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Crystal structure and antitumor activity of the novel zwitterionic complex of tri-n-Butyltin(IV) with 2-thiobarbituric acid

Crystal structure and antitumor activity of the novel zwitterionic complex of tri-n-Butyltin(IV) with 2-thiobarbituric acid
Crystal structure and antitumor activity of the novel zwitterionic complex of tri-n-Butyltin(IV) with 2-thiobarbituric acid
A novel tri-n-butyl(IV) derivative of 2-thiobarbituric acid (HTBA) of formula [(n-Bu)3Sn(TBA) H2O] (1) has been synthesized and characterized by elemental analysis and 119Sn-NMR and FT-IR spectroscopic techniques. The crystal structure of complex 1 has been determined by single crystal X-ray diffraction analysis at 120(2) K. The geometry around Sn(IV) is trigonal bipyramidal. Three n-butyl groups and one oxygen atom from a deprotonated 2-thiobarbituric ligand are bonded to the metal center. The geometry is completed with one oxygen from a water molecule. Compound 1 exhibits potent, in vitro, cytotoxicity against sarcoma cancer cells (mesenchymal tissue) from the Wistar rat, polycyclic aromatic hydrocarbons (PAH, benzo[a]pyrene) carcinogenesis. In addition, the inhibition caused by 1, in the rate of lipoxygenase (LOX) catalyzed oxidation reaction of linoleic acid to hyperoxolinoleic acid, has been also kinetically and theoretically studied. The results are compared to that of cisplatin.
donor ligands, c-13, derivatives, organotin(iv) complexes
1565-3633
Balas, V.I.
a43fe572-d91c-4a08-99e6-61dc7c9f5a7d
Hadjikakou, S.K.
bb3ad0f2-fdaf-4a9a-9352-2b168072ac80
Hadjiliadis, N.
066ce2ee-96db-47c2-87c8-98cb87b9f80e
Kourkoumelis, N.
801063f6-6e66-4f9e-9b4d-4f82429a2089
Light, M.E.
cf57314e-6856-491b-a8d2-2dffc452e161
Hursthouse, M.
57a2ddf9-b1b3-4f38-bfe9-ef2f526388da
Metsios, A.K.
3b415f33-afb2-4007-ad16-3027cb6ad1f6
Karkabounas, S.
55be6da7-8a08-47ba-b9e3-60a30964e725
Balas, V.I.
a43fe572-d91c-4a08-99e6-61dc7c9f5a7d
Hadjikakou, S.K.
bb3ad0f2-fdaf-4a9a-9352-2b168072ac80
Hadjiliadis, N.
066ce2ee-96db-47c2-87c8-98cb87b9f80e
Kourkoumelis, N.
801063f6-6e66-4f9e-9b4d-4f82429a2089
Light, M.E.
cf57314e-6856-491b-a8d2-2dffc452e161
Hursthouse, M.
57a2ddf9-b1b3-4f38-bfe9-ef2f526388da
Metsios, A.K.
3b415f33-afb2-4007-ad16-3027cb6ad1f6
Karkabounas, S.
55be6da7-8a08-47ba-b9e3-60a30964e725

Balas, V.I., Hadjikakou, S.K., Hadjiliadis, N., Kourkoumelis, N., Light, M.E., Hursthouse, M., Metsios, A.K. and Karkabounas, S. (2008) Crystal structure and antitumor activity of the novel zwitterionic complex of tri-n-Butyltin(IV) with 2-thiobarbituric acid. Bioinorganic Chemistry and Applications, 2008. (doi:10.1155/2008/654137).

Record type: Article

Abstract

A novel tri-n-butyl(IV) derivative of 2-thiobarbituric acid (HTBA) of formula [(n-Bu)3Sn(TBA) H2O] (1) has been synthesized and characterized by elemental analysis and 119Sn-NMR and FT-IR spectroscopic techniques. The crystal structure of complex 1 has been determined by single crystal X-ray diffraction analysis at 120(2) K. The geometry around Sn(IV) is trigonal bipyramidal. Three n-butyl groups and one oxygen atom from a deprotonated 2-thiobarbituric ligand are bonded to the metal center. The geometry is completed with one oxygen from a water molecule. Compound 1 exhibits potent, in vitro, cytotoxicity against sarcoma cancer cells (mesenchymal tissue) from the Wistar rat, polycyclic aromatic hydrocarbons (PAH, benzo[a]pyrene) carcinogenesis. In addition, the inhibition caused by 1, in the rate of lipoxygenase (LOX) catalyzed oxidation reaction of linoleic acid to hyperoxolinoleic acid, has been also kinetically and theoretically studied. The results are compared to that of cisplatin.

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More information

Submitted date: 2 October 2007
Published date: 2008
Keywords: donor ligands, c-13, derivatives, organotin(iv) complexes

Identifiers

Local EPrints ID: 54418
URI: https://eprints.soton.ac.uk/id/eprint/54418
ISSN: 1565-3633
PURE UUID: 2f55a9da-710a-4fde-8a44-ac05d19063cf
ORCID for M.E. Light: ORCID iD orcid.org/0000-0002-0585-0843

Catalogue record

Date deposited: 05 Aug 2008
Last modified: 19 Nov 2019 01:53

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