Design, Synthesis, and Anti-Cancer Evaluation of Novel Water-Soluble Copper(I) Complexes Bearing Terpyridine and PTA Ligands
Abstract
:1. Introduction
2. Results and Discussion
2.1. Synthesis and Characterization
2.2. Crystal Structure of 2
2.3. Cytotoxic Activity
2.4. Apo-Transferrin Interactions
3. Materials and Methods
3.1. Chemicals
3.2. Synthesis of 1 and 2
3.3. X-ray Crystallography
3.4. X-ray Crystal Structure Determination
3.5. Cell Cultures
3.6. Cytotoxicity Assay
3.7. Apo-Transferrin Interactions
3.7.1. Fluorescence Measurements
3.7.2. Circular Dichroism Spectroscopy
3.7.3. Zeta Potential Measurements
4. Conclusions
Supplementary Materials
Author Contributions
Funding
Institutional Review Board Statement
Informed Consent Statement
Data Availability Statement
Acknowledgments
Conflicts of Interest
References
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Bond Distances [Å] | Valence Angles [°] | ||
---|---|---|---|
Cu1-P11 | 2.1854(5) | P11-Cu1-P21 | 119.48(2) |
Cu1-P21 | 2.2126(5) | P11-Cu1-N31 | 118.43(5) |
Cu1-N31 | 2.0785(16) | P11-Cu1-N41 | 117.71(5) |
Cu1-N41 | 2.0674(15) | P21-Cu1-N31 | 104.86(5) |
P21-Cu1-N41 | 109.43(5) | ||
N31-Cu1-N41 | 79.87(6) |
Formula | C27H35CuF6N9P3 |
---|---|
Moiety formula | [Cu(C15H11N3){P(CH2)6N3}2][PF6] |
FW [g·mol−1] | 756.09 |
T [K] | 100(2) |
Wavelength [Å] | 1.54184 |
Cryst. Syst. | Monoclinic |
Space group | P21/n |
a [Å] | 10.4364(3) |
b [Å] | 13.7629(4) |
c [Å] | 21.5413(5) |
β [°] | 98.343(3) |
V [Å3] | 3061.34(15) |
Z | 4 |
Calc d [g·cm−3] | 1.640 |
µ [mm−1] | 3.150 |
Tmin/Tmax | 0.706/0.860 |
θ range [°] | 3.823–75.785 |
Reflns collected | 30003 |
Indep refunds (Rint) | 6287 (0.0195) |
GOF on F2 | 1.057 |
Final R1/wR2 indices | 0.0331/0.0877 |
CCDC No. | 2291627 |
THCDA/100 [43] | FCGP/100 [44] | τ4 [45] | |
---|---|---|---|
Tetrahedron | 1.00 | 0.00 | 1.00 |
Trigonal pyramid | 0.00 | 1.00 | 0.85 |
[Cu(terpy)(PTA)2]+ | 0.32 | 0.45 | 0.87 |
Cell Line | 1 | 2 | [Cu(MeCN)4][PF6] | terpy | PTA | [Ag(terpy)(PTA)][NO3] [30] | Cisplatin [30] |
---|---|---|---|---|---|---|---|
NHDF | 152.36 ± 2.82 | 171.72 ± 4.77 | 24.75 ± 3.64 | 1.71 ± 0.95 | 127.39 ± 7.84 | 50.07 ± 4.74 | 16.65 ± 2.17 |
A549 | 0.64 ± 0.35 | 49.87 ± 1.14 | 0.89 ± 1.14 | 0.75 ± 0.23 | 141.84 ± 3.62 | 1.67 ± 2.53 | 33.30 ± 4.23 |
HeLa | 0.31 ± 0.61 | 5.09 ± 0.79 | 5.02 ± 1.72 | 0.33 ± 0.41 | 110.73 ± 4.77 | 1.67 ± 3.21 | 16.65 ± 3.19 |
MCF-7 | 1.29 ± 2.47 | 0.23 ± 1.39 | 22.02 ± 2.49 | 0.38 ± 0.17 | 148.19 ± 7.43 | 26.75 ± 2.81 | 33.30 ± 4.28 |
Compound | T [K] | Ksv [M−1] | Kq [M−1s−1] | Ka [M−1] | n | ∆H [kJ/mol] | ∆S [J/mol] | ∆G [kJ/mol] |
---|---|---|---|---|---|---|---|---|
1 | 300 | 6.26 × 103 | 2.50 × 1012 | 5.39 × 105 | 1.25 | −69.30 | −121.28 | −32.92 |
310 | 2.26 × 104 | 9.02 × 1012 | 2.20 × 105 | 1.16 | −31.70 | |||
2 | 300 | 4.86 × 103 | 1.94 × 1012 | 1.08 × 106 | 1.34 | −141.20 | −355.17 | −34.65 |
310 | 1.40 × 104 | 5.60 × 1012 | 1.74 × 105 | 1.16 | −31.10 |
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Smoleński, P.; Śliwińska-Hill, U.; Kwiecień, A.; Wolińska, J.; Poradowski, D. Design, Synthesis, and Anti-Cancer Evaluation of Novel Water-Soluble Copper(I) Complexes Bearing Terpyridine and PTA Ligands. Molecules 2024, 29, 945. https://doi.org/10.3390/molecules29050945
Smoleński P, Śliwińska-Hill U, Kwiecień A, Wolińska J, Poradowski D. Design, Synthesis, and Anti-Cancer Evaluation of Novel Water-Soluble Copper(I) Complexes Bearing Terpyridine and PTA Ligands. Molecules. 2024; 29(5):945. https://doi.org/10.3390/molecules29050945
Chicago/Turabian StyleSmoleński, Piotr, Urszula Śliwińska-Hill, Anna Kwiecień, Joanna Wolińska, and Dominik Poradowski. 2024. "Design, Synthesis, and Anti-Cancer Evaluation of Novel Water-Soluble Copper(I) Complexes Bearing Terpyridine and PTA Ligands" Molecules 29, no. 5: 945. https://doi.org/10.3390/molecules29050945