Pentafluorophenyl Platinum(II) Complexes of PTA and Its N-Allyl and N-Benzyl Derivatives: Synthesis, Characterization and Biological Activity
"> Figure 1
<p>New PTA-based pentafluorophenyl Pt(II) complexes <b>2a–c</b>.</p> "> Figure 2
<p>Molecular structure of complex <b>2a</b> with a partial atom labeling scheme. Ellipsoids are drawn at 30% probability level. Selected distances (Å) and angles (°): Pt–P1 2.2788(8), Pt–Cl1 2.3688(12), Pt–C7 2.016(4); P1–Pt1–P1<span class="html-italic"><sup>i</sup></span> 175.15(4), P1–Pt1–Cl1 92.43(2), C7–Pt1–Cl1 180.0 and C7–Pt1–P1 87.57(2). Relevant non-classical hydrogen bond interactions C–H⋅⋅⋅N (represented in dashed light blue color; <span class="html-italic">d</span>(C⋅⋅⋅N) in Å, ∠(C–H⋅⋅⋅N) in °): C3–H3A⋅⋅⋅N3 3.465(4), 144 and C3–H3B⋅⋅⋅N1 3.440(4), 172. Symmetry codes to generate equivalent atoms: (i) 1 − x, y, 1.5 − z; (ii) x, −y, ½ + z; (iii) 1.5 − x, ½ − y, 2 − z; (iv) −1/2 + x, ½ − y, −1/2 + z and (v) 1 − x, −y, 1 − z.</p> "> Figure 3
<p>Fluorescence emission spectra of HSA-<b>2b</b> (left) and -<b>2c</b> (right) systems. Experimental conditions: (1) HSA (10 μM) and (2)–(10) HSA 10 μM with Pt complex at 5, 10, 30, 50, 60, 70, 80, 90 and 100 μM; pH = 7.40, 0.05 M phosphate buffer, incubation at 37 <sup>o</sup>C during 24 h, <span class="html-italic">λ</span><sub>ex</sub> = 295 nm.</p> "> Scheme 1
<p>Synthesis of allyl (<b>1b</b>) and benzyl (<b>1c</b>) PTA derivatives.</p> "> Scheme 2
<p>Synthesis of the pentafluorophenyl Pt(II) complexes <b>2a–c.</b></p> ">
Abstract
:1. Introduction
2. Experimental
2.1. General
2.2. Materials and Methods
2.3. Cell Cultures
2.4. Cell Viability Assays
2.5. Cytotoxic Assay-Quantitative Suspension Test According to EN 14476
2.6. Octanol–Water Partition Coefficient Determination
2.7. HSA Interaction
2.7.1. Fluorescence Measurements
2.7.2. CD Measurement
2.8. Synthesis and Analytical Data
2.9. X-ray Crystallography
3. Results and Discussion
3.1. Synthesis and Characterization
3.2. Biologic Assays
3.3. HSA Interactions
4. Conclusions
Supplementary Materials
Author Contributions
Funding
Acknowledgments
Conflicts of Interest
References
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Formula Unit | C18H24ClF5N6P2Pt |
---|---|
Formula weight | 711.91 |
Crystal system | Monoclinic |
Space group | C2/c |
a (Å) | 19.9537(17) |
b (Å) | 12.2786(9) |
c (Å) | 10.2981(9) |
β (°) | 115.314(5) |
Z | 4 |
Volume (Å3) | 2280.8(3) |
T (K) | 153(2) |
Dc (g cm−3) | 2.073 |
μ (mm−1) | 6.471 |
θmax, θmin (°) | 25.349, 2.589 |
Rfls. total, unique, observed | 10377, 2082, 1928 |
Rint | 0.0383 |
R1 *,wR2 # (I > 2σ(I)) | 0.0183, 0.0427 |
R1, wR2 (all data) | 0.0214, 0.0440 |
GOF | 1.043 |
Entry | Cell Line | 2a | 2b | 2c | 1a [100] | 1b | 1c | Cisplatin [100] |
---|---|---|---|---|---|---|---|---|
1 | NHDF | 26.07 ± 0.68 | 26.91 ± 3.5 | 11.16 ± 3.1 | nda | >263.13 ± 13 | >223.82 ± 5.7 | 16.65 ± 2.1 |
2 | A549 | 15.41 ± 5.3 | 7.79 ± 1.7 | >28.10 ± 1.9 | nda | >263.13 ± 0.42 | >223.82 ± 23 | 33.30 ± 4.2 |
3 | HeLa | >42.14 ± 5.5 | 29.48 ± 1.3 | 8.89 ± 4.1 | nda | 65.78 ± 6.6 | 55.96 ± 16 | 16.65 ± 3.1 |
4 | MCF7 | >42.14 ± 7.9 | >31.00 ± 11 | >28.10 ± 7.3 | nda | >263.13 ± 7.5 | 72.40 ± 2.4 | 33.30 ± 4.2 |
T (K) | KSV (M−1) | Kq (M−1·s−1) | KA (M−1) | n | ||||
---|---|---|---|---|---|---|---|---|
2b | 2c | 2b | 2c | 2b | 2c | 2b | 2c | |
300 | 8.85 × 103 | 1.36 × 104 | 1.77 × 1012 | 2.72 × 1012 | 9.88 × 103 | 1.45 × 104 | 1.26 | 1.25 |
305 | 9.78 × 103 | 1.48 × 104 | 1.96 × 1012 | 2.96 × 1012 | 9.90 × 103 | 1.52 × 104 | 0.96 | 0.99 |
310 | 1.04 × 104 | 1.62 × 104 | 2.08 × 1012 | 3.24 × 1012 | 1.10 × 104 | 1.59 × 104 | 1.24 | 1.59 |
T (K) | ΔH0 (kJ mol−1) | ΔG0 (kJ mol−1) | ΔS0 (J mol−1·K−1) | |||
---|---|---|---|---|---|---|
2b | 2c | 2b | 2c | 2b | 2c | |
300 | 16.8 | 7.15 | −22.7 | −23.9 | 131.4 | 103.5 |
305 | −23.3 | −24.4 |
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Sgarbossa, P.; Śliwińska-Hill, U.; Guedes da Silva, M.F.C.; Bażanów, B.; Pawlak, A.; Jackulak, N.; Poradowski, D.; Pombeiro, A.J.L.; Smoleński, P. Pentafluorophenyl Platinum(II) Complexes of PTA and Its N-Allyl and N-Benzyl Derivatives: Synthesis, Characterization and Biological Activity. Materials 2019, 12, 3907. https://doi.org/10.3390/ma12233907
Sgarbossa P, Śliwińska-Hill U, Guedes da Silva MFC, Bażanów B, Pawlak A, Jackulak N, Poradowski D, Pombeiro AJL, Smoleński P. Pentafluorophenyl Platinum(II) Complexes of PTA and Its N-Allyl and N-Benzyl Derivatives: Synthesis, Characterization and Biological Activity. Materials. 2019; 12(23):3907. https://doi.org/10.3390/ma12233907
Chicago/Turabian StyleSgarbossa, Paolo, Urszula Śliwińska-Hill, M. Fátima C. Guedes da Silva, Barbara Bażanów, Aleksandra Pawlak, Natalia Jackulak, Dominik Poradowski, Armando J. L. Pombeiro, and Piotr Smoleński. 2019. "Pentafluorophenyl Platinum(II) Complexes of PTA and Its N-Allyl and N-Benzyl Derivatives: Synthesis, Characterization and Biological Activity" Materials 12, no. 23: 3907. https://doi.org/10.3390/ma12233907
APA StyleSgarbossa, P., Śliwińska-Hill, U., Guedes da Silva, M. F. C., Bażanów, B., Pawlak, A., Jackulak, N., Poradowski, D., Pombeiro, A. J. L., & Smoleński, P. (2019). Pentafluorophenyl Platinum(II) Complexes of PTA and Its N-Allyl and N-Benzyl Derivatives: Synthesis, Characterization and Biological Activity. Materials, 12(23), 3907. https://doi.org/10.3390/ma12233907