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Synthesis and characterization of photoactivatable doxycycline analogues bearing two-photon-sensitive photoremovable groups suitable for light-induced gene expression

We report the synthesis and photolytic properties of caged 9-aminodoxycycline derivatives modified with 2-4′-bis-[2-(2methoxyethoxy)ethyl]-4-nitrobiphenyl-3-ylprop-1-oxy (EANBP) and PEG7-ylated (7-diethylamino-2-oxo-2H-chromen-4-yl)methyl (PEG7-DEACM) groups. 9-Aminodoxycycline is a tetracycline ana...

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Bibliographic Details
Main Authors: Goegan, Bastien (Author) , Terzi, Firat (Author) , Cambridge, Sidney (Author)
Format: Article (Journal)
Language:English
Published: 17 January 2018
In: ChemBioChem
Year: 2018, Volume: 19, Issue: 12, Pages: 1341-1348
ISSN:1439-7633
DOI:10.1002/cbic.201700628
Online Access:Verlag, Volltext: https://doi.org/10.1002/cbic.201700628
Verlag, Volltext: https://onlinelibrary.wiley.com/doi/abs/10.1002/cbic.201700628
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Author Notes:Bastien Goegan, Firat Terzi, Frédéric Bolze, Sidney Cambridge, and Alexandre Specht
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Summary:We report the synthesis and photolytic properties of caged 9-aminodoxycycline derivatives modified with 2-4′-bis-[2-(2methoxyethoxy)ethyl]-4-nitrobiphenyl-3-ylprop-1-oxy (EANBP) and PEG7-ylated (7-diethylamino-2-oxo-2H-chromen-4-yl)methyl (PEG7-DEACM) groups. 9-Aminodoxycycline is a tetracycline analogue capable of activating transcription through the inducible TetOn transgene expression system and can be regioselectively coupled to two-photon-sensitive photo-removable protecting groups by carbamoylation. The EANBP-based caged 9-aminodoxycycline showed complex photochemical reactions but did release 10 % of 9-aminodoxycycline. However, 9-(PEG7-DEACMamino)doxycycline exhibited excellent photolysis efficiency at 405 nm with quantitative release of 9-aminodoxycycline and a 0.21 uncaging quantum yield. Thanks to the good two-photon sensitivity of the DEACM chromophore, 9-aminodoxycycline release by two-photon photolysis is possible, with calculated action cross-sections of up to 4.0 GM at 740 nm. Therefore, 9-(PEG7-DEACMamino)doxycycline represents a very attractive tool for the development of a light-induced gene expression method in living cells.
Item Description:Gesehen am 08.05.2019
Physical Description:Online Resource
ISSN:1439-7633
DOI:10.1002/cbic.201700628

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