New Look on 3-Hydroxyiminoflavanone and Its Palladium(II) Complex: Crystallographic and Spectroscopic Studies, Theoretical Calculations and Cytotoxic Activity
Abstract
:1. Introduction
2. Results and Discussion
2.1. Synthesis of the Compounds 1 and 2
2.2. Crystallography and Theoretical Calculations
2.3. NMR Spectroscopic Analysis and Solution Stability Studies
2.3.1. Compound 1
2.3.2. Compound 2
2.4. Cytotoxicity Assay (3-(4,5-Dimethylthiazol-2-yl)-2,5-diphenyltetrazolium Bromide or MTT Assay)
3. Materials and Methods
3.1. Synthetic Procedures
3.1.1. Synthesis of Compound 1—(3-Hydroxyminoflavanone or 3-HIF)
3.1.2. Synthesis of Compound 2—[cis-(bis)(3-Nitrosoflavanone)-palladium(II)]
3.2. Crystallography and Theoretical Calculations
3.2.1. X-ray Measurements and Spherical Structure-Refinements (IAM-Independent-Atom Models)
3.2.2. X-ray Wavefunction Refinement (XWR)
3.2.3. Theoretical Calculations
3.2.4. QTAIM (Quantum Theory of Atoms in Molecules) and ELI-D (Electron Localizability Indicator) Analyses
3.3. NMR Spectroscopic Analysis
3.4. Solution Stability Studies: UV-Vis Spectroscopy
3.5. Cell Culture and Cytotoxicity Assay
3.5.1. Cell Culture
3.5.2. Cytotoxicity Assay (3-(4,5-Dimethylthiazol-2-yl)-2,5-diphenyltetrazolium Bromide or MTT Assay)
4. Conclusions
Supplementary Materials
Acknowledgments
Author Contributions
Conflicts of Interest
Abbreviations
1 | 3-hydroxyiminoflavanone |
2 | cis-(bis)(3-nitrosoflavanone)palladium(II) |
CDDP | cis-diaminnadichloridoplatinum(II) or cisplatin |
DMF | N′-N′-dimethylformamide |
DMSO | dimethylsulfoxide |
ELI-D | Electron Localizability Indicator |
HAR | Hirshfeld Atom Refinement |
IAM | Independent Atom Model |
MTT | 3-(4,5-dimethylthiazol-2-yl)-2,5-diphenyltetrazolium bromide |
NAMI-A | New Anti-tumor Metastasis Inhibitor or imidazolium trans-DMSO-imidazole-tetrachlororuthenate(III) |
NMR | Nuclear Magnetic Resonance |
QTAIM | Quantum Theory of Atoms in Molecules |
XWR | X-ray wavefunction refinement |
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1 | 2 | |
---|---|---|
Empirical formula | C15H11NO3 | C30H20N2O6Pd·CHCl3 |
Formula weight | 253.25 | 730.25 |
Crystal system, space group | Monoclinic, P21/n | Triclinic, P |
a, b, c (Å) | 8.6182(17), 5.7715(12), 23.468(5) | 10.3894(7), 10.9265(8), 13.1736(8) |
α, β, γ (°) | 90.00, 94.06(3), 90.00 | 83.848(6), 80.996(5), 86.933(6) |
V (Å3) | 1164.4(4) | 1467.50(17) |
Z | 4 | 2 |
Dx (Mg/m3) | 1.445 | 1.653 |
Crystal size (mm) | 0.25 × 0.06 × 0.03 | 0.24 × 0.13 × 0.07 |
Crystal habit and color | Plate, colorless | Plate, red |
λ (Å) | 0.71073 (MoKα) | 0.71073 (MoKα) |
μ (mm−1) | 0.10 | 0.95 |
T (K) | 100(2) | 100(2) |
Measured/unique reflections | 18731/3055 | 12395/6905 |
Rint | 0.021 | 0.023 |
θ range (°) | 2.5–29.0 | 3.1–28.0 |
Completeness to θmax (%) | 98.9 | 97.2 |
IAM model (spherical) | ||
Observed reflections [I > 2σ(I)] | 2741 | 5695 |
Data/restraints/parameters | 3055/0/176 | 6905/0/429 |
Refinement method | Full-matrix least-squares on F2 | Full-matrix least-squares on F2 |
S | 1.112 | 0.927 |
R [I > 2σ(I)], wR [I > 2σ(I)] | 0.0452, 0.1009 | 0.0257, 0.0517 |
R (all data), wR (all data) | 0.0497, 0.1034 | 0.0351, 0.0527 |
(Δ/σ)max | <0.001 | 0.001 |
Δρmax (eÅ−3), Δρmin (eÅ−3) | 0.40, −0.19 | 0.50, −0.75 |
XWR: HAR model (aspherical) | ||
Refinement method | on F with weight = 1/σ(|F|) | |
Functional/basis-set | blyp/cc-pVTZ | |
Data/restraints/parameters | 2974/0/216 | |
χ2 | 10.17 | |
S | 3.19 | |
R (F), wR (F) | 0.0340, 0.0233 | |
XWR: XCW (fitting procedure) | ||
Refinement method | on F with weight = 1/σ(|F|) | |
Functional/basis-set | blyp/cc-pVTZ | |
Data/restraints/parameters | 2974/0/1 | |
χ2 (λ = 0.10) | 6.42 | |
S | 2.53 | |
R (F), wR (F) | 0.0303, 0.0192 |
Interaction | D-H | H···A | D···A | D-H···A |
---|---|---|---|---|
1 | ||||
O3-H3A···O2 i | 0.96(2) | 2.49(2) | 3.3359(18) | 146(2) |
O3-H3A···N1 i | 0.96(2) | 1.98(2) | 2.7996(18) | 142(2) |
C9-H9···O2 ii | 0.98 | 2.41 | 3.283(2) | 147 |
C3-H3···O2 iii | 0.93 | 2.46 | 3.297(2) | 149 |
C1-H1···Cg ii,b | 0.93 | 2.79 | 3.628(2) | 150 |
2 | ||||
C31-H31···O3 | 0.99(2) | 2.26(2) | 2.990(4) | 130(2) |
C31-H31···O6 | 0.99(2) | 1.29(3) | 2.964(4) | 124(2) |
C26-H26···O2 i | 0.93 | 2.51 | 3.259(2) | 137 |
C27-H27···O3 ii | 0.93 | 2.63 | 3.395(2) | 140 |
Bond | d | ρbcp | ∇2ρbcp | ε | G/ρbcp | H/ρbcp | δ | VELI | ELIpop | Ymax | ΔELI | RJI |
---|---|---|---|---|---|---|---|---|---|---|---|---|
(1-XWR) | ||||||||||||
O1-C5 | 1.3520(6) | 1.94 | −7.6 | 0.04 | 1.15 | −1.43 | 0.96 | 1.16 | 1.39 | 1.56 | 0.06 | 78.4 |
O1-C9 | 1.4405(6) | 1.61 | −9.6 | 0.07 | 0.87 | −1.29 | 0.80 | 1.21 | 1.40 | 1.58 | 0.06 | 82.3 |
O2-C7 | 1.2218(5) | 2.75 | −10.9 | 0.16 | 1.42 | −1.70 | 1.37 | 4.28 | 2.29 | 1.54 | 0.04 | 73.2 |
O3-N1 | 1.3641(5) | 2.24 | −7.6 | 0.03 | 0.67 | −0.90 | 1.34 | 0.56 | 0.99 | 1.46 | 0.02 | 55.0 |
N1-C8 | 1.2856(6) | 2.57 | −22.8 | 0.39 | 0.92 | −1.54 | 1.50 | 6.88 | 3.08 | 1.71 | 0.17 | 69.2 |
C5-C6 | 1.4026(6) | 2.09 | −23.3 | 0.25 | 0.36 | −1.14 | 1.25 | 7.92 | 2.87 | 1.82 | 0.03 | 54.2 |
C6-C7 | 1.4614(7) | 1.96 | −21.7 | 0.12 | 0.27 | −1.05 | 1.04 | 4.84 | 2.38 | 1.95 | 0.01 | 50.8 |
C7-C8 | 1.4839(7) | 1.89 | −20.2 | 0.15 | 0.26 | −1.01 | 0.95 | 5.22 | 2.40 | 1.97 | 0.03 | 52.1 |
C8-C9 | 1.5015(7) | 1.79 | −17.9 | 0.15 | 0.26 | −0.96 | 0.94 | 3.82 | 2.21 | 1.95 | 0.05 | 55.9 |
(2-OPT) | ||||||||||||
N1-Pd1 | 2.032 | 0.80 | 8.2 | 0.07 | 1.07 | −0.36 | 0.76 | 6.42 | 2.53 | 1.77 | 0.09 | 94.5 |
O2-Pd1 | 2.112 | 0.57 | 8.6 | 0.04 | 1.27 | −0.22 | 0.56 | 2.80 | 2.02 | 1.61 | 0.03 | 97.1 |
O1-C5 | 1.364 | 1.97 | −14.1 | 0.05 | 0.95 | −1.45 | 0.97 | 1.23 | 1.47 | 1.59 | 0.05 | 76.1 |
O1-C9 | 1.485 | 1.51 | −11.3 | 0.03 | 0.61 | −1.14 | 0.83 | 1.10 | 1.24 | 1.56 | 0.06 | 76.4 |
O2-C7 | 1.286 | 2.40 | −15.5 | 0.07 | 1.14 | −1.60 | 1.19 | 1.94 | 1.82 | 1.57 | 0.01 | 73.7 |
N1-O3 | 1.249 | 3.15 | −21.7 | 0.06 | 0.74 | −1.22 | 1.66 | 0.90 | 1.50 | 1.50 | 0.02 | 56.8 |
N1-C8 | 1.359 | 2.18 | −19.6 | 0.34 | 0.77 | −1.40 | 1.22 | 3.86 | 2.51 | 1.72 | 0.05 | 75.1 |
C5-C6 | 1.420 | 2.05 | −22.2 | 0.20 | 0.32 | −1.08 | 1.23 | 7.68 | 2.79 | 1.87 | 0.04 | 53.5 |
C7-C6 | 1.458 | 1.92 | −19.8 | 0.14 | 0.27 | −0.99 | 1.07 | 5.57 | 2.46 | 1.95 | 0.03 | 53.2 |
C8-C7 | 1.423 | 2.07 | −22.6 | 0.22 | 0.31 | −1.07 | 1.14 | 10.21 | 3.16 | 1.90 | 0.01 | 56.7 |
C8-C9 | 1.508 | 1.74 | −16.0 | 0.09 | 0.24 | −0.88 | 0.95 | 3.51 | 2.16 | 1.98 | 0.02 | 52.4 |
Cell Line | 1 IC50 (µM) | 1 15 µM (%) a | 2 15 µM (%) a | CDDP 15 µM (%) a | CDDP IC50 (µM) |
---|---|---|---|---|---|
A2780 | 57 ± 3 | ni | 54 ± 9 b | <10 c | 0.6 ± 0.03 |
A2780cis | 50 ± 6 | ni | 65 ± 3 | 65 ± 1 | 20.2 ± 0.7 |
A549 | 79 ± 13 | ni | 71 ± 13 b | 21 ± 1.5 | 3.9 ± 0.5 |
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Kasprzak, M.; Fabijańska, M.; Chęcińska, L.; Szmigiero, L.; Ochocki, J. New Look on 3-Hydroxyiminoflavanone and Its Palladium(II) Complex: Crystallographic and Spectroscopic Studies, Theoretical Calculations and Cytotoxic Activity. Molecules 2016, 21, 455. https://doi.org/10.3390/molecules21040455
Kasprzak M, Fabijańska M, Chęcińska L, Szmigiero L, Ochocki J. New Look on 3-Hydroxyiminoflavanone and Its Palladium(II) Complex: Crystallographic and Spectroscopic Studies, Theoretical Calculations and Cytotoxic Activity. Molecules. 2016; 21(4):455. https://doi.org/10.3390/molecules21040455
Chicago/Turabian StyleKasprzak, Maria, Małgorzata Fabijańska, Lilianna Chęcińska, Leszek Szmigiero, and Justyn Ochocki. 2016. "New Look on 3-Hydroxyiminoflavanone and Its Palladium(II) Complex: Crystallographic and Spectroscopic Studies, Theoretical Calculations and Cytotoxic Activity" Molecules 21, no. 4: 455. https://doi.org/10.3390/molecules21040455