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The mechanisms of interaction of inorganic complexes with DNA are important in the design and development of new metal-based drug molecules. The limitations of cis-platin have encouraged the design and development of new metal-based target-specific anticancer drugs having reduced side effects. The complex cis-dichloridobis(1,2,5-thiadiazolo[3,4-f][1,10]phenanthroline-κ2N1,N10)copper(II), [CuCl2(C12H6N4S)2], has been synthesized and characterized. The complex crystallizes in the monoclinic space group C2/c. The covalent binding of the complex with DNA was studied by absorption spectroscopy. The anticancer activity of the complex on the Human Lung Carcinoma (A549) cell line was investigated by MTT assay. The complex exhibits higher toxicity than cis-platin and induces an apoptotic mode of cell death.
Supporting information
CCDC reference: 1563768
Data collection: SMART (Bruker, 2014); cell refinement: SMART (Bruker, 2014); data reduction: SAINT (Bruker, 2014); program(s) used to solve structure: SHELXT (Sheldrick, 2015a); program(s) used to refine structure: SHELXL2014 (Sheldrick, 2015b); molecular graphics: OLEX2 (Dolomanov et al., 2009); software used to prepare material for publication: OLEX2 (Dolomanov et al., 2009).
cis-Dichloridobis(1,2,5-thiadiazolo[3,4-
f][1,10]phenanthroline-
κ2N1,
N10)copper(II)
top
Crystal data top
[CuCl2(C12H6N4S)2] | F(000) = 1228 |
Mr = 610.98 | Dx = 1.775 Mg m−3 |
Monoclinic, C2/c | Mo Kα radiation, λ = 0.71073 Å |
a = 8.181 (4) Å | Cell parameters from 4383 reflections |
b = 12.168 (5) Å | θ = 3.0–25.7° |
c = 22.99 (1) Å | µ = 1.41 mm−1 |
β = 92.197 (7)° | T = 298 K |
V = 2286.8 (17) Å3 | Plate, blue |
Z = 4 | 0.28 × 0.24 × 0.16 mm |
Data collection top
Bruker SMART CCD area detector diffractometer | 1974 reflections with I > 2σ(I) |
phi and ω scans | Rint = 0.033 |
Absorption correction: empirical (using intensity measurements) sadabs | θmax = 26.1°, θmin = 1.8° |
Tmin = 0.694, Tmax = 0.806 | h = −10→10 |
11562 measured reflections | k = −14→14 |
2250 independent reflections | l = −28→28 |
Refinement top
Refinement on F2 | Primary atom site location: dual |
Least-squares matrix: full | Hydrogen site location: inferred from neighbouring sites |
R[F2 > 2σ(F2)] = 0.043 | H-atom parameters constrained |
wR(F2) = 0.116 | w = 1/[σ2(Fo2) + (0.059P)2 + 4.722P] where P = (Fo2 + 2Fc2)/3 |
S = 1.04 | (Δ/σ)max = 0.001 |
2250 reflections | Δρmax = 0.59 e Å−3 |
168 parameters | Δρmin = −0.60 e Å−3 |
0 restraints | |
Special details top
Geometry. All esds (except the esd in the dihedral angle between two l.s. planes)
are estimated using the full covariance matrix. The cell esds are taken
into account individually in the estimation of esds in distances, angles
and torsion angles; correlations between esds in cell parameters are only
used when they are defined by crystal symmetry. An approximate (isotropic)
treatment of cell esds is used for estimating esds involving l.s. planes. |
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top | x | y | z | Uiso*/Ueq | |
Cu1 | 0.5000 | 0.57810 (5) | 0.7500 | 0.0462 (2) | |
Cl1 | 0.66036 (11) | 0.72346 (9) | 0.80884 (4) | 0.0685 (3) | |
S1 | 0.66218 (14) | 0.34721 (8) | 0.45450 (4) | 0.0648 (3) | |
N1 | 0.6788 (3) | 0.5646 (2) | 0.69073 (10) | 0.0417 (6) | |
N2 | 0.3942 (3) | 0.4572 (2) | 0.68896 (12) | 0.0530 (7) | |
N3 | 0.7753 (4) | 0.4210 (2) | 0.49855 (11) | 0.0518 (7) | |
N4 | 0.5045 (4) | 0.3292 (2) | 0.49399 (13) | 0.0588 (7) | |
C5 | 0.6413 (3) | 0.5034 (2) | 0.64287 (12) | 0.0362 (6) | |
C4 | 0.7471 (3) | 0.4960 (2) | 0.59694 (12) | 0.0372 (6) | |
C11 | 0.6915 (4) | 0.4333 (2) | 0.54656 (12) | 0.0400 (6) | |
C6 | 0.4837 (3) | 0.4471 (2) | 0.64110 (13) | 0.0391 (6) | |
C3 | 0.8977 (4) | 0.5490 (3) | 0.60191 (13) | 0.0454 (7) | |
H3 | 0.9707 | 0.5449 | 0.5720 | 0.054* | |
C7 | 0.4298 (4) | 0.3880 (2) | 0.59198 (14) | 0.0441 (7) | |
C12 | 0.5365 (4) | 0.3814 (2) | 0.54411 (13) | 0.0446 (7) | |
C1 | 0.8235 (4) | 0.6141 (3) | 0.69432 (13) | 0.0484 (7) | |
H1 | 0.8500 | 0.6556 | 0.7273 | 0.058* | |
C2 | 0.9369 (4) | 0.6071 (3) | 0.65127 (14) | 0.0508 (8) | |
H2 | 1.0382 | 0.6414 | 0.6559 | 0.061* | |
C8 | 0.2742 (4) | 0.3401 (3) | 0.5925 (2) | 0.0632 (10) | |
H8 | 0.2323 | 0.3020 | 0.5603 | 0.076* | |
C10 | 0.2498 (5) | 0.4079 (3) | 0.6886 (2) | 0.0701 (12) | |
H10 | 0.1886 | 0.4122 | 0.7218 | 0.084* | |
C9 | 0.1856 (4) | 0.3503 (3) | 0.6409 (2) | 0.0759 (13) | |
H9 | 0.0822 | 0.3188 | 0.6421 | 0.091* | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
Cu1 | 0.0457 (3) | 0.0633 (4) | 0.0304 (3) | 0.000 | 0.0113 (2) | 0.000 |
Cl1 | 0.0583 (5) | 0.0901 (7) | 0.0585 (5) | 0.0259 (5) | 0.0216 (4) | 0.0145 (5) |
S1 | 0.0986 (8) | 0.0612 (6) | 0.0344 (4) | 0.0161 (5) | −0.0014 (4) | −0.0080 (4) |
N1 | 0.0422 (13) | 0.0533 (14) | 0.0300 (12) | 0.0028 (11) | 0.0043 (10) | −0.0009 (10) |
N2 | 0.0418 (14) | 0.0692 (18) | 0.0493 (16) | 0.0116 (13) | 0.0177 (12) | 0.0173 (13) |
N3 | 0.0660 (18) | 0.0557 (16) | 0.0345 (13) | 0.0086 (13) | 0.0153 (12) | 0.0011 (11) |
N4 | 0.0701 (19) | 0.0513 (16) | 0.0538 (16) | 0.0059 (14) | −0.0147 (14) | −0.0089 (13) |
C5 | 0.0359 (14) | 0.0429 (15) | 0.0301 (13) | 0.0053 (11) | 0.0051 (10) | 0.0030 (11) |
C4 | 0.0362 (14) | 0.0425 (15) | 0.0331 (14) | 0.0039 (11) | 0.0061 (11) | 0.0031 (11) |
C11 | 0.0446 (16) | 0.0428 (15) | 0.0329 (14) | 0.0064 (12) | 0.0050 (12) | 0.0024 (11) |
C6 | 0.0334 (14) | 0.0443 (15) | 0.0400 (15) | 0.0052 (11) | 0.0079 (11) | 0.0077 (12) |
C3 | 0.0359 (15) | 0.0567 (18) | 0.0444 (17) | 0.0031 (13) | 0.0116 (12) | 0.0035 (13) |
C7 | 0.0365 (15) | 0.0390 (15) | 0.0568 (18) | 0.0014 (12) | −0.0008 (13) | 0.0071 (13) |
C12 | 0.0499 (17) | 0.0393 (15) | 0.0442 (16) | 0.0050 (13) | −0.0046 (13) | −0.0002 (13) |
C1 | 0.0472 (17) | 0.0589 (19) | 0.0388 (16) | −0.0002 (14) | −0.0021 (13) | −0.0054 (14) |
C2 | 0.0375 (16) | 0.0615 (19) | 0.0532 (19) | −0.0056 (14) | 0.0004 (14) | 0.0007 (16) |
C8 | 0.0439 (18) | 0.0489 (19) | 0.096 (3) | −0.0049 (15) | −0.0023 (18) | 0.0049 (19) |
C10 | 0.048 (2) | 0.077 (3) | 0.088 (3) | 0.0127 (18) | 0.032 (2) | 0.032 (2) |
C9 | 0.0360 (18) | 0.061 (2) | 0.131 (4) | −0.0055 (16) | 0.015 (2) | 0.024 (2) |
Geometric parameters (Å, º) top
Cu1—Cl1 | 2.5579 (14) | C4—C11 | 1.446 (4) |
Cu1—Cl1i | 2.5579 (14) | C4—C3 | 1.391 (4) |
Cu1—N1 | 2.043 (2) | C11—C12 | 1.415 (4) |
Cu1—N1i | 2.043 (2) | C6—C7 | 1.396 (4) |
Cu1—N2 | 2.189 (3) | C3—H3 | 0.9300 |
Cu1—N2i | 2.189 (3) | C3—C2 | 1.365 (4) |
S1—N3 | 1.617 (3) | C7—C12 | 1.433 (4) |
S1—N4 | 1.620 (4) | C7—C8 | 1.401 (4) |
N1—C5 | 1.354 (4) | C1—H1 | 0.9300 |
N1—C1 | 1.329 (4) | C1—C2 | 1.385 (4) |
N2—C6 | 1.350 (4) | C2—H2 | 0.9300 |
N2—C10 | 1.324 (5) | C8—H8 | 0.9300 |
N3—C11 | 1.330 (4) | C8—C9 | 1.356 (6) |
N4—C12 | 1.333 (4) | C10—H10 | 0.9300 |
C5—C4 | 1.394 (4) | C10—C9 | 1.387 (6) |
C5—C6 | 1.460 (4) | C9—H9 | 0.9300 |
| | | |
Cl1i—Cu1—Cl1 | 92.51 (6) | N3—C11—C4 | 124.6 (3) |
N1i—Cu1—Cl1 | 93.93 (8) | N3—C11—C12 | 114.0 (3) |
N1—Cu1—Cl1i | 93.93 (8) | C12—C11—C4 | 121.4 (3) |
N1—Cu1—Cl1 | 92.44 (8) | N2—C6—C5 | 116.1 (3) |
N1i—Cu1—Cl1i | 92.44 (8) | N2—C6—C7 | 122.8 (3) |
N1—Cu1—N1i | 170.78 (15) | C7—C6—C5 | 121.0 (3) |
N1i—Cu1—N2 | 95.62 (10) | C4—C3—H3 | 120.4 |
N1—Cu1—N2i | 95.62 (10) | C2—C3—C4 | 119.2 (3) |
N1—Cu1—N2 | 78.11 (10) | C2—C3—H3 | 120.4 |
N1i—Cu1—N2i | 78.11 (10) | C6—C7—C12 | 117.9 (3) |
N2—Cu1—Cl1 | 170.44 (7) | C6—C7—C8 | 117.7 (3) |
N2—Cu1—Cl1i | 86.76 (8) | C8—C7—C12 | 124.4 (3) |
N2i—Cu1—Cl1i | 170.44 (7) | N4—C12—C11 | 113.1 (3) |
N2i—Cu1—Cl1 | 86.76 (8) | N4—C12—C7 | 125.8 (3) |
N2—Cu1—N2i | 95.52 (15) | C11—C12—C7 | 121.0 (3) |
N3—S1—N4 | 99.95 (14) | N1—C1—H1 | 118.4 |
C5—N1—Cu1 | 116.15 (19) | N1—C1—C2 | 123.2 (3) |
C1—N1—Cu1 | 125.5 (2) | C2—C1—H1 | 118.4 |
C1—N1—C5 | 118.3 (3) | C3—C2—C1 | 118.9 (3) |
C6—N2—Cu1 | 111.7 (2) | C3—C2—H2 | 120.5 |
C10—N2—Cu1 | 129.8 (3) | C1—C2—H2 | 120.5 |
C10—N2—C6 | 117.7 (3) | C7—C8—H8 | 120.5 |
C11—N3—S1 | 106.3 (2) | C9—C8—C7 | 119.0 (4) |
C12—N4—S1 | 106.6 (2) | C9—C8—H8 | 120.5 |
N1—C5—C4 | 121.6 (3) | N2—C10—H10 | 118.5 |
N1—C5—C6 | 116.9 (2) | N2—C10—C9 | 123.0 (4) |
C4—C5—C6 | 121.5 (3) | C9—C10—H10 | 118.5 |
C5—C4—C11 | 117.1 (3) | C8—C9—C10 | 119.7 (3) |
C3—C4—C5 | 118.8 (3) | C8—C9—H9 | 120.1 |
C3—C4—C11 | 124.1 (3) | C10—C9—H9 | 120.1 |
Symmetry code: (i) −x+1, y, −z+3/2. |
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