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摘要
<jats:p>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)CH<jats:sub>2</jats:sub>CH<jats:sub>2</jats:sub>–thymine (<jats:bold>2</jats:bold>) conjugate reveals dimers of molecules <jats:bold>2</jats:bold> 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 T<jats:sub>10</jats:sub> template in water, compounds <jats:bold>3</jats:bold> and <jats:bold>5</jats:bold> both show a self-assembling behavior according to canonical base–base pairing. However, in buffer solution, derivative <jats:bold>5</jats:bold> was much more effective than <jats:bold>3</jats:bold> in binding to the T<jats:sub>10</jats:sub> template. Furthermore the adenine derivative <jats:bold>5</jats:bold> binds to the double-stranded (dA)<jats:sub>10</jats:sub>–T<jats:sub>10</jats:sub> 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 <jats:bold>5</jats:bold> also shows dual staining pattern in living HeLa cells. Confocal microscopy confirmed that <jats:bold>5</jats:bold> predominantly stains mitochondria but it also accumulates in the nucleoli of the cells.</jats:p>
- 出版日期2017-11-28
