Home Physical Sciences Diorganotin(iv) benzyldithiocarbamate complexes: synthesis, characterization, and thermal and cytotoxicity study
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Diorganotin(iv) benzyldithiocarbamate complexes: synthesis, characterization, and thermal and cytotoxicity study

  • Jerry O. Adeyemi , Damian C. Onwudiwe EMAIL logo , Nirasha Nundkumar and Moganavelli Singh
Published/Copyright: June 18, 2020
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Open Chemistry
From the journal Open Chemistry Volume 18 Issue 1

Abstract

Ammonium benzyldithiocarbamate, represented as NH4L, was prepared and used in the complexation reaction involving three organotin(iv) salts, represented as R2SnCl2 (R = CH3, C4H9, and C6H5). The structures of the synthesized complexes [(CH3)2SnL2] (1), [(C4H9)2SnL2] (2), and [(C6H5)2SnL2] (3) were established using various spectroscopic techniques (Fourier transform infrared spectroscopy, 1H NMR, 13C NMR, and 119Sn NMR) and elemental analysis. Thermal decomposition of the complexes using thermogravimetric analysis under nitrogen showed no definite pathway in the pattern of the complexes even though they are structurally related. X-ray diffraction studies of the final residue showed a common diffraction pattern for the complexes and confirmed SnS as the product of the thermal treatment. Cytotoxicity studies of these complexes against the human tumor cell lines (HeLa and MCF-7) compared favorably with the used standard 5-fluorouracil drug, with complexes 2 and 3 showing very good activity toward the used cell lines.

Keywords: dithiocarbamate; organotin(iv); thermal decomposition; X-ray diffraction; cytotoxicity

1 Introduction

Interest in the chemistry of ligands bearing sulfur atom(s) has been on the rise due to their diverse applications in various industrial and biological fields [1]; there is also interest in the chemistry of sulfur (S) atom compared with its congener oxygen (O). Sulfur possesses different donor properties, characterized by a lower electronegative property than that of oxygen. This in turn decreases its ionic character, alters the stability of various bonds, and reduces the influence of hydrogen in compounds where they exist [1]. Notable in this group of sulfur ligands are xanthates, dithiocarbamates, and dithiophosphates [1]. Among these, dithiocarbamate compounds have gained more attention due to their versatility. These have proved to be a useful structural motif, lending themselves to the metal-directed assembly of a range of structures [2]. These compounds are capable of stabilizing the different oxidation states of various metal ions due to their small bite angle (usually found to be ≈2.8–2.9 Å) [2]. Even though the transition metal complexes of this ligand have been predominantly studied, the tin(iv) complexes of dithiocarbamate have been only rarely explored until recently when these compounds began to gain attention due to their increased applications and interesting variable structural chemistry [3,4].

Understanding the thermal behavior of the metal complexes of dithiocarbamate has become pertinent due to their widespread applications as effective heat stabilizers, fungicides, antioxidants, foam rubber, polymers, etc. [5]. The thermal studies of these complexes have shown that they either volatilize, leaving a negligible amount of residue, or form metal sulfide/oxide, depending on the selected conditions (air or inert) [6]. A notable intermediate product often obtained in the thermal decomposition of metal dithiocarbamate is metal thiocyanate [5]. Furthermore, the trends in the decomposition pattern have been reported to be influenced by the electronic effects of the ligands and the environment of the coordinated metal [7]. Tin(iv) dithiocarbamate has become an important synthetic precursor for a wide range of organometallic complexes, especially those involved in ligand replacement. It is, thus, pertinent to understand their thermal behavior due to their commercial application in materials of high thermal conditions and as active ingredients in fungicides and pesticides [7]. Dithiocarbamate complexes of organotin(iv) derivatives have attracted attention due to their diverse applications as biological agents [6], their chemistry [6], and their supramolecular chemistry [3,8]. Furthermore, they have also been used as a single-source precursor for the nanoparticle synthesis of the different tin sulfide phases (SnS, SnS2, and Sn2S3), because their thermal decomposition under nitrogen often leaves a residue of tin sulfide [9,10,11,12]. Tin sulfide has a very good semiconducting property and a good band gap energy in all its phases; therefore, it is supported to use it as a semiconductor in solar cells [6,12]. The SnS phase has attracted more attention than the other phases due to its electronic band gap (1.3 eV), which lies between that of Ga and Si [12,13]. As such, it has become more imperative to continue to study the thermal behavior of derivatives of tin(iv) dithiocarbamate group such as organotin(iv) dithiocarbamate complexes with the goal of understanding the possible trend in the decomposition pattern of the compound.

Molecules containing sulfur atoms have been widely studied as chemoprotectants in Pt-based chemotherapy due to their promising modulating activity in cisplatin nephrotoxicity, which has shown improved therapeutic indices under acidic conditions. This may have significant implications in the treatment of cancer due to the acidic conditions often observed in a solid tumor, which is caused by the fermentation of glucose-secreting acid in the tumor tissue [8]. Both organotin and dithiocarbamate moieties have been reported to play a significant role in the cytotoxic activities of various cancerous cell lines. This may be attributed to the increased lipophilicity due to the complexation or the transportation role played by the ligand, which facilitates the movement of the metal to the site of action, where the cytotoxic effect can be induced [6].

This study reports the thermal and cytotoxicity studies of new dithiocarbamate complexes derived from benzyldithiocarbamate and selected diorganotin(iv) salts.

2 Materials and methods

The chemicals used in this work were all purchased from Sigma-Aldrich Chemical, Co, and used as recommended. The percentages of C, H, N, and S in the obtained complexes were determined using an elementar, Vario EL Cube. The infrared (IR) spectra, in the range 400–4,000 cm−1, were obtained with an Alpha Bruker FTIR spectrophotometer. The NMR spectra (1H and 13C) of the complexes (in CDCl3) were obtained at room temperature with a Bruker Avance III NMR spectrometer (600 MHz). Similarly, the 119Sn NMR spectra were obtained with Bruker Ascend Avance III (500 MHz) HD using broadband observe (BBO) as a probe and (CH3)4Sn reference as an external standard. SDT Q600 Thermal Analyzer (under N2 flow) was used for the thermal study [thermogravimetric analysis (TGA) and derivative thermogravimetry] between 50 and 700°C at a heating rate of 10°C min−1. The crystalline phases of the obtained residues from the TGA measurement were identified using a Rőntgen PW3040/60 X’Pert Pro X-ray diffractometer, equipped with a nickel filtered Cu Kα radiation (k = 1.5418 Å) at room temperature and a scanning rate of 0.0018° min−1.

2.1 Preparation of ammonium N-benzyldithiocarbamate (NH4L)

The ligand was synthesized according to a guided procedure with slight modifications [14]. A mixture of benzylaniline (5.50 mL, 0.05 mol) and ammonium hydroxide (15 mL, 0.05 mol) was stirred in an ice bath for 30 min, followed by the dropwise addition of cold carbon disulfide (3 mL, 0.05 mol). The resulting mixture was stirred for 3 h at an approximate temperature of 4°C. Using a suction pump, a pale yellow solid precipitate was extracted, which was thoroughly rinsed with a mixture of absolute ethanol and ether. This precipitate was stored at low temperature.

2.2 Preparation of diorganotin(iv) complexes (R2SnL2 [R = CH3, C4H9, C6H5])

The respective diorganotin(iv) chloride salts (0.025 mol) were dissolved in 10 mL ethanol, and the resulting mixture was added to an already stirred solution of ethanolic ammonium N-benzyldithiocarbamate (0.01 mol). This mixture was stirred for 2 h, and the white precipitates obtained were filtered and rinsed with cold ethanol to remove the unreacted substances in the solution.

2.2.1 [(CH3)2Sn(L)2]

Yield, 2.21 g (71.29%); M. pt., 125–126°C; FTIR, ν (cm−1): 1,503 (C═N), 1,241 (C2–N), 981 (C═S), 2,908 (–CH), 3,147 (═CH), 3,333 (N–H), 507 (Sn–C), 451 (Sn–S); 1H NMR (DMSO) d (ppm) = 7.30−7.19 (m, 10H, C6H̲5–CH2–NH), 4.65 (s, 2H, C6H5–CH2–NH̲), 3.94 (s, 4H, C6H5–CH̲2–NH), 1.53 (s, 6H, Sn–CH̲3); 13C NMR (DMSO) d (ppm) = 202.7 (–NC̲S2), 135.6, 129.0, 128.1, 127.5 (C̲6H5–CH2–NH), 52.8 (C6H5–C̲H2–NH), 15.0 (Sn–(C̲H3)2); 119Sn NMR (CDCl3): δ ppm = −335.0; C18H22N2S4Sn (513.35); C, 42.11; H, 4.32; N, 5.46; S, 24.98, found; C, 41.91; H, 4.02; N, 5.06; S, 24.49.

2.2.2 [(C4H9)2Sn(L)2]

Yield, 2.68 g (74.65%); M. pt., 133–134°C; FTIR, ν (cm−1): 1,487 (C═N), 1,237 (C2–N), 1,008 (C═S), 2,954 (–CH), 3,117 (═CH), 3,300 (N–H), 512 (Sn–C), 440 (Sn–S); 1H NMR (DMSO) d (ppm) = 7.47–7.24 (m, 10H, C6H̲5–CH2–NH), 4.85 (s, 2H, C6H5–CH2–NH̲), 3.56 (s, 4H, C6H5–CH̲2–NH), 2.35 (t, 4H, Sn–CH̲2CH2CH2CH3), 1.76 (m, 4H, Sn–CH2CH̲2CH2CH3), 1.48 (m, 4H, Sn–CH2CH2CH̲2CH3), 0.88 (t, 6H, Sn–CH2CH2CH2CH̲3); 13C NMR (DMSO) d (ppm) = 201.0 (–NC̲S2), 135.6, 129.0, 128.4, 127.1 (C̲6H5–CH2–NH), 52.8 (C6H5–C̲H2–NH), 31.2 (Sn–CH2CH2CH2CH3), 27.8 (Sn–CH2C̲H2CH2CH3), 23.3 (Sn–CH2CH2C̲H2CH3) 13.9 (Sn–CH2CH2CH2C̲H3); 119Sn NMR (CDCl3): δ ppm = −351.0; C18H22N2S4Sn (598.06); C, 48.34; H, 5.75; N, 4.68; S, 21.67; found; C, 47.94; H, 5.24; N, 4.26; S, 22.07.

2.2.3 [(C6H5)2Sn(L)2]

Yield, 2.93 g (78.76%); M. pt., 135–137°C; FTIR, ν (cm−1): 1,478 (C═N), 1,229 (C2–N), 996 (C═S), 2,932 (–CH), 3,119 (═CH), 3,318 (N–H), 510 (Sn–C), 443 (Sn–S); 1H NMR (DMSO) d (ppm) = 7.47–7.24 (m, 10H, C6H̲5–CH2–NH), 4.62 (s, 2H, C6H5–CH2–NH̲), 3.93 (s, 4H, C6H5–CH̲2–NH), 8.06–7.78 (m, 10H, Sn–(C6H̲5)2); 13C NMR (DMSO) d (ppm) = 200.6 (–NC̲S2), 135, 129.2, 128.1, 127.6 (C̲6H5–CH2–NH), 52.8 (C6H5–C̲H2–NH), 136.2, 135.3, 129.4, 128.9 (Sn–(C̲6H5)2); 119Sn NMR (CDCl3): δ ppm = −343.9; C28H26N2S4Sn (638.00); C, 52.75; H, 4.11; N, 4.39; S, 20.12; found; C, 52.45; H, 3.99; N, 4.01; S, 20.32.

2.3 Cytotoxicity evaluation using MTT assay

A similar method used in this study has already been reported by our group [15]. The human cervical carcinoma (HeLa) cells were obtained from the ATCC, Manassas, USA. These cells were cultured in a 25 cm2 tissue flasks with Dulbecco's Modified eagles's medium (DMEM), already containing 10% fetal bovine serum, 100 U mL−1 penicillin, and 100 μg mL−1 streptomycin. The MTT assay (3-(4,5-dimethylthiazol-2-yl)-2,6-diphenyltetrazolium bromide) was performed in a 96-well plate containing 2.5 × 102 cells/well in 100 μL DMEM. The cells were used to investigate the viability of the HeLa cells. These cells were incubated at 37°C overnight, followed by the addition of the respective complexes at various concentrations of 20, 40, 80, and 100 μg  mL−1. Then, the cells were incubated at 37°C for 48 h, followed by the MTT assay. The untreated cells were used as positive control 1 and the untreated cells with DMSO were used as positive control 2, while 5-fluorouracil (5-FU) was used as a standard. The fresh medium containing 10% MTT reagent was used to replace the medium in the assay, followed by incubation at 37°C for 4 h. After these were removed, insoluble formazan crystals were dissolved in 100 μL of DMSO, then the absorbance was studied at 570 nm with DMSO as a blank. These assays were carried out in triplicates.

  1. Ethical approval: The research conducted is not related to either human or animal use.

3 Results and discussion

3.1 Synthesis

Dithiocarbamate ligands obtained from primary amines are generally less stable compared with those obtained from secondary amines. This is due to the presence of the acidic hydrogen on the nitrogen [16,17]. Hence, their synthesis may sometimes require an inert atmosphere [17]. However, in this study, the reaction proceeded in air, as reported in Su et al. [18]. The complexes were synthesized as shown in Scheme 1. Good yields of about 70–78% were obtained, and the data from the elemental analytical corresponded with the stoichiometry of the complexes. The complexes were white, stable at room temperature, and soluble in dichloromethane, chloroform, and dimethyl sulfoxide but sparingly soluble in alcohol.

Scheme 1 General synthetic route of diorganotin(iv) N-benzyl dithiocarbamate complexes.
Scheme 1

General synthetic route of diorganotin(iv) N-benzyl dithiocarbamate complexes.

3.2 IR spectral study

The IR spectra of the three complexes showed the characteristic dithiocarbamate bands, as presented in Figure 1a. A strong band assigned to the C–N vibration of the thioureide bond was found in the region between 1,503 and 1,478 cm−1 for all the complexes, due to the delocalization of electron toward the tin center in the complexes [19]. A single band in the region 1,008–996 cm−1 was attributed to the vibrational mode of C–S, which is suggestive of a bidentate mode of coordination [20]. A stretching vibration due to the aromatic ring (═C–H) was found in the region of 3,147–3,030 cm−1, while the stretching vibration due to the CH2 bond appeared in the region 2,954–2,912 cm−1 [21]. The N–H stretching vibration was found in the region 3,300–3,378 cm−1 [22]. In the far-IR region, the characteristic peaks associated with organotin dithiocarbamate complexes were found in the regions 512–508 cm−1 and 451–440 cm−1, ascribed to the stretching vibrations of Sn–C and Sn–S, respectively [23].

Figure 1 The (a) FTIR, (b) 1H NMR, (c) 13C NMR, and (d) 119Sn NMR (ppm) spectra of [(CH3)2SnL2] (1).
Figure 1

The (a) FTIR, (b) 1H NMR, (c) 13C NMR, and (d) 119Sn NMR (ppm) spectra of [(CH3)2SnL2] (1).

3.3 NMR (1H, 13C, and 119Sn) spectral study

In the 1H NMR spectra of the complexes, the expected chemical shifts were found at their appropriate regions. A representative spectrum of the complex ([(CH3)2SnL2]) is presented in Figure 1b. The signals due to the aromatic protons of the ligand moiety were found as multiplets around the region 7.47–7.24 ppm for the complexes. The signals attributed to the methylene protons of the methylene group appeared in the region 3.93–3.56 ppm due to the electronegative N atom, while the signals in the region 4.85–4.62 ppm attributed to the proton on the N atom were found in all the spectra of the complexes. The proton signals in the organotin moiety appeared in the high field region as a singlet at 1.53 ppm for the dimethyltin(iv) derivative and as a complex multiplet in the region 8.06–7.78 ppm for the diphenyltin(iv) derivative. In the dibutyltin(iv) derivative, the proton signals were found in the range 2.35–0.88 ppm, attributed to the methylene and methyl protons of the butyl group [24].

The 13C NMR spectra showed a weak signal of the thioureide carbon (–NCS2) for all the complexes in the region between 202 and 200 ppm [19], while carbon signals of the phenyl moiety resonated between 135 and 125 ppm. The signal in the region 59.8–57.0 ppm, found in the spectra of the complexes, has been attributed to the methylene carbon close to the electronegative N atom. Carbons of the alkyl substituents in the complexes resonated at 13.94 ppm [25] in the spectra of the dimethyl complex; the diphenyl complex was found in the region 135 to 127 ppm; and the dibutyl complex was found between 31.2 and 13.9 ppm [22]. The 119Sn chemical shift values (δ) for this group of complexes ranged from −335 to −350 ppm, which indicates a hexacoordinated geometry around the Sn metal.

3.4 Thermal study

The thermogravimetric plots of the complexes are presented in Figure 2(a–c). The change in the composition of each complex based on mass losses with respective temperature changes is summarized in Table 1. These complexes decomposed in a two-step pathway, except for 3, which has a single step. In complexes 1 and 2, the first decomposition step occurred from approximately 90 to 168°C and 122 to 171°C, respectively. These cause the respective mass losses of about 17.30% (1) and 10.43% (2) of the starting masses. These mass losses have been attributed to the two –C6H5 group in complex 1 emanating from the ligand moiety and the mass of one –C4H9 group in complex 2 emanating from the organotin(iv) moiety. The masses found (1: 82.70% and 2: 89.57%) at this stage were in close agreement with the calculated values (1: 83.74% and 2: 90.55%). The remaining mass underwent more decomposition in the second and final steps for both complexes in the temperature range of 172–263 and 184–293°C, respectively. The masses of the obtained residues were 14.42% and 24.12% of the starting masses for complexes 1 and 2, respectively, and this concurred with the theoretical estimated value of SnS (16.87% (1) and 25.0% (2)). The thermogravimetric graph of complex 3 showed the decomposition to proceed in a single step pathway in the temperature range of 57–296°C. The remaining mass was found to be 21.30% of the starting mass; this concurred with the calculated weight of SnS (23.43%).

Figure 2 TG/DTG curves of complexes (a) 1, (b) 2, and (c) 3 obtained under a nitrogen atmosphere (75 mL min−1) and heating rate of 10°C min−1 at a temperature range of 50–700°C.
Figure 2

TG/DTG curves of complexes (a) 1, (b) 2, and (c) 3 obtained under a nitrogen atmosphere (75 mL min−1) and heating rate of 10°C min−1 at a temperature range of 50–700°C.

Table 1

Thermal analysis data of complexes 1–3

Complex123
Temperature range of decomposition (°C)
1st stage89–168122–17157–296
2nd stage172–263184–293—
DTG peak T (°C)
1st stage167161253
2nd stage242274—
Product obtained
1st decomposition(CH2–NHCS2)2Sn(CH3)2(Ph–CH3–NHCS2)2Sn(C4H9)SnS
2nd decompositionSnSSnS—
Mass of residues (mg), found (calc)
1st stage8.09 (8.10)9.17 (9.27)1.71 (1.87)
2nd stage1.41 (1.65)2.47 (2.56)—

Therefore, the only rational trend observed in the thermal decomposition of these complexes is as follows: for the alkyltin(iv) derivatives, two decomposition steps were found, while a single decomposition step was found for the aryltin(iv) derivative. Furthermore, there appears to be some intrinsic features in the ligand and its binding mode to the metal center, which in turn governs the decomposition mechanism. Hence, the structural feature of the complexes appears to have very little effect on the mechanism of decomposition. As previously reported by Hill et al. [7], the thermal decomposition pattern of tin dithiocarbamate complexes is unpredictable and complicated even for a series of structurally similar complexes. It is often difficult to rationalize a trend [7]. However, in the thermal decomposition study of these complexes, a stable SnS residue was found at the end of their decomposition. A representative X-ray diffraction pattern obtained from the residue of complex 1 is presented in Figure 3, and this clearly confirms that the SnS Herzenbergite (JCPDS no. 39-0354) phase was obtained after the decomposition.

Figure 3 A representative X-ray diffraction pattern of [(CH3)2SnL2] (1) residue showing a herzenbergite structure of SnS (JCPDS no. 39-0354).
Figure 3

A representative X-ray diffraction pattern of [(CH3)2SnL2] (1) residue showing a herzenbergite structure of SnS (JCPDS no. 39-0354).

3.5 Cytotoxicity study

The HeLa cell lines were obtained from human cervical cancer cells [26], while the MCF-7 are cell lines were obtained from human breast cancer cells [27]. These cell lines are often used for research purposes. Table 2 shows the activity of the complexes at different concentrations and the estimated minimum inhibitory concentration (IC50) values against the cell lines. The plots of the percentage viability against the concentration are also depicted in Figures 4a and b. These results show a concentration-dependent profile with some good activities toward the used cell lines. These are better than the standard drug, with an IC50 value of 40 and 58 µM for the Hela and MCF-7, respectively. For HeLa cell lines, complex 1 had a good cytotoxic activity, which is comparable to that of the standard 5-FU drug, and complex 2 had outstanding IC50 values, which were 2,100 times better than that of the standard drug. However, complex 3 displayed a high IC50 value, which may be due to its selectivity toward the HeLa cell lines, contrary to the expected trend within the group of organotin(iv) complexes. Thus, the diphenyl derivative (3) had poor activity against the HeLa cell lines.

Table 2

In vitro cytotoxicity of the complexes on the HeLa and MCF-7 cells (IC50)

HeLa cell line25 µg mL−150 µg mL−1100 µg mL−1150 µg mL−1IC50 (µM)
Control 1a100.00 ± 0.79100.00 ± 0.79100.00 ± 0.79100.00 ± 0.79—
Control 2b104.09 ± 2.43104.09 ± 2.43104.09 ± 2.43104.09 ± 2.43—
5-FU36.57 ± 4.1527.47 ± 6.1423.54 ± 2.9017.72 ± 4.3440
117.17 ± 6.7311.34 ± 13.808.49 ± 4.987.41 ± 1.8140
29.05 ± 13.984.75 ± 9.646.87 ± 14.815.14 ± 10.680.019
310.81 ± 6.3517.67 ± 5.0930.978 ± 9.1837.51 ± 4.85330
MCF-7 cell line25 µg mL−150 µg mL−1100 µg mL−1150 µg mL−1IC50 (µM)
Control 1a100.00 ± 0.71100.00 ± 0.71100.00 ± 0.71100.00 ± 0.71—
Control 2b99.87 ± 1.0599.87 ± 1.0599.87 ± 1.0599.87 ± 1.05—
5-FU82.40 ± 0.8758.37 ± 2.8048.88 ± 1.2642.99 ± 1.2856.2
167.74 ± 6.7864.68 ± 6.2365.40 ± 0.9366.90 ± 4.03185
264.02 ± 11.2953.52 ± 2.1251.01 ± 8.7544.80 ± 9.2157.3
350.82 ± 7.4234.12 ± 7.9933.81 ± 6.8027.03 ± 13.9920
  1. a

    Control 1: cell only.

  2. b

    Control 2: cell + DMSO.

Figure 4 Plot of percentage (%) viability against the complexes showing concentration-dependent profile.
Figure 4

Plot of percentage (%) viability against the complexes showing concentration-dependent profile.

Furthermore, for the MCF-7, the observed IC50 value obtained for complex 3 showed that it possesses better activity than the standard drug used, while complex 2 exhibited almost equal activity compared with the standard drug. Complex 1 showed weak activity. These trends concur with the previous reports for most organotin(iv) complexes, in which longer alkyl chains or aryl groups induced better cytotoxicity than their shorter chain counterparts [28]. However, this trend has also been observed to be a hindrance due to the selectivity toward the used cell lines, as observed in the HeLa cell lines reported in this study [29].

Generally, both organotin and dithiocarbamate moieties have been reported to play useful roles in the cytotoxicity of various cancer cell lines. This has been suggested to be due to complexation, which leads to increased lipophilicity and consequently facilitates the movement of the metal to the site of action, where the cytotoxic effect can be induced [28]. The electronic effect induced by the ligand in addition to the lipophilicity of the complexes has also been reported to play crucial roles in the cytoselectivity exhibited by these complexes [28]. In their right mix, these properties often give outstanding cytotoxic activities [30]. Therefore, the obtained results from this study show that on further screening in vivo and other clinical trials, these complexes may become useful compounds in the development of a new drug against cancer cells.

4 Conclusion

We have successfully synthesized and characterized three new organotin(iv) complexes using a benzyldithiocarbamate ligand. This ligand appears to bond in a bidentate fashion to the tin metal of the organotin(iv) moiety, as suggested by the presence of a single peak of the carbon sulfide (C═S) bond in the IR spectra. Furthermore, the 119Sn NMR also suggested a hexacoordinated geometry around the Sn atom, which indicated that two ligands moiety bonded to the tin atom. The noticeable trend observed in the thermal study showed that the two alkyltin(iv) derivatives followed two decomposition patterns, but the aryltin(iv) derivative followed a single decomposition pattern. Furthermore, all the complexes gave a final residue of SnS with a herzenbergite structure. Thus, the as-synthesized complexes can be a good single precursor source for the SnS nanoparticle synthesis. The study on the cytotoxicity of these complexes showed a concentration-dependent profile with some good activities toward the HeLa and MCF-7 cell lines, which compared favorably with the standard drug. However, further studies with different cell lines and on the mechanism of action are needed for these complexes to be considered leading anticancer agents.

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  1. Conflicts of interest: The authors declare no conflict of interest.

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Received: 2019-07-06
Revised: 2019-12-18
Accepted: 2020-02-05
Published Online: 2020-06-18

© 2020 Jerry O. Adeyemi et al., published by De Gruyter

This work is licensed under the Creative Commons Attribution 4.0 International License.

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  6. Molecular dynamics simulation of sI methane hydrate under compression and tension
  7. Spatial distribution and potential ecological risk assessment of some trace elements in sediments and grey mangrove (Avicennia marina) along the Arabian Gulf coast, Saudi Arabia
  8. Amino-functionalized graphene oxide for Cr(VI), Cu(II), Pb(II) and Cd(II) removal from industrial wastewater
  9. Chemical composition and in vitro activity of Origanum vulgare L., Satureja hortensis L., Thymus serpyllum L. and Thymus vulgaris L. essential oils towards oral isolates of Candida albicans and Candida glabrata
  10. Effect of excess Fluoride consumption on Urine-Serum Fluorides, Dental state and Thyroid Hormones among children in “Talab Sarai” Punjab Pakistan
  11. Design, Synthesis and Characterization of Novel Isoxazole Tagged Indole Hybrid Compounds
  12. Comparison of kinetic and enzymatic properties of intracellular phosphoserine aminotransferases from alkaliphilic and neutralophilic bacteria
  13. Green Organic Solvent-Free Oxidation of Alkylarenes with tert-Butyl Hydroperoxide Catalyzed by Water-Soluble Copper Complex
  14. Ducrosia ismaelis Asch. essential oil: chemical composition profile and anticancer, antimicrobial and antioxidant potential assessment
  15. DFT calculations as an efficient tool for prediction of Raman and infra-red spectra and activities of newly synthesized cathinones
  16. Influence of Chemical Osmosis on Solute Transport and Fluid Velocity in Clay Soils
  17. A New fatty acid and some triterpenoids from propolis of Nkambe (North-West Region, Cameroon) and evaluation of the antiradical scavenging activity of their extracts
  18. Antiplasmodial Activity of Stigmastane Steroids from Dryobalanops oblongifolia Stem Bark
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https://doi.org/10.1515/chem-2020-0037
Keywords for this article
dithiocarbamate; organotin(iv); thermal decomposition; X-ray diffraction; cytotoxicity
Creative Commons
BY 4.0

Articles in the same Issue

  1. Regular Articles
  2. Electrochemical antioxidant screening and evaluation based on guanine and chitosan immobilized MoS2 nanosheet modified glassy carbon electrode (guanine/CS/MoS2/GCE)
  3. Kinetic models of the extraction of vanillic acid from pumpkin seeds
  4. On the maximum ABC index of bipartite graphs without pendent vertices
  5. Estimation of the total antioxidant potential in the meat samples using thin-layer chromatography
  6. Molecular dynamics simulation of sI methane hydrate under compression and tension
  7. Spatial distribution and potential ecological risk assessment of some trace elements in sediments and grey mangrove (Avicennia marina) along the Arabian Gulf coast, Saudi Arabia
  8. Amino-functionalized graphene oxide for Cr(VI), Cu(II), Pb(II) and Cd(II) removal from industrial wastewater
  9. Chemical composition and in vitro activity of Origanum vulgare L., Satureja hortensis L., Thymus serpyllum L. and Thymus vulgaris L. essential oils towards oral isolates of Candida albicans and Candida glabrata
  10. Effect of excess Fluoride consumption on Urine-Serum Fluorides, Dental state and Thyroid Hormones among children in “Talab Sarai” Punjab Pakistan
  11. Design, Synthesis and Characterization of Novel Isoxazole Tagged Indole Hybrid Compounds
  12. Comparison of kinetic and enzymatic properties of intracellular phosphoserine aminotransferases from alkaliphilic and neutralophilic bacteria
  13. Green Organic Solvent-Free Oxidation of Alkylarenes with tert-Butyl Hydroperoxide Catalyzed by Water-Soluble Copper Complex
  14. Ducrosia ismaelis Asch. essential oil: chemical composition profile and anticancer, antimicrobial and antioxidant potential assessment
  15. DFT calculations as an efficient tool for prediction of Raman and infra-red spectra and activities of newly synthesized cathinones
  16. Influence of Chemical Osmosis on Solute Transport and Fluid Velocity in Clay Soils
  17. A New fatty acid and some triterpenoids from propolis of Nkambe (North-West Region, Cameroon) and evaluation of the antiradical scavenging activity of their extracts
  18. Antiplasmodial Activity of Stigmastane Steroids from Dryobalanops oblongifolia Stem Bark
  19. Rapid identification of direct-acting pancreatic protectants from Cyclocarya paliurus leaves tea by the method of serum pharmacochemistry combined with target cell extraction
  20. Immobilization of Pseudomonas aeruginosa static biomass on eggshell powder for on-line preconcentration and determination of Cr (VI)
  21. Assessment of methyl 2-({[(4,6-dimethoxypyrimidin-2-yl)carbamoyl] sulfamoyl}methyl)benzoate through biotic and abiotic degradation modes
  22. Stability of natural polyphenol fisetin in eye drops Stability of fisetin in eye drops
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  24. Molecular Properties of Carbon Crystal Cubic Structures
  25. Synthesis and characterization of calcium carbonate whisker from yellow phosphorus slag
  26. Study on the interaction between catechin and cholesterol by the density functional theory
  27. Analysis of some pharmaceuticals in the presence of their synthetic impurities by applying hybrid micelle liquid chromatography
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  29. Incorporation of silver stearate nanoparticles in methacrylate polymeric monoliths for hemeprotein isolation
  30. Development of ultrasound-assisted dispersive solid-phase microextraction based on mesoporous carbon coated with silica@iron oxide nanocomposite for preconcentration of Te and Tl in natural water systems
  31. N,N′-Bis[2-hydroxynaphthylidene]/[2-methoxybenzylidene]amino]oxamides and their divalent manganese complexes: Isolation, spectral characterization, morphology, antibacterial and cytotoxicity against leukemia cells
  32. Determination of the content of selected trace elements in Polish commercial fruit juices and health risk assessment
  33. Diorganotin(iv) benzyldithiocarbamate complexes: synthesis, characterization, and thermal and cytotoxicity study
  34. Keratin 17 is induced in prurigo nodularis lesions
  35. Anticancer, antioxidant, and acute toxicity studies of a Saudi polyherbal formulation, PHF5
  36. LaCoO3 perovskite-type catalysts in syngas conversion
  37. Comparative studies of two vegetal extracts from Stokesia laevis and Geranium pratense: polyphenol profile, cytotoxic effect and antiproliferative activity
  38. Fragmentation pattern of certain isatin–indole antiproliferative conjugates with application to identify their in vitro metabolic profiles in rat liver microsomes by liquid chromatography tandem mass spectrometry
  39. Investigation of polyphenol profile, antioxidant activity and hepatoprotective potential of Aconogonon alpinum (All.) Schur roots
  40. Lead discovery of a guanidinyl tryptophan derivative on amyloid cascade inhibition
  41. Physicochemical evaluation of the fruit pulp of Opuntia spp growing in the Mediterranean area under hard climate conditions
  42. Electronic structural properties of amino/hydroxyl functionalized imidazolium-based bromide ionic liquids
  43. New Schiff bases of 2-(quinolin-8-yloxy)acetohydrazide and their Cu(ii), and Zn(ii) metal complexes: their in vitro antimicrobial potentials and in silico physicochemical and pharmacokinetics properties
  44. Treatment of adhesions after Achilles tendon injury using focused ultrasound with targeted bFGF plasmid-loaded cationic microbubbles
  45. Synthesis of orotic acid derivatives and their effects on stem cell proliferation
  46. Chirality of β2-agonists. An overview of pharmacological activity, stereoselective analysis, and synthesis
  47. Fe3O4@urea/HITh-SO3H as an efficient and reusable catalyst for the solvent-free synthesis of 7-aryl-8H-benzo[h]indeno[1,2-b]quinoline-8-one and indeno[2′,1′:5,6]pyrido[2,3-d]pyrimidine derivatives
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  49. Enhancement of thermal properties of bio-based microcapsules intended for textile applications
  50. Exploring the effect of khat (Catha edulis) chewing on the pharmacokinetics of the antiplatelet drug clopidogrel in rats using the newly developed LC-MS/MS technique
  51. A green strategy for obtaining anthraquinones from Rheum tanguticum by subcritical water
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  64. Study of the remediation effects of passivation materials on Pb-contaminated soil
  65. Saliva proteomic analysis reveals possible biomarkers of renal cell carcinoma
  66. Withania frutescens: Chemical characterization, analgesic, anti-inflammatory, and healing activities
  67. Design, synthesis and pharmacological profile of (−)-verbenone hydrazones
  68. Synthesis of magnesium carbonate hydrate from natural talc
  69. Stability-indicating HPLC-DAD assay for simultaneous quantification of hydrocortisone 21 acetate, dexamethasone, and fluocinolone acetonide in cosmetics
  70. A novel lactose biosensor based on electrochemically synthesized 3,4-ethylenedioxythiophene/thiophene (EDOT/Th) copolymer
  71. Citrullus colocynthis (L.) Schrad: Chemical characterization, scavenging and cytotoxic activities
  72. Development and validation of a high performance liquid chromatography/diode array detection method for estrogen determination: Application to residual analysis in meat products
  73. PCSK9 concentrations in different stages of subclinical atherosclerosis and their relationship with inflammation
  74. Development of trace analysis for alkyl methanesulfonates in the delgocitinib drug substance using GC-FID and liquid–liquid extraction with ionic liquid
  75. Electrochemical evaluation of the antioxidant capacity of natural compounds on glassy carbon electrode modified with guanine-, polythionine-, and nitrogen-doped graphene
  76. A Dy(iii)–organic framework as a fluorescent probe for highly selective detection of picric acid and treatment activity on human lung cancer cells
  77. A Zn(ii)–organic cage with semirigid ligand for solvent-free cyanosilylation and inhibitory effect on ovarian cancer cell migration and invasion ability via regulating mi-RNA16 expression
  78. Polyphenol content and antioxidant activities of Prunus padus L. and Prunus serotina L. leaves: Electrochemical and spectrophotometric approach and their antimicrobial properties
  79. The combined use of GC, PDSC and FT-IR techniques to characterize fat extracted from commercial complete dry pet food for adult cats
  80. MALDI-TOF MS profiling in the discovery and identification of salivary proteomic patterns of temporomandibular joint disorders
  81. Concentrations of dioxins, furans and dioxin-like PCBs in natural animal feed additives
  82. Structure and some physicochemical and functional properties of water treated under ammonia with low-temperature low-pressure glow plasma of low frequency
  83. Mesoscale nanoparticles encapsulated with emodin for targeting antifibrosis in animal models
  84. Amine-functionalized magnetic activated carbon as an adsorbent for preconcentration and determination of acidic drugs in environmental water samples using HPLC-DAD
  85. Antioxidant activity as a response to cadmium pollution in three durum wheat genotypes differing in salt-tolerance
  86. A promising naphthoquinone [8-hydroxy-2-(2-thienylcarbonyl)naphtho[2,3-b]thiophene-4,9-dione] exerts anti-colorectal cancer activity through ferroptosis and inhibition of MAPK signaling pathway based on RNA sequencing
  87. Synthesis and efficacy of herbicidal ionic liquids with chlorsulfuron as the anion
  88. Effect of isovalent substitution on the crystal structure and properties of two-slab indates BaLa2−xSmxIn2O7
  89. Synthesis, spectral and thermo-kinetics explorations of Schiff-base derived metal complexes
  90. An improved reduction method for phase stability testing in the single-phase region
  91. Comparative analysis of chemical composition of some commercially important fishes with an emphasis on various Malaysian diets
  92. Development of a solventless stir bar sorptive extraction/thermal desorption large volume injection capillary gas chromatographic-mass spectrometric method for ultra-trace determination of pyrethroids pesticides in river and tap water samples
  93. A turbidity sensor development based on NL-PI observers: Experimental application to the control of a Sinaloa’s River Spirulina maxima cultivation
  94. Deep desulfurization of sintering flue gas in iron and steel works based on low-temperature oxidation
  95. Investigations of metallic elements and phenolics in Chinese medicinal plants
  96. Influence of site-classification approach on geochemical background values
  97. Effects of ageing on the surface characteristics and Cu(ii) adsorption behaviour of rice husk biochar in soil
  98. Adsorption and sugarcane-bagasse-derived activated carbon-based mitigation of 1-[2-(2-chloroethoxy)phenyl]sulfonyl-3-(4-methoxy-6-methyl-1,3,5-triazin-2-yl) urea-contaminated soils
  99. Antimicrobial and antifungal activities of bifunctional cooper(ii) complexes with non-steroidal anti-inflammatory drugs, flufenamic, mefenamic and tolfenamic acids and 1,10-phenanthroline
  100. Application of selenium and silicon to alleviate short-term drought stress in French marigold (Tagetes patula L.) as a model plant species
  101. Screening and analysis of xanthine oxidase inhibitors in jute leaves and their protective effects against hydrogen peroxide-induced oxidative stress in cells
  102. Synthesis and physicochemical studies of a series of mixed-ligand transition metal complexes and their molecular docking investigations against Coronavirus main protease
  103. A study of in vitro metabolism and cytotoxicity of mephedrone and methoxetamine in human and pig liver models using GC/MS and LC/MS analyses
  104. A new phenyl alkyl ester and a new combretin triterpene derivative from Combretum fragrans F. Hoffm (Combretaceae) and antiproliferative activity
  105. Erratum
  106. Erratum to: A one-step incubation ELISA kit for rapid determination of dibutyl phthalate in water, beverage and liquor
  107. Review Articles
  108. Sinoporphyrin sodium, a novel sensitizer for photodynamic and sonodynamic therapy
  109. Natural products isolated from Casimiroa
  110. Plant description, phytochemical constituents and bioactivities of Syzygium genus: A review
  111. Evaluation of elastomeric heat shielding materials as insulators for solid propellant rocket motors: A short review
  112. Special Issue on Applied Biochemistry and Biotechnology 2019
  113. An overview of Monascus fermentation processes for monacolin K production
  114. Study on online soft sensor method of total sugar content in chlorotetracycline fermentation tank
  115. Studies on the Anti-Gouty Arthritis and Anti-hyperuricemia Properties of Astilbin in Animal Models
  116. Effects of organic fertilizer on water use, photosynthetic characteristics, and fruit quality of pear jujube in northern Shaanxi
  117. Characteristics of the root exudate release system of typical plants in plateau lakeside wetland under phosphorus stress conditions
  118. Characterization of soil water by the means of hydrogen and oxygen isotope ratio at dry-wet season under different soil layers in the dry-hot valley of Jinsha River
  119. Composition and diurnal variation of floral scent emission in Rosa rugosa Thunb. and Tulipa gesneriana L.
  120. Preparation of a novel ginkgolide B niosomal composite drug
  121. The degradation, biodegradability and toxicity evaluation of sulfamethazine antibiotics by gamma radiation
  122. Special issue on Monitoring, Risk Assessment and Sustainable Management for the Exposure to Environmental Toxins
  123. Insight into the cadmium and zinc binding potential of humic acids derived from composts by EEM spectra combined with PARAFAC analysis
  124. Source apportionment of soil contamination based on multivariate receptor and robust geostatistics in a typical rural–urban area, Wuhan city, middle China
  125. Special Issue on 13th JCC 2018
  126. The Role of H2C2O4 and Na2CO3 as Precipitating Agents on The Physichochemical Properties and Photocatalytic Activity of Bismuth Oxide
  127. Preparation of magnetite-silica–cetyltrimethylammonium for phenol removal based on adsolubilization
  128. Topical Issue on Agriculture
  129. Size-dependent growth kinetics of struvite crystals in wastewater with calcium ions
  130. The effect of silica-calcite sedimentary rock contained in the chicken broiler diet on the overall quality of chicken muscles
  131. Physicochemical properties of selected herbicidal products containing nicosulfuron as an active ingredient
  132. Lycopene in tomatoes and tomato products
  133. Fluorescence in the assessment of the share of a key component in the mixing of feed
  134. Sulfur application alleviates chromium stress in maize and wheat
  135. Effectiveness of removal of sulphur compounds from the air after 3 years of biofiltration with a mixture of compost soil, peat, coconut fibre and oak bark
  136. Special Issue on the 4th Green Chemistry 2018
  137. Study and fire test of banana fibre reinforced composites with flame retardance properties
  138. Special Issue on the International conference CosCI 2018
  139. Disintegration, In vitro Dissolution, and Drug Release Kinetics Profiles of k-Carrageenan-based Nutraceutical Hard-shell Capsules Containing Salicylamide
  140. Synthesis of amorphous aluminosilicate from impure Indonesian kaolin
  141. Special Issue on the International Conf on Science, Applied Science, Teaching and Education 2019
  142. Functionalization of Congo red dye as a light harvester on solar cell
  143. The effect of nitrite food preservatives added to se’i meat on the expression of wild-type p53 protein
  144. Biocompatibility and osteoconductivity of scaffold porous composite collagen–hydroxyapatite based coral for bone regeneration
  145. Special Issue on the Joint Science Congress of Materials and Polymers (ISCMP 2019)
  146. Effect of natural boron mineral use on the essential oil ratio and components of Musk Sage (Salvia sclarea L.)
  147. A theoretical and experimental study of the adsorptive removal of hexavalent chromium ions using graphene oxide as an adsorbent
  148. A study on the bacterial adhesion of Streptococcus mutans in various dental ceramics: In vitro study
  149. Corrosion study of copper in aqueous sulfuric acid solution in the presence of (2E,5E)-2,5-dibenzylidenecyclopentanone and (2E,5E)-bis[(4-dimethylamino)benzylidene]cyclopentanone: Experimental and theoretical study
  150. Special Issue on Chemistry Today for Tomorrow 2019
  151. Diabetes mellitus type 2: Exploratory data analysis based on clinical reading
  152. Multivariate analysis for the classification of copper–lead and copper–zinc glasses
  153. Special Issue on Advances in Chemistry and Polymers
  154. The spatial and temporal distribution of cationic and anionic radicals in early embryo implantation
  155. Special Issue on 3rd IC3PE 2020
  156. Magnetic iron oxide/clay nanocomposites for adsorption and catalytic oxidation in water treatment applications
  157. Special Issue on IC3PE 2018/2019 Conference
  158. Exergy analysis of conventional and hydrothermal liquefaction–esterification processes of microalgae for biodiesel production
  159. Advancing biodiesel production from microalgae Spirulina sp. by a simultaneous extraction–transesterification process using palm oil as a co-solvent of methanol
  160. Topical Issue on Applications of Mathematics in Chemistry
  161. Omega and the related counting polynomials of some chemical structures
  162. M-polynomial and topological indices of zigzag edge coronoid fused by starphene
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