Organic and Biomolecular Chemistry, volume 18, issue 13, pages 2416-2431
Exploring the relationship between structure and activity in BODIPYs designed for antimicrobial phototherapy.
Hohlfeld Benjamin F
1, 2, 3
,
Gitter Burkhard
3
,
Flanagan Keith J.
4
,
Kingsbury Christopher J
4
,
Kulak N
2, 5
,
Senge Mathias O.
4
,
Wiehe Arno
1, 3
2
3
Biolitec research GmbH, Otto-Schott-Str. 15, 07745 Jena, Germany
|
4
Medicinal Chemistry, Trinity Translational Medicine Institute, Trinity Centre for Health Sciences, Trinity College Dublin, The University of Dublin, St James's Hospital, Dublin 8, Ireland
|
5
Institut für Chemie, Otto-von-Guericke-Universität Magdeburg, Universitätsplatz 2, 39106 Magdeburg, Germany
|
Publication type: Journal Article
Publication date: 2020-03-06
Journal:
Organic and Biomolecular Chemistry
Quartile SCImago
Q1
Quartile WOS
Q2
Impact factor: 3.2
ISSN: 14770520, 14770539
Organic Chemistry
Biochemistry
Physical and Theoretical Chemistry
Abstract
A synthetic strategy to BODIPY dyes is presented giving access to a range of new compounds relevant in the context of antimicrobial photodynamic therapy (aPDT). BODIPYs with the 8-(4-fluoro-3-nitrophenyl) and the 8-pentafluorophenyl substituents were used for the synthesis of new mono- and dibrominated BODIPYs. The para-fluorine atoms in these electron-withdrawing groups facilitate functional modification via nucleophilic aromatic substitution (SNAr) with a number of amines and thio-carbohydrates. Subsequently, the antibacterial phototoxic activity of these BODIPYs has been assessed in bacterial assays against the Gram-positive germ S. aureus and also against the Gram-negative germ P. aeruginosa. The bacterial assays allowed to identify substitution patterns which ensured antibacterial activity not only in phosphate-buffered saline (PBS) but also in the presence of serum, hereby more realistically modelling the complex biological environment that is present in clinical applications.
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Citations by publishers
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1
2
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3 publications, 27.27%
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3 publications, 27.27%
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2 publications, 18.18%
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Springer Nature
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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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Royal Society of Chemistry (RSC)
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Royal Society of Chemistry (RSC)
1 publication, 9.09%
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1
2
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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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Hohlfeld B. F. et al. Exploring the relationship between structure and activity in BODIPYs designed for antimicrobial phototherapy. // Organic and Biomolecular Chemistry. 2020. Vol. 18. No. 13. pp. 2416-2431.
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Hohlfeld B. F., Gitter B., Flanagan K. J., Kingsbury C. J., Kulak N., Senge M. O., Wiehe A. Exploring the relationship between structure and activity in BODIPYs designed for antimicrobial phototherapy. // Organic and Biomolecular Chemistry. 2020. Vol. 18. No. 13. pp. 2416-2431.
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TY - JOUR
DO - 10.1039/D0OB00188K
UR - https://doi.org/10.1039%2FD0OB00188K
TI - Exploring the relationship between structure and activity in BODIPYs designed for antimicrobial phototherapy.
T2 - Organic and Biomolecular Chemistry
AU - Hohlfeld, Benjamin F
AU - Gitter, Burkhard
AU - Flanagan, Keith J.
AU - Kingsbury, Christopher J
AU - Kulak, N
AU - Senge, Mathias O.
AU - Wiehe, Arno
PY - 2020
DA - 2020/03/06 00:00:00
PB - Royal Society of Chemistry (RSC)
SP - 2416-2431
IS - 13
VL - 18
SN - 1477-0520
SN - 1477-0539
ER -
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@article{2020_Hohlfeld,
author = {Benjamin F Hohlfeld and Burkhard Gitter and Keith J. Flanagan and Christopher J Kingsbury and N Kulak and Mathias O. Senge and Arno Wiehe},
title = {Exploring the relationship between structure and activity in BODIPYs designed for antimicrobial phototherapy.},
journal = {Organic and Biomolecular Chemistry},
year = {2020},
volume = {18},
publisher = {Royal Society of Chemistry (RSC)},
month = {mar},
url = {https://doi.org/10.1039%2FD0OB00188K},
number = {13},
pages = {2416--2431},
doi = {10.1039/D0OB00188K}
}
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MLA
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Hohlfeld, Benjamin F., et al. “Exploring the relationship between structure and activity in BODIPYs designed for antimicrobial phototherapy..” Organic and Biomolecular Chemistry, vol. 18, no. 13, Mar. 2020, pp. 2416-2431. https://doi.org/10.1039%2FD0OB00188K.