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Probing of DNA Photochemistry with C-Nucleosides of Xanthones and Triphenylene as Photosensitizers To Study the Formation of Cyclobutane Pyrimidine Dimers

Häcker, Sebastian 1; Schrödter, Maren 1; Kuhlmann, Arthur 1; Wagenknecht, Hans-Achim 1
1 Institut für Organische Chemie (IOC), Karlsruher Institut für Technologie (KIT)

Abstract:

The direct and sequence-dependent investigation of photochemical processes in DNA on the way to cyclobutane pyrimidine dimers (CPDs) as DNA damage requires the probing by photochemically different photosensitizers. The C-nucleosides of xanthone, thioxanthone, 3-methoxyxanthone, and triphenylene as photosensitizers were synthesized by Heck couplings and incorporated into ternary photoactive DNA architectures. This structural approach allows the site-selective excitation of the DNA by UV light. Together with a single defined site for T–T dimerization, not only the direct CPD formation but also the distance-dependent CPD formation in DNA as well as the possibility for energy transport processes could be investigated. Direct CPD formation was observed with xanthone, 3-methoxyxanthone, and triphenylene as sensitizers but not with thioxanthone. Only xanthone was able to induce CPDs remotely by a triplet energy transfer over up to six intervening A-T base pairs. Taken together, more precise information on the sequence dependence of the DNA triplet photochemistry was obtained.


Verlagsausgabe §
DOI: 10.5445/IR/1000160559
Veröffentlicht am 21.08.2023
Originalveröffentlichung
DOI: 10.1021/jacsau.3c00167
Scopus
Zitationen: 2
Dimensions
Zitationen: 3
Cover der Publikation
Zugehörige Institution(en) am KIT Institut für Organische Chemie (IOC)
Publikationstyp Zeitschriftenaufsatz
Publikationsjahr 2023
Sprache Englisch
Identifikator ISSN: 2691-3704
KITopen-ID: 1000160559
Erschienen in JACS Au
Verlag ACS Publications
Band 3
Heft 7
Seiten 1843–1850
Bemerkung zur Veröffentlichung Gefördert durch den KIT-Publikationsfonds
Vorab online veröffentlicht am 26.05.2023
Schlagwörter Genetics,Irradiation,Photosensitization,Quantum mechanics,Xanthones
Nachgewiesen in Scopus
Dimensions
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