Naphthylated LEGO-lipophosphonoxin antibiotics used as a fluorescent tool for the observation of target membrane perturbations preceding its disruption

Result code in IS VaVaI

<a href="https://www.isvavai.cz/riv?ss=detail&h=RIV%2F61388963%3A_____%2F25%3A00600353" target="_blank" >RIV/61388963:_____/25:00600353 - isvavai.cz</a>

Alternative codes found

RIV/61388955:_____/25:00600353 RIV/00216208:11310/25:10488180

Result on the web

<a href="https://doi.org/10.1088/2050-6120/ad8abf" target="_blank" >https://doi.org/10.1088/2050-6120/ad8abf</a>

DOI - Digital Object Identifier

<a href="http://dx.doi.org/10.1088/2050-6120/ad8abf" target="_blank" >10.1088/2050-6120/ad8abf</a>

Result language

angličtina

Original language name

Naphthylated LEGO-lipophosphonoxin antibiotics used as a fluorescent tool for the observation of target membrane perturbations preceding its disruption

Original language description

Linker-Evolved-Group-Optimized-Lipophosphonoxins (LEGO-LPPO) are small synthetic modular peptidomimetics with promising antimicrobial activity. The LEGO-LPPO mechanism of antibacterial action has been determined to be the depolarization and disruption of bacterial membranes. Their modular nature is advantageous for fine tuning their biological properties. In order to optimize the structure of LEGO-LPPO even further, it is important to understand the interaction of LEGO-LPPO with bacterial membranes at the molecular level. In this work, we present the synthesis of five LEGO-LPPO (designated as1_naph2-4-G to5_naph2-4-G) molecules bearing fluorescent naphtylethyl moieties and their usage in the study of LEGO-LPPO behaviour in the membrane. Our goal was to characterize fluorescently labelled LEGO-LPPO under conditions that do not completely disrupt the membrane, mostly in the form of membrane-bound monomers. We observed the intramolecular interactions of hydrophobic modules of1_naph2-4-G in the buffer by detecting dynamic naphthyl excimers and their disappearance after1_naph2-4-G bind into the membranes. In the membrane, the molecule1_naph2-4-G slightly affects the membrane fluidity of DOPG membranes above the phase transition. The naphthyl fluorophore itself has fast and almost unrestricted rotation around ethylene linking groups (rinf= 0.010), which indicates a considerable chaotropic effect of the hydrophobic modules of1_naph2-4-G at the given depth of the membrane.1_naph2-4-G proved to be a useful model for observing the interaction of LEGO-LPPO antibiotics with the phospholipid bilayer enabling us to decipher its effects on membrane state and dynamics, its binding and penetration into the membrane, its structure and the particular depth that it occupies.

Czech name

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Czech description

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Type

J_imp - Article in a specialist periodical, which is included in the Web of Science database

CEP classification

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OECD FORD branch

10401 - Organic chemistry

Project

Result was created during the realization of more than one project. More information in the Projects tab.

Continuities

I - Institucionalni podpora na dlouhodoby koncepcni rozvoj vyzkumne organizace

Publication year

2025

Confidentiality

S - Úplné a pravdivé údaje o projektu nepodléhají ochraně podle zvláštních právních předpisů

Name of the periodical

Methods and Applications in Fluorescence

ISSN

2050-6120

e-ISSN

2050-6120

Volume of the periodical

13

Issue of the periodical within the volume

1

Country of publishing house

US - UNITED STATES

Number of pages

18

Pages from-to

015001

UT code for WoS article

001349710200001

EID of the result in the Scopus database

2-s2.0-85208688377