Nanomedical Applications: Update and Future Directions)

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9 pages, 3132 KiB

Open AccessArticle

Importance of Binding Affinity for the Activity of a Metallodendritic Chemical Nuclease

by Yi-Hsuan Tang, Sodio C. N. Hsu, Po-Yu Chen, Si-ting Liou, Hui-Ting Chen, Carol Hsin-Yi Wu and Chai-Lin Kao

Pharmaceutics 2018, 10(4), 258; https://doi.org/10.3390/pharmaceutics10040258 - 03 Dec 2018

Viewed by 2724

Abstract

A family of bis(2-pyridyl)amino-modified poly(amidoamine) dendrimer Cu complexes was prepared, and their chemical nuclease activities and binding affinity (K_b) levels for DNA plasmid were investigated. The K_b values of the G2 to G6 apodendrimers for DNA plasmid were found to be 7.4, 23, 48, 70, and 280 µM⁻¹, respectively, using ethidium bromide (EtBr) displacement experiments. The chemical nuclease activities of the corresponding complexes were determined by gel electrophoresis, and a clear positive dendritic effect was observed. Further analysis indicated a linear correlation between the K_b values of the G2 to G5 apodendrimers and the nuclease activity of the corresponding complexes. This observation indicated the importance of substrate binding affinity for macromolecular nuclease activity. In addition, an experiment using 3′-(p-hydroxyphenyl) fluorescein suggested that hydroxyl radicals formed under the tested conditions. Subsequently performed inhibition studies indicated that the hydroxyl radical was the active species responsible for the plasmid cleavage. Full article

(This article belongs to the Special Issue Dendrimers in Nanomedical Applications: Update and Future Directions)

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10 pages, 2223 KiB

Open AccessArticle

l-Cysteine and l-Serine Modified Dendrimer with Multiple Reduced Thiols as a Kidney-Targeting Reactive Oxygen Species Scavenger to Prevent Renal Ischemia/Reperfusion Injury

by Satoru Matsuura, Hidemasa Katsumi, Hiroe Suzuki, Natsuko Hirai, Rie Takashima, Masaki Morishita, Toshiyasu Sakane and Akira Yamamoto

Pharmaceutics 2018, 10(4), 251; https://doi.org/10.3390/pharmaceutics10040251 - 01 Dec 2018

Cited by 18 | Viewed by 3756

Abstract

l-cysteine (Cys)- and l-serine (Ser)-modified, third-generation polyamidoamine (PAMAM) dendrimer with multiple reduced thiols (Ser-PAMAM-Cys) was synthesized as a kidney-targeting reactive oxygen species (ROS) scavenger to help prevent renal ischemia/reperfusion injury. Ser-PAMAM-Cys effectively scavenged 2,2-diphenyl-1-picrylhydrazyl (DPPH) radical and ROS (hydrogen peroxide and hydroxyl radical) in phosphate-buffered saline (PBS). In addition, ~64% of ¹¹¹In-labeled Ser-PAMAM-Cys accumulated in mouse kidney 3 h after intravenous administration. An in vivo imaging system (IVIS) study indicated that near-infrared fluorescence dye (NIR)-labeled Ser-PAMAM-Cys specifically accumulated in the kidney. In a mouse renal ischemia/reperfusion injury model, increases in the kidney damage markers creatinine (Cre) and blood urea nitrogen (BUN) were significantly inhibited by intravenous Ser-PAMAM-Cys administration. In contrast, Cys injection had no statistically significant effect of preventing Cre or BUN elevation relative to the control. Ser-PAMAM-Cys also effectively downregulated the inflammatory factors NGAL, IL-18, ICAM-1, and VCAM-1 in the renal ischemia/reperfusion injury model. These results indicate that Ser-PAMAM-Cys is a promising kidney-targeting ROS scavenger which could prevent ischemia/reperfusion-induced renal failure. Full article

(This article belongs to the Special Issue Dendrimers in Nanomedical Applications: Update and Future Directions)

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13 pages, 3102 KiB

Open AccessArticle

Doxorubicin-Conjugated PAMAM Dendrimers for pH-Responsive Drug Release and Folic Acid-Targeted Cancer Therapy

by Mengen Zhang, Jingyi Zhu, Yun Zheng, Rui Guo, Shige Wang, Serge Mignani, Anne-Marie Caminade, Jean-Pierre Majoral and Xiangyang Shi

Pharmaceutics 2018, 10(3), 162; https://doi.org/10.3390/pharmaceutics10030162 - 19 Sep 2018

Cited by 73 | Viewed by 7261

Abstract

We present here the development of multifunctional doxorubicin (DOX)-conjugated poly(amidoamine) (PAMAM) dendrimers as a unique platform for pH-responsive drug release and targeted chemotherapy of cancer cells. In this work, we covalently conjugated DOX onto the periphery of partially acetylated and folic acid (FA)-modified generation 5 (G5) PAMAM dendrimers through a pH-sensitive cis-aconityl linkage to form the G5.NHAc-FA-DOX conjugates. The formed dendrimer conjugates were well characterized using different methods. We show that DOX release from the G5.NHAc-FA-DOX conjugates follows an acid-triggered manner with a higher release rate under an acidic pH condition (pH = 5 or 6, close to the acidic pH of tumor microenvironment) than under a physiological pH condition. Both in vitro cytotoxicity evaluation and cell morphological observation demonstrate that the therapeutic activity of dendrimer-DOX conjugates against cancer cells is absolutely related to the DOX drug released. More importantly, the FA conjugation onto the dendrimers allowed a specific targeting to cancer cells overexpressing FA receptors (FAR), and allowed targeted inhibition of cancer cells. The developed G5.NHAc-FA-DOX conjugates may be used as a promising nanodevice for targeted cancer chemotherapy. Full article

(This article belongs to the Special Issue Dendrimers in Nanomedical Applications: Update and Future Directions)

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10 pages, 2611 KiB

Open AccessArticle

Lysine Dendrigraft Nanocontainers. Influence of Topology on Their Size and Internal Structure

by Boris Okrugin, Maxim Ilyash, Denis Markelov and Igor Neelov

Pharmaceutics 2018, 10(3), 129; https://doi.org/10.3390/pharmaceutics10030129 - 13 Aug 2018

Cited by 15 | Viewed by 2819

Abstract

Poly-l-ysine dendrigrafts are promising systems for biomedical applications due to their biodegradability, biocompatibility, and similarity to dendrimers. There are many papers about the use of dendrigrafts as nanocontainers for drug delivery. At the same time, the number of studies about their physical properties is limited, and computer simulations of dendrigrafts are almost absent. This paper presents the results of a systematic molecular dynamics simulation study of third-generation lysine dendrigrafts with different topologies. The size and internal structures of the dendrigrafts were calculated. We discovered that the size of dendrigrafts of the same molecular weight depends on their topology. The shape of all studied dendrigrafts is close to spherical. Density profile of dendrigrafts depends on their topology. Full article

(This article belongs to the Special Issue Dendrimers in Nanomedical Applications: Update and Future Directions)

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13 pages, 2204 KiB

Open AccessArticle

Hydrogels of Polycationic Acetohydrazone-Modified Phosphorus Dendrimers for Biomedical Applications: Gelation Studies and Nucleic Acid Loading

by Evgeny K. Apartsin, Alina E. Grigoryeva, Audrey Malrin-Fournol, Elena I. Ryabchikova, Alya G. Venyaminova, Serge Mignani, Anne-Marie Caminade and Jean-Pierre Majoral

Pharmaceutics 2018, 10(3), 120; https://doi.org/10.3390/pharmaceutics10030120 - 06 Aug 2018

Cited by 8 | Viewed by 3185

Abstract

In this work, we report the assemblage of hydrogels from phosphorus dendrimers in the presence of biocompatible additives and the study of their interactions with nucleic acids. As precursors for hydrogels, phosphorus dendrimers of generations 1–3 based on the cyclotriphosphazene core and bearing ammonium or pyridinium acetohydrazones (Girard reagents) on the periphery have been synthesized. The gelation was done by the incubation of dendrimer solutions in water or phosphate-buffered saline in the presence of biocompatible additives (glucose, glycine or polyethylene glycol) to form physical gels. Physical properties of gels have been shown to depend on the gelation conditions. Transmission electron microscopy revealed structural units and well-developed network structures of the hydrogels. The hydrogels were shown to bind nucleic acids efficiently. In summary, hydrogels of phosphorus dendrimers represent a useful tool for biomedical applications. Full article

(This article belongs to the Special Issue Dendrimers in Nanomedical Applications: Update and Future Directions)

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9 pages, 2722 KiB

Open AccessArticle

Cellular Uptake Behaviors of Rigidity-Tunable Dendrimers

by Hui Liu, Jingjing Wang, Wenchao Li, Jie Hu, Min Wang and Yuejun Kang

Pharmaceutics 2018, 10(3), 99; https://doi.org/10.3390/pharmaceutics10030099 - 19 Jul 2018

Cited by 4 | Viewed by 3657

Abstract

Understanding of the interaction between cells and nanoparticles (NPs) is critical. Despite numerous attempts to understand the effect of several parameters of NPs on their cellular uptake behaviors, such as size, shape, surface chemistry, etc., limited information is available regarding NP rigidity. Herein, we investigate the effect of rigidity on cellular uptake behaviors of NPs, using generation 5 poly(amidoamine) dendrimer as a model. By harnessing the abundant inner cavity, their rigidity could be effectively regulated by forming size-tunable gold NPs. The NPs thus formed were well characterized and displayed similar hydrodynamic size, surface potential, fluorescence intensity, and distinct rigidity (owing to differences in the size of the Au core). Flow cytometry analysis revealed a positive correlation between NP rigidity and cellular uptake of NPs. Confocal microscopic evaluation revealed that the entrapped gold NPs may affect the intracellular localization of the internalized dendrimers. The present findings can potentially guide the preparation of suitable NPs for biomedical applications. Full article

(This article belongs to the Special Issue Dendrimers in Nanomedical Applications: Update and Future Directions)

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12 pages, 11443 KiB

Open AccessArticle

Loading IR820 Using Multifunctional Dendrimers with Enhanced Stability and Specificity

by Hui Liu and Jingjing Wang

Pharmaceutics 2018, 10(3), 77; https://doi.org/10.3390/pharmaceutics10030077 - 28 Jun 2018

Cited by 9 | Viewed by 3558

Abstract

Cyanine dyes are promising candidates in biomedical applications. Although various delivery systems have been developed to enhance their properties, their dendrimer-based delivery systems are seldom investigated. Herein, amine-terminated generation 5 poly(amidoamine) (G5.NH₂) dendrimers and new indocyanine green (IR820) dyes were chosen as models to study the loading ability of dendrimers for cyanine dynes. G5.NH₂ dendrimers were pre-modified with arginine-glycine-aspartic (RGD) peptides, poly(ethylene glycol) chains, and acetyl groups to be endowed with cancer cell specificity and biocompatibility. The formed Ac-PR dendrimers were used to load IR820, followed by thorough characterization. The loaded number of IR820 was estimated to be 6.7 per dendrimer. The stability of IR820 was improved through dendrimer loading, which was proved by their UV-vis spectra under different kinds of storage conditions. In addition, the formed Ac-PR dendrimers can retain the loaded IR820 effectively. Their cytocompatibility was desirable under the studied conditions. Their cellular uptake behaviors were demonstrated to be enhanced by RGD modification, showing concentration-, co-incubation time-, and α_vβ₃ integrin receptor-dependent properties, displaying a cytoplasm-location. The findings from this work demonstrated the versatile loading and delivery capacity of dendrimers for near-infrared (NIR) dyes, providing fundamental data for the development of dendrimer/NIR dye systems for biomedical applications, especially for cancer theranostic applications. Full article

(This article belongs to the Special Issue Dendrimers in Nanomedical Applications: Update and Future Directions)

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Review

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27 pages, 1919 KiB

Open AccessReview

Targeting Groups Employed in Selective Dendrons and Dendrimers

by Rodrigo Vieira Gonzaga, Soraya Da Silva Santos, Joao Vitor Da Silva, Diego Campos Prieto, Debora Feliciano Savino, Jeanine Giarolla and Elizabeth Igne Ferreira

Pharmaceutics 2018, 10(4), 219; https://doi.org/10.3390/pharmaceutics10040219 - 08 Nov 2018

Cited by 12 | Viewed by 3873

Abstract

The design of compounds with directed action to a defined organ or tissue is a very promising approach, since it can decrease considerably the toxicity of the drug/bioactive compound. For this reason, this kind of strategy has been greatly important in the scientific community. Dendrimers, on the other hand, comprise extremely organized macromolecules with many peripheral functionalities, stepwise controlled synthesis, and defined size. These nanocomposites present several biological applications, demonstrating their efficiency to act in the pharmaceutical field. Considering that, the main purpose of this review was describing the potential of dendrons and dendrimers as drug targeting, applying different targeting groups. This application has been demonstrated through interesting examples from the literature considering the last ten years of publications. Full article

(This article belongs to the Special Issue Dendrimers in Nanomedical Applications: Update and Future Directions)

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17 pages, 17442 KiB

Open AccessReview

The Delivery Challenge in Neurodegenerative Disorders: The Nanoparticles Role in Alzheimer’s Disease Therapeutics and Diagnostics

by Cristina De la Torre and Valentín Ceña

Pharmaceutics 2018, 10(4), 190; https://doi.org/10.3390/pharmaceutics10040190 - 17 Oct 2018

Cited by 28 | Viewed by 5105

Abstract

Alzheimer’s disease (AD) is one of the main causes of disability and dependency among elderly people. AD is a neurodegenerative disorder characterized by a progressive and irreversible cognitive impairment, whose etiology is unclear because of the complex molecular mechanisms involved in its pathophysiology. A global view of the AD pathophysiology is described in order to understand the need for an effective treatment and why nanoparticles (NPs) could be an important weapon against neurodegenerative diseases by solving the general problem of poor delivery into the central nervous system (CNS) for many drugs. Drug delivery into the CNS is one of the most challenging objectives in pharmaceutical design, due to the limited access to the CNS imposed by the blood-brain barrier (BBB). The purpose of this review is to present a comprehensive overview of the use of NPs as delivery systems for therapeutic and diagnostic purposes in models of AD. Full article

(This article belongs to the Special Issue Dendrimers in Nanomedical Applications: Update and Future Directions)

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25 pages, 1272 KiB

Open AccessReview

Dendrimers Show Promise for siRNA and microRNA Therapeutics

by Volha Dzmitruk, Evgeny Apartsin, Aliaksei Ihnatsyeu-Kachan, Viktar Abashkin, Dzmitry Shcharbin and Maria Bryszewska

Pharmaceutics 2018, 10(3), 126; https://doi.org/10.3390/pharmaceutics10030126 - 08 Aug 2018

Cited by 76 | Viewed by 5442

Abstract

The lack of an appropriate intracellular delivery system for therapeutic nucleic acids (TNAs) is a major problem in molecular biology, biotechnology, and medicine. A relatively new class of highly symmetrical hyperbranched polymers, called dendrimers, shows promise for transporting small TNAs into both cells and target tissues. Dendrimers have intrinsic advantages for this purpose: their physico-chemical and biological properties can be controlled during synthesis, and they are able to transport large numbers of TNA molecules that can specifically suppress the expression of single or multiple targeted genes. Numerous chemical modifications of dendrimers extend the biocompatibility of synthetic materials and allow targeted vectors to be designed for particular therapeutic purposes. This review summarizes the latest experimental data and trends in the medical application of various types of dendrimers and dendrimer-based nanoconstructions as delivery systems for short small interfering RNAs (siRNAs) and microRNAs at the cell and organism levels. It provides an overview of the structural features of dendrimers, indicating their advantages over other types of TNA transporters. Full article

(This article belongs to the Special Issue Dendrimers in Nanomedical Applications: Update and Future Directions)

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10 pages, 1449 KiB

Open AccessReview

New Ways to Treat Tuberculosis Using Dendrimers as Nanocarriers

by Serge Mignani, Rama Pati Tripathi, Liang Chen, Anne-Marie Caminade, Xiangyang Shi and Jean-Pierre Majoral

Pharmaceutics 2018, 10(3), 105; https://doi.org/10.3390/pharmaceutics10030105 - 26 Jul 2018

Cited by 27 | Viewed by 11494

Abstract

Tuberculosis (TB) is a contagious infection that usually attacks not only the lungs, but also brain and spine. More than twenty drugs have been developed for the treatment of TB, but most of them were developed some years ago. They are used in different combinations. Isoniazid and Rifampicin are examples of the five first line TB drugs, whereas, for instance, Levofloxacin, Kanamycin and Linezolid belong to the second line drugs that are used for the treatment of drug resistant TB. Several new bicyclic nitroimidazoles (e.g., Delamanid) without mutagenic effects were developed. New TB drugs need to provide several main issues such as more effective, less toxic, and less expensive for drug resistant TB. Besides polymeric, metal-based nanoparticles, polymeric micelles and polymers, dendrimer nanostructures represent ideal delivery vehicles and offer high hopes for the future of nanomedicine. In this original review, we present and analyze the development of anti-TB drugs in combination with dendrimers. Few articles have highlighted the encapsulation of anti-TB drugs with dendrimers. Due to their unique structure, dendrimers represent attractive candidates for the encapsulation and conjugation of other anti-TB drugs presenting important drawbacks (e.g., solubility, toxicity, low bioavailability) that hinder their development, including clinic trials. Full article

(This article belongs to the Special Issue Dendrimers in Nanomedical Applications: Update and Future Directions)

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