Syntheses and Antibacterial Activities of Gramicidin S Analogs Containing<scp>L</scp>-Ornithine in Place of<scp>L</scp>-Valine

Soejima, Yasuhiro; Hashiguchi, Atsuko; Izumiya, Nobuo

doi:10.1271/bbb.58.826

Cited by 6 publications

(2 citation statements)

References 3 publications

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“…By adopting the “inverted” β-strand approach, Kapoerchan et al. synthesized a series of hydrophobic and hydrophilic GS analogues with two or four positive charges (Figure ).…”

Section: Structure–activity Relationship Of Gramicidin S and Its Anal...mentioning

confidence: 99%

“…Gram-positive bacteria and was absolutely inactive against Gram-negative bacteria, highlighting the importance of hydrophobicity in the β-strand regions. By adopting the "inverted" β-strand approach, 64 Kapoerchan et al synthesized a series of hydrophobic and hydrophilic GS analogues with two or four positive charges (Figure 2). 37,60 Since all of the peptides shared the same β-hairpin content, the hydrophobicities of the analogues were evaluated using the RP-HPLC retention times as an empirical method.…”

Section: Journal Of Medicinal Chemistrymentioning

confidence: 99%

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Recent Advances in the Exploration of Therapeutic Analogues of Gramicidin S, an Old but Still Potent Antimicrobial Peptide

et al. 2019

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Gramicidin S (GS), one of the oldest commercially used peptide antibiotics, is known for its robust antibacterial activity against both Gram-positive and Gram-negative bacterial strains. Although it was discovered well over 70 years ago, its clinical potential was limited to topical applications because of its high hemolytic activity. To overcome this side effect, significant efforts have been invested in the chase for GS analogues with high therapeutic index (e.g., high antimicrobial activity and low hemolytic activity) in the past decades. In this Perspective, the structural properties and biological profiles (including the recently discovered activities) of representative GS analogues designed by different approaches are described and analyzed. We also present how the general structure–activity relationships were established and how they could help in the design of more efficient GS analogues.

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“…By adopting the “inverted” β-strand approach, Kapoerchan et al. synthesized a series of hydrophobic and hydrophilic GS analogues with two or four positive charges (Figure ).…”

Section: Structure–activity Relationship Of Gramicidin S and Its Anal...mentioning

confidence: 99%

Section: Journal Of Medicinal Chemistrymentioning

confidence: 99%

Recent Advances in the Exploration of Therapeutic Analogues of Gramicidin S, an Old but Still Potent Antimicrobial Peptide

et al. 2019

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An Adamantyl Amino Acid Containing Gramicidin S Analogue with Broad Spectrum Antibacterial Activity and Reduced Hemolytic Activity

Kapoerchan

Knijnenburg

Niamat

et al. 2010

Chemistry A European J

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The cyclic cationic antimicrobial peptide gramicidin S (GS) is an effective topical antibacterial agent that is toxic for human red blood cells (hemolysis). Herein, we present a series of amphiphilic derivatives of GS with either two or four positive charges and characteristics ranging between very polar and very hydrophobic. Screening of this series of peptide derivatives identified a compound that combines effective antibacterial activity with virtually no toxicity within the same concentration range. This peptide acts against both Gram-negative and Gram-positive bacteria, including several MRSA strains, and represents an interesting lead for the development of a broadly applicable antibiotic.

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‘Inverted’ analogs of the antibiotic gramicidin S with an improved biological profile

Kapoerchan

Knijnenburg

Keizer

et al. 2012

Bioorganic & Medicinal Chemistry

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Syntheses and Antibacterial Activities of Gramicidin S Analogs ContainingL-Ornithine in Place ofL-Valine

Cited by 6 publications

References 3 publications

Recent Advances in the Exploration of Therapeutic Analogues of Gramicidin S, an Old but Still Potent Antimicrobial Peptide

Recent Advances in the Exploration of Therapeutic Analogues of Gramicidin S, an Old but Still Potent Antimicrobial Peptide

An Adamantyl Amino Acid Containing Gramicidin S Analogue with Broad Spectrum Antibacterial Activity and Reduced Hemolytic Activity

‘Inverted’ analogs of the antibiotic gramicidin S with an improved biological profile

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