Synthesis and biological activity of novel heavy metal complexes
of 5-amino-1,10-phenanthroline and 1,10-phenanthroline
5
-nitro-1,10-phenanthroline by reduction with hydrazine solution was hot filtered, cooled to room temperature
hydrate using Raney-nickel as a catalyst. All other and water added to 25 mL. The filtrate stayed
chemicals used were of the highest available quality. in a refrigerator at 2–3°C for one week. Amorphous
Composition of the products was determined by yellow
elemental analysis on a VarioEl (Elemental analysen washed with cold distilled water and ether,
systeme GmbH). FAB-mass spectra were taken on a and dried in desiccator over P O .
VG autospec mass spectrometer. The samples were Yield: 0.065 g.
dissolved in NBA and lactic acid. Infrared spectra Anal. calcd. for C H N O ClSn (C, H, N): Calculated
were recorded on a Perkin-Elmer 1600 Series FTIR (%): C, 37.49; H, 3.12; N, 10.93. Found (%): C, 37.89; H,
residue
formed,
were
filtered
off,
a
4
10
12
12
3
2
−
1
-1
spectrophotometer in the range of 4400–450 cm , 2.72; N, 11.26. FTIR (cm ): 3404, 3324, 3225, 1638,
−1
+
resolution 4 cm , in KBr pellets.
1516. FAB-mass (m/z): 154 (SnCl) , 196 (5-NH -phen).
2
+
+
+
H , 385 Sn(5-NH -phen).H Cl , 391 (5-NH -phen) .H ,
2
2
2
2
+
2
0
0
.1.2. Synthesis of Sr(5-NH -phen) (NO )(OH)(H O) (1) 413 (5-NH -phen) .Na .
.096g(0.450mmol)5-amino-1,10-phenanthroline•H O,
.355 g (1.677 mmol) Sr(NO ) and 2.5 mL of 96% 2.1.5. Synthesis of Pb(5-NH -phen)(NO ) (H O) (4)
2 4 3 2 2
2
2
2
3
2
2
3
2
2
ethanol were dissolved in 20 mL distilled water at 0.096g(0.450mmol)5-amino-1,10-phenanthroline•H O,
2
70°С. The solution was hot filtered, cooled to room 0.148
g (0.627 mmol) Ca(NO ) •4H O, 0.237 g
3 2 2
temperature and water was added to 25 mL. The filtrate (0.625 mmol) Pb(CH COO) •3H O and 2.5 mL of
3
2
2
stayed in a refrigerator at 2–3°C for one month. Yellow 96% ethanol were dissolved in 20 mL distilled water
crystals formed, filtered off, washed with cold distilled at 70°С. The mixture was hot filtered, cooled to room
water and dried in a desiccator over P O . Yield: temperature and water added to 25 mL. The filtrate
4
10
0.052 g.
stayed in a refrigerator at 2–3°C for one week. Yellow
Anal. calcd. for C H N O Sr (C, H, N): Calculated crystals formed, were filtered off, washed with cold
4
8
41 13
6
(
%): C, 58.56; H, 4.16; N, 18.50. Found (%): C, 58.70; distilled water and dried in a desiccator over P O .
4 10
-1
H, 4.57; N, 18.53. FTIR (cm ): 3440, 3350, 3226, 1636, Yield: 0.099 g.
513, 1384, 824. FAB-mass (m/z): 196 (5-NH -phen). Anal. calcd. for C H N O Pb (C, H, N):
1
2
12 11
4
7
+
+
+
H , 391 (5-NH -phen) .H , 413 (5-NH -phen) .Na , 476 Calculated (%): C, 46.38; H, 2.89; N, 18.03. Found (%):
2
2
2
2
+
+
-1
[
Sr(5-NH -phen) -H ] .
C, 46.43; H, 2.87; N, 17.79. FTIR (cm ): 3430, 3342,
227, 1635, 1515, 1362, 822. FAB-mass (m/z): 196
2
2
3
+
+
2
0
0
.1.3. Synthesis of Sn(phen)(NO )(OH)(H O) (2)
(5-NH -phen).H , 465 [Pb(5-NH -phen) (NO )] , 660
2 2 3
3
2
+
.386
g
(1.950 mmol) 1,10-phenanthroline•H O, [Pb(5-NH -phen) (NO )] .
2 2 2 3
.519
g
(2.301 mmol) SnCl •2H O, 0.590
g
2
2
(
2.498 mmol) Ca(NO ) •4H O and 10 mL of 96% 2.2. Citotoxicity assays
3
2
2
ethanol were diluted in 80 mL distilled water at 70°С for The cytotoxicity of the substances was measured
0 min. The solution was hot filtered, cooled to in vitro using the cultivated human tumour
3
room temperature and water added to 100 mL. cell lines: epithelial colorectal carcinoma HT-29,
The filtrate stayed in a refrigerator at 2–3°C for breast cancer epithelial-like morphology MDA-
24
h. Amorphous yellow residue formed was MB-231, epithelial cervix adenocarcinoma HeLa,
filtered off, washed with cold distilled water, diethyl hepatocellular carcinoma liver HepG2 and non-tumour
ether and dried in a desiccator over P O . Yield: diploid cell line Lep-3 (as a control). Compounds 1, 2,
4
10
0.137 g.
3 and 4 were evaluated for their cytotoxicity in vitro,
Anal. calcd. for C H N O Sn (C, H, N): Calculated towards the following cultivated human tumour and
12
11
3
5
(
%): C, 36.32; H, 2.78; N, 10.60. Found (%): C, 36.21; non-tumour cell lines, using MTS-test [18]:
-1
H, 2.85; N, 10.54. FTIR (cm ): 3490, 3327, 1519, 1385,
8
H .2H O, 235 (phen).H .3H O, 361 [Sn(phen)(NO )] , HTB-26).
5
- Breast cancer cells, epithelial-like morphology
24. FAB-mass (m/z): 181 (phen).H , 217 (phen). MDA-MB-231 (American Type Culture Collection ATCC
+
+
+
+
2
2
3
+
41 [Sn(phen) (NO )] .
- Human epithelial colorectal carcinoma HT-29
American Type Culture Collection ATCC HTB-38).
- Epithelial cervix adenocarcinoma HeLa (American
2
3
(
2
0
0
.1.4. Synthesis of Sn(5-NH -phen)(OH)(Cl)(H O) (3)
2 2
.096g(0.450mmol)5-amino-1,10-phenanthroline•H O, Type Culture Collection ATCC CCL-2).
2
.148
g
(0.627 mmol) Ca(NO ) •4H O, 0.141
g
- Differentiated hepatocellular liver carcinoma
3
2
2
(
0.625 mmol) SnCl •2H O and 2.5 mL of 96% ethanol HepG2 (American Type Culture Collection, Rockville,
2 2
were dissolved in 20 mL distilled water at 70°С. The MD, USA).
1036