Design of Bisphosphonate‐Terminated Dendrimers

Cavero, Emma; Zabłocka, Maria; Caminade, Anne‐Marie; Majoral, Jean Pierre

doi:10.1002/ejoc.200901291

Cited by 25 publications

(27 citation statements)

References 25 publications

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“…The click reaction was carried out using an alkyne bearing two phosphonate groups (AP(O)(OMe) 2 ), which is shown in Scheme 2, and was prepared according to literature. 37 Methyl phosphonate-terminated dendrimers were treated with TMSBr in excess for 1 h, then washed with MeOH and finally the resulting solids were treated with an aqueous NaOH solution (see Scheme 2). In this way, sodium phosphonate-decorated dendrimers G n {(CH 2 ) 4 (C 2 H N 3 )CH 2 N[(CH 2 ) 2 N(CH 2 P(O)(ONa) 2 ] 2 } m ; (where n 5 1, m 5 4 (10); n 5 2, m 5 8 (11); n 5 3, m 5 16 (12)) were obtained in moderate yields.…”

Section: Click Coupling Of Neutral Alkynesmentioning

confidence: 99%

Synthesis of anionic carbosilane dendrimers via “click chemistry” and their antiviral properties against HIV

Arnáiz

Vacas-Córdoba

Galán

et al. 2014

J. Polym. Sci. Part A: Polym. Chem.

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The synthesis and characterization of four families of anionic carbosilane dendrimers bearing carboxylate, phosphonate, naphthylsulfonate, and sulfate terminal groups prepared by cycloaddition of azide–alkyne catalyzed by copper (CuAAC) are presented here. For the preparation of these anionic carbosilane dendrimers, two strategies starting from azide‐terminated carbosilane dendrimers were followed: (i) click coupling of neutral alkynes followed by derivatization into anionic moieties or (ii) click coupling of anionic alkynes. Both strategies require different reaction conditions in order to accommodate the different substrate polarities. These anionic dendrimers, in general, do not present cell toxicity in vitro until concentration up to 20 µM. Therefore, they can be used in inhibition experiments in concentrations below this limit. We have observed that dendrimers bearing phosphonate groups possess poor anti‐HIV capabilities in vitro in PBMCs, while carboxylate dendrimers can reduce HIV infection levels moderately. On the other hand, sulfate and naphthylsulfonate dendrimers are powerful anti‐HIV agents and their antiviral activity is generation and concentration dependent. © 2014 Wiley Periodicals, Inc. J. Polym. Sci., Part A: Polym. Chem. 2014, 52, 1099–1112

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Section: Click Coupling Of Neutral Alkynesmentioning

confidence: 99%

Synthesis of anionic carbosilane dendrimers via “click chemistry” and their antiviral properties against HIV

Arnáiz

Vacas-Córdoba

Galán

et al. 2014

J. Polym. Sci. Part A: Polym. Chem.

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“…The synthesis of the intermediates A and B was carried out according to a previously reported procedure, with some modifications [ 27 , 28 ]. A dry hydroquinone solution (24.03 mmol) in DMF (250 mL) was refluxed for 30 min at 72 °C, K 2 CO 3 (30.04 mmol) was added and the mixture was refluxed for 1 h. To this mixture, alkyne (12.02 mmol) was added dropwise over 2 h. The resulting mixture was refluxed for 36 h, then cooled to 25 °C and filtered.…”

Section: Methodsmentioning

confidence: 99%

First Class of Phosphorus Dendritic Compounds Containing β-Cyclodextrin Units in the Periphery Prepared by CuAAC

et al. 2020

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A new class of phosphorus dendritic compounds (PDCs) having a cyclotriphosphazene (P3N3) core and decorated with six β-cyclodextrin (βCD) units, named P3N3-[O-C6H4-O-(CH2)n-βCD]6, where n = 3 or 4 was designed, and the synthesis was performed using copper (I) catalyzed alkyne-azide cycloaddition (CuAAC). To obtain the complete substitution of the P3N3, two linkers consisting of an aromatic ring and an aliphatic chain of two different lengths were assessed. We found that, with both linkers, the total modification of the periphery was achieved. The two new obtained dendritic compounds presented a considerably high water solubility (>1 g/mL). The compounds comprised in this new class of PDCs are potential drug carrier candidates, since the conjugation of the βCD units to the P3N3 core through the primary face will not only serve as surface cover but, also, provide them the faculty to encapsulate various drugs inside the βCDs cavities.

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“…Monopropagyloxyphenol ( 13 ) [ 50 ]. Hydroquinone (10.28 g, 93.37 mmol) was dissolved in acetone (150 mL) followed by the addition of K 2 CO 3 (15.42 g, 111.58 mmol).…”

Section: Methodsmentioning

confidence: 99%

Effect of Dendrimer Generation and Aglyconic Linkers on the Binding Properties of Mannosylated Dendrimers Prepared by a Combined Convergent and Onion Peel Approach

et al. 2018

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An efficient study of carbohydrate-protein interactions was achieved using multivalent glycodendrimer library. Different dendrimers with varied peripheral sugar densities and linkers provided an arsenal of potential novel therapeutic agents that could be useful for better specific action and greater binding affinities against their cognate protein receptors. Highly effective click chemistry represents the basic method used for the synthesis of mannosylated dendrimers. To this end, we used propargylated scaffolds of varying sugar densities ranging from 2 to 18 for the attachment of azido mannopyranoside derivatives using copper catalyzed click cycloaddition. Mannopyranosides with short and pegylated aglycones were used to evaluate their effects on the kinetics of binding. The mannosylated dendrons were built using varied scaffolds toward the accelerated and combined “onion peel” strategy These carbohydrates have been designed to fight E. coli urinary infections, by inhibiting the formation of bacterial biofilms, thus neutralizing the adhesion of FimH type 1 lectin present at the tip of their fimbriae against the natural multiantennary oligomannosides of uroplakin 1a receptors expressed on uroepithelial tissues. Preliminary DLS studies of the mannosylated dendrimers to cross- link the leguminous lectin Con A used as a model showed their high potency as candidates to fight the E. coli adhesion and biofilm formation.

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Design of Bisphosphonate‐Terminated Dendrimers

Abstract: Several new methods for the synthesis of phosphorus dendrimers capped with biologically active azabisphosphonates are reported. Monomers bearing either azido or acetylenic groups were designed as building blocks either for attach-

Cited by 25 publications

References 25 publications

Synthesis of anionic carbosilane dendrimers via “click chemistry” and their antiviral properties against HIV

Synthesis of anionic carbosilane dendrimers via “click chemistry” and their antiviral properties against HIV

First Class of Phosphorus Dendritic Compounds Containing β-Cyclodextrin Units in the Periphery Prepared by CuAAC

Effect of Dendrimer Generation and Aglyconic Linkers on the Binding Properties of Mannosylated Dendrimers Prepared by a Combined Convergent and Onion Peel Approach

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