UV-induced electron transfer between triethylamine and 5-bromo-2′-deoxyuridine. A puzzle concerning the photochemical debromination of labeled DNA
PBN-AR
Instytucja
Wydział Chemii (Uniwersytet Gdański)
Źródłowe zdarzenia ewaluacyjne
Informacje podstawowe
Główny język publikacji
en
Czasopismo
Journal of Pharmaceutical and Biomedical Analysis (35pkt w roku publikacji)
ISSN
0731-7085
EISSN
1873-264X
Wydawca
Elsevier BV
DOI
Rok publikacji
2017
Numer zeszytu
Strony od-do
262-269
Numer tomu
142
Identyfikator DOI
Liczba arkuszy
0.5
Słowa kluczowe
en
triethylamine
photoinduced electron transfer
synthetic oligonucleotides
mass spectrometry
debromination
strand break
Streszczenia
Język
en
Treść
5-Bromo-2′-deoxyuridine (BrdU) photosensitizes DNA to strand break formation. However, this type of photodamage is completely quenched by the presence of triethylamine (TEA) which originates from RP-HPLC purification commonly employed by oligonucleotide providers. While the presence of TEA in oligonucleotide samples does not interfere with PCR or other molecular biology applications, the mechanism of photochemical reaction proceeding in the labeled DNA is dramatically changed due to the photoinduced electron transfer (PET) between the photoexcited BrdU and the ground state TEA. For the first time, we demonstrated that the latter process produces 2′-deoxyuridne2′-deoxyuridine (debromination) in the labeled DNA instead of the expected strand break. PET between TEA and BrdU was additionally confirmed by the UV irradiations of aqueous solutions containing both species. Indeed, the efficient formation of 2′-deoxyuridine was observed in the studied photolytes. Moreover, we showed the formation of an additional product in these binary mixtures, i.e. imidazole derivative, that is not formed in DNA and was reported in the literature in the context of dark rather than photochemical processes. Using mass spectrometry we demonstrated that the amount of TEA impurity in the commercial samples of oligos exceeds up to 3 orders of magnitude that of the purchased DNA.
Inne
System-identifier
UOG5cf4c225c1e34e4896145ab794c0b908
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