Photosensitised biphotonic chemistry of pyrimidine derivatives
- Resource Type
- Authors
- Jean Cadet; M. Consuelo Cuquerella; Ofelia R. Alzueta; Miguel A. Miranda
- Source
- Digital.CSIC. Repositorio Institucional del CSIC
instname
- Subject
- Pyrimidine
Absorption spectroscopy
010405 organic chemistry
Organic Chemistry
Substituent
Uracil
010402 general chemistry
Photochemistry
01 natural sciences
Biochemistry
0104 chemical sciences
Nucleobase
chemistry.chemical_compound
chemistry
Excited state
Irradiation
Physical and Theoretical Chemistry
Absorption (electromagnetic radiation)
- Language
- ISSN
- 1477-0539
1477-0520
Photosensitised biphotonic irradiation of DNA has been rarely addressed, probably due to the difficulties in the experimental design. This is associated with the selection of nucleobases and sensitisers with appropriate absorption spectra and photochemical reactivity, in combination with a laser source emitting intense UVA light of the adequate wavelength. The present paper presents a new strategy involving absorption of a first UVA photon by an adequate sensitiser followed by triplet energy transfer to a pyrimidine (Pyr) derivative and absorption of a second UVA photon by the resulting Pyr triplet excited state. The feasibility of the proposed strategy has been demonstrated using two model reactions: (i) the Norrish-Yang photocyclisation of a tert-butyluracil and (ii) the photohydration of its uracil analogue, lacking the tert-butyl substituent.
Financial support by the Spanish Government (O. R-A. for FPU14/05294) and Generalitat Valenciana (PROMETEO/2017/075) is gratefully acknowledged. We also thank Dr Lhiaubet-Vallet for her help with the UPLC-MS/MS experiments.