An emerging class of amphiphilic dendrimers for pharmaceutical and biomedical applications: Janus amphiphilic dendrimers

Sikwal, Dhiraj R.; Kalhapure, Rahul S.; Govender, Thirumala

doi:10.1016/j.ejps.2016.11.013

Cited by 68 publications

(65 citation statements)

References 72 publications

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“…1 CuSO 4 ·5H 2 O (0.763 g, 3.05 mmol, 3.3 equiv) was dissolved in 20 ml of distilled water, and was then injected into the above THF solution.…”

Section: Synthesis Ofmentioning

confidence: 99%

“…1 CuSO 4 ·5H 2 O (3.05 g, 12.2 mmol, 3.3 equiv) dissolved in 20 ml distilled water was added into the obtained reaction mixture, followed by the dropwise injection of a freshly prepared sodium ascorbate (4.84 g, 24.4 mmol, 6.6 equiv) aqueous solution (30 ml) to obtain a THF/water in a ratio of 1:1 (v/v).…”

Section: Synthesis Ofmentioning

confidence: 99%

“…1 2.5 | Synthesis of JD 9 by using 5 and 8 The obtained mixture was stirred at 80°C overnight, poured into 1 M HCl (40 ml) below 5°C, and then extracted with CH 2 Cl 2 (3 × 50 ml).…”

Section: Synthesis Ofmentioning

confidence: 99%

“…1 The obtained mixture was stirred at r. t. under N 2 atmosphere for 12 hr, and then concentrated under reduced pressure to give the crude acyl chloride of 8 that was used in the next step without further purification.…”

Section: Synthesis Of 10mentioning

confidence: 99%

“…[1][2][3] and are attracting wide attention owing to their combination of properties of the constituting blocks in a unique way. [1][2][3] and are attracting wide attention owing to their combination of properties of the constituting blocks in a unique way.…”

Section: Introductionmentioning

confidence: 99%

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Ferrocenyl amphiphilic Janus dendrimers as redox‐responsive micellar carriers

Ling

et al. 2019

Applied Organom Chemis

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Amphiphilic Janus dendrimers have attracted increasing attention due to their asymmetric structures and various functional properties compared to the conventional symmetric macromolecules. Herein, a novel ferrocenyl-terminated amphiphilic Janus dendrimer containing nine hydrophilic triethylene glycol branches was synthesized by two synthetic routes, namely the typical chemo selective coupling method and the mixed modular approach. Chemical redox triggers, namely Fe 2 (SO 4 ) 3 as oxidant and ascorbic acid as reductant, could regulate the self-assembly behavior of the Janus dendrimer in water through the redox-switching between ferrocene and ferricinium cations, and the change of micelles formed were investigated and confirmed through scanning electron microscopy and dynamic light scattering. The cargo-loading property of the micelles self-assembled by the Janus dendrimer was further proved by the successful fabrication of Rhodamine B (RhB)-loaded micelles, and the oxidation-triggered release behavior of the encapsulated RhB could be mediated by changing the concentration of oxidants. This work provides an effective approach to prepare ferrocenyl-terminated amphiphilic Janus dendrimers and the self-assembled micelles might be used as a promising molecular carrier in areas such as drug delivery and catalysis.

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“…1 CuSO 4 ·5H 2 O (0.763 g, 3.05 mmol, 3.3 equiv) was dissolved in 20 ml of distilled water, and was then injected into the above THF solution.…”

Section: Synthesis Ofmentioning

confidence: 99%

Section: Synthesis Ofmentioning

confidence: 99%

“…1 2.5 | Synthesis of JD 9 by using 5 and 8 The obtained mixture was stirred at 80°C overnight, poured into 1 M HCl (40 ml) below 5°C, and then extracted with CH 2 Cl 2 (3 × 50 ml).…”

Section: Synthesis Ofmentioning

confidence: 99%

Section: Synthesis Of 10mentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

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Ferrocenyl amphiphilic Janus dendrimers as redox‐responsive micellar carriers

Ling

et al. 2019

Applied Organom Chemis

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Multifunctional triazolylferrocenyl Janus dendron: Nanoparticle stabilizer, smart drug carrier and supramolecular nanoreactor

Zhao

Ling

Liu

et al. 2017

Applied Organom Chemis

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Owing to their unique broken symmetry, amphiphilic Janus dendrimers and dendons provide fascinating properties for material, biological, pharmaceutical and biomedical applications. The integration of various organometallic moieties into these macromolecules will further offer the opportunity to form complex and intelligent architectures and materials. Here, we report a novel, simple and multifunctional Janus dendron containing redox‐reversible hydrophobic ferrocene (Fc) unit, complexing‐effective 1,2,3‐triazole ligand and biocompatible hydrophilic triethylene glycol termini. Silver and gold nanoparticles were firstly successfully prepared by using the Janus dendron as the reducing agent of Au(III) and Ag(I), and the stabilizer of the corresponding nanoparticles. The redox response of the Fc moiety was then employed to trigger the release of model drug, rhodamine B, encapsulated in supramolecular micelles formed by the self‐assembly of the Janus dendron. Finally, the precise and excellent metal‐complexing ability of the triazole group in this dendron was fully utilized to stabilize a water‐soluble Cu(I) catalyst, forming supramolecular nanoreactors for the catalysis of the copper(I)‐catalyzed azide alkyne cycloaddition click reaction in only water. The multifunctional characteristics of this dendron highlight the potential for organometallic Janus dendrimers and dendrons in the fields of functional materials and nanomedicines.

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Structural and Surface Properties of Polyamidoamine (PAMAM) – Fatty Acid‐based Nanoaggregates Derived from Self‐assembling Janus Dendrimers

et al. 2020

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This study summarizes the synthesis, characterization, and evaluation of a library of biocompatible selfassembling Janus dendrimers (JDs) and their resulting nanostructures possessing either a cationic (NH 3 +), anionic (COO À), or neutral (OH) surface. Strategically designed for applications in therapeutic delivery, the dendrimers are comprised of a polyamidoamine (PAMAM) dendron as the hydrophilic portion and fatty acid (FA) functionalized dendrons as the hydrophobic portion. The physicochemical characterization and in vitro cell viability of amphiphilic JDs were performed. Microscopy (TEM) and dynamic light scattering (DLS) analysis indicate the size (i. e., diameters) of spherical nanoaggregates ranging from 40 to 100 nm with zeta-potential values ranging from À 17.9 to + 58.7 mV with respect to the terminal functional group of the JD employed. Furthermore, these systems exhibited spherical nanoaggregates with critical aggregate concentrations (CAC) ranging from 2.8 to 7.0 mg/L. At low concentrations (< 200 μg/mL), JDs nanoaggregates showed minimal cell growth inhibitory properties in the in vitro testing, demonstrating their safety. The results of this study prove that a simple yet strategic combination of chemically distinctive dendritic segments can afford a versatile library of unique JDs nanoplatforms with excellent potential for biomedical applications.

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An emerging class of amphiphilic dendrimers for pharmaceutical and biomedical applications: Janus amphiphilic dendrimers

Cited by 68 publications

References 72 publications

Ferrocenyl amphiphilic Janus dendrimers as redox‐responsive micellar carriers

Ferrocenyl amphiphilic Janus dendrimers as redox‐responsive micellar carriers

Multifunctional triazolylferrocenyl Janus dendron: Nanoparticle stabilizer, smart drug carrier and supramolecular nanoreactor

Structural and Surface Properties of Polyamidoamine (PAMAM) – Fatty Acid‐based Nanoaggregates Derived from Self‐assembling Janus Dendrimers

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