Synthesis and cellular penetration properties of new phosphonium based cationic amphiphilic peptides

Silva Nigenda, E., Postma, T., Hezwani, M., Pirvan, A., Gannon, S., Smith, C.-A., Riehle, M. and Liskamp, R. M.J. (2018) Synthesis and cellular penetration properties of new phosphonium based cationic amphiphilic peptides. MedChemComm, 9(6), pp. 982-987. (doi:10.1039/c8md00113h)

[img]
Preview
Text
162534.pdf - Published Version
Available under License Creative Commons Attribution Non-commercial.

3MB

Abstract

A new category of phosphonium based cationic amphiphilic peptides has been developed and evaluated as potential antimicrobial peptides and cell penetrating peptides. The required building blocks were conveniently accessible from cysteine and could be applied in a solid phase peptide synthesis protocol for incorporation into peptide sequences. Evaluation of the antimicrobial properties and cellular toxicity of these phosphonium based peptides showed that these “soft” cationic side-chain containing peptides have poor antimicrobial properties and most of them were virtually non toxic (on HEK cells tested at 256 and 512 μM) and non-haemolytic (on horse erythrocytes tested at 512 μM), hinting at an interesting potential application as cell penetrating peptides. This possibility was evaluated using fluorescent peptide derivatives and showed that these phosphonium based peptide derivatives were capable of entering HEK cells and depending on the sequence confined to specific cellular areas.

Item Type:Articles
Additional Information:E. S. N thanks the National Council of Science and Technology of Mexico (CONACyT) for financial support. Assistance by Dr Alex Hoose with MS-interpretation is gratefully acknowledged.
Status:Published
Refereed:Yes
Glasgow Author(s) Enlighten ID:Riehle, Dr Mathis and Liskamp, Professor Robert and Hezwani, Dr Mohammed and Silva Nigenda, Mr Ezequiel and Pirvan, Alin and Smith, Mrs Carol-Anne and Gannon, Dr Susan and Postma, Dr Tobias
Authors: Silva Nigenda, E., Postma, T., Hezwani, M., Pirvan, A., Gannon, S., Smith, C.-A., Riehle, M., and Liskamp, R. M.J.
College/School:College of Medical Veterinary and Life Sciences > Institute of Molecular Cell and Systems Biology
College of Science and Engineering
College of Science and Engineering > School of Chemistry
Journal Name:MedChemComm
Publisher:Royal Society of Chemistry
ISSN:2040-2503
ISSN (Online):2040-2511
Published Online:09 May 2018
Copyright Holders:Copyright © 2018 The Royal Society of Chemistry
First Published:First published in MedChemComm 9(6):982-987
Publisher Policy:Reproduced under a Creative Commons License

University Staff: Request a correction | Enlighten Editors: Update this record