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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| Main Authors: | , , |
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| Format: | Article (Journal) |
| Language: | English |
| Published: |
17 January 2018
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| 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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| 245 | 1 | 0 | |a Synthesis and characterization of photoactivatable doxycycline analogues bearing two-photon-sensitive photoremovable groups suitable for light-induced gene expression |c Bastien Goegan, Firat Terzi, Frédéric Bolze, Sidney Cambridge, and Alexandre Specht |
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| 520 | |a 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. | ||
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