Combining Orthogonal Reactive Groups in Block Copolymers for Functional Nanoparticle Synthesis in a Single Step,ACS Macro Letters

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Combining Orthogonal Reactive Groups in Block Copolymers for Functional Nanoparticle Synthesis in a Single Step
ACS Macro Letters ( IF 5.1 ) Pub Date : 2017-09-28 00:00:00 , DOI: 10.1021/acsmacrolett.7b00678
Olga Schäfer ₁ , Kristina Klinker _{1,

2} , Lydia Braun ₁ , David Huesmann ₁ , Jennifer Schultze ₃ , Kaloian Koynov ₃ , Matthias Barz ₁

Affiliation

We report on the synthesis of polysarcosine-block-poly(S-alkylsulfonyl)-l-cysteine block copolymers, which combine three orthogonal addressable groups enabling site-specific conversion of all reactive entities in a single step. The polymers are readily obtained by ring-opening polymerization (ROP) of corresponding α-amino acid N-carboxyanhydrides (NCAs) combining azide and amine chain ends, with a thiol-reactive S-alkylsulfonyl cysteine. Functional group interconversion of chain ends using strain-promoted azide–alkyne cycloaddition (SPAAC) and activated ester chemistry with NHS- and DBCO-containing fluorescent dyes could be readily performed without affecting the cross-linking reaction between thiols and S-alkylsulfonyl protective groups. Eventually, all three functionalities can be combined in the formation of multifunctional disulfide core cross-linked nanoparticles bearing spatially separated functionalities. The simultaneous attachment of dyes in core and corona during the formation of core-cross-linked nanostructures with controlled morphology is confirmed by fluorescence cross-correlation spectroscopy (FCCS).

中文翻译：

结合嵌段共聚物中的正交反应基团，一步合成功能性纳米粒子

我们报告了聚肌氨酸-嵌段-聚( S-烷基磺酰基) -l-半胱氨酸嵌段共聚物的合成，该共聚物结合了三个正交可寻址基团，能够在一个步骤中实现所有反应实体的位点特异性转化。聚合物很容易通过相应的 α-氨基酸N-羧基酸酐 (NCA) 的开环聚合 (ROP) 与叠氮化物和胺链末端与硫醇反应性S-烷基磺酰基半胱氨酸结合而获得。使用应变促进的叠氮化物 - 炔烃环加成 (SPAAC) 和活化酯化学与含有 NHS 和 DBCO 的荧光染料的链端官能团相互转化可以很容易地进行，而不会影响硫醇和之间的交联反应。S-烷基磺酰基保护基团。最终，所有三种功能可以结合形成具有空间分离功能的多功能二硫键交联纳米颗粒。荧光互相关光谱 (FCCS) 证实了在形成具有受控形态的核心交联纳米结构期间染料在核心和电晕中的同时附着。

更新日期：2017-09-28

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