Journal of Fluorescence, volume 24, issue 1, pages 213-230

Synthesis of BODIPY Derivatives Substituted with Various Bioconjugatable Linker Groups: A Construction Kit for Fluorescent Labeling of Receptor Ligands

Heisig Fabian 1
Gollos Sabrina 1
Freudenthal Sven J
El Tayeb Ali
Iqbal Jamshed
Müller Christa E. 1
1
 
PharmaCenter Bonn, Pharmaceutical Institute, Pharmaceutical Chemistry I, University Bonn, Bonn, Germany
Publication typeJournal Article
Publication date2013-09-20
Quartile SCImago
Q1
Quartile WOS
Q3
Impact factor2.7
ISSN10530509, 15734994
Biochemistry
Spectroscopy
Clinical Biochemistry
Law
Sociology and Political Science
Social Sciences (miscellaneous)
Clinical Psychology
Abstract
The goal of the present study was to design small, functionalized green-emitting BODIPY dyes, which can readily be coupled to target molecules such as receptor ligands, or even be integrated into their pharmacophores. A simple two-step one-pot procedure starting from 2,4-dimethylpyrrole and ω-bromoalkylcarboxylic acid chlorides was used to obtain new ω-bromoalkyl-substituted BODIPY fluorophores (1a–1f) connected via alkyl spacers of different length to the 8-position of the fluorescent dye. The addition of radical inhibitors reduced the amount of side products. The ω-bromoalkyl-substituted BODIPYs were further converted to introduce various functional groups: iodo-substituted dyes were obtained by Finkelstein reaction in excellent yields; microwave-assisted reaction with methanolic ammonia led to fast and clean conversion to the amino-substituted dyes; a hydroxyl-substituted derivative was prepared by reaction with sodium ethylate, and thiol-substituted BODIPYs were obtained by reaction of 1a–1f with potassium thioacetate followed by alkaline cleavage of the thioesters. Water-soluble derivatives were prepared by introducing sulfonate groups into the 2- and 6-position of the BODIPY core. The synthesized BODIPY derivatives showed high fluorescent yields and appeared to be stable under basic, reducing and oxidative conditions. As a proof of concept, 2-thioadenosine was alkylated with bromoethyl-BODIPY 1b. The resulting fluorescent 2-substituted adenosine derivative 15 displayed selectivity for the A3 adenosine receptor (ARs) over the other AR subtypes, showed agonistic activity, and may thus become a useful tool for studying A3ARs, or a lead structure for further optimization. The new functionalized dyes may be widely used for fluorescent labeling allowing the investigation of biological targets and processes.

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Heisig F. et al. Synthesis of BODIPY Derivatives Substituted with Various Bioconjugatable Linker Groups: A Construction Kit for Fluorescent Labeling of Receptor Ligands // Journal of Fluorescence. 2013. Vol. 24. No. 1. pp. 213-230.
GOST all authors (up to 50) Copy
Heisig F., Gollos S., Freudenthal S. J., El Tayeb A., Iqbal J., Müller C. E. Synthesis of BODIPY Derivatives Substituted with Various Bioconjugatable Linker Groups: A Construction Kit for Fluorescent Labeling of Receptor Ligands // Journal of Fluorescence. 2013. Vol. 24. No. 1. pp. 213-230.
RIS |
Cite this
RIS Copy
TY - JOUR
DO - 10.1007/s10895-013-1289-4
UR - https://doi.org/10.1007%2Fs10895-013-1289-4
TI - Synthesis of BODIPY Derivatives Substituted with Various Bioconjugatable Linker Groups: A Construction Kit for Fluorescent Labeling of Receptor Ligands
T2 - Journal of Fluorescence
AU - Heisig, Fabian
AU - Gollos, Sabrina
AU - Freudenthal, Sven J
AU - El Tayeb, Ali
AU - Iqbal, Jamshed
AU - Müller, Christa E.
PY - 2013
DA - 2013/09/20 00:00:00
PB - Springer Nature
SP - 213-230
IS - 1
VL - 24
SN - 1053-0509
SN - 1573-4994
ER -
BibTex |
Cite this
BibTex Copy
@article{2013_Heisig
author = {Fabian Heisig and Sabrina Gollos and Sven J Freudenthal and Ali El Tayeb and Jamshed Iqbal and Christa E. Müller},
title = {Synthesis of BODIPY Derivatives Substituted with Various Bioconjugatable Linker Groups: A Construction Kit for Fluorescent Labeling of Receptor Ligands},
journal = {Journal of Fluorescence},
year = {2013},
volume = {24},
publisher = {Springer Nature},
month = {sep},
url = {https://doi.org/10.1007%2Fs10895-013-1289-4},
number = {1},
pages = {213--230},
doi = {10.1007/s10895-013-1289-4}
}
MLA
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Heisig, Fabian, et al. “Synthesis of BODIPY Derivatives Substituted with Various Bioconjugatable Linker Groups: A Construction Kit for Fluorescent Labeling of Receptor Ligands.” Journal of Fluorescence, vol. 24, no. 1, Sep. 2013, pp. 213-230. https://doi.org/10.1007%2Fs10895-013-1289-4.
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