Synthesis, Crystal Structure, and Cytotoxic Activity of a Novel Eight-Coordinated Dinuclear Ca(II)-Schiff Base Complex
College of Chemistry and Chemical Engineering, Weifang University, Weifang 261061, China
*
Author to whom correspondence should be addressed.
Crystals 2016, 6(9), 109; https://doi.org/10.3390/cryst6090109
Submission received: 14 July 2016
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Revised: 1 September 2016
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Accepted: 5 September 2016
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Published: 7 September 2016
(This article belongs to the Section Biomolecular Crystals)
Abstract
:A novel eight-coordinated dinuclear Ca(II) complex, [Ca2(L)2(H2O)10]·H2O (L = 4-formylbenzene-1,3-disulfonate-3-pyridinecarboxylic hydrazone) (1), was synthesized by the reaction of 3-pyridinecarboxylic hydrazide, disodium 4-formylbenzene-1,3-disulfonate, and Ca(ClO4)2·4H2O in ethanol-water solution (v:v = 3:1) at 50 °C. Complex 1 was characterized by elemental analysis, IR, 1H-NMR, 13C-NMR, and X-ray single crystal diffraction analysis. Dinuclear Ca(II) complex 1 belongs to triclinic, space group P-1 with a = 7.186(3) Å, b = 11.978(5) Å, c = 12.263(5) Å, α = 90.318(5)°, β = 91.922(5)°, γ = 96.797(5)°, V = 1047.5(8) Å3, Z = 1, Dc = 1.685 mg·m−3, μ = 0.572 mm−1, F(000) = 552, and final R1 = 0.0308, ωR2 = 0.0770. Dinuclear Ca(II) molecules form a 1D chained structure by π–π stacking interaction. The 1D chains form a 3D framework structure by the π–π stacking interaction and hydrogen bonds. The in vitro cytotoxic activity activity of 1 against HL-60 and MLTC-1 was also investigated.
1. Introduction
The biological activities of metal complexes have been a hot research topic since cisplatin was used as an antitumor drug. Many metal complexes with transition metals as center ions show excellent antibacterial and antitumor activities, such as Cu(II) [1,2,3], Zn(II) [4,5,6], Mn(II) [7,8,9], Ni(II) [10,11,12], Ag(I) [13,14,15], and so on. Meanwhile, hydrazone compounds also exhibit good biological activities and are a kind of good ligand [16,17,18]. Hence, the design and synthesis of novel hydrazone compounds and their transition metal complexes have received more attention. However, compared with transition metal complexes, the studies on the antibacterial and antitumor activities of Ca(II) complexes are rare. The investigations of the synthesis and properties of Ca(II) complexes have always been one of our goals [19,20,21,22,23,24,25]. In this work, we synthesized a novel eight-coordinated dinuclear Ca(II) complex, [Ca2(L)2(H2O)10]·H2O (1), by the reaction of 3-pyridinecarboxylic hydrazide, disodium 4-formylbenzene-1,3-disulfonate, and Ca(ClO4)2·4H2O. Complex 1 was characterized by elemental analysis, IR spectrum, 1H-NMR, 13C-NMR, and single crystal X-ray crystallography. The in vitro cytotoxic activity of 1 against HL-60 and MLTC-1 was also investigated.
2. Results and Discussion
2.1. Properties of 1
The data of elemental analysis for C, H, and N are C, 29.35; H, 3.95; N, 7.90% (Calcd.); C, 29.17; H, 4.28; N, 7.75% (Found). Thus, the dinuclear Ca(II) complex conforms to the formula C26H42Ca2N6O26S4.
The dinuclear Ca(II) complex are soluble in DMF, DMSO, H2O, and CH3OH, insoluble in THF, CHCl3, and benzene.
2.2. IR Spectrum of 1
The IR spectrum of the dinuclear Ca(II) complex is shown in Figure 1. The strong peak at 3473 cm−1 corresponds to the ν(OH) vibration of H2O molecules in 1. The peaks at 1683 cm−1 and 1561 cm−1 can be assigned to ν(C=O) and ν(C=N), showing that the C=O and C=N groups do not coordinate to Ca(II) ion [26]. The peaks at 1253 cm−1 and 1,192 cm−1 demonstrate the existence of coordination bonds between SO3− groups and Ca(II) [27].
2.3. 1HNMR and 13CNMR Spectra of 1
The 1HNMR and 13CNMR data of dinuclear Ca(II) complex are as follows: 1H NMR (400 MHz, DMSO-d6): δ 12.10 (s, 1 H, CONH), 9.37 (s, 1 H, N=CH), 8.71 (d, J = 4.8 Hz, 1 H, H-C11A of pyridine), 8.03–8.15 (m, 3 H, H-C10A, H-C12A, H-C13A of pyridine), 7.96 (d, J = 8.0 Hz, H-C6A of Ph), 7.65–7.68 (m, 2 H,H-C3A, H-C2A of Ph). 13C NMR (100 MHz, DMSO-d6): δ 161.07 (C8A), 150.14 (C1A), 149.38 (C10A), 148.99 (C11A), 148.57 (C5A), 146.90 (C7A), 138.35 (C2A), 131.67 (C4A), 127.36 (C9A), 126.29 (C13A), 126.04 (C6A), 124.97 (C12A), 123.00 (C3A).
2.4. Description of 1
The result of X-ray single-crystal diffraction reveals that the novel eight-coordinated dinuclear Ca(II) complex 1 crystallizes in a triclinic P-1 space group. The coordination environment of Ca(II) of 1 is shown in Figure 2. From Figure 2, the asymmetric unit of 1 contains two Ca(II) ions, two 4-formylbenzene-1,3-disulfonate-3-pyridinecarboxylic hydrazone ligands, ten coordinated H2O molecules, and one uncoordinated H2O molecule. Each Ca(II) ion in 1 is eight-coordinated to three oxygen atoms (O2A, O5, O6 or O2, O5A, O6A) from two 4-formylbenzene-1,3-disulfonate-3-pyridinecarboxylic hydrazone ligands and five coordinated H2O molecules (O8, O9, O10, O11, O12 or O8A, O9A, O10A, O11A, O12A). The coordination geometry of Ca(II) can be described as a distorted trigonal dodecahedron. In 1, the two sulfonate groups of each 4-formylbenzene-1,3-disulfonate-3-pyridinecarboxylic hydrazone ligand adopt different coordination modes, one is monodentate and the other is bidentate. The molecules of 1 form a 1D chained structure by the π–π stacking interaction, as shown in Figure 3, and the distance of two planes is 3.428 Å. The 1D chains form a 3D framework structure by the π–π stacking interaction and hydrogen bonds, as shown in Figure 4. The π–π stacking interaction and hydrogen bonds play an important role in stabilizing the 3D framework structure. The main bond lengths (Å) and angles (°) for 1 are given in Table 1. The lengths (Å) and angles (°) of hydrogen bonds for 1 are listed in Table 2.
2.5. In Vitro Cytotoxic Activity
The data of in vitro cytotoxic activity of dinuclear Ca(II) complex 1 against HL-60 and MLTC-1 are given in Table 3. The concentration of DMSO was controlled under 1% to assure not to affect the results. The results show that the dinuclear Ca(II) complex 1 has an obvious cytotoxic effect against HL-60 cells and MLTC-1 cells. The dinuclear Ca(II) complex 1 has a stronger cytotoxicity against MLTC-1 cells with lower IC50 (19.51 μg/mL).
3. Experimental Section
3.1. Materials and Instrumentation
3-Pyridinecarboxylic hydrazide, disodium 4-formylbenzene-1,3-disulfonate, Ca(ClO4)2·4H2O, and solvents were obtained from commercial sources and used without further purification. Elemental analysis was carried out on an Elementar Vario EL III analyzer (Elementar, Hanau, Germany). The IR spectrum was recorded in the 4000–400 cm−1 range on an infrared spectrophotometer (Beijing Purkinje General Instrument, Beijing, China). 1H NMR and 13CNMR spectra were recorded on a Bruker Avance-400 spectrometer with DMSO-d6 as the solvent. Crystal data of the dinuclear Ca(II) complex 1 were collected by a Bruker Smart CCD diffractometer (Bruker, Billerica, MA, USA).
3.2. Synthesis of [Ca2(L)2(H2O)10]·H2O (1)
A mixture of 3-pyridinecarboxylic hydrazide (0.1371 g, 1.0 mmol), disodium 4-formylbenzene-1,3-disulfonate (0.310 g, 1.0 mmol), and Ca(ClO4)2·4H2O (0.119 g, 0.5 mmol) were dissolved in 15-mL mixed solvents of H2O:CH3CH2OH (v:v = 1:3). The mixture was stirred for 5 h at 50 °C and was then cooled to obtain colorless crystals. The product was filtered and dried in the air. Anal. Calcd for C26H42Ca2N6O26S4 (Mr = 1063.06): C, 29.35; H, 3.95; N, 7.90%. Found: C, 29.17; H, 4.28; N, 7.75%. Main IR (cm−1, KBr Pellet): ν(H2O) 3473 cm−1 (s), ν(C=O): 1683 cm−1 (s), ν(SO3−): 1253 (s), 1,192 cm−1 (s), ν(C=N): 1561 cm−1 (s), ν(Ca–O): 447 cm−1 (w).
3.3. Crystal Structure Determination
A single crystal of dinuclear Ca(II) complex 1 with dimensions of 0.22 mm × 0.21 mm × 0.20 mm was chosen for data collection. The X-ray diffraction data of dinuclear Ca(II) complex 1 were collected on a Bruker Smart CCD diffractometer with a graphite-monochromatized MoKα (λ = 0.71073 Å) radiation using the ω–φ scan mode (1.66° ≤ θ ≤ 25.09°). The structure was solved by direct methods with SHELXL-97 [28] and refined on F2 by full-matrix least-squares procedures with SHELXTL-97 [29]. The crystal data of 1 are given in Table 4.
3.4. In Vitro Cytotoxic Activity
The tested cells (HL-60 and MLTC-1) were provided by Taishan Medical University. The harvested HL-60 and MLTC-1 cells were incubated for 48 h at 37 °C in a humidified 5%CO2-90%N2-5%O2 atmosphere. The drug (complex 1) with different concentrations (5, 10, 20, 30, 40, and 60 μg ml−1) was tested for its IC50 against HL-60 and MLTC-1 cells, following the procedure previously described [23].
4. Conclusions
In this paper, a novel eight-coordinated dinuclear Ca(II) complex, [Ca2(L)2(H2O)10]·H2O (L = 4-formylbenzene-1,3-disulfonate-3-pyridinecarboxylic hydrazone) (1), was synthesized by the reaction of 3-pyridinecarboxylic hydrazide, disodium 4-formylbenzene-1,3-disulfonate, and Ca(ClO4)2·4H2O in ethanol–water solution (v:v = 3:1) at 50 °C. Dinuclear Ca(II) complex 1 was characterized by elemental analysis, IR, and X-ray single crystal diffraction analysis. The molecules of 1 form a 1D chained structure by π–π stacking. 1D chains form a 3D framework structure by the interaction of π–π stacking and hydrogen bonds. The dinuclear Ca(II) complex 1 has marked cytotoxic effect against HL-60 cells and MLTC-1 cells.
Acknowledgments
This project was supported by the National Natural Science Foundation of China (No. 21171132), the National Natural Science Foundation of Shandong (ZR2014BL003), the Project of Shandong Province Higher Educational Science and Technology Program (J14LC01), and Science Foundation of Weifang.
Author Contributions
Meng Qing-Guo synthesized the complex 1. Liu Li-Li analyzed the crystal data. Tai Xi-Shi designed the experiments and wrote the manuscript.
Conflicts of Interest
The authors declare that this article content has no conflict of interest.
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Figure 1.
The IR spectrum of 1.
Figure 2.
The coordination environment of 1.
Figure 3.
1D chained structure of 1.
Figure 4.
3D network structure of 1.
| Bond | Distance | Bond | Distance |
|---|---|---|---|
| Ca1-O11 | 2.3882 (18) | Ca1-O6 | 2.688 (2) |
| Ca1-O10 | 2.4110 (17) | S2-O4 | 1.4396 (14) |
| Ca1-O2i | 2.4221 (15) | S2-O6 | 1.4504 (15) |
| Ca1-O8 | 2.4333 (18) | S2-O5 | 1.4556 (17) |
| Ca1-O9 | 2.4448 (19) | S1-O1 | 1.4454 (16) |
| Ca1-O12 | 2.4799 (19) | S1-O2 | 1.4501 (16) |
| Ca1-O5 | 2.5823 (16) | S1-O3 | 1.4546 (17) |
| C7-N1 | 1.266 (3) | N1-N2 | 1.381 (2) |
| Angle | ° | Angle | ° |
| O11-Ca1-O10 | 139.72 (7) | O11-Ca1-O2i | 114.65 (7) |
| O10-Ca1-O2i | 79.62 (6) | O11-Ca1-O8 | 140.87 (6) |
| O10-Ca1-O8 | 76.19 (7) | O8-Ca1-O2i | 80.77 (6) |
| O11-Ca1-O9 | 72.33 (6) | O10-Ca1-O9 | 73.73 (6) |
| O9-Ca1-O2i | 80.05 (6) | O8-Ca1-O9 | 146.67 (5) |
| O11-Ca1-O12 | 72.44 (6) | O12-Ca1-O10 | 147.10 (6) |
| O12-Ca1-O2i | 78.36 (6) | O8-Ca1-O12 | 76.39 (6) |
| O12-Ca1-O9 | 125.36 (6) | O11-Ca1-O5 | 75.96 (6) |
| O10-Ca1-O5 | 108.77 (6) | O5-Ca1-O2i | 153.19 (6) |
| O8-Ca1-O5 | 76.89 (6) | O9-Ca1-O5 | 126.56 (6) |
| O5-Ca1-O12 | 82.12 (6) | O11-Ca1-O6 | 84.33 (6) |
| O10-Ca1-O6 | 69.68 (5) | O6-Ca1-O2i | 147.52 (95) |
| O8-Ca1-O6 | 101.30 (6) | O9-Ca1-O6 | 81.40 (6) |
| O12-Ca1-O6 | 133.92 (6) | O5-Ca1-O9 | 53.40 (5) |
Symmetry codes: (i) = –x + 1, −y + 2, −z.
| Hydrogen Bonds | d(D-H) | d(H…A) | d(D…A) | DHA | Symmetry Code |
|---|---|---|---|---|---|
| O(8)-H(8WB)…O(3) | 0.853 | 2.05 | 2.812(2) | 149 | 1 − x, 2 − y, −z |
| O(8)-H(8WA)…N(3) | 0.849 | 1.94 | 2.771(3) | 166 | 1 − x, 3 − y, 1 − z |
| N(2)-H(2B)…O(13) | 0.86 | 1.97 | 2.766(3) | 153 | x, y, z |
| O(9)-H(9WB)…O(7) | 0.856 | 1.99 | 2.815(2) | 159 | x, −1 + y, z |
| O(9)-H(9WA)…O(1) | 0.85 | 2.03 | 2.869(2) | 170 | 2 − x, 2 − y, −z |
| O(11)-H(1WB)…O(5) | 0.85 | 2.01 | 2.817(2) | 160 | 1 − x, 2 − y, 1 − z |
| O(11)-H(1WA)…O(7) | 0.85 | 1.90 | 2.717(3) | 163 | x, −1 + y, z |
| O(12)-H(2WA)…O(6) | 0.86 | 2.06 | 2.910(3) | 169 | −1 + x, y, z |
| O(12)-H(2WB)…O(4) | 0.85 | 2.06 | 2.887(2) | 163 | 1 − x, 2 − y, 1 − z |
| O(10)-H(10C)…O(8) | 0.85 | 2.14 | 2.900(2) | 149 | 1 − x, 2 − y, − z |
| O(10)-H(10D)…O(3) | 0.86 | 1.95 | 2.801(3) | 170 | 2 − x, 2 − y, − z |
| O(13)-H(13B)…O(1) | 0.96 | 2.45 | 3.187(3) | 133 | x, y, 1 + z |
| O(13)-H(13B)…O(2) | 0.96 | 2.41 | 3.079(3) | 126 | x, y, 1 + z |
| O(13)-H(13C)…O(12) | 0.96 | 2.16 | 3.039(3) | 152 | 1 − x, 2 − y, 1 − z |
| Compound | IC50 (μg/mL) | |
| HL-60 | MLTC-1 | |
| Ca(II) complex | 27.68 ± 0.9 | 19.51 ± 1.2 |
| Empirical Formula | C26H42Ca2N6O26S4 |
|---|---|
| Formula weight | 1063.06 |
| Temperature/K | 296(2) |
| Crystal system | Triclinic |
| Space group | P-1 |
| a/Å | 7.186(3) |
| b/Å | 11.978(5) |
| c/Å | 12.263(5) |
| α/° | 90.318(5) |
| β/° | 91.922(5) |
| γ/° | 96.797(5) |
| Volume/Å3 | 1047.5(8) |
| Z | 1 |
| ρcalcmg/mm3 | 1.685 |
| μ/mm‑1 | 0.572 |
| S | 1.093 |
| F(000) | 552 |
| Index ranges | −8 ≤ h ≤ 8, −14 ≤ k ≤ 13, −14 ≤ l ≤ 13 |
| Reflections collected | 5175 |
| Independent reflections | 3646 [R(int) = 0.0169] |
| Data/restraints/parameters | 3646/10/329 |
| Goodness-of-fit on F2 | 1.094 |
| Final R indexes [I ≥ 2σ (I)] | R1 = 0.0308, wR2 = 0.0770 |
| Final R indexes [all data] | R1 = 0.0355, wR2 = 0.0792 |
| Largest diff. peak/hole / e Å−3 | 0.354/−0.358 |
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Tai, X.-S.; Meng, Q.-G.; Liu, L.-L. Synthesis, Crystal Structure, and Cytotoxic Activity of a Novel Eight-Coordinated Dinuclear Ca(II)-Schiff Base Complex. Crystals 2016, 6, 109. https://doi.org/10.3390/cryst6090109
AMA Style
Tai X-S, Meng Q-G, Liu L-L. Synthesis, Crystal Structure, and Cytotoxic Activity of a Novel Eight-Coordinated Dinuclear Ca(II)-Schiff Base Complex. Crystals. 2016; 6(9):109. https://doi.org/10.3390/cryst6090109
Chicago/Turabian StyleTai, Xi-Shi, Qing-Guo Meng, and Li-Li Liu. 2016. "Synthesis, Crystal Structure, and Cytotoxic Activity of a Novel Eight-Coordinated Dinuclear Ca(II)-Schiff Base Complex" Crystals 6, no. 9: 109. https://doi.org/10.3390/cryst6090109
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