TY - JOUR A1 - Jabłoński, Artur A1 - Fritz, Yannic A1 - Wagenknecht, Hans-Achim A1 - Czerwieniec, Rafał A1 - Bernaś, Tytus A1 - Trzybiński, Damian A1 - Woźniak, Krzysztof A1 - Kowalski, Konrad T1 - Pyrene–nucleobase conjugates: synthesis, oligonucleotide binding and confocal bioimaging studies JF - Beilstein Journal of Organic Chemistry PY - 2017/// VL - 13 SP - 2521 EP - 2534 SN - 1860-5397 DO - 10.3762/bjoc.13.249 PB - Beilstein-Institut JA - Beilstein J. Org. Chem. UR - https://doi.org/10.3762/bjoc.13.249 KW - confocal microscopy KW - luminescence KW - nucleobases KW - oligonucleotide binding KW - pyrene KW - X-ray N2 - Fluorescent pyrene–linker–nucleobase (nucleobase = thymine, adenine) conjugates with carbonyl and hydroxy functionalities in the linker were synthesized and characterized. X-ray single-crystal structure analysis performed for the pyrene–C(O)CH2CH2–thymine (2) conjugate reveals dimers of molecules 2 stabilized by hydrogen bonds between the thymine moieties. The photochemical characterization showed structure-dependent fluorescence properties of the investigated compounds. The conjugates bearing a carbonyl function represent weak emitters as compared to compounds with a hydroxy function in the linker. The self-assembly properties of pyrene nucleobases were investigated in respect to their binding to single and double strand oligonucleotides in water and in buffer solution. In respect to the complementary oligothymidine T10 template in water, compounds 3 and 5 both show a self-assembling behavior according to canonical base–base pairing. However, in buffer solution, derivative 5 was much more effective than 3 in binding to the T10 template. Furthermore the adenine derivative 5 binds to the double-stranded (dA)10–T10 template with a self-assembly ratio of 112%. Such a high value of a self-assembly ratio can be rationalized by a triple-helix-like binding, intercalation, or a mixture of both. Remarkably, compound 5 also shows dual staining pattern in living HeLa cells. Confocal microscopy confirmed that 5 predominantly stains mitochondria but it also accumulates in the nucleoli of the cells. ER -