1,4-Dihydropyridine Cationic Peptidomimetics with Antibacterial Activity

Inbal Lapidot; Amnon Albeck; Gary Gellerman; Shimon Shatzmiller; Flavio Grynszpan

doi:https://doi.org/10.1007/s10989-015-9460-1

1,4-Dihydropyridine Cationic Peptidomimetics with Antibacterial Activity

Inbal Lapidot, Amnon Albeck, Gary Gellerman, Shimon Shatzmiller, Flavio Grynszpan

Ariel University, Bar-Ilan University

Research output: Contribution to journal › Article › peer-review

Abstract

We synthesized new broad spectrum antibacterial cationic peptidomimetics centered on a hydrophobic 1,4-dihydropyridine (1,4-DHP) scaffold. The synthesis involves the preparation of the scaffold in a three step Hantzsch reaction followed by simultaneous coupling of the 1,4-DHP scaffold to two dipeptides bearing cationic side chains. The synthesized peptidomimetics were found to have no measurable toxic hemolytic effect against mammalian red blood cells. The compounds were found to have antibacterial activity against Gram-(-) and Gram-(+) bacteria with MICs in the range of 35-100 μg/mL. These cationic antimicrobial peptidomimetics will lead to more effective antibacterial drug candidates based on a synthetically accessible scaffold.

Original language	English
Pages (from-to)	243-247
Number of pages	5
Journal	International Journal of Peptide Research and Therapeutics
Volume	21
Issue number	3
DOIs	https://doi.org/10.1007/s10989-015-9460-1
State	Published - 27 Sep 2015

Keywords

1, 4-dihydropyridine scaffold
Anti-microbial
Broad spectrum anti-bacterial
Cationic peptides
Drug design
Peptidomimetics

All Science Journal Classification (ASJC) codes

Analytical Chemistry
Bioengineering
Biochemistry
Molecular Medicine
Drug Discovery

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Cite this

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title = "1,4-Dihydropyridine Cationic Peptidomimetics with Antibacterial Activity",

abstract = "We synthesized new broad spectrum antibacterial cationic peptidomimetics centered on a hydrophobic 1,4-dihydropyridine (1,4-DHP) scaffold. The synthesis involves the preparation of the scaffold in a three step Hantzsch reaction followed by simultaneous coupling of the 1,4-DHP scaffold to two dipeptides bearing cationic side chains. The synthesized peptidomimetics were found to have no measurable toxic hemolytic effect against mammalian red blood cells. The compounds were found to have antibacterial activity against Gram-(-) and Gram-(+) bacteria with MICs in the range of 35-100 μg/mL. These cationic antimicrobial peptidomimetics will lead to more effective antibacterial drug candidates based on a synthetically accessible scaffold.",

keywords = "1, 4-dihydropyridine scaffold, Anti-microbial, Broad spectrum anti-bacterial, Cationic peptides, Drug design, Peptidomimetics",

author = "Inbal Lapidot and Amnon Albeck and Gary Gellerman and Shimon Shatzmiller and Flavio Grynszpan",

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year = "2015",

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doi = "https://doi.org/10.1007/s10989-015-9460-1",

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T1 - 1,4-Dihydropyridine Cationic Peptidomimetics with Antibacterial Activity

AU - Lapidot, Inbal

AU - Albeck, Amnon

AU - Gellerman, Gary

AU - Shatzmiller, Shimon

AU - Grynszpan, Flavio

PY - 2015/9/27

Y1 - 2015/9/27

N2 - We synthesized new broad spectrum antibacterial cationic peptidomimetics centered on a hydrophobic 1,4-dihydropyridine (1,4-DHP) scaffold. The synthesis involves the preparation of the scaffold in a three step Hantzsch reaction followed by simultaneous coupling of the 1,4-DHP scaffold to two dipeptides bearing cationic side chains. The synthesized peptidomimetics were found to have no measurable toxic hemolytic effect against mammalian red blood cells. The compounds were found to have antibacterial activity against Gram-(-) and Gram-(+) bacteria with MICs in the range of 35-100 μg/mL. These cationic antimicrobial peptidomimetics will lead to more effective antibacterial drug candidates based on a synthetically accessible scaffold.

AB - We synthesized new broad spectrum antibacterial cationic peptidomimetics centered on a hydrophobic 1,4-dihydropyridine (1,4-DHP) scaffold. The synthesis involves the preparation of the scaffold in a three step Hantzsch reaction followed by simultaneous coupling of the 1,4-DHP scaffold to two dipeptides bearing cationic side chains. The synthesized peptidomimetics were found to have no measurable toxic hemolytic effect against mammalian red blood cells. The compounds were found to have antibacterial activity against Gram-(-) and Gram-(+) bacteria with MICs in the range of 35-100 μg/mL. These cationic antimicrobial peptidomimetics will lead to more effective antibacterial drug candidates based on a synthetically accessible scaffold.

KW - 1, 4-dihydropyridine scaffold

KW - Anti-microbial

KW - Broad spectrum anti-bacterial

KW - Cationic peptides

KW - Drug design

KW - Peptidomimetics

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U2 - https://doi.org/10.1007/s10989-015-9460-1

DO - https://doi.org/10.1007/s10989-015-9460-1

M3 - مقالة

SN - 1573-3149

VL - 21

SP - 243

EP - 247

JO - International Journal of Peptide Research and Therapeutics

JF - International Journal of Peptide Research and Therapeutics

IS - 3

ER -

1,4-Dihydropyridine Cationic Peptidomimetics with Antibacterial Activity

Abstract

Keywords

All Science Journal Classification (ASJC) codes

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