UV-induced electron transfer between triethylamine and 5-bromo-2′-deoxyuridine. A puzzle concerning the photochemical debromination of labeled DNA

Paweł Wityk , Magdalena Zdrowowicz , Justyna Wiczk , Janusz Rak

Abstract

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.
Autor Paweł Wityk (WCh / KChF / PSB)
Paweł Wityk
- Pracownia Sensybilizatorów Biologicznych
, Magdalena Zdrowowicz (WCh / KChF / PSB)
Magdalena Zdrowowicz
- Pracownia Sensybilizatorów Biologicznych
, Justyna Wiczk (WCh / KChF / PSB)
Justyna Wiczk
- Pracownia Sensybilizatorów Biologicznych
, Janusz Rak (WCh / KChF / PSB)
Janusz Rak
- Pracownia Sensybilizatorów Biologicznych
Inne wersje tytułu
Tytuł czasopisma/seriiJournal of Pharmaceutical and Biomedical Analysis, ISSN 0731-7085, (A 35 pkt)
Rok wydania2017
Tom142
Paginacja262-269
Objętość publikacji w arkuszach wydawniczych0.5
Słowa kluczowe w języku angielskimtriethylamine, photoinduced electron transfer, synthetic oligonucleotides, mass spectrometry, debromination, strand break
Klasyfikacja ASJC1308 Clinical Biochemistry; 1607 Spectroscopy; 3002 Drug Discovery; 3003 Pharmaceutical Science; 1602 Analytical Chemistry
DOIDOI:10.1016/j.jpba.2017.04.044
URL https://doi.org/10.1016/j.jpba.2017.04.044
Języken angielski
Punktacja (całkowita)35
PunktacjaPunktacja MNiSW = 35.0, 24-07-2019, ArticleFromJournal
Wskaźniki publikacji Scopus SNIP (Source Normalised Impact per Paper): 2017 = 1.179; Impact Factor WoS: 2017 = 2.831 (2) - 2017=2.863 (5)
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