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The high functional group density at the chain ends of dendrimers, coupled with unprecedented control over molecular structure, makes these synthetic materials extremely attractive candidates for a variety of surface active applications

Multivalent, bifunctional dendrimers prepared by click chemistry.

CHEMICAL COMMUNICATIONS, no. 46 (2006): 5775-5777

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摘要

Unsymmetrical dendrimers, containing both mannose binding units and coumarin fluorescent units, have been prepared using click chemistry and shown to be highly efficient, dual-purpose recognition/detection agents for the inhibition of hemagglutination.

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简介
  • Received 24th August 2005, Accepted 21st October 2005 First published as an Advance Article on the web 4th November 2005 DOI: 10.1039/b512021g.
  • Unsymmetrical dendrimers, containing both mannose binding units and coumarin fluorescent units, have been prepared using click chemistry and shown to be highly efficient, dualpurpose recognition/detection agents for the inhibition of hemagglutination.
重点内容
  • Received 24th August 2005, Accepted 21st October 2005 First published as an Advance Article on the web 4th November 2005 DOI: 10.1039/b512021g
  • The high functional group density at the chain ends of dendrimers, coupled with unprecedented control over molecular structure, makes these synthetic materials extremely attractive candidates for a variety of surface active applications.[1]
  • A general strategy for the facile synthesis of chemically differentiated dendrimers which allows for the introduction of functional groups at defined locations has not been reported
  • The high efficiency of this process is exploited to couple the dendritic blocks together, while its tolerance of a wide variety of functional groups allows the introduction of reactive units at the periphery without the use of protecting groups.[9]
  • Coupling of the differentiated dendritic blocks containing a variety of chain end
  • Quantitative modification and sequential differentiation of the chain ends by the introduction of mannose and coumarin unit derivatives to the periphery of individual blocks allowed preparation of agents with dual function, recognition and detection, which may prove useful in identification and treatment of pathological conditions via multivalent interactions
结果
  • While a number of approaches have been reported for combining all of these elements into a single system,[5] the structural control and monodispersity of dendrimer-based macromolecules promise superior performance.[6] A general strategy for the facile synthesis of chemically differentiated dendrimers which allows for the introduction of functional groups at defined locations has not been reported.
  • The key chemical transformation which allows simple and facile preparation of these dual-purpose, multifunctional materials is the copper(I)-catalyzed azide–alkyne cycloaddition, a premier ‘‘click’’ reaction.[8] The high efficiency of this process is exploited to couple the dendritic blocks together, while its tolerance of a wide variety of functional groups allows the introduction of reactive units at the periphery without the use of protecting groups.[9]
  • See DOI: 10.1039/b512021g block and the resulting anhydride 1 provides easy access to both the alkyne 2 and the azide 3 by condensation with the appropriate alcohol.[10] Removal of the acetonide protecting groups and subsequent acylation with the anhydride 1 allows for facile generation growth of the dendritic blocks containing either a single acetylene 4 or azide group 5 at the focal point.
  • The efficiency of this polymer coupling reaction was further proved by GPC, NMR and MALDI analysis, the latter showing a single peak at 1985 (MH+) for 8.11 Using the same methodology, a series of amphiphilic dendrimers from generation 1 to 4 were prepared from dendrons of varied sizes.
  • The acetylene functionalized, fluorescently labelled dendrimer 13 showed a single molecular ion (MH+ = 4184; MNa+ = 4206) in the MALDI spectrum which correlates with 2 coumarin and 16 acetylene chain end groups (Fig. 1).
  • Copper(I)-catalyzed azide–acetylene cycloaddition[15] has proven to be a powerful tool for both the preparation of unsymmetric diblock dendrimers and for efficient differentiation of the dendritic chain end groups.
结论
  • By preparing dendrons with unique acetylenic and azide groups at the focal point, highly efficient coupling of these blocks was achieved through the formation of a stable [1,2,3]-triazole linkage.
  • Quantitative modification and sequential differentiation of the chain ends by the introduction of mannose and coumarin unit derivatives to the periphery of individual blocks allowed preparation of agents with dual function, recognition and detection, which may prove useful in identification and treatment of pathological conditions via multivalent interactions.
总结
  • Received 24th August 2005, Accepted 21st October 2005 First published as an Advance Article on the web 4th November 2005 DOI: 10.1039/b512021g.
  • Unsymmetrical dendrimers, containing both mannose binding units and coumarin fluorescent units, have been prepared using click chemistry and shown to be highly efficient, dualpurpose recognition/detection agents for the inhibition of hemagglutination.
  • While a number of approaches have been reported for combining all of these elements into a single system,[5] the structural control and monodispersity of dendrimer-based macromolecules promise superior performance.[6] A general strategy for the facile synthesis of chemically differentiated dendrimers which allows for the introduction of functional groups at defined locations has not been reported.
  • The key chemical transformation which allows simple and facile preparation of these dual-purpose, multifunctional materials is the copper(I)-catalyzed azide–alkyne cycloaddition, a premier ‘‘click’’ reaction.[8] The high efficiency of this process is exploited to couple the dendritic blocks together, while its tolerance of a wide variety of functional groups allows the introduction of reactive units at the periphery without the use of protecting groups.[9]
  • See DOI: 10.1039/b512021g block and the resulting anhydride 1 provides easy access to both the alkyne 2 and the azide 3 by condensation with the appropriate alcohol.[10] Removal of the acetonide protecting groups and subsequent acylation with the anhydride 1 allows for facile generation growth of the dendritic blocks containing either a single acetylene 4 or azide group 5 at the focal point.
  • The efficiency of this polymer coupling reaction was further proved by GPC, NMR and MALDI analysis, the latter showing a single peak at 1985 (MH+) for 8.11 Using the same methodology, a series of amphiphilic dendrimers from generation 1 to 4 were prepared from dendrons of varied sizes.
  • The acetylene functionalized, fluorescently labelled dendrimer 13 showed a single molecular ion (MH+ = 4184; MNa+ = 4206) in the MALDI spectrum which correlates with 2 coumarin and 16 acetylene chain end groups (Fig. 1).
  • Copper(I)-catalyzed azide–acetylene cycloaddition[15] has proven to be a powerful tool for both the preparation of unsymmetric diblock dendrimers and for efficient differentiation of the dendritic chain end groups.
  • By preparing dendrons with unique acetylenic and azide groups at the focal point, highly efficient coupling of these blocks was achieved through the formation of a stable [1,2,3]-triazole linkage.
  • Quantitative modification and sequential differentiation of the chain ends by the introduction of mannose and coumarin unit derivatives to the periphery of individual blocks allowed preparation of agents with dual function, recognition and detection, which may prove useful in identification and treatment of pathological conditions via multivalent interactions.
引用论文
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