Facile Synthesis of Amphiphilic Fluorescent Phosphorus Dendron-Based Micelles as Antiproliferative Agents: First Investigations

Qiu, Jieru; Chen, Liang; Zhan, Mengsi; Laurent, Régis; Bignon, Jérôme; Mignani, Serge; Shi, Xiangyang; Caminade, Anne‐Marie; Majoral, Jean‐Pierre

doi:10.1021/acs.bioconjchem.0c00716

Cited by 20 publications

(43 citation statements)

References 45 publications

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“…In the theranostic nanomedicine realm, the design and synthesis of first-in-class amphiphilic fluorescent phosphorus dendron-based micelles has been studied by the teams of Shi and Majoral [ 39 ]. As shown in Figure 7 , 12 amphiphilic phosphorus dendrons bearing 10 protonated cyclic amino groups (G1) or 20 protonated cyclic amino groups (G2) and one hydrophobic chain carrying one fluorophore moiety were prepared and screened through phenotypic screening.…”

Section: Polycationic Phosphorus Dendrimersmentioning

confidence: 99%

“… Self-assembly of D2G1.HCl amphiphilic dendrons to form nanostructured aggregates (micelles). Reproduced with permission from reference [ 39 ], American Chemical Society. …”

Section: Figurementioning

confidence: 99%

“…Interestingly, these fluorescent amphiphilic phosphorus dendron-based micelles exhibited the Previously, as markers of phosphorus dendrimers, several types of fluorophores have been used, such as pyrene, naphthol, anthracene, dansyl, diketone, phthalocyanine, maleimide, julolidine, rhodamine, fluorescein or fluorene derivatives [42,43]. Interestingly, these fluorescent amphiphilic phosphorus dendron-based micelles exhibited the capacity to aggregate in solution, mediated by hydrophilic/hydrophobic interactions, which promoted the formation of well-characterized polymeric micelles (Figure 8) [39].…”

Section: As Anti-cancer Agentsmentioning

confidence: 99%

“…Molecules 2021, 26, x FOR PEER REVIEW 9 of 15 capacity to aggregate in solution, mediated by hydrophilic/hydrophobic interactions, which promoted the formation of well-characterized polymeric micelles (Figure 8) [39]. Reproduced with permission from reference [39], American Chemical Society.…”

Section: As Anti-cancer Agentsmentioning

confidence: 99%

“…The main therapeutic domains developed by J.-P. Majoral and A.-M. Caminade are as follows: anti-inflammatory [ 27 , 28 ], anti-tuberculosis [ 29 ], against Alzheimer’s disease [ 30 ], antiprion [ 31 ] and anti-cancer [ 32 , 33 , 34 , 35 ]. The theragnostic realm in oncology [ 36 ] has also been developed using phosphorus dendrimers and dendrons [ 37 , 38 , 39 ].…”

Section: Introductionmentioning

confidence: 99%

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First-in-Class Phosphorus Dendritic Framework, a Wide Surface Functional Group Palette Bringing Noteworthy Anti-Cancer and Anti-Tuberculosis Activities: What Lessons to Learn?

et al. 2021

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Based on phenotypic screening, the major advantages of phosphorus dendrimers and dendrons as drugs allowed the discovery of new therapeutic applications, for instance, as anti-cancer and anti-tuberculosis agents. These biological activities depend on the nature of the chemical groups (neutral or cationic) on their surface as well as their generation. As lessons to learn, in the oncology domain, the increase in the generation of metallo-dendrimers is in the same direction as the anti-proliferative activities, in contrast to the development of polycationic dendrimers, where the most potent anti-tuberculosis phosphorus dendrimer was observed to have the lowest generation (G0). The examples presented in this original analysis of phosphorus dendrimers and dendrons provide support for the lessons learned and for the development of new nanoparticles in nanomedicine.

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Section: Polycationic Phosphorus Dendrimersmentioning

confidence: 99%

“… Self-assembly of D2G1.HCl amphiphilic dendrons to form nanostructured aggregates (micelles). Reproduced with permission from reference [ 39 ], American Chemical Society. …”

Section: Figurementioning

confidence: 99%

Section: As Anti-cancer Agentsmentioning

confidence: 99%

Section: As Anti-cancer Agentsmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

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First-in-Class Phosphorus Dendritic Framework, a Wide Surface Functional Group Palette Bringing Noteworthy Anti-Cancer and Anti-Tuberculosis Activities: What Lessons to Learn?

et al. 2021

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Phosphorous Dendron Micelles as a Nanomedicine Platform for Cooperative Tumor Chemoimmunotherapy via Synergistic Modulation of Immune Cells

et al. 2022

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Design of effective nanomedicines to modulate multiple immune cells to overcome the immune‐suppressive tumor microenvironment is desirable to improve the overall poor clinical outcomes of immunotherapy. Herein, a nanomedicine platform is reported based on chemotherapeutic drug doxorubicin (DOX)‐loaded phosphorus dendron micelles (M‐G1‐TBPNa@DOX, TBP, tyramine bearing two dimethylphosphonate) with inherent immunomodulatory activity for synergistic tumor chemoimmunotherapy. The M‐G1‐TBPNa@DOX micelles with good stability and a mean particle size of 86.4 nm can deliver DOX to solid tumors to induce significant tumor cell apoptosis and immunogenic cell death (ICD). With the demonstrated intrinsic activity of M‐G1‐TBPNa that can promote the proliferation of natural killer (NK) cells, the ICD‐resulted maturation of dendritic cells of the DOX‐loaded micelles, and the combination of anti‐PD‐L1 antibody, the synergistic modulation of multiple immune cells through NK cell proliferation, recruitment of tumor‐infiltrating NK cells and cytotoxic T cells, and decrease of regulatory T cells for effective tumor chemoimmunotherapy with strong antitumor immunity and immune memory effect for effective prevention of lung metastasis are demonstrated. The developed phosphorous dendron micelles may hold great promise to be used as an advanced nanomedicine formulation for synergistic modulation of multiple immune cells through NK cell proliferation for effective chemoimmunotherapy of different tumor types.

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Supramolecular Self‐Associations of Amphiphilic Dendrons and Their Properties

Apartsin

Caminade

2021

Chemistry A European J

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This review presents precisely defined amphiphilic dendrons, their self‐association properties, and their different uses. Dendrons, also named dendritic wedges, are composed of a core having two different types of functions, of which one type is used for growing or grafting branched arms, generally multiplied by 2 at each layer by using 1→2 branching motifs. A large diversity of structures has been already synthesized. In practically all cases, their synthesis is based on the synthesis of known dendrimers, such as poly(aryl ether), poly(amidoamine) (in particular PAMAM), poly(amide) (in particular poly(L‐lysine)), 1→3 branching motifs (instead of 1→2), poly(alkyl ether) (poly(glycerol) and poly(ethylene glycol)), poly(ester), and those containing main group elements (poly(carbosilane) and poly(phosphorhydrazone)). In most cases, the hydrophilic functions are on the surface of the dendrons, whereas one or two hydrophobic tails are linked to the core. Depending on the structure of the dendrons, and on the experimental conditions used, the amphiphilic dendrons can self‐associate at the air‐water interface, or form micelles (eventually tubular, but most generally spherical), or form vesicles. These associated dendrons are suitable for the encapsulation of low‐molecular or macromolecular bioactive entities to be delivered in cells. This review is organized depending on the nature of the internal structure of the amphiphilic dendrons (aryl ether, amidoamine, amide, quaternary carbon atom, alkyl ether, ester, main group element). The properties issued from their self‐associations are described all along the review.

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Facile Synthesis of Amphiphilic Fluorescent Phosphorus Dendron-Based Micelles as Antiproliferative Agents: First Investigations

Cited by 20 publications

References 45 publications

First-in-Class Phosphorus Dendritic Framework, a Wide Surface Functional Group Palette Bringing Noteworthy Anti-Cancer and Anti-Tuberculosis Activities: What Lessons to Learn?

First-in-Class Phosphorus Dendritic Framework, a Wide Surface Functional Group Palette Bringing Noteworthy Anti-Cancer and Anti-Tuberculosis Activities: What Lessons to Learn?

Phosphorous Dendron Micelles as a Nanomedicine Platform for Cooperative Tumor Chemoimmunotherapy via Synergistic Modulation of Immune Cells

Supramolecular Self‐Associations of Amphiphilic Dendrons and Their Properties

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