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Synthesis, structural characterization, and anticancer activity of a monobenzyltin compound against MCF-7 breast cancer cells.

Fani S, Kamalidehghan B, Lo KM, Hashim NM, Chow KM, Ahmadipour F - Drug Des Devel Ther (2015)

Bottom Line: A significant increase of lactate dehydrogenase release in treated cells was observed via fluorescence analysis.Luminescent analysis showed significant growth in intracellular reactive oxygen species production after treatment.DNA fragmentation was observed as a characteristic of apoptosis in treated cells.

View Article: PubMed Central - PubMed

Affiliation: Department of Pharmacy, Faculty of Medicine, University of Malaya, Kuala Lumpur, Malaysia.

ABSTRACT
A new monoorganotin Schiff base compound, [N-(3,5-dichloro-2-oxidobenzylidene)-4-chlorobenzyhydrazidato](o-methylbenzyl)aquatin(IV) chloride, (compound C1), was synthesized, and its structural features were investigated by spectroscopic techniques and single-crystal X-ray diffractometry. Compound C1 was exposed to several human cancer cell lines, including breast adenocarcinoma cell lines MCF-7 and MDA-MB-231, ovarian adenocarcinoma cell lines Skov3 and Caov3, and prostate cancer cell line PC3, in order to examine its cytotoxic effect for different forms of cancer. Human hepatic cell line WRL-68 was used as a normal cell line. We concentrated on the MCF-7 cell line to detect possible underlying mechanism involvement of compound C1. 3-(4,5-dimethylthiazol-2-yl)-2,5-diphenyltetrazolium bromide (MTT) assay revealed the strongest cytotoxicity of compound C1 against MCF-7 cells, with a half maximal inhibitory concentration (IC50) value of 2.5±0.50 μg/mL after 48 hours treatment. The IC50 value was >30 μg/mL in WRL-68 cells. Induced antiproliferative activity of compound C1 for MCF-7 cells was further confirmed by lactate dehydrogenase, reactive oxygen species, acridine orange/propidium iodide staining, and DNA fragmentation assays. A significant increase of lactate dehydrogenase release in treated cells was observed via fluorescence analysis. Luminescent analysis showed significant growth in intracellular reactive oxygen species production after treatment. Morphological changes of necrosis and early and late apoptosis stages were observed in treated cells after staining with acridine orange/propidium iodide. DNA fragmentation was observed as a characteristic of apoptosis in treated cells. Results of the present study obviously reveal potential cytotoxic effects of compound C1 against human breast cancer MCF-7 cells.

No MeSH data available.


Related in: MedlinePlus

Synthetic route for benzyltin compound C1.Abbreviation: C1, compound 1 [N-(3,5-dichloro-2-oxidobenzylidene)-4-chlorobenzyhydrazidato](o-methylbenzyl)aquatin(IV) chloride.
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f1-dddt-9-6191: Synthetic route for benzyltin compound C1.Abbreviation: C1, compound 1 [N-(3,5-dichloro-2-oxidobenzylidene)-4-chlorobenzyhydrazidato](o-methylbenzyl)aquatin(IV) chloride.

Mentions: The condensation reaction of 4-chlorobenzhydrazide with 3,5-dichlorosalicylaldehyde yielded the ligand N-(3,5- dichloro-2-oxidobenzylidene)-4-chlorobenzyhydrazide (L), which is a yellow crystalline solid. Subsequent reaction of ligand L with di(o-methylbenzyl)tin dichloride gave the monobenzyltin Schiff base compound C1 (Figure 1). The melting point; elemental analytical data; 1H, 13C, and 119Sn NMR chemical shifts; and IR stretching frequencies of selected functional groups are presented in the “Materials and methods” section. The molecular structure, which was determined by single X-ray diffraction, is depicted in Figure 2, while its crystal packing showing the hydrogen-bonding interaction is presented in Figure 3. Tables 1–3 list the crystallographic data, bond distances and bond angles, and hydrogen-bond parameters of the compound, respectively.


Synthesis, structural characterization, and anticancer activity of a monobenzyltin compound against MCF-7 breast cancer cells.

Fani S, Kamalidehghan B, Lo KM, Hashim NM, Chow KM, Ahmadipour F - Drug Des Devel Ther (2015)

Synthetic route for benzyltin compound C1.Abbreviation: C1, compound 1 [N-(3,5-dichloro-2-oxidobenzylidene)-4-chlorobenzyhydrazidato](o-methylbenzyl)aquatin(IV) chloride.
© Copyright Policy
Related In: Results  -  Collection

License
Show All Figures
getmorefigures.php?uid=PMC4664434&req=5

f1-dddt-9-6191: Synthetic route for benzyltin compound C1.Abbreviation: C1, compound 1 [N-(3,5-dichloro-2-oxidobenzylidene)-4-chlorobenzyhydrazidato](o-methylbenzyl)aquatin(IV) chloride.
Mentions: The condensation reaction of 4-chlorobenzhydrazide with 3,5-dichlorosalicylaldehyde yielded the ligand N-(3,5- dichloro-2-oxidobenzylidene)-4-chlorobenzyhydrazide (L), which is a yellow crystalline solid. Subsequent reaction of ligand L with di(o-methylbenzyl)tin dichloride gave the monobenzyltin Schiff base compound C1 (Figure 1). The melting point; elemental analytical data; 1H, 13C, and 119Sn NMR chemical shifts; and IR stretching frequencies of selected functional groups are presented in the “Materials and methods” section. The molecular structure, which was determined by single X-ray diffraction, is depicted in Figure 2, while its crystal packing showing the hydrogen-bonding interaction is presented in Figure 3. Tables 1–3 list the crystallographic data, bond distances and bond angles, and hydrogen-bond parameters of the compound, respectively.

Bottom Line: A significant increase of lactate dehydrogenase release in treated cells was observed via fluorescence analysis.Luminescent analysis showed significant growth in intracellular reactive oxygen species production after treatment.DNA fragmentation was observed as a characteristic of apoptosis in treated cells.

View Article: PubMed Central - PubMed

Affiliation: Department of Pharmacy, Faculty of Medicine, University of Malaya, Kuala Lumpur, Malaysia.

ABSTRACT
A new monoorganotin Schiff base compound, [N-(3,5-dichloro-2-oxidobenzylidene)-4-chlorobenzyhydrazidato](o-methylbenzyl)aquatin(IV) chloride, (compound C1), was synthesized, and its structural features were investigated by spectroscopic techniques and single-crystal X-ray diffractometry. Compound C1 was exposed to several human cancer cell lines, including breast adenocarcinoma cell lines MCF-7 and MDA-MB-231, ovarian adenocarcinoma cell lines Skov3 and Caov3, and prostate cancer cell line PC3, in order to examine its cytotoxic effect for different forms of cancer. Human hepatic cell line WRL-68 was used as a normal cell line. We concentrated on the MCF-7 cell line to detect possible underlying mechanism involvement of compound C1. 3-(4,5-dimethylthiazol-2-yl)-2,5-diphenyltetrazolium bromide (MTT) assay revealed the strongest cytotoxicity of compound C1 against MCF-7 cells, with a half maximal inhibitory concentration (IC50) value of 2.5±0.50 μg/mL after 48 hours treatment. The IC50 value was >30 μg/mL in WRL-68 cells. Induced antiproliferative activity of compound C1 for MCF-7 cells was further confirmed by lactate dehydrogenase, reactive oxygen species, acridine orange/propidium iodide staining, and DNA fragmentation assays. A significant increase of lactate dehydrogenase release in treated cells was observed via fluorescence analysis. Luminescent analysis showed significant growth in intracellular reactive oxygen species production after treatment. Morphological changes of necrosis and early and late apoptosis stages were observed in treated cells after staining with acridine orange/propidium iodide. DNA fragmentation was observed as a characteristic of apoptosis in treated cells. Results of the present study obviously reveal potential cytotoxic effects of compound C1 against human breast cancer MCF-7 cells.

No MeSH data available.


Related in: MedlinePlus