TY - JOUR

T1 - Anthracene-thymine luminophores: Synthesis, photophysical properties, and imaging in living HeLa cells

AU - Jabłoński, Artur

AU - Kowalczyk, Aleksandra

AU - Fik, Marta A.

AU - Trzybiński, Damian

AU - Woźniak, Krzysztof

AU - Vinogradova, Katerina

AU - Glińska, Sława

AU - Vrček, Valerije

AU - Czerwieniec, Rafał

AU - Kowalski, Konrad

N1 - Publisher Copyright: © 2019 Elsevier Ltd

PY - 2019/11/1

Y1 - 2019/11/1

N2 - This paper presents a report of the synthesis and chemical transformations of anthracene-thymine and 4-thiothymine derivatives. In a reaction of 1-(anthracen-9-yl)-1-hydroxy-3-(N1-thyminyl)-propane with ethylene glycol either an elimination or substitution product is preferentially formed depending on reaction conditions. In the presence of Yb(OTf) 3 , the elimination product was the major one; while in the absence of Yb(OTf) 3 , the substitution reaction product prevailed. Thus, six fluorescent nucleic base derivatives were obtained. The three anthracene-thymine derivatives (2, 3, and 4) show strong fluorescence with emission quantum yields from 65% to about 100% in solution at ambient temperature. The emission of anthracene-thymine 1 and two anthracene-thiothymines is weaker due to the carbonyl substituents and the sulphur atom of thiothymine. Tests of antiproliferative activity on human cancer HeLa cells performed at 24 h and 5 h treatment times, respectively, revealed no detectable toxicity at the latter interval. Thus, confocal microscopy imaging studies were carried out on HeLa cells at 5 h incubation time. All six compounds under study were found in the interior of the cells, albeit the intensity of the compounds’ luminescence stemming from the interiors was different. All compounds localised in the lipid membranes of cytoplasmic compartments in general follow the same staining pattern. In addition, compounds 3 and 6 were also detected in the nucleus. Notably, no signs of photocytotoxicity or photobleaching in the timespan of imaging studies were observed. The new fluorescent nucleic base derivatives represent attractive leading structures for the development of preferably more selective luminescent probes in the future.

AB - This paper presents a report of the synthesis and chemical transformations of anthracene-thymine and 4-thiothymine derivatives. In a reaction of 1-(anthracen-9-yl)-1-hydroxy-3-(N1-thyminyl)-propane with ethylene glycol either an elimination or substitution product is preferentially formed depending on reaction conditions. In the presence of Yb(OTf) 3 , the elimination product was the major one; while in the absence of Yb(OTf) 3 , the substitution reaction product prevailed. Thus, six fluorescent nucleic base derivatives were obtained. The three anthracene-thymine derivatives (2, 3, and 4) show strong fluorescence with emission quantum yields from 65% to about 100% in solution at ambient temperature. The emission of anthracene-thymine 1 and two anthracene-thiothymines is weaker due to the carbonyl substituents and the sulphur atom of thiothymine. Tests of antiproliferative activity on human cancer HeLa cells performed at 24 h and 5 h treatment times, respectively, revealed no detectable toxicity at the latter interval. Thus, confocal microscopy imaging studies were carried out on HeLa cells at 5 h incubation time. All six compounds under study were found in the interior of the cells, albeit the intensity of the compounds’ luminescence stemming from the interiors was different. All compounds localised in the lipid membranes of cytoplasmic compartments in general follow the same staining pattern. In addition, compounds 3 and 6 were also detected in the nucleus. Notably, no signs of photocytotoxicity or photobleaching in the timespan of imaging studies were observed. The new fluorescent nucleic base derivatives represent attractive leading structures for the development of preferably more selective luminescent probes in the future.

KW - Anthracene

KW - Bioimaging

KW - Luminescence

KW - Nucleic bases

KW - DNA-BINDING

KW - SPECIFICITY

KW - DERIVATIVES

KW - OLIGONUCLEOTIDES

KW - PROBES

UR - http://www.scopus.com/inward/record.url?scp=85065736654&partnerID=8YFLogxK

U2 - 10.1016/j.dyepig.2019.107554

DO - 10.1016/j.dyepig.2019.107554

M3 - Article

AN - SCOPUS:85065736654

VL - 170

JO - Dyes and Pigments

JF - Dyes and Pigments

SN - 0143-7208

M1 - 107554

ER -