Specific Bifunctionalization on the Surface of Phosphorus Dendrimers Syntheses and Properties
Massimo Petriccone, Régis Laurent, Cédric-Olivier Turrin, Rosa Maria Sebastián, Anne-Marie Caminade
Organics · pp. 240–261 · Published 3 Aug 2022
10.3390/org3030018Abstract
Dendrimers are highly branched macromolecules possessing, in most cases, identical terminal functions. However, it is sometimes desirable to have two types of surface functions in order to fulfil specific properties. The stochastic functionalization is frequently used for such purposes, but the presence of an uncontrolled number of each type of terminal function, albeit acceptable for research purposes, has no practical use. Thus, it is highly desirable to find strategies suitable for the precise grafting of two different functional groups on the surface of dendrimers. The easiest way, and the most widely used, consists in using a bifunctional monomer to be grafted to all of the surface functions of the dendrimers. Two other strategies are known but are rarely used: the modification of an existing function, to generate two functions, and the sequential grafting of one function then of a second function. The three methods are illustrated in this review with polyphosphorhydrazone (PPH) dendrimers, together with their properties as catalysts, for materials, and as biological tools.
References (79)
- 1 Tomalia, 1985, A New Class of Polymers–Starburst-Dendritic Macromolecules [DOI]
- 2 Caminade, A.M., Turrin, C.O., Laurent, R., Ouali, A., and Delavaux-Nicot, B. (2011). Dendrimers: Towards Catalytic, Material and Biomedical Uses, John Wiley & Sons Ltd. [DOI]
- 3 Newkome, 2008, Poly(amidoamine), Polypropylenimine, and Related Dendrimers and Dendrons Possessing Different 1 → 2 Branching Motifs: An overview of the Divergent Procedures [DOI]
- 4 Newkome, 2010, Dendrimers Derived from 1 → 3 Branching Motifs [DOI]
- 5 Mullen, 2010, Isolation and Characterization of Dendrimers with Precise Numbers of Functional Groups [DOI]
- 6 Thomas, 2012, Polyvalent Dendrimer-Methotrexate as a Folate Receptor-Targeted Cancer Therapeutic [DOI]
- 7 Thomas, 2005, Energy and Electron Transfer in Bifunctional Non-Conjugated Dendrimers [DOI]
- 8 Navath, 2010, Amino Acid-Functionalized Dendrimers with Heterobifunctional Chemoselective Peripheral Groups for Drug Delivery Applications [DOI]
- 9 Montanez, 2011, Bifunctional Dendronized Cellulose Surfaces as Biosensors [DOI]
- 10 Hed, 2013, Multipurpose Heterofunctional Dendritic Scaffolds as Crosslinkers towards Functional Soft Hydrogels and Implant Adhesives in Bone Fracture Applications [DOI]
- 11 Sharma, 2011, Facile Construction of Multifunctional Nanocarriers Using Sequential Click Chemistry for Applications in Biology [DOI]
- 12 Castelar, 2015, Multifunctional Ionic Hybrid Poly (propyleneimine) Dendrimers Surrounded by Carbazole Dendrons: Liquid Crystals, Optical and Electrochemical Properties [DOI]
- 13 Kaufman, 2017, Synthesis of Well-Defined Bifunctional Newkome-Type Dendrimers [DOI]
- 14 Floyd, 2010, Design, Synthesis, and Biological Evaluation of a Robust, Biodegradable Dendrimer [DOI]
- 15 Floyd, 2011, Conjugation Effects of Various Linkers on Gd(III) MRI Contrast Agents with Dendrimers: Optimizing the Hydroxypyridinonate (HOPO) Ligands with Nontoxic, Degradable Esteramide (EA) Dendrimers for High Relaxivity [DOI]
- 16 Klemm, 2012, Improving T1 and T2 Magnetic Resonance Imaging Contrast Agents through the Conjugation of an Esteramide Dendrimer to High-Water-Coordination Gd (III) Hydroxypyridinone Complexes [DOI]
- 17 Klemm, 2012, Conjugation to Biocompatible Dendrimers Increases Lanthanide T2 Relaxivity of Hydroxypyridinone Complexes for Magnetic Resonance Imaging [DOI]
- 18 Andolina, 2012, Analysis of Lanthanide Complex Dendrimer Conjugates for Bimodal NIR and MRI Imaging [DOI]
- 19 Floyd, 2011, Chemotherapeutic Evaluation of a Synthetic Tubulysin Analogue-Dendrimer Conjugate in C26 Tumor Bearing Mice [DOI]
- 20 Luo, 2011, Gadolinium-labeled Peptide Dendrimers with Controlled Structures as Potential Magnetic Resonance Imaging Contrast Agents [DOI]
- 21 Luo, 2011, Multifunctional Gadolinium-based Dendritic Macromolecules as Liver Targeting Imaging Probes [DOI]
- 22 Li, 2014, A Smart and Versatile Theranostic Nanomedicine Platform Based on Nanoporphyrin [DOI]
- 23 Goodwin, 2007, Rapid, Efficient Synthesis of Heterobifunctional Biodegradable Dendrimers [DOI]
- 24 Patra, 2013, Dendrimers Terminated with Dichlorotriazine Groups Provide a Route to Compositional Diversity [DOI]
- 25 Lim, 2012, Gadolinium MRI Contrast Agents Based on Triazine Dendrimers: Relaxivity and In Vivo Pharmacokinetics [DOI]
- 26 Launay, 1994, A General Synthetic Strategy for Neutral Phosphorus-Containing Dendrimers [DOI]
- 27 Launay, 1997, Synthesis of Bowl-Shaped Dendrimers from Generation 1 to Generation 8 [DOI]
- 28 Blattes, 2013, Mannodendrimers Prevent Acute Lung Inflammation by Inhibiting Neutrophil Recruitment [DOI]
- 29 Poupot, 2006, Design of Phosphorylated Dendritic Architectures to Promote Human Monocyte Activation [DOI]
- 30 Mignani, 2013, Original Multivalent Copper(II)-Conjugated Phosphorus Dendrimers and Corresponding Mononuclear Copper(II) Complexes with Antitumoral Activities [DOI]
- 31 Mignani, 2017, Original Multivalent Gold (III) and Dual Gold (III)-Copper (II) Conjugated Phosphorus Dendrimers as Potent Antitumoral and Antimicrobial Agents [DOI]
- 32 Mignani, 2017, Anticancer Copper (II) Phosphorus Dendrimers are Potent Proapoptotic Bax Activators [DOI]
- 33 Prevote, 1997, Application of the Horner-Wadsworth-Emmons Reaction to the Functionalization of Dendrimers: Synthesis of Amino Acid Terminated Dendrimers [DOI]
- 34 Caminade, 2008, Dendrimeric Phosphines in Asymmetric Catalysis [DOI]
- 35 Slany, 1995, Dendrimer Surface-Chemistry-Facile Route to Polyphosphines and their Gold Complexes [DOI]
- 36 Koprowski, 2002, Iminophosphine Palladium Complexes in Catalytic Stille Coupling Reactions: From Monomers to Dendrimers [DOI]
- 37 Keller, 2012, An Efficient and Recyclable Dendritic Catalyst Able to Dramatically Decrease Palladium Leaching in Suzuki Couplings [DOI]
- 38 Garcia, 2012, Dendritic Phosphoramidite Ligands for Rh-Catalyzed 2+2+2 Cycloaddition Reactions: Unprecedented Enhancement of Enantiodiscrimination [DOI]
- 39 Keller, 2013, Pyrene-Tagged Dendritic Catalysts Noncovalently Grafted onto Magnetic Co/C Nanoparticles: An Efficient and Recyclable System for Drug Synthesis [DOI]
- 40 Neumann, 2015, Redox Control of a Dendritic Ferrocenyl-Based Homogeneous Catalyst [DOI]
- 41 Laurent, 2005, A Third Generation Chiral Phosphorus-Containing Dendrimer as Ligand in Pd-Catalyzed Asymmetric Allylic Alkylation [DOI]
- 42 Popp, 2020, Redox-Switchable Transfer Hydrogenations with P-Chiral Dendritic Ferrocenyl Phosphine Complexes [DOI]
- 43 Bardaji, 1997, Phosphorus-Containing Dendrimers as Multidentate Ligands: Palladium, Platinum, and Rhodium Complexes [DOI]
- 44 Bardaji, 1997, Ruthenium Hydride and Dihydrogen Complexes with Dendrimeric Multidentate Ligands [DOI]
- 45 Maraval, 2000, Phosphorus-Containing Dendrimers and their Transition Metal Complexes as Efficient Recoverable Multicenter Homogeneous Catalysts in Organic Synthesis [DOI]
- 46 Servin, 2008, Synthesis of Dendrimers Terminated by Bis(diphenylphosphinomethyl)amino Ligands and Use of their Palladium Complexes for Catalyzing C-C Cross-Coupling Reactions [DOI]
- 47 Caminade, 2012, Organocatalysis with Dendrimers [DOI]
- 48 Rull, 2015, (+)-Cinchonine-Decorated Dendrimers as Recoverable Organocatalysts
- 49 Rull, 2016, Recoverable Dendritic Phase-Transfer Catalysts that Contain (+)-Cinchonine-Derived Ammonium Salts
- 50 Franc, 2010, An Efficient Synthesis Combining Phosphorus Dendrimers and 15-Membered Triolefinic Azamacrocycles: Towards the Stabilization of Platinum Nanoparticles [DOI]
- 51 Franc, 2009, Dendritic Structures within Dendritic Structures: Dendrimer-Induced Formation and Self-Assembly of Nanoparticle Networks [DOI]
- 52 Badetti, 2008, Palladium (0) Nanoparticles Stabilized by Phosphorus Dendrimers Containing Coordinating 15-Membered Triolefinic Macrocycles in Periphery [DOI]
- 53 Hincapie, 2014, Supermolecular Columnar Liquid-Crystalline Phosphorus Dendrimers Decorated with Sulfonamide [DOI]
- 54 Blanzat, 2002, Phosphorus-Containing Dendrimers Bearing Galactosylceramide Analogs: Self-Assembly Properties [DOI]
- 55 Spataro, 2009, Phosphonate Terminated PPH Dendrimers: Influence of Pendant Alkyl Chains on the In Vitro Anti-HIV-1 Properties [DOI]
- 56 Stefaniu, 2010, Multivalent Catanionic GalCer Analogs Derived from First Generation Dendrimeric Phosphonic Acids [DOI]
- 57 Rodrigues, 2015, Influence of Structural Parameters on the Self-Association Properties of Anti-HIV Catanionic Dendrimers [DOI]
- 58 Mazeres, 2015, Use of a Fluorescent Aminodeoxylactitol to Measure the Stability of Anti-HIV Catanionic Dendrimers by Spectrofluorimetry [DOI]
- 59 Fruchon, 2009, Anti-Inflammatory and Immunosuppressive Activation of Human Monocytes by a Bioactive Dendrimer [DOI]
- 60 Griffe, 2007, Multiplication of Human Natural Killer Cells by Nanosized Phosphonate-Capped Dendrimers [DOI]
- 61 Hayder, 2011, A Phosphorus-Based Dendrimer Targets Inflammation and Osteoclastogenesis in Experimental Arthritis [DOI]
- 62 Hayder, 2015, Phosphorus-Based Dendrimer ABP Treats Neuroinflammation by Promoting IL-10-Producing CD4 (+) T Cells [DOI]
- 63 Fruchon, 2013, An Azabisphosphonate-Capped Poly(phosphorhydrazone) Dendrimer for the Treatment of Endotoxin-Induced Uveitis [DOI]
- 64 Jebbawi, R., Oukhrib, A., Clement, E., Blanzat, M., Turrin, C.O., Caminade, A.M., Lacoste, E., Fruchon, S., and Poupot, R. (2020). An Anti-Inflammatory Poly (PhosphorHydrazone) Dendrimer Capped with AzaBisPhosphonate Groups to Treat Psoriasis. Biomolecules, 10. [DOI]
- 65 Caminade, 2015, The Key Role of the Scaffold on the Efficiency of Dendrimer Nanodrugs [DOI]
- 66 Marchand, 2009, Dendrimers Ended by Non-Symmetrical Azadiphosphonate Groups: Synthesis and Immunological Properties [DOI]
- 67 Slany, 1996, Specific Functionalization on the Surface of Dendrimers [DOI]
- 68 Lartigue, 1997, Chiroptical Properties of Dendrimers with Stereogenic End Groups [DOI]
- 69 Hameau, 2015, Theoretical and Experimental Characterization of Amino-PEG-Phosphonate-Terminated Polyphosphorhydrazone Dendrimers: Influence of Size and PEG Capping on Cytotoxicity Profiles [DOI]
- 70 Hameau, 2013, PPH Dendrimers Grafted on Silica Nanoparticles: Surface Chemistry, Characterization, Silver Colloids Hosting and Antibacterial Activity [DOI]
- 71 Brahmi, 2011, Hierarchically Porous Nanostructures through Phosphonate-Metal Alkoxide Condensation and Growth Using Functionalized Dendrimeric Building Blocks [DOI]
- 72 Brahmi, 2013, Low Temperature Synthesis of Ordered Mesoporous Stable Anatase Nanocrystals: The Phosphorus Dendrimer Approach [DOI]
- 73 Lartigue, 1996, Phosphorus-Containing Dendrimers: Synthesis of Macromolecules with Multiple Tri- and Tetrafunctionalization [DOI]
- 74 Riegert, 2013, Diversified Strategies for the Synthesis of Bifunctional Dendrimeric Structures [DOI]
- 75 Riegert, 2016, Silica Functionalized by Bifunctional Dendrimers: Hybrid Nanomaterials for Trapping CO2 [DOI]
- 76 Lartigue, 1997, Synthesis and Reactivity of Dendrimers Based on Phosphoryl (P= O) Groups [DOI]
- 77 Severac, 2004, A New Way for the Internal Functionalization of Dendrimers [DOI]
- 78 Mignani, 2015, Investigations on Dendrimer Space Reveal Solid and Liquid Tumor Growth-Inhibition by Original Phosphorus-Based Dendrimers and the Corresponding Monomers and Dendrons with Ethacrynic Acid Motifs [DOI]
- 79 Mignani, 2017, Symmetrical and Unsymmetrical Incorporation of Active Biological Monomers on the Surface of Phosphorus Dendrimers [DOI]
Cited by 21
Sahar Peiman, Behrooz Maleki, Milad Ghani · Scientific Reports · 2024
Joel Cejas-Sánchez, Anna Kajetanowicz, Karol Grela · Molecules · 2023
Anbazhagan Thirumalai, Noureddine Ali Elboughdiri, Karthick Harini · TURKISH JOURNAL OF CHEMISTRY · 2023
Joel Cejas-Sánchez, Anne‐Marie Caminade, Anna Kajetanowicz · Dalton Transactions · 2024
Massimo Petriccone, Régis Laurent, Anne‐Marie Caminade · ACS Macro Letters · 2024
Fatemeh Aminian, Alireza Hemmati · Journal of environmental chemical engineering · 2025
Anne‐Marie Caminade · Polymers · 2025
Cédric‐Olivier Turrin, Régis Laurent, Valérie Maraval · European Polymer Journal · 2025
Chantal J. Abou‐Fayssal, Rinaldo Poli, Karine Philippot · Comptes Rendus Chimie · 2024
Massimo Petriccone, Régis Laurent, Rosa Maria Sebastián · European Polymer Journal · 2026
Showing 12 of 21 known citations — external sources report more than can currently be individually listed.
Related research
- Boranils: Versatile Multifunctional Organic Fluorophores for Innovative Applications — shares topic coverage
- Thienothiophene Scaffolds as Building Blocks for (Opto)Electronics — shares topic coverage
- Looking for a Safe Bridge: Synthesis of P3HT-Bridge-TBO Block-Copolymers and Their Performance in Perovskite Solar Cells — shares topic coverage
- Triple Benefits of Cardanol as Chain Stopper, Flame Retardant and Reactive Diluent for Greener Alkyd Coating — shares topic coverage
- Cell Viability Study of ZnCuInS/ZnS–TPPS4 Conjugates against Different Cell Lines as a Promising Fluorescent Probe — shares topic coverage
Article metrics
Real usage data collected on this platform.
0
Page views
0
PDF downloads
0
Outbound clicks
21
Citations
Views by country
Approximate, from request IP at view time — not citizenship or institution. Countries with fewer than 5 views are grouped as "Other".
No views recorded yet.
Traffic sources
Referring site, by host.
No traffic recorded yet.
Views and downloads exclude known bots/crawlers. Citations combines this platform's own DOI-resolved index with each external source's own reported total — see Cited by above for individually listed citing works. Last refreshed 0 seconds ago.