Site-specific N-terminus conjugation of poly(mPEG1100) methacrylates to salmon calcitonin: synthesis and preliminary biological evaluation

Claire T. Sayers; Giuseppe Mantovani; Sinead M. Ryan; Rajan K. Randev; Odin Keiper; Oksana I. Leszczyszyn; Claudia Blindauer; David J. Brayden; David M. Haddleton

doi:10.1039/B905335B

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Site-specific N-terminus conjugation of poly(mPEG₁₁₀₀) methacrylates to salmon calcitonin: synthesis and preliminary biological evaluation†

Claire T. Sayers,^a Giuseppe Mantovani,^b Sinead M. Ryan,^c Rajan K. Randev,^a Odin Keiper,^a Oksana I. Leszczyszyn,^a Claudia Blindauer,^a David J. Brayden^c and David M. Haddleton*^a

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* Corresponding authors

^a Department of Chemistry, University of Warwick, Coventry, UK
E-mail: d.m.haddleton@warwick.ac.uk
Fax: +44 (0)24 7652 3256
Tel: +44 (0)24 7652 3256

^b School of Pharmacy, University of Nottingham, Nottingham, UK

^c UCD School of Agriculture, Food Science and Veterinary Medicine and UCD Conway Institute, University College Dublin, Belfield, Dublin, Ireland

Abstract

Recent advances in polymerization strategies have led to the development of novel polymer–(poly)peptide biohybrid materials with potential application in the field of macromolecular therapeutics. In this current work, comb-shaped α-aldehyde poly(monomethoxy polyethylene glycol)methacrylates (p(mPEG)MA) with molecular masses in the 6.5–109 kDa range were prepared and conjugated, via reductive amination, to the Cys1N-terminus of salmon calcitonin (sCT), a calcitropic hormone currently administered for the treatment of a number of hypercalcaemia-related diseases. The conjugation site was determined by tryptic digestion of the sCT–p(mPEG₁₁₀₀)MA biohybrids in conjunction with LC-MS MALDI-TOF spectrometry. Preliminary in vitro biological tests show that the polymer conjugation does not interfere with the biological activity of the sCT.

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Supplementary files

MALDI-TOF mass spectrum of conjugating p(mPEG)MA (1a), influence of the p(mPEG₁₁₀₀)MA polymers on the conjugation rate plot andIE-FPLC, RP-HPLC, SEC-HPLC chromatograms and NMR data of the sCTconjugates are reported. PDF (1821K)

Article information

DOI: https://doi.org/10.1039/B905335B
Article type: Paper
Submitted: 16 Mar 2009
Accepted: 22 May 2009
First published: 01 Jul 2009

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Soft Matter, 2009,5, 3038-3046

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Site-specific N-terminus conjugation of poly(mPEG₁₁₀₀) methacrylates to salmon calcitonin: synthesis and preliminary biological evaluation

C. T. Sayers, G. Mantovani, S. M. Ryan, R. K. Randev, O. Keiper, O. I. Leszczyszyn, C. Blindauer, D. J. Brayden and D. M. Haddleton, Soft Matter, 2009, 5, 3038 DOI: 10.1039/B905335B

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