Journal of Photochemistry and Photobiology B: Biology, volume 212, pages 112049
BODIPYs bearing a dimethylaminopropoxy substituent for imaging and photodynamic inactivation of bacteria.
Palacios Yohana B
1
,
Santamarina Sofia C
1
,
Durantini Javier E
2
,
Durantini Edgardo N.
1
,
Durantini Andres
1
1
IDAS‐CONICET, Departamento de Química, Facultad de Ciencias Exactas, Físico‐Químicas y Naturales Universidad Nacional de Río Cuarto, Ruta Nacional 36 Km 601, X5804BYA Río Cuarto Córdoba Argentina
|
2
IITEMA-CONICET, Departamento de Química Facultad de Ciencias Exactas, Físico-Químicas y Naturales, Universidad Nacional de Río Cuarto, Ruta Nacional 36 Km 601, X5804BYA, Río Cuarto, Córdoba, Argentina.
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Publication type: Journal Article
Publication date: 2020-11-01
Quartile SCImago
Q1
Quartile WOS
Q1
Impact factor: 5.4
ISSN: 10111344, 18732682
Biophysics
Radiation
Radiological and Ultrasound Technology
Radiology, Nuclear Medicine and imaging
Abstract
A new BODIPY (BDP 1) bearing a dimethylaminopropoxy group attached to a phenylene unit was synthesized. This compound was brominated to obtain the halogenated analog BDP 2, which was designed to enhance the photodynamic effect of BODIPY to kill bacteria without an intrinsic cationic charge. The basic amino group located at the end of the propoxy bridge can acquire a positive charge by protonation in an aqueous medium, increasing the binding to bacterial cells. Interaction and photokilling activity mediated by these compounds was evaluated in Staphylococcus aureus and Escherichia coli . BDP 1 and BDP 2 were rapidly bound to bacterial cells, showing bioimages with green emission. Complete elimination of S. aureus was detected when cells were incubated with 1 μM BDP 2 and irradiated for 5 min. Comparable photoinactivation was obtained with E. coli , after an irradiation of 30 min. Furthermore, BDP 2 was effective to kill bacteria at very low concentration (0.5 μM). Thus, BDP 1 showed mainly interesting properties as a fluorophore, whereas BDP 2 was highly effective photosensitizer as a broad-spectrum antibacterial agent. BODIPY derivatives are a promising molecular architecture for use as a broad-spectrum antimicrobial photosensitizer. The presence of a basic amine group in the BODIPY structure allows a better binding to bacterial cells, leading to a highly effective photoinactivation. This molecular design of a phototherapeutic agent augurs very well for possible future clinical applications. • New BODIPYs containing a dimethylaminopropoxy group were synthesized. • The basic aliphatic amino group provides effective binding to bacterial cells. • The highly fluorescent BODIPY is an interesting fluorophore for bioimaging. • Brominated BODIPY was highly effective to eradicate bacteria at low concentrations.
Citations by journals
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Journal of Photochemistry and Photobiology B: Biology
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ACS Applied Nano Materials
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Microbiology spectrum
1 publication, 9.09%
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1
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Citations by publishers
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4
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Elsevier
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4 publications, 36.36%
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Wiley
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Wiley
2 publications, 18.18%
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Multidisciplinary Digital Publishing Institute (MDPI)
1 publication, 9.09%
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Springer Nature
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Springer Nature
1 publication, 9.09%
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American Chemical Society (ACS)
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American Chemical Society (ACS)
1 publication, 9.09%
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American Society for Microbiology
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American Society for Microbiology
1 publication, 9.09%
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- We do not take into account publications that without a DOI.
- Statistics recalculated only for publications connected to researchers, organizations and labs registered on the platform.
- Statistics recalculated weekly.
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Palacios Y. B. et al. BODIPYs bearing a dimethylaminopropoxy substituent for imaging and photodynamic inactivation of bacteria. // Journal of Photochemistry and Photobiology B: Biology. 2020. Vol. 212. p. 112049.
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Palacios Y. B., Santamarina S. C., Durantini J. E., Durantini E. N., Durantini A. BODIPYs bearing a dimethylaminopropoxy substituent for imaging and photodynamic inactivation of bacteria. // Journal of Photochemistry and Photobiology B: Biology. 2020. Vol. 212. p. 112049.
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TY - JOUR
DO - 10.1016/j.jphotobiol.2020.112049
UR - https://doi.org/10.1016%2Fj.jphotobiol.2020.112049
TI - BODIPYs bearing a dimethylaminopropoxy substituent for imaging and photodynamic inactivation of bacteria.
T2 - Journal of Photochemistry and Photobiology B: Biology
AU - Palacios, Yohana B
AU - Santamarina, Sofia C
AU - Durantini, Javier E
AU - Durantini, Edgardo N.
AU - Durantini, Andres
PY - 2020
DA - 2020/11/01 00:00:00
PB - Elsevier
SP - 112049
VL - 212
SN - 1011-1344
SN - 1873-2682
ER -
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@article{2020_Palacios,
author = {Yohana B Palacios and Sofia C Santamarina and Javier E Durantini and Edgardo N. Durantini and Andres Durantini},
title = {BODIPYs bearing a dimethylaminopropoxy substituent for imaging and photodynamic inactivation of bacteria.},
journal = {Journal of Photochemistry and Photobiology B: Biology},
year = {2020},
volume = {212},
publisher = {Elsevier},
month = {nov},
url = {https://doi.org/10.1016%2Fj.jphotobiol.2020.112049},
pages = {112049},
doi = {10.1016/j.jphotobiol.2020.112049}
}