Self-assembly to function: design, synthesis, and broad spectrum antimicrobial properties of short hybrid E-vinylogous lipopeptides

S Shiva Shankar; Sushil N Benke; Narem Nagendra; Prabhakar Lal Srivastava; Hirekodathakallu V Thulasiram; Hosahudya N Gopi

doi:10.1021/jm400884w

Self-assembly to function: design, synthesis, and broad spectrum antimicrobial properties of short hybrid E-vinylogous lipopeptides

S Shiva Shankar, Sushil N Benke, Narem Nagendra, Prabhakar Lal Srivastava, Hirekodathakallu V Thulasiram, Hosahudya N Gopi

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

Abstract

Nonribosomal E-vinylogous γ-amino acids are widely present in many peptide natural products and have been exploited as inhibitors for serine and cysteine proteases. Here, we are reporting the broad spectrum antimicrobial properties and self-assembled nanostructures of various hybrid lipopeptides composed of 1:1 alternating α- and E-vinylogous residues. Analysis of the results revealed that self-assembled nanostructures also play a significant role in the antimicrobial and hemolytic activities. In contrast to the α-peptide counterparts, vinylogous hybrid peptides displayed excellent antimicrobial properties against various bacterial and fungal strains. Peptides that adopted nanofiber structures displayed less hemolytic activity, while peptides that adopted nanoneedle structures displayed the highest hemolytic activity.

Original language	English
Pages (from-to)	8468-74
Number of pages	7
Journal	Journal of Medicinal Chemistry
Volume	56
Issue number	21
Early online date	31 Oct 2013
DOIs	https://doi.org/10.1021/jm400884w
Publication status	Published - 14 Nov 2013
Externally published	Yes

Keywords

Anti-Bacterial Agents/chemical synthesis
Antifungal Agents/chemical synthesis
Candida albicans/drug effects
Dose-Response Relationship, Drug
Drug Design
Escherichia coli/cytology
Hemolysis
Lipopeptides/chemical synthesis
Microbial Sensitivity Tests
Microscopy, Atomic Force
Molecular Structure
Particle Size
Structure-Activity Relationship
Surface Properties

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10.1021/jm400884w

Cite this

@article{007f0726cc6b457db3e356e84b715a05,

title = "Self-assembly to function: design, synthesis, and broad spectrum antimicrobial properties of short hybrid E-vinylogous lipopeptides",

abstract = "Nonribosomal E-vinylogous γ-amino acids are widely present in many peptide natural products and have been exploited as inhibitors for serine and cysteine proteases. Here, we are reporting the broad spectrum antimicrobial properties and self-assembled nanostructures of various hybrid lipopeptides composed of 1:1 alternating α- and E-vinylogous residues. Analysis of the results revealed that self-assembled nanostructures also play a significant role in the antimicrobial and hemolytic activities. In contrast to the α-peptide counterparts, vinylogous hybrid peptides displayed excellent antimicrobial properties against various bacterial and fungal strains. Peptides that adopted nanofiber structures displayed less hemolytic activity, while peptides that adopted nanoneedle structures displayed the highest hemolytic activity.",

keywords = "Anti-Bacterial Agents/chemical synthesis, Antifungal Agents/chemical synthesis, Candida albicans/drug effects, Dose-Response Relationship, Drug, Drug Design, Escherichia coli/cytology, Hemolysis, Lipopeptides/chemical synthesis, Microbial Sensitivity Tests, Microscopy, Atomic Force, Molecular Structure, Particle Size, Structure-Activity Relationship, Surface Properties",

author = "Shankar, \{S Shiva\} and Benke, \{Sushil N\} and Narem Nagendra and Srivastava, \{Prabhakar Lal\} and Thulasiram, \{Hirekodathakallu V\} and Gopi, \{Hosahudya N\}",

year = "2013",

month = nov,

day = "14",

doi = "10.1021/jm400884w",

language = "English",

volume = "56",

pages = "8468--74",

journal = "Journal of Medicinal Chemistry",

issn = "0022-2623",

publisher = "American Chemical Society",

number = "21",

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TY - JOUR

T1 - Self-assembly to function

T2 - design, synthesis, and broad spectrum antimicrobial properties of short hybrid E-vinylogous lipopeptides

AU - Shankar, S Shiva

AU - Benke, Sushil N

AU - Nagendra, Narem

AU - Srivastava, Prabhakar Lal

AU - Thulasiram, Hirekodathakallu V

AU - Gopi, Hosahudya N

PY - 2013/11/14

Y1 - 2013/11/14

N2 - Nonribosomal E-vinylogous γ-amino acids are widely present in many peptide natural products and have been exploited as inhibitors for serine and cysteine proteases. Here, we are reporting the broad spectrum antimicrobial properties and self-assembled nanostructures of various hybrid lipopeptides composed of 1:1 alternating α- and E-vinylogous residues. Analysis of the results revealed that self-assembled nanostructures also play a significant role in the antimicrobial and hemolytic activities. In contrast to the α-peptide counterparts, vinylogous hybrid peptides displayed excellent antimicrobial properties against various bacterial and fungal strains. Peptides that adopted nanofiber structures displayed less hemolytic activity, while peptides that adopted nanoneedle structures displayed the highest hemolytic activity.

AB - Nonribosomal E-vinylogous γ-amino acids are widely present in many peptide natural products and have been exploited as inhibitors for serine and cysteine proteases. Here, we are reporting the broad spectrum antimicrobial properties and self-assembled nanostructures of various hybrid lipopeptides composed of 1:1 alternating α- and E-vinylogous residues. Analysis of the results revealed that self-assembled nanostructures also play a significant role in the antimicrobial and hemolytic activities. In contrast to the α-peptide counterparts, vinylogous hybrid peptides displayed excellent antimicrobial properties against various bacterial and fungal strains. Peptides that adopted nanofiber structures displayed less hemolytic activity, while peptides that adopted nanoneedle structures displayed the highest hemolytic activity.

KW - Anti-Bacterial Agents/chemical synthesis

KW - Antifungal Agents/chemical synthesis

KW - Candida albicans/drug effects

KW - Dose-Response Relationship, Drug

KW - Drug Design

KW - Escherichia coli/cytology

KW - Hemolysis

KW - Lipopeptides/chemical synthesis

KW - Microbial Sensitivity Tests

KW - Microscopy, Atomic Force

KW - Molecular Structure

KW - Particle Size

KW - Structure-Activity Relationship

KW - Surface Properties

U2 - 10.1021/jm400884w

DO - 10.1021/jm400884w

M3 - Article

C2 - 24117107

SN - 0022-2623

VL - 56

SP - 8468

EP - 8474

JO - Journal of Medicinal Chemistry

JF - Journal of Medicinal Chemistry

IS - 21

ER -

Self-assembly to function: design, synthesis, and broad spectrum antimicrobial properties of short hybrid E-vinylogous lipopeptides

Abstract

Keywords

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