Synthesis, Crystal Structures and Anticancer Studies of Morpholinyldithiocarbamato Cu(II) and Zn(II) Complexes
Abstract
:1. Introduction
2. Results and Discussion
2.1. Syntheses
2.2. Spectral Studies of the Morpholine Dithiocarbamate and Its Cu(II) and Zn(II) Complexes
2.3. Molecular Structures of the Cu(II) and Zn(II) Morpholinyldithiocarbamate Complexes
2.4. Anticancer Studies
3. Materials and Methods
3.1. Apparatus, Materials and Analysis
3.2. Synthesis of Bis(Morpholinyldithiocarbamato) Cu(II) Complex [Cu(MphDTC)2]
3.3. Synthesis of Bis(Morpholinyldithiocarbamato) Zn(II) Complex [Zn(MphDTC)2]
3.4. Anticancer Studies
4. Conclusions
Supplementary Materials
Author Contributions
Funding
Acknowledgments
Conflicts of Interest
References
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Sample Availability: Samples of the compounds; morpholinyl dithiocarbamate, and the corresponding Cu(II) and Zn(II) complexes are available from the authors. |
Compound | [Cu(MphDTC)2] | [Zn(μ-MphDTC)2(MphDTC)2] |
---|---|---|
Formula | C10H16CuN2O2S4 | C20H32N4O4S8Zn2 |
Dcalc./g cm−3 | 1.806 | 1.734 |
μ/mm−1 | 2.113 | 2.208 |
Formula Weight | 388.03 | 779.76 |
Size/mm3 | 0.34 × 0.22 × 0.14 | 0.33 × 0.22 × 0.14 |
T/K | 100(2) | 100(2) |
Crystal System | monoclinic | triclinic |
Space Group | P21/n | P-1 |
a/Å | 4.1987(5) | 7.9581(6) |
b/Å | 20.646(3) | 8.7769(6) |
c/Å | 8.3714(10) | 11.8945(9) |
α/° | 90 | 103.680(2) |
β/° | 100.564(8) | 91.204(1) |
γ/° | 90 | 111.329(3) |
V/Å3 | 713.39(16) | 746.67(10) |
Z | 2 | 1 |
Z’ | 0.5 | 0.5 |
Θmin/° | 1.973 | 1.778 |
Θmax/° | 26.497 | 27.412 |
Measured Refl. | 6298 | 12596 |
Independent Refl. | 1473 | 3370 |
Reflections Used | 1222 | 3208 |
Rint | 0.0672 | 0.0345 |
Parameters | 88 | 172 |
Largest Peak | 0.496 | 0.849 |
Deepest Hole | −0.468 | −0.359 |
GooF | 1.088 | 1.078 |
wR2 (all data) | 0.0930 | 0.0725 |
wR2 | 0.0873 | 0.0718 |
R1 (all data) | 0.0448 | 0.0271 |
R1 | 0.0359 | 0.0260 |
[Cu(MphDTC)2] | [Zn(μ-MphDTC)2(MphDTC)2] | ||
---|---|---|---|
Bond | Length(Å) | Bonds | Length(Å) |
Cu1–S1 | 2.3019(7) | S1–Zn1 | 2.4373(5) |
Cu1–S2 | 2.3119(8) | S2–Zn1 | 2.3347(5) |
S2–C1 | 1.717(3) | S3–Zn1 | 2.342(5) |
O1–C3 | 1.436(3) | S4–Zn1 | 2.3169(5) |
O1–C4 | 1.423(3) | C1–S1 | 1.7290(19) |
N1–C1 | 1.332(3) | C3–O1 | 1.426(2) |
C8–O2 | 1.428(2) | ||
C1–N1 | 1.323(2) | ||
Bond | Angle(°) | Bonds | Angle(°) |
S11–Cu1–S1 | 180.0 | S2–Zn1–S1 | 76.408(16) |
S11–Cu1–S2 | 77.22(2) | S2–Zn1–S3 | 115.480(18) |
S1–Cu1–S2 | 102.78(2) | S1–Zn1–S3 | 112.705(18) |
S11–Cu–S21 | 102.78(2) | S1–Zn1–S4 | 107.689(18) |
S1–Cu1–S21 | 77.22(2) | S2–Zn1–S4 | 130.37(2) |
S2–Cu1–S21 | 180.0 | S3–Zn1–S4 | 108.203(19) |
C11–S1–Cu1 | 84.58(9) | C1–Zn1–S1 | 81.75(7) |
C1–S2–Cu1 | 84.37(9) | S2–Zn1–S1 | 76.408(16) |
Compounds/Cancer Cells | Renal (TK-10) IC50, µM | Melanoma (UACC-62) IC50, µM | Breast (MCF-7) IC50, µM |
---|---|---|---|
Mphdtc | 1.51 | 12.73 | 2.65 |
[Cu(Mphdtc)2] | 4.64 | 4.47 | 4.37 |
[Zn(μ-MphDTC)2(MphDTC)2] | 8.70 | 16.54 | 3.17 |
Parthenolide | 4.64 | 11.37 | 3.52 |
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Ajibade, P.A.; Andrew, F.P.; Botha, N.L.; Solomane, N. Synthesis, Crystal Structures and Anticancer Studies of Morpholinyldithiocarbamato Cu(II) and Zn(II) Complexes. Molecules 2020, 25, 3584. https://doi.org/10.3390/molecules25163584
Ajibade PA, Andrew FP, Botha NL, Solomane N. Synthesis, Crystal Structures and Anticancer Studies of Morpholinyldithiocarbamato Cu(II) and Zn(II) Complexes. Molecules. 2020; 25(16):3584. https://doi.org/10.3390/molecules25163584
Chicago/Turabian StyleAjibade, Peter A., Fartisincha P. Andrew, Nandipha L. Botha, and Nolwazi Solomane. 2020. "Synthesis, Crystal Structures and Anticancer Studies of Morpholinyldithiocarbamato Cu(II) and Zn(II) Complexes" Molecules 25, no. 16: 3584. https://doi.org/10.3390/molecules25163584