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)

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: Liskamp, Professor Robert and Pirvan, Alin and Hezwani, Dr Mohammed and Riehle, Dr Mathis and Silva Nigenda, Mr Ezequiel and Postma, Dr Tobias and Smith, Mrs Carol-Anne and Gannon, Dr Susan
• 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 > School of Molecular Biosciences; 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