Optimisation of two-photon induced cleavage of molecular linker systems for drug delivery

• Verfasst von: Buckup, Tiago [VerfasserIn]
• Verfasst von: Southan, A. [VerfasserIn]
• Verfasst von: Kim, H. -C. [VerfasserIn]
• Verfasst von: Hampp, N. [VerfasserIn]
• Verfasst von: Motzkus, Marcus [VerfasserIn]
• Titel: Optimisation of two-photon induced cleavage of molecular linker systems for drug delivery
• Verf.angabe: T. Buckup, A. Southan, H.-C. Kim, N. Hampp, M. Motzkus
• Jahr: 2010
• Umfang: 5 S.
• Fussnoten: Erstmals am 23. Dezember 2009 online veröffentlicht ; Gesehen am 15.03.2023
• Titel Quelle: Enthalten in: Journal of photochemistry and photobiology
• Ort Quelle: New York, NY [u.a.] : Elsevier, 1987
• Jahr Quelle: 2010
• Band/Heft Quelle: 210(2010), 2, Seite 188-192
• ISSN Quelle: 1873-2666
• DOI: doi:10.1016/j.jphotochem.2009.12.016
• Datenträger: Online-Ressource
• Sprache: eng
• Sach-SW: Photo-induced cleavage
• Sach-SW: Reaction quantum yield
• K10plus-PPN: 183924321X

Abstract

Photoreactive linker systems for drug delivery in modern ophthalmology are crucial for the efficiency of such applications. We compare 5 different linker molecule candidates (truxillic acid and 4 dimers of coumarin derivates) in solution regarding their chemical stability and two-photon induced cleavage efficiency, and shed light into the role of molecular structure in the cleavage reaction. Dimers of the coumarin family showed much higher two-photon induced cleavage efficiency, achieving the highest reaction cross-section when tert-Butyldimethylsilyl (TBS) was used as a substituent, being almost 5-times higher than the unsubstituted coumarin dimer. Coumarin-based linker systems react promptly with nucleophilic solvents, in particular with short chain alcohols. The polarity of such solvents which do not cause a lactone ring opening seems not to influence the cleavage of the cyclobutane ring in coumarin dimers.