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Direct peptide bioconjugation/PEGylation at tyrosine with linear and branched polymeric diazonium salts
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Jones, Mathew W., Mantovani, Giuseppe, Blindauer, Claudia A., Ryan, Sinead M., Wang, Xuexuan, Brayden, David J. and Haddleton, David M. (2012) Direct peptide bioconjugation/PEGylation at tyrosine with linear and branched polymeric diazonium salts. Journal of the American Chemical Society, 134 (17). pp. 7406-7413. doi:10.1021/ja211855q ISSN 0002-7863.
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Official URL: http://dx.doi.org/10.1021/ja211855q
Abstract
Direct polymer conjugation at peptide tyrosine residues is described. In this study Tyr residues of both leucine enkephalin and salmon calcitonin (sCT) were targeted using appropriate diazonium salt-terminated linear monomethoxy poly(ethylene glycol)s (mPEGs) and poly(mPEG) methacrylate prepared by atom transfer radical polymerization. Judicious choice of the reaction conditions-pH, stoichiometry, and chemical structure of diazonium salt-led to a high degree of site-specificity in the conjugation reaction, even in the presence of competitive peptide amino acid targets such as histidine, lysines, and N-terminal amine. In vitro studies showed that conjugation of mPEG 2000 to sCT did not affect the peptide's ability to increase intracellular cAMP induced in T47D human breast cancer cells bearing sCT receptors. Preliminary in vivo investigation showed preserved ability to reduce [Ca 2+] plasma levels by mPEG 2000-sCT conjugate in rat animal models. © 2012 American Chemical Society.
Item Type: | Journal Article | ||||
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Subjects: | Q Science > QP Physiology Q Science > QR Microbiology T Technology > TP Chemical technology |
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Divisions: | Faculty of Science, Engineering and Medicine > Science > Chemistry | ||||
Library of Congress Subject Headings (LCSH): | Bioconjugates, Immunological tolerance, Recombinant proteins--Therapeutic use | ||||
Journal or Publication Title: | Journal of the American Chemical Society | ||||
Publisher: | American Chemical Society | ||||
ISSN: | 0002-7863 | ||||
Official Date: | 2 May 2012 | ||||
Dates: |
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Volume: | 134 | ||||
Number: | 17 | ||||
Page Range: | pp. 7406-7413 | ||||
DOI: | 10.1021/ja211855q | ||||
Status: | Peer Reviewed | ||||
Publication Status: | Published | ||||
Access rights to Published version: | Restricted or Subscription Access | ||||
Date of first compliant deposit: | 22 August 2016 | ||||
Date of first compliant Open Access: | 22 August 2016 | ||||
Funder: | Engineering and Physical Sciences Research Council (EPSRC), Warwick Effect Polymers Limited, Coventry, European Regional Development Fund (ERDF) |
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