Amphiphilicity-Controlled Localization of Red Emitting Bicationic Fluorophores in Tumor Cells Acting as Bio-Probes and Anticancer Drugs
Abstract
:1. Introduction
2. Results
2.1. Spectrophotometric and Fluorimetric Investigation of the Interaction with Nucleic Acids
2.2. Femtosecond Transient Absorption Spectroscopy of Complexes with Nucleic Acids
2.3. Antiproliferative Effect and Cellular Localization in Tumor Cells
3. Discussion
4. Materials and Methods
4.1. Materials
4.2. Spectroscopic Titrations
4.3. TA Measurements
4.4. Cell Culture
4.5. Antiproliferative Assay
4.6. Fluorescence Microscopy
5. Conclusions
Supplementary Materials
Author Contributions
Funding
Data Availability Statement
Conflicts of Interest
Sample Availability
References
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Comp. | W | tRNA | ct-DNA | |||||||||||
---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|
λabs/ nm | λem/ nm | Δν/ cm−1 | ΦF | λabs/ nm | λem/nm | ΦF | Δν/ cm−1 | r | λabs/ nm | λem/ nm | ΦF | Δν/ cm−1 | r | |
1 | 352, 427 | 583 | 6270 | 0.16 | 368, 467 | 577 | 0.025 | 4080 | 0.0052 | 365, 464 | 578 | 0.084 | 4250 | 0.0075 |
2 | 359, 446 | 605 | 5890 | 0.36 | 372, 471 377, 488 | 600 595 | 0.066 0.12 | 4560 3690 | 0.081 0.0027 | 374, 481 | 591 | 0.17 | 3870 | 0.0081 |
3 | 393, 485 | 680 | 5910 | 0.010 | 407, 524 | 655 | 0.028 | 3820 | 0.0028 | 405, 520 | 645 | 0.058 | 3730 | 0.0050 |
4 | 389, 498 | 710 | 6000 | 0.003 | 408, 543 | 680 | 0.0068 | 3710 | 0.0025 | 405, 532 | 670 | 0.012 | 3870 | 0.0040 |
5 | 464 | 600 | 4890 | 0.026 | 495 | 615 | 0.057 | 3940 | 0.0036 | 486 | 595 | 0.10 | 3770 | 0.0025 |
6 | 540 | 700 | 4230 | 0.058 | 500 571 | 665 705 | 0.002 0.018 | 4960 3330 | 0.63 0.0028 | 567 | 700 | 0.56 | 3350 | 0.0017 |
Compound | tRNA | ct-DNA |
---|---|---|
logK | logK | |
1 | 5.49 ± 0.06 | 7.11 ± 0.04 |
2 | 6.4 ± 0.2 4.3 ± 0.5 | 6.85 ± 0.04 |
3 | 5.2 ± 0.1 | 4.66 ± 0.09 |
4 | 4.4 ± 0.3 | 4.5 ± 0.1 |
5 | 5.19 ± 0.07 | 5.0 ± 0.1 |
6 | 8.0 ± 0.8 4.4 ± 0.2 | 5.3 ± 0.3 |
Compound | Free (W) a | tRNA | ct-DNA | Assignment |
---|---|---|---|---|
τ (ps) | ||||
1 b | 0.79 | 0.74 | 2.0 | Solv. |
6.1 | Solv./VR | |||
8.0 | 8.1 | S1 (Complex) | ||
190 | 72 | 51 | CR | |
1100 | S1 (Complex) | |||
2700 | S1 (Free) | |||
1600 | 3500 | S1 (Complex) | ||
2 b | 0.60 | 0.13 | Solv. | |
1.1 | 1.7 | Solv. | ||
5.2 | 12 | Solv./VR | ||
57 | 68 | S1 (Complex) | ||
190 | CR | |||
1500 | 1200 | S1 (Free) | ||
1200 | 4500 | S1 (Complex) | ||
3 | 0.22 | Solv. | ||
1.7 | 2.2 | 2.6 | Solv. | |
23 | 32 | 57 | CR | |
110 | S1 (Free) | |||
300 | 770 | S1 (Complex) | ||
4 | 0.90 | 0.78 | Solv. | |
3.3 | 4.4 | 2.1 | Solv. | |
25 | 20 | CR | ||
39 | S1 (Free) | |||
240 | 270 | S1 (Complex) | ||
Inf | T1 | |||
5 | 0.66 | Solv. | ||
4.9 | 2.6 | 2.9 | Solv. | |
38 | 55 | CR | ||
92 | S1 (Free) | |||
300 | 310 | S1 (Complex) | ||
Inf | Inf | Inf | T1 | |
6 | 0.53 | 1.2 | Solv. | |
19 | 7.0 | Solv./VR | ||
160 | 60 | 330 | CR | |
910 | S1 (Free) | |||
260 | 3600 | S1 (Complex) | ||
Inf | T1 |
Compound | IC50/µM | ||||||
---|---|---|---|---|---|---|---|
Cell | 1 | 2 | 3 | 4 | 5 | 6 | |
A549 | - | >100 | 12 ± 2 | - | 27 ± 9 | 19 ± 5 | |
HeLa | - | 53 ± 2 | 1.7 ± 0.1 | 13 ± 2 | 18 ± 6 | 0.7 ± 0.2 |
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Cesaretti, A.; Mencaroni, L.; Bonaccorso, C.; Botti, V.; Calzoni, E.; Carlotti, B.; Fortuna, C.G.; Montegiove, N.; Spalletti, A.; Elisei, F. Amphiphilicity-Controlled Localization of Red Emitting Bicationic Fluorophores in Tumor Cells Acting as Bio-Probes and Anticancer Drugs. Molecules 2022, 27, 3713. https://doi.org/10.3390/molecules27123713
Cesaretti A, Mencaroni L, Bonaccorso C, Botti V, Calzoni E, Carlotti B, Fortuna CG, Montegiove N, Spalletti A, Elisei F. Amphiphilicity-Controlled Localization of Red Emitting Bicationic Fluorophores in Tumor Cells Acting as Bio-Probes and Anticancer Drugs. Molecules. 2022; 27(12):3713. https://doi.org/10.3390/molecules27123713
Chicago/Turabian StyleCesaretti, Alessio, Letizia Mencaroni, Carmela Bonaccorso, Valentina Botti, Eleonora Calzoni, Benedetta Carlotti, Cosimo Gianluca Fortuna, Nicolò Montegiove, Anna Spalletti, and Fausto Elisei. 2022. "Amphiphilicity-Controlled Localization of Red Emitting Bicationic Fluorophores in Tumor Cells Acting as Bio-Probes and Anticancer Drugs" Molecules 27, no. 12: 3713. https://doi.org/10.3390/molecules27123713