Trimeric and Tetrameric Cationic Styryl Dyes as Novel Fluorescence and CD Probes for ds-DNA and ds-RNA
Abstract
:1. Introduction
- (a)
- multiplicity of styryl motif through attaching three or four styryl moieties to one central aromatic core;
- (b)
- type of positive charge by comparing heterocyclic cationic species with exocyclic per-alkylated amines;
- (c)
- steric shielding of positive charge by the introduction of smaller or larger alkylating groups.
2. Results and Discussion
2.1. Synthesis
2.2. Photophysical Studies of the New Dyes in Aqueous Solutions
2.3. Interactions of New Dyes with ds-DNA and ds-RNA
2.3.1. Thermal Denaturation of ds-DNA/RNA
2.3.2. Spectrophotometric Titrations of the New Dyes with Polynucleotides
2.3.3. Circular Dichroism (CD) Experiments
2.4. Biological Experiments
Confocal Microscopy
3. Materials and Methods
3.1. General
3.2. Synthesis
3.3. Spectrophotometric Characterization
3.4. Study of DNA/RNA Interactions
3.5. Biology
4. Conclusions
Supplementary Materials
Author Contributions
Funding
Institutional Review Board Statement
Informed Consent Statement
Data Availability Statement
Conflicts of Interest
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Compd. | maxλabs/[nm] (ε × 103/[M−1 cm−1]) | b Φf | a λexc [nm] | λem [nm] | a τ [ns] | χ2 |
---|---|---|---|---|---|---|
T1 | 314 (91.5) | 0.27 ± 0.05 | 340 | 412 | 10.68 (14.04%) 20.33 (85.96%) | 0.960 |
T2 | 315 (80.0) | 0.41 ± 0.05 | 340 | 480 | 13.05 (33.74%) 21.50 (66.26%) | 0.918 |
T3 | 348 (88.8) | 0.04 ± 0.05 | 340 | 454 | 0.78 (90.42%) 5.03 (9.58%) | 1.055 |
T4 | 314 (86.3) | 0.37 ± 0.05 | 340 | 411 | 10.67 (18.28%) 20.24 (81.72%) | 0.931 |
T5 | 348 (79.5) | 0.29 ± 0.05 | 340 | 448 | 0.69 (98.06%) 4.55 (1.94%) | 1.062 |
F1 | 333 (75.4) | 0.57 ± 0.05 | 340 | 460 | 2.89 (21.82%) 7.03 (78.18%) | 0.941 |
F2 | 335 (66.5) | 0.20 ± 0.05 | 340 | 460 | 2.55 (20.77%) 6.69 (79.23%) | 1.050 |
F3 | 366 (83.0) | 0.07 ± 0.05 | 340 | 485 | 0.64 (59.91%) 3.56 (40.09%) | 0.963 |
F4 | 334 (60.6) | 0.35 ± 0.05 | 340 | 460 | 2.60 (28.08%) 6.58 (71.92%) | 0.985 |
F5 | 366 (53.8) | 0.06 ± 0.05 | 340 | 485 | 0.68 (55.54%) 3.63 (44.46%) | 0.906 |
c dimer | 446 (35.0) | 0.21 ± 0.05 | 457 | 605 | 0.19 (21%) 1.60 (79%) | 0.98 < χ2 < 1.02 |
Compd. | ctDNA | pApU |
---|---|---|
T1 | +11.9 | +23.2 |
T2 | +6.2 | +5.1 |
T3 | >+15.0 | +8.5 |
T4 | +12.0 | +18.1 |
T5 | +14.3 | +1.5 |
F1 | >+15.0 | +12.5 |
F2 | 0 | 0 |
F3 | +6.6 | +6.4 |
F4 | +4.8 | +10.4 |
F5 | +3.2 | +1.7 |
b dimer | +3.1 | +1.8 |
Compd. | ctDNA | pApU |
---|---|---|
T1 | 8.6 (0.23) | 8.9 (0.30) |
T2 | 8.6 (0.04) | 8.9 (0.16) |
T3 | 8.2 (0.24) | 8.7 (0.13) |
T4 | 8.9 (0.10) | 8.6 (0.35) |
T5 | 8.9 (0.10) | 8.7 (0.14) |
F1 | 9.3 (0.17) | 8.6 (0.17) |
F2 | 8.0 (0.09) | 8.6 (0.08) |
F3 | 7.1 (0.11) | 8.2 (0.28) |
F4 | 8.6 (0.17) | 8.9 (0.17) |
F5 | 8.9 (0.30) | 7.6 (0.26) |
c dimer | 6.9 (0.80) | 7.5 (0.5) |
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Pavlović Saftić, D.; Krošl Knežević, I.; de Lera Garrido, F.; Tolosa, J.; Majhen, D.; Piantanida, I.; García Martínez, J.C. Trimeric and Tetrameric Cationic Styryl Dyes as Novel Fluorescence and CD Probes for ds-DNA and ds-RNA. Int. J. Mol. Sci. 2024, 25, 5724. https://doi.org/10.3390/ijms25115724
Pavlović Saftić D, Krošl Knežević I, de Lera Garrido F, Tolosa J, Majhen D, Piantanida I, García Martínez JC. Trimeric and Tetrameric Cationic Styryl Dyes as Novel Fluorescence and CD Probes for ds-DNA and ds-RNA. International Journal of Molecular Sciences. 2024; 25(11):5724. https://doi.org/10.3390/ijms25115724
Chicago/Turabian StylePavlović Saftić, Dijana, Ivona Krošl Knežević, Fernando de Lera Garrido, Juan Tolosa, Dragomira Majhen, Ivo Piantanida, and Joaquín Calixto García Martínez. 2024. "Trimeric and Tetrameric Cationic Styryl Dyes as Novel Fluorescence and CD Probes for ds-DNA and ds-RNA" International Journal of Molecular Sciences 25, no. 11: 5724. https://doi.org/10.3390/ijms25115724