Fluorescein Derivatives as Antibacterial Agents Acting via Membrane Depolarization

Pavel A. Nazarov; Roman S. Kirsanov; Stepan S. Denisov; Ljudmila S. Khailova; Marina Karakozova; Konstantin G. Lyamzaev; Galina A. Korshunova; Konstantin A. Lukyanov; Elena A. Kotova; Yuri N. Antonenko

doi:10.3390/biom10020309

Fluorescein Derivatives as Antibacterial Agents Acting via Membrane Depolarization

Pavel A. Nazarov^*, Roman S. Kirsanov, Stepan S. Denisov, Ljudmila S. Khailova, Marina Karakozova, Konstantin G. Lyamzaev, Galina A. Korshunova, Konstantin A. Lukyanov, Elena A. Kotova^*, Yuri N. Antonenko

^*Corresponding author for this work

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

Abstract

Appending a lipophylic alkyl chain by ester bond to fluorescein has been previously shown to convert this popular dye into an effective protonophoric uncoupler of oxidative phosphorylation in mitochondria, exhibiting neuro- and nephroprotective effects in murine models. In line with this finding, we here report data on the pronounced depolarizing effect of a series of fluorescein decyl esters on bacterial cells. The binding of the fluorescein derivatives to Bacillus subtilis cells was monitored by fluorescence microscopy and fluorescence correlation spectroscopy (FCS). FCS revealed the energy-dependent accumulation of the fluorescein esters with decyl(triphenyl)- and decyl(tri-p-tolyl)phosphonium cations in the bacterial cells. The latter compound proved to be the most potent in suppressing B. subtilis growth.

Original language	English
Article number	309
Number of pages	14
Journal	Biomolecules
Volume	10
Issue number	2
DOIs	https://doi.org/10.3390/biom10020309
Publication status	Published - 15 Feb 2020

Keywords

fluorescein derivative
antibacterial agent
bacterial membrane depolarization
mitochondria
membrane potential
fluorescent uncoupler
OXIDATIVE-PHOSPHORYLATION
BACILLUS-SUBTILIS
MITOCHONDRIA
UNCOUPLERS
TRIPHENYLPHOSPHONIUM
PLATFORM
CATIONS
EFFLUX
PROBE

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title = "Fluorescein Derivatives as Antibacterial Agents Acting via Membrane Depolarization",

abstract = "Appending a lipophylic alkyl chain by ester bond to fluorescein has been previously shown to convert this popular dye into an effective protonophoric uncoupler of oxidative phosphorylation in mitochondria, exhibiting neuro- and nephroprotective effects in murine models. In line with this finding, we here report data on the pronounced depolarizing effect of a series of fluorescein decyl esters on bacterial cells. The binding of the fluorescein derivatives to Bacillus subtilis cells was monitored by fluorescence microscopy and fluorescence correlation spectroscopy (FCS). FCS revealed the energy-dependent accumulation of the fluorescein esters with decyl(triphenyl)- and decyl(tri-p-tolyl)phosphonium cations in the bacterial cells. The latter compound proved to be the most potent in suppressing B. subtilis growth.",

keywords = "fluorescein derivative, antibacterial agent, bacterial membrane depolarization, mitochondria, membrane potential, fluorescent uncoupler, OXIDATIVE-PHOSPHORYLATION, BACILLUS-SUBTILIS, MITOCHONDRIA, UNCOUPLERS, TRIPHENYLPHOSPHONIUM, PLATFORM, CATIONS, EFFLUX, PROBE",

author = "Nazarov, {Pavel A.} and Kirsanov, {Roman S.} and Denisov, {Stepan S.} and Khailova, {Ljudmila S.} and Marina Karakozova and Lyamzaev, {Konstantin G.} and Korshunova, {Galina A.} and Lukyanov, {Konstantin A.} and Kotova, {Elena A.} and Antonenko, {Yuri N.}",

note = "Funding Information: Funding: This work was financially supported by the Russian Science Foundation (project No. 16-14-10025). Publisher Copyright: {\textcopyright} 2020 by the authors. Licensee MDPI, Basel, Switzerland.",

year = "2020",

month = feb,

day = "15",

doi = "10.3390/biom10020309",

language = "English",

volume = "10",

journal = "Biomolecules",

issn = "2218-273X",

publisher = "Multidisciplinary Digital Publishing Institute (MDPI)",

number = "2",

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TY - JOUR

T1 - Fluorescein Derivatives as Antibacterial Agents Acting via Membrane Depolarization

AU - Nazarov, Pavel A.

AU - Kirsanov, Roman S.

AU - Denisov, Stepan S.

AU - Khailova, Ljudmila S.

AU - Karakozova, Marina

AU - Lyamzaev, Konstantin G.

AU - Korshunova, Galina A.

AU - Lukyanov, Konstantin A.

AU - Kotova, Elena A.

AU - Antonenko, Yuri N.

N1 - Funding Information: Funding: This work was financially supported by the Russian Science Foundation (project No. 16-14-10025). Publisher Copyright: © 2020 by the authors. Licensee MDPI, Basel, Switzerland.

PY - 2020/2/15

Y1 - 2020/2/15

N2 - Appending a lipophylic alkyl chain by ester bond to fluorescein has been previously shown to convert this popular dye into an effective protonophoric uncoupler of oxidative phosphorylation in mitochondria, exhibiting neuro- and nephroprotective effects in murine models. In line with this finding, we here report data on the pronounced depolarizing effect of a series of fluorescein decyl esters on bacterial cells. The binding of the fluorescein derivatives to Bacillus subtilis cells was monitored by fluorescence microscopy and fluorescence correlation spectroscopy (FCS). FCS revealed the energy-dependent accumulation of the fluorescein esters with decyl(triphenyl)- and decyl(tri-p-tolyl)phosphonium cations in the bacterial cells. The latter compound proved to be the most potent in suppressing B. subtilis growth.

AB - Appending a lipophylic alkyl chain by ester bond to fluorescein has been previously shown to convert this popular dye into an effective protonophoric uncoupler of oxidative phosphorylation in mitochondria, exhibiting neuro- and nephroprotective effects in murine models. In line with this finding, we here report data on the pronounced depolarizing effect of a series of fluorescein decyl esters on bacterial cells. The binding of the fluorescein derivatives to Bacillus subtilis cells was monitored by fluorescence microscopy and fluorescence correlation spectroscopy (FCS). FCS revealed the energy-dependent accumulation of the fluorescein esters with decyl(triphenyl)- and decyl(tri-p-tolyl)phosphonium cations in the bacterial cells. The latter compound proved to be the most potent in suppressing B. subtilis growth.

KW - fluorescein derivative

KW - antibacterial agent

KW - bacterial membrane depolarization

KW - mitochondria

KW - membrane potential

KW - fluorescent uncoupler

KW - OXIDATIVE-PHOSPHORYLATION

KW - BACILLUS-SUBTILIS

KW - MITOCHONDRIA

KW - UNCOUPLERS

KW - TRIPHENYLPHOSPHONIUM

KW - PLATFORM

KW - CATIONS

KW - EFFLUX

KW - PROBE

U2 - 10.3390/biom10020309

DO - 10.3390/biom10020309

M3 - Article

C2 - 32075319

SN - 2218-273X

VL - 10

JO - Biomolecules

JF - Biomolecules

IS - 2

M1 - 309

ER -

Fluorescein Derivatives as Antibacterial Agents Acting via Membrane Depolarization

Abstract

Keywords

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