Chemical synthesis and biological evaluation of an antimicrobial peptide gonococcal growth inhibitor

Amino Acids
J D WadeRaymond M Dawson

Abstract

Gonococcal growth inhibitor 1 (GGI-1) is a 44-residue peptide with potent anti-Legionella activity. It has been isolated from Staphylococcus haemolyticus but, to date, its chemical synthesis has not been reported. Acquisition of this peptide via this means would enable a more detailed examination of its antimicrobial properties. However, its synthesis represents a significant challenge because of two predicted "difficult sequences" within the peptide. Its successful solid-phase assembly is reported in this paper, and was accomplished by use of simple palliative measures including the introduction of a single pseudo-proline isostere in order to counteract on-resin aggregation. The peptide had moderate antimicrobial activity against Escherichia coli but was inactive against another Gram-negative bacterium and two Gram-positive bacteria (Bacillus species). It had significant haemolytic activity, with a H(50) (concentration of peptide that causes 50 % haemolysis) of 20 and 125 μM for two blood samples from different donors. An alternative therapeutic index to that proposed for GGI-1 in a recent publication is proposed.

References

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Jan 1, 2010·Amino Acids·Mohammed Akhter HossainRoss A D Bathgate
Oct 16, 2010·International Journal of Antimicrobial Agents·Raymond Murray Dawson, Chun-Qiang Liu
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Mar 8, 2011·International Journal of Antimicrobial Agents·Raymond M Dawson, Chun-Qiang Liu
Jul 12, 2011·International Journal of Antimicrobial Agents·Raymond M DawsonChun-Qiang Liu

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Citations

Mar 5, 2013·Amino Acids·Mohammed Akhter HossainJohn D Wade
Jun 25, 2013·Journal of Agricultural and Food Chemistry·Giuseppe ForlaniPaweł Kafarski
Sep 10, 2014·Amino Acids·Elaheh JamasbiMohammed Akhter Hossain
Mar 8, 2013·ChemMedChem·Andreas F G GlawarGeorge W J Fleet
Jun 9, 2015·Biochimica Et Biophysica Acta·Elaheh JamasbiFrances Separovic
May 12, 2016·Interdisciplinary Sciences, Computational Life Sciences·Rui-Fang LiChao-Nan Li
Nov 30, 2013·Pharmaceuticals·Ali Adem Bahar, Dacheng Ren
Oct 27, 2018·Molecules : a Journal of Synthetic Chemistry and Natural Product Chemistry·Neda RiahifardRakesh Kumar Tiwari
Sep 11, 2021·Biochimica Et Biophysica Acta. Biomembranes·Jun Hee OhYoonkyung Park
Oct 5, 2021·Journal of Applied Microbiology·Mine Erdem Büyükkiraz, Zülal Kesmen

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