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Synthesis of Heterotelechelic Polymers for Conjugation of Two Different Proteins.

ABSTRACT: In this report we describe a straightforward approach to synthesize polymers with end-groups that bind site-specifically to two different proteins. Telechelic biotin, maleimide poly(N-isopropylacrylamide) (pNIPAAm) was synthesized for the formation of streptavidin (SAv)-bovine serum albumin (BSA) polymer conjugates. Reversible addition-fragmentation chain transfer (RAFT) polymerization of NIPAAm was conducted in the presence of biotinylated chain transfer agents (CTAs) with either ester or amide linkages, and the resultant ?-biotinylated pNIPAAm were formed with low polydispersity indices (PDI ? 1.09). UV-Vis analysis of the trithiocarbonate chain-ends indicated 88% or greater retention of the group. A maleimide was introduced to the ? chain-end via a radical cross-coupling reaction with a functionalized azo-initiator. The polymer structures were characterized by 1H NMR spectroscopy and gel permeation chromatography (GPC). The resultant biotin-maleimide heterotelechelic polymer was used to form a SAv-BSA heterodimer conjugate. Bioconjugate formation was confirmed by gel electrophoresis.

SUBMITTER: Heredia KL

PROVIDER: S-EPMC4219831 | biostudies-literature | 2009

REPOSITORIES: biostudies-literature

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Synthesis of Heterotelechelic Polymers for Conjugation of Two Different Proteins.

Heredia Karina L KL Grover Gregory N GN Tao Lei L Maynard Heather D HD

Macromolecules 20090101 7

In this report we describe a straightforward approach to synthesize polymers with end-groups that bind site-specifically to two different proteins. Telechelic biotin, maleimide poly(<i>N</i>-isopropylacrylamide) (pNIPAAm) was synthesized for the formation of streptavidin (SAv)-bovine serum albumin (BSA) polymer conjugates. Reversible addition-fragmentation chain transfer (RAFT) polymerization of NIPAAm was conducted in the presence of biotinylated chain transfer agents (CTAs) with either ester o ...[more]

PMID: 25378715

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Project description:Pyrazinacenes are next generation N-heteroacenes and represent a novel class of stable n-type materials capable of accepting more than one electron and displaying intriguing features, including prototropism, halochromism, and redox chromism. Astonishingly, despite a century since their discovery, there have been no reports on the conjugated polymers of pyrazinacenes due to unknown substrate scope and lack of pyrazinacene monomers that are conducive to condensation polymerization. Breaking through these challenges, in this work, we report the synthesis of previously undiscovered and highly coveted conjugated polymers of pyrazinacenes. In order to understand the intricacies of conjugation extension within the acene and along the polymer backbone, a series of electronically diverse four pyrazinacene conjugated polymers were synthesized. Polymers synthesis required optimizing a few synthetic steps along the 12-step synthetic pathway. The generated pyrazinacene monomers are not amenable to the popular condensation polymerizations involving Pd or Cu catalysts. Gratifyingly, Pd and Cu free dehydrohalogenation polymerization of the monomer with HgCl2 resulted in high molecular weight organometallic conjugated pyrazinacene polymers within a few minutes at room temperature. The dual role played by the Hg(ii) during the polymerization, combined with the self-coupling of the RHgCl (intermediate), is at the core of successful polymerization. Notably, the self-coupling of intermediates challenges the strict stoichiometric balance typically required for step-growth polymerization and offers a novel synthetic strategy to generate high molecular weight conjugated polymers even with imbalanced monomer stoichiometries. A combination of electrochemical studies and DFT-B3LYP simulations indicated that the presence of the reduced pyrazine ring promotes interacene π-conjugation through the metal center, in contrast to completely oxidized tetrazaazaanthracene. The extension of conjugation results in ca. 2 eV lower reduction potential for polymers compared to the monomer, placing the LUMO energy levels of these polymers on par with some of the best-known n-type polymers. Also, the presence of NH protons in the pyrazinacene polymers show ionochromism and red-shift UV-vis absorption maximum by ca. 100 nm. This work not only shows a way to realize highly desirable and elusive pyrazinacene conjugated polymers but also paves the way for a library of n-type conjugated polymers that can undergo multi-electron reduction.

Dataset Information

Synthesis of Heterotelechelic Polymers for Conjugation of Two Different Proteins.

Publications

Synthesis of Heterotelechelic Polymers for Conjugation of Two Different Proteins.

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