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University of Groningen

Controlling Biological Function with Light

Hansen, Mickel Jens

IMPORTANT NOTE: You are advised to consult the publisher's version (publisher's PDF) if you wish to cite from it. Please check the document version below.

Document Version

Publisher's PDF, also known as Version of record

Publication date: 2018

Link to publication in University of Groningen/UMCG research database

Citation for published version (APA):

Hansen, M. J. (2018). Controlling Biological Function with Light. Rijksuniversiteit Groningen.

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Downloaded from the University of Groningen/UMCG research database (Pure): http://www.rug.nl/research/portal. For technical reasons the number of authors shown on this cover page is limited to 10 maximum.

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Controlling Biological Function

with Light

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Mickel Jens Hansen PhD Thesis

Rijksuniversiteit Groningen First edition, December 2018

The work described in this thesis was carried out at the Stratingh Insititute for Chemistry, University of Groningen, Groningen, The Netherlands

The work was financially supported by the Netherlands Organization for Scientific Research (NWO), the European Research Council and the Ministry of Education, Culture and Science

Cover picture by Dusan Kolarski

Printed by Ipskamp Drukkers BV, Enschede, The Netherlands ISBN: 978-94-034-1249-8

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Controlling Biological Function with Light

Proefschrift

ter verkrijging van de graad van doctor aan de Rijksuniversiteit Groningen

op gezag van de

rector mangificus prof. dr. E. Sterken en volgens besluit van het College voor Promoties.

De openbare verdediging zal plaatsvinden op

vrijdag 14 december 2018 om 12.45 uur

door

Mickel Jens Hansen

geboren op 18 februari 1991

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 Promotores Prof. dr. B. L. Feringa Prof. dr. A. J. M. Driessen Beoordelingscommissie Prof. dr. G. A. Woolley Prof. dr. H. S. Overkleeft Prof. dr. ir. A. J. Minnaard

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Table of Contents

Table of Contents

Chapter 1 Perspective and Outline

1

ͳǤͳ ‹‘ˆ–Š‡‡•‡ƒ”…Š‡•…”‹„‡†‹Š‹•Š‡•‹• ʹ ͳǤʹ Š‡•‹•—–Ž‹‡ ʹ ͳǤ͵ ‡ˆ‡”‡…‡• Ͷ

Chapter 2 Photopharmacology

7

ʹǤͳ Š‡‘…‡’–‘ˆŠ‘–‘’Šƒ”ƒ…‘Ž‘‰› ͺ ʹǤʹ ‹‰Š–‹‡†‹…ƒŽ”ƒ…–‹…‡ǣ’’‘”–—‹–‹‡•ƒ†ŠƒŽŽ‡‰‡• ͳͳ ʹǤ͵ Š‘–‘†”—‰‰ƒ„‹Ž‹–›ƒ†Žƒ••‹ˆ‹…ƒ–‹‘‘ˆƒ”‰‡–•Ǥ ͳʹ ʹǤͶ ‘…Ž—•‹‘ƒ†—–Ž‘‘ ͵͹ ʹǤͷ ‡ˆ‡”‡…‡• ͵ͻ

Chapter 3 Ciprofloxacin-Photoswitch Conjugates: a Facile

Strategy for Photopharmacology

49

͵Ǥͳ –”‘†—…–‹‘ ͷͲ ͵Ǥʹ ‡•—Ž–•ƒ†‹•…—••‹‘ ͷͳ ͵Ǥ͵ Š‘–‘…Š‡‹…ƒŽ‡Šƒ˜‹‘” ͷʹ ͵ǤͶ ‹‘Ž‘‰‹…ƒŽ˜ƒŽ—ƒ–‹‘ ͷͶ ͵Ǥͷ ‘…Ž—•‹‘• ͷ͸ ͵Ǥ͸ š’‡”‹‡–ƒŽ‡…–‹‘ ͷ͹ ͵Ǥ͹ ‡ˆ‡”‡…‡• ͸Ͳ

Chapter 4 Direct and Versatile Synthesis of Red-shifted

Azobenzenes 63

ͶǤͳ –”‘†—…–‹‘ ͸Ͷ ͶǤʹ ‡•—Ž–•ƒ†‹•…—••‹‘ ͸͸ ͶǤ͵ ‘…Ž—•‹‘• ͹Ͳ ͶǤͶ š’‡”‹‡–ƒŽ‡…–‹‘ ͹ͳ ͶǤͷ ‡ˆ‡”‡…‡• ͺͲ

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Chapter 5 Photocontrol of Antibacterial Activity: Shifting

from UV to Red Light Activation

85

ͷǤͳ –”‘†—…–‹‘ ͺ͸

ͷǤʹ ‡•—Ž–•ƒ†‹•…—••‹‘ ͺͺ

ͷǤ͵ ‘…Ž—•‹‘• ͻͶ

ͷǤͶ š’‡”‹‡–ƒŽ‡…–‹‘ ͻͷ

ͷǤͷ ‡ˆ‡”‡…‡• ͳͲͳ

Chapter 6 Easily Accessible, Highly Potent, Photocontrolled

Modulators of Bacterial Communication

107

͸Ǥͳ –”‘†—…–‹‘ ͳͲͺ

͸Ǥʹ ‡•—Ž–•ƒ†‹•…—••‹‘ ͳͲͻ

͸Ǥ͵ ‘…Ž—•‹‘• ͳͳͷ

͸ǤͶ š’‡”‹‡–ƒŽ‡…–‹‘ ͳͳͷ

͸Ǥͷ ‡ˆ‡”‡…‡• ͳʹ͹

Chapter 7 Wavelength-Selective Cleavage of Photoprotecting

Groups: Strategies and Applications

131

͹Ǥͳ –”‘†—…–‹‘ ͳ͵ʹ ͹Ǥʹ Š‘–‘Ǧ…Ž‡ƒ˜ƒ„Ž‡”‘–‡…–‹‰”‘—’• ͳ͵͵ ͹Ǥ͵ ‡•‹‰‘ˆ”–Š‘‰‘ƒŽ›•–‡•™‹–Š—Ž–‹’Ž‡ —…–‹‘ƒŽ‡˜‡Ž• ͳͶͲ ͹ǤͶ ›–Š‡–‹…‘•‹†‡”ƒ–‹‘• ͳͶͶ ͹Ǥͷ ŽŽ—•–”ƒ–‹˜‡šƒ’Ž‡•ƒ†’’Ž‹…ƒ–‹‘• ͳͶ͸ ͹Ǥ͸ —Ž–‹’Ž‡ —…–‹‘ƒŽ‡˜‡Ž• ͳͷͲ ͹Ǥ͹ ‘…Ž—•‹‘•ƒ†—–Ž‘‘ ͳͷ͵ ͹Ǥͺ ‡ˆ‡”‡…‡• ͳͷͶ

Chapter 8 Photo-activation of MDM2-inhibitors: Controlling

Protein-Protein Interaction with Light

159

ͺǤͳ –”‘†—…–‹‘ ͳ͸Ͳ

ͺǤʹ ‡•—Ž–•ƒ†‹•…—••‹‘ ͳ͸ͳ

ͺǤ͵ ‘…Ž—•‹‘• ͳ͸ͺ

ͺǤͶ š’‡”‹‡–ƒŽ‡…–‹‘ ͳ͸ͺ

ͺǤͷ ‡ˆ‡”‡…‡• ͳ͹ͷ

Chapter 9 A Photocleavable Trojan Horse Strategy; Fighting

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 ͻǤͳ –”‘†—…–‹‘ ͳͺͲ ͻǤʹ ‡•—Ž–•ƒ†‹•…—••‹‘ ͳͺʹ ͻǤ͵ ‘…Ž—•‹‘• ͳͺͷ ͻǤͶ š’‡”‹‡–ƒŽ‡…–‹‘ ͳͺ͸ ͻǤͷ ‡ˆ‡”‡…‡• ͳͻ͸

Summary, Prospect and Conclusion

199

Samenvatting en Conclusie

203

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