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Preparation and in vitro investigations of triphenyl[ω‐(tetrahydro‐2 H ‐pyran‐2‐yloxy)alkyl]tin(IV) compounds
Author(s) -
Edeler David,
Bensing Christian,
Schmidt Harry,
Kaluđerović Goran N.
Publication year - 2017
Publication title -
applied organometallic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.53
H-Index - 71
eISSN - 1099-0739
pISSN - 0268-2605
DOI - 10.1002/aoc.3630
Subject(s) - chemistry , hela , in vitro , pyran , cisplatin , stereochemistry , mass spectrometry , alkyl , a549 cell , carbon 13 nmr , biochemistry , organic chemistry , chromatography , medicine , surgery , chemotherapy
The reaction of SnPh 3 Li with X(CH 2 ) n O–THP (THP = tetrahydro‐2 H ‐pyran‐2‐yl; n = 3, 4, 6, 8, 11; X = Cl, Br) afforded organotin(IV) compounds with the general formula Ph 3 Sn(CH 2 ) n O–THP ( 1 – 5 ). The tetraorganotin(IV) compounds were characterized using multinuclear NMR and infrared spectroscopies and high‐resolution mass spectrometry. Anticancer activity of the synthesized compounds was tested in vitro against the A2780 (ovarian), A549 (lung), HeLa (adenocarcinoma) and SW480 (colon) tumour cell lines with SRB assay. The in vitro investigations revealed that when a shorter chain was present a higher activity was achieved; however compounds 1 – 5 were found to be less active than cisplatin. In addition, the most active compound, 1 , enters A2780 cells and causes apoptosis by triggering both intrinsic and extrinsic caspase pathways.