Phosphorus‐containing dendrimers: From material science to biology

Abstract

Various methods of synthesis ofphosphorus-containing dendrimers are described. The reactivity of several of these macromolecules is then studied at several levels, mainly on the surface, and also at the level of the branches and of the core. Functionalizations confer to these macromolecules interesting properties, and allow the development of new applications, which are emphasized in this review.

Dendrimers Show Promise for siRNA and microRNA Therapeutics

“…Phosphorus-containing dendrimers generally consist of a thiophosphate or cyclotriphosphazene core and extended branches containing stable aromatic thiophosphohydrazones [ 58 , 59 ]. Such a structure allows steric limitations to be overcome during synthesis: phosphorus dendrimers can be grown up to generation 12 [ 60 ], in contrast to PAMAM dendrimers for which the maximum generation number is 10 [ 61 ]. Also, because of their specific structure, phosphorus dendrimers possess voluminous internal cavities in which small molecules can be encapsulated [ 60 ].…”

“…Such a structure allows steric limitations to be overcome during synthesis: phosphorus dendrimers can be grown up to generation 12 [ 60 ], in contrast to PAMAM dendrimers for which the maximum generation number is 10 [ 61 ]. Also, because of their specific structure, phosphorus dendrimers possess voluminous internal cavities in which small molecules can be encapsulated [ 60 ]. On the other hand, the extended branches make the density of functional groups on the periphery of the dendrimer comparatively low.…”

Phosphines and Related Tervalent Phosphorus Systems

“…572 The Staudinger reaction has found further application in the synthesis of phosphorus-functional dendrimers 573,574 and work in this area has also been reviewed. 575 An interesting new approach to unsymmetrical binol-derived bidentate P,N-ligands is afforded by the reaction of the phosphino-nonaflate (191) with an azide, which proceeds with intramolecular nucleophilic displacement of the nonaflate group by the nitrogen of the intermediate aza-ylide to give, after hydrolysis, the aminoarylphosphine oxide (192), subsequently reduced to the related phosphine with phenylsilane. 576 Further examples of linked Staudingeraza-Wittig synthetic schemes have also appeared, 577,578 including the first example of such reactions involving a non-cumulated sulfoxy group.…”

Dendrimers in Anti-HIV Therapy

“…Besides PPI, another popular abbreviation of these dendrimers is DAB (diaminobutyl), based on the name of the nucleus, and these are commercially available. Phosphorus dendrimers were synthesized by the Majoral and Caminade group [Majoral et al, 2002]. Phosphorus atoms are present in the nucleus and branches of these dendrimers.…”